culture

“Founder Mode” and the Art of Mythmaking

mipsytipsy, , , , , , 31 Comments

I’ve never been good at “hot takes”. Anyone who knows anything about marketing can tell you that the best time to share your opinion about something is when everyone is all worked up about it. Hot topics drive clicks and eyeballs and attention en masse.

Unfortunately, my internal combustion engine doesn’t run that way. If anything, my fuel runs the other way. If everybody’s already buzzing about something, I feel like chances are, everything that needs to be said is already being said by someone else, so why should I bother?

Earlier this year I started writing a piece on why “hire great people and get out of their way” is such terrible, dangerous, counterproductive advice to give anyone in a leadership role. Then Paul Graham dropped his famous essay on “founder mode”, inspired by a talk given at a YC event by Brian Chesky. PG called it “a talk everyone who was there will remember…Most founders I talked to afterward said it was the best they’d ever heard.” The internet went nuts for it.

What I should have done: put my head down and finished the fucking piece. 🙄

What I actually did: ragetweeted a long thread from bed, read a bunch of other people’s takes, then went “well, all the bases seem to be covered” and lost all interest in finishing.

For the curious, here are the takes I really liked:

A month and a half later, we all got to see what the fuss was about. Keith Rabois interviewed Brian Chesky at a Khosla Ventures event in NYC and posted the ensuing 45 min video to YouTube, calling it “Founder Mode and the Art of Hiring”.

The gripping tale of Airbnb’s dramatic rise, crash, and rebirth

Chesky starts off by relating a story about how Airbnb in its early years hired way too many people, way too fast, and buckled under all the nasty consequences of hypergrowth. Lack of clarity and direction, excessive coordination costs, lack of focus, layers of bureaucracy that added no value or expertise, empire building, you name it. 

So it’s 2019, and it’s just starting to dawn on Brian Chesky that he has this massive clusterfuck on his hands. But Airbnb is barrelling towards an IPO, so he feels like his hands are tied. Then COVID hits. Airbnb loses 80% of its business in 8 weeks, going from “the hottest IPO since Uber” to facing possible bankruptcy and dissolution, practically overnight. You never want to let a crisis go to waste, so Chesky seizes the opportunity to restructure the company and make a bunch of massive changes.

This is a fascinating story, right? It is! Or it should be. A young, first-time founder hits it big with his first startup, barrels through a decade of hypergrowth and free money towards a white hot IPO, then belatedly realizes everything he’s done has resulted in a big, bloated, horrendously inefficient company where nobody can get shit done and all the top talent is leaving. Then comes the pandemic. Holy shit! How will he turn things around??

This is an incredible story. I want to hear this story. 

The problem is that he somehow manages to tell it in the most aggravating possible way, where he is a lone hero, buffeted by mediocrity and held back by his own employees at every turn. Actual quote:

“Oh my god, I guess I’m not crazy. I’m just made to believe I’m crazy by my own employees. You’re not crazy. Even though people who work for you tell you you are. You’re not crazy.” 

He talks about the people who worked for him in supremely belittling terms — “C players”, “incapable”, “mediocre”, “worst people”. And he takes absolutely zero responsibility for the corporate disaster that developed in slow motion under his watch, while taking ALL the credit for its recovery.

How might another person have told this story?

I mean…if it was me, I might have started off by confessing that “Wow, I did not do a good job as CEO for the first decade of running my company. I over-hired, underspecified the roles, did a terrible job of setting expectations and rewarding the skills and behaviors that really mattered, didn’t know what org charts were for, and in general just completely failed to build a company that valued efficiency, or had any kind of effective strategy or culture of high performance”.

If Brian Chesky had done that I would have been like, “THIS MAN IS A HERO, EVERYONE STOP WHAT YOU ARE DOING AND COME HEAR HIS HARD WON WISDOM”. Instead, the way he tells the story, the problem is always everyone else, and the solution is always more Brian Chesky.

But Brian Chesky created the fucking problems, by being bad at running the business! 

There is actually no shame in this! He is right: being a CEO is fucking hard. It does not come naturally. Nobody is born good at it. It takes a lot of hard work and pain and suffering to become someone who is good at running a company. I was CEO of Honeycomb for 3.5 years, and it almost killed me. I never got good at it. I have immense respect for the people who do it well.

But this attitude he has, where the buck stops literally everywhere but him — is one I find so fucking repellent. Ethics aside, I also feel like it constitutes a material risk to any company when the CEO is so lacking in humility and self-awareness. (I can leave room for the possibility that he is actually humble as fuck and he just…chose not to share those reflections with us in this talk. 🤷)

It took me a month to make it through the entire recording

I’ll be honest, I made it about three minutes into the video before I blew my fucking top and closed the tab. It made me so angry. This fucking guy. It pushes all my buttons.

But then I had a few conversations with other founders who did watch the whole thing, people I genuinely respect. I kept hearing there was great advice in the piece, if you can just get past the attitude and total lack of accountability.

It took me over a month to make it through the full thing, in fits and starts, but once I finally did, I had to admit that they were right. There is good advice inside, and there are reasonable principles embedded in this talk. Chesky seems to have successfully turned his company around, after all. That’s a really hard thing to do!

In the end, I forced myself to buckle down and get this piece out because … between PG’s “founder mode” essay and the wide distribution of the Chesky interview, these opinions have already imprinted onto generations of Silicon Valley founders and leaders. They have seeped into the water table, and there’s no going back.

I would PREFER the enduring legacy of both “founder mode” and Brian Chesky’s “The Art of Hiring” to be one that moves the industry forward in material ways, and not one that further entrenches the Silicon Valley cult of the founder, Great Man of History, 10x engineer Lone Ranger superhero John Galt type bullshit that has dogged our heels for decades. And there is some decent material here! We can work with this.

So let’s take the major points he makes, one at a time, and mine them for gold nuggets. Here we go!

The story, in Brian Chesky’s words

My apologies for the extremely long quotes, but I think they set the stage well. (Lightly edited for readability.)

“You know, we were one of the first ‘unicorns’, before that was a term. And it was amazing for a bit, from like 2009-2014. It was awesome. It was fun. It was exciting. And then one day it was horrible. And that day went on for like six years (emphasis mine). And basically what happened was I realized you can kind of be born a good founder…I think I was a pretty good founder the day we started the company…But I’m not sure any of us are born good CEOs.

But the other problem with being a CEO is I think almost all the advice and everything they teach at like Harvard Business School…is wrong. For example, the role of a great leader is to hire great people and empower them to do their job…If you do that, your company will be destroyed.”

I’ve never been to Harvard Business School, but I would be pretty surprised to learn that they don’t cover things like organizational structure, span of control, or operational efficiency.

We had a company where we were like a matrix organization. And so like we had all these different teams. And by the way, there’s no governor of how many teams there are. So teams can create teams, can create sub teams, can create sub teams, that people can decide how many manager levels they create. Like if you’re not careful people do this. And why do they do this? Because they want to have new teams.”

(The “governor of how many teams there are” is whoever leads your People team or HR, btw, who in turn rolls up to the CEO. Again, org design is a pretty traditional and well-studied aspect of operating a company.)

So let’s take a marketing or creative department. There’s a team in Airbnb doing graphics and different parts of the site need graphics, advertising needs graphics. And when it was five teams, the five teams would ask the graphics department for graphics and they’d have like five requests. And then pretty soon it’s 20 teams and once it’s 20 teams…they’re like the deli, there’s a line out the block, there’s a multi-month wait. And then what happens is the graphics team, the central service, kind of like gives up and everything seems pointless. And the teams waiting forever give up and they say, ‘give me my own people’. So now they get their own graphics team. So now you have 5 or 10 graphics teams. And you can do the same thing with technology. And product. Oh, you can have 10 data teams that have different metrics and we can go down the list. 

So now you have 10 divisions. Now those 10 divisions are wanting to go in different directions. And they have general managers. And GMs are like little Russian babushka dolls. They want to create miniature GMs and miniature-miniature GMs. And so now you don’t have 10 teams, you’ve got actually 100 teams, because you’ve got these little babushkas running around and they’re going in 100 directions with different technology…

You end up with a lot of bureaucracy. You end up with a company where there’s meetings about meetings where metrics and strategic priorities are the only thing that bind the company together. There’s no cohesive product roadmap, everything is a different time horizon. It’s all short term oriented. And the biggest problem of all is a CEO gets separated from their own product.

And I noticed this thing where there was more bureaucracy, there were these divisions, the divisions then they have to advocate for resources. That advocacy creates politics. And then you have a situation where it’s hard to track what everyone’s doing. So you have like this free for all. There’s not a lot of accountability, which leads to complacency. The complacency means that, like the bad people, the good people are indistinguishable. So the good people tend to move on. They say the company’s changed, the company slows down, and one day you wake up.

Sounds like a mess, all right.

(Chesky’s use of the passive voice here is truly spectacular. Who was in charge for those horrible six years while all this organizational fuckery and uncontrolled sprawl was happening? Oh right, you were.)

To sum up: before the pandemic, Airbnb seems to have had multiple business divisions, each of which had its own GM and a whole ass org structure, with its own engineering, design, marketing teams, etc. This seems wildly weird and inefficient and crazy to me, given that Airbnb only has one product, which is Airbnb? But, they did. So yeah, I am unsurprised that this did not work well.

Which brings us to our first lesson on efficiency.

You should have as few employees as possible

“So what did I do? The first thing I did is I went from a divisional structure to a functional organization. Functional organizations are when you have design and engineering and product management or product marketing and sales. So we went back to a functional organization where our goal was to have as few employees as possible…We said we were the Navy Seals, not the Navy. We want a small, lean, elite, highly skilled team, not a team of kind of mid-level battalion type people. And the reason why is that every person brings with them a communication tax.” 

Basically, Brian Chesky is rediscovering this graphic and it’s blowing his mind.

Brooks’ Law

I feel like this should be really fucking obvious, but I guess the legacy of hypergrowth companies proves that it is not: You should ALWAYS have as few employees as possible. Always. Hiring more people should never be the first lever you reach for, it’s what you do after exhausting your other options. Doing great things with a small team is always something to brag about.

(Okay…maybe not ALWAYS-always. There are some business models where your revenue scales linearly along with headcount, but for your average VC-funded technology startup, “we want a small, lean, elite, highly skilled team” is like saying “you should eat vegetables”.)

Your managers should be subject matter experts

“Oh and by the way, you have leaders that are, quote, managers. I don’t like managers. We don’t have a single manager at Airbnb. And I put that in air quotes. A manager that doesn’t know how to do the job is like a cavalry general that can’t ride a horse. A lot of companies do that. So we only allowed managers that were experts but for a long time we had managers. And one day I woke up and I realized I had 50 year olds, managing 40 year olds, managing 30 year olds, managing interns, doing the job with all these layers that weren’t adding any value.”

The disgust in his voice when he says the word “managers” is palpable. And it’s gross. You can talk about the importance of managers being highly skilled in their domain — and I have, many times! — without treating people with contempt, or disparaging them in public for performing the exact jobs that, again, your own company defined and hired them to do, and they faithfully did, for years.

The moral of the story is valid. The tone is unwarranted and disrespectful (and the whiff of ageism is just the rotten little cherry on top).

As for his claim that “A lot of companies do that” — hire managers that aren’t experts in their field, who just do pure people management — no? Maybe? Not that I’m aware of, not in the past decade. Citation needed.

You don’t manage people, you manage people through the work

“I got rid of all quote managers or they left the company and we said you can only manage the function if you’re an expert. So like the head of design has to actually manage the work first. You don’t manage people. You manage people through the work. I learned this from Johnny Ive because most heads of design, at most tech companies don’t actually manage design. They manage the people. Johnny Ive would say no, my main job is to manage the work and I build a team and we design together. But I’m mostly looking at the work. I’m not like having career conversations all day long. That’s crazy.”

Again, I’m not sure where he gets this idea that at “most tech companies”, the head of design is just like…hired from Starbucks or something for their people management skills? So mystifying.

“The best way to get rid of meetings is to not have so many people”

“The reason there’s too many meetings in a company isn’t because they don’t have no-meeting Wednesdays, it’s because they have too many people. People create meetings, and the best way to get rid of meetings is to not have so many people. There’s no other better way to do that (emphasis mine).”

Um…it might be a mistake to read this too literally, but this is a really stupid thing to say. People do incur coordination costs, but just to be clear, there are lots of ways to get rid of meetings, no matter how many people you do or don’t have, and you should absolutely be investing in some of them in an ongoing way. For example,

  • Develop a rich written culture and rituals around async work
  • Make recordings available, use AI transcription and summaries, or take notes and send them around
  • Use calendar plugins to visualize where your time is going, or even automatically reschedule meetings to compact your calendar and create blocks of focus time (e.g. Clockwise)
  • Declare calendar bankruptcy for meetings with >3 people every quarter, like Spotify does
  • Use ‘optional’ invites to be clear whether you’re inviting someone because you need them there vs for awareness purposes, or because you think they might be interested
  • Simply remind people that they own their calendar, and it’s okay to decline!

Synchronous meetings are one of many, many ways to coordinate between people and groups. There are others. Explore and experiment.

Maybe don’t call your employees “C players”, “incapable people” or “non world class”

“So you end up with this situation where non world class people, you know the old saying ‘A players hire A players, B players hire C players’, I would like to amend it. B players hire LOTS of C players, not just a few but a lot, because those are the kind of people that like building empires. If you can’t capably do your job, you don’t hire people better than you, and a person less capable than you can’t do the job. 

So you need three incapable people because one incapable person can’t actually do all the work. But now three incapable people are just going in three different directions, creating all these meetings and all this administrative tax.”

Deep breaths.

Ok. My goal for this piece is NOT to spend the whole time complaining about Brian Chesky and his lack of accountability, empathy, or respect (or as a friend of mine put it: “I am prepared to argue that he has no theory of mind for any actor at the company that is not the CEO. The search for the deep truth can stop, Brian doesn’t actually know what people are.”)

I want to invest my own limited time and energy into plucking out the bits of advice he gives that are solid, practical, and actionable, so I can contextualize and expound upon them. 

With that in mind, let’s skip right past the insults and acknowledge the fact that there are real challenges here. It’s extremely difficult to evaluate people who are more skilled than you are in the interview process, and harder still to evaluate those who are skilled in a different domain. Developing these muscles as an organization, figuring out what excellence looks like for each level in each role, maintaining a high bar of quality and employee-role fit…these are investments, and they take time and attention.

Constraints fuel creativity. Constraints also fuel efficiency. One of the biggest pathologies of hypergrowth is that when money is free, and everybody is telling you to go go go, grow grow grow! discipline tends to fly out the window. These things are hard to do well even under the best of circumstances; when everyone’s being given unlimited budgets and told to hire their way out of their backlog, well, can you blame them for doing exactly as they’ve been told?

Pretty shitty to retroactively decide they were all losers, if you ask me.

Great leadership is presence, not absence

“Founder mode at its core, though, is about the single principle to be in the details. Great leadership is presence, not absence. So to go back to my lesson, it is not good for you to hire great people and trust them to do their job. How do you know if they’re doing a good job if you’re not in the details?

You should start in the details. And no one does this (emphasis mine). Everyone hires executives and they let them do their thing, and then they find out a year later, the whole thing has been wrong. They’ve hired people they shouldn’t have hired. Now you got to get in the details. And of course, now their confidence goes down. They always inevitably leave the company. And you should actually start in the details, develop trust, develop muscle memory and then let go. So great leadership is presence not absence.”

A-fucking-men.

…Except for the one small fact that Chesky keeps repeating, “no one does this”. My dude, everyone does this. Nobody just hires an executive and sets them loose and doesn’t look over their shoulder for a year. What the flying fuck? That is lunacy. I love that you are discovering basic leadership principles and it is just fucking flooring you, but have you ever cracked a book about management, or talked to another leader? Ever?

Christine and I learned a long time ago not to tell our execs, “I’m not going to tell you how to run your org.” The goal is to do the work to be in alignment so that you don’t have to tell someone how to run their org, because you have a shared idea of what “great” looks like — and what “good enough” looks like — and you can catch deviations early, while they’re easy enough to fix.

Great leadership is presence, not absence; agreed, absolutely. But what does that mean exactly? Fortunately, he’s about to tell us.

“I review every single thing in the company. If I don’t review it, it doesn’t ship.”

“There was this paradox of CEO involvement. The less involved I got in a project, the more dysfunctional it got; the more dysfunctional it got, the more people assumed the dysfunction came from leadership…And then it would get so screwed up, then I would get involved. So what I ended up doing, I took a playbook of Steve Jobs, Elon Musk does this, Jensen Huang does this, Walt Disney does this, all of them do this. (emphasis mine) 

If the CEO is the chief product officer in the company, then you should review all of the work. So I review every single thing in the company. If I don’t review it, it doesn’t ship. I review everything on a cadence…If you’re not actually good at product, you don’t have good judgment and you’re not a super skilled product leader, then maybe you shouldn’t be CEO of the company, I don’t know. So let’s assume you’re actually good at what you do, then I think you should review all the work.”

Whuf.

Let’s back up a second. Brian Chesky has led Airbnb on an incredible journey over the past 17 years — from idea to startup to bloated, sprawling post-unicorn behemoth; through a near-death experience, restructuring and IPO; and emerged on the other side of it all as a public company with a share price of $130. He didn’t do this alone (I really loathe the trope where we treat companies like the extension and embodiment of one man’s will to power), but this also doesn’t happen by accident or happenstance.

He deserves credit for this. It’s more than I’ve done! Who cares what I have to say about any of this, really? I don’t have the same degree of believability as Brian Chesky when it comes to how to build a resilient, enduring, high-quality product company.

So let’s listen to someone who does have believability. Here’s what Reed Hastings says in “No Rules Rules: Netflix and the Culture of Reinvention” (share price: $921):

“There’s a whole mythology about CEOs and other senior leaders who are so involved in the details of the business that their product or service becomes amazing. The legend of Steve Jobs was that his micromanagement made the iPhone a great product…Of course, at most companies, even at those who have leaders who don’t micromanage, employees seek to make the decision the boss is most likely to support.

We don’t emulate those top-down models, because we believe we are fastest and most innovative when employees throughout the company make and own decisions. At Netflix, we strive to develop good decision-making muscles everywhere in our company — and we pride ourselves on how few decisions senior management makes (emphasis mine).”

His co-author, Erin Meyer, chimes in:

“People desire and thrive on jobs that give them control over their own decisions. Since the 1980s, management literature has been filled with instructions for how to delegate more and ‘empower employees to empower themselves’…The more people are given control over their own projects, the more ownership they feel, and the more motivated they are to do their best work.”

OMG, confusing!! Evidently ALL of them do NOT do it. What even IS the moral of the story here?! Well…it’s not a simple one, unfortunately. It turns out that you can’t just copy what Brian Chesky did at Airbnb, or what Reed Hastings did at Netflix, and paste it into your company and expect the same results. Bummer!

There are many paths up the mountain

This is an architecture problem. The Chesky/Airbnb architecture is like a monolith application, or a single-threaded process. Everything goes through the CEO, and that’s how they maintain quality. The Hastings/Netflix architecture is more like a microservices application or a threaded, highly concurrent process.

Either can work. Both have tradeoffs and implications. If you try to import either philosophy wholesale, it will break in unexpected ways; if you try to mix and match, it will probably be an unfettered nightmare.

Your architecture will only work if it solves for your problems, utilizing your resources, values, and contingencies. It needs to be authentic, consistent, and internally coherent. This doesn’t mean you can’t learn anything from either of these companies. You can — I have! But you should probably treat them like reference architectures — just-so stories about how individual cultures have successfully evolved in response to their unique challenges and threats, not recipe books.

And I can tell you right away that as an employee, one of these models looks a whole hell of a lot more appealing than the other.

But wait — it gets worse. 😅

Should the CEO interview every candidate?

“I interviewed the first 400 people and I wish I interviewed longer. Maybe my biggest regret is not interviewing the first thousand. I think you should interview every candidate until the recruiting team stages an intervention. Once they stage an intervention, you should interview for two more years after that until everyone threatens to resign…and then you should step away.”

Well. If this is the kind of company you’re choosing to build, then I suppose you may as well be consistent.

Can you be calibrated as an interviewer on every single opening, for every role? My God, no, not even close. 

The thing is…I have talked to so many people who work at companies where the CEO insists on interviewing every candidate. It seems to be a trend that is gaining steam rather than losing steam, much to everyone’s misfortune.

Which means that I have personally heard so many anguished stories from angry, frustrated engineering managers who have had their decisions overturned by arrogant CEOs who lacked the skills to evaluate their candidate’s experience, who were biased in blatant and embarrassing ways, who were so fucking overconfident in their own judgment that their teams are constantly having to compensate and apologize and mop up after them.

Want an example? Sure. I recently heard from a director at a 500-person company who spent six months cultivating and recruiting an exceptional hire with an unusual skill set. The candidate made it through their interview loop with flying colors, only for the CEO to reject them because they had recently had a child and were forthright about the fact that work/life balance was a meaningful consideration for them at this point in time. (The director did their best to do damage control, but even though the CEO ultimately relented, the candidate was no longer willing to leave their job. Can you blame them?!?)

It keeps getting worse! Here comes the low point.

“If they would come work for you, they’re not good enough. They’re only good enough if they come to work for me.”

“Can I give you an example of what I do today that no one else, not no one but maybe 95% of public company CEOs don’t do. I have an executive team, right?…I have like seven execs and 40 or 50 VPs. All the directs to my directs dual report to me. I am the co-hiring manager of all the directs to my directs and so we meet and I often tell my directs, ‘I don’t want somebody that you could hire without me. If they would come to work for you, they’re not good enough. They’re only good enough if they come to work for me. So if you can hire them without my help, they’re not good enough.’”

I just about lost my shit over this. Do you hear yourself, bud? 

The irony is…I am actually the world’s hugest proponent of skip level 1x1s. I have two or three half-written blog posts in my drafts folder preaching the value of skip levels. I’ve written MULTIPLE twitter threads over the years, talking about how important it is to build relationships with your manager’s managers and your direct reports’ direct reports. 

I’ve said that I think skip levels are like end-to-end health checks. It’s important to open a line of communication and explicitly invite critical feedback and bad news. It’s a way to verify that managers are doing a good job managing their teams. It’s how you help iron out telephone games and ensure packets are being transmitted and received up and down the org chart. They are such a critical contribution to organizational health and clear communications, and not enough places invest in them.

I’m also a big proponent of promoting from within, of hiring ambitious people — all of it. 

But this attitude towards hierarchy that locates the CEO at the center of every universe, and ranks people in importance according to their proximity…it’s just gross. It’s an attitude that’s contagious; it spreads, like syphilis. And I do not think it unlocks intrinsic motivation or excellence in most humans. It mostly incentivizes a bunch of maladaptive behaviors like sucking up to the CEO.

UGH. Okay, this is getting really long. I’m going to jump rapid-fire through a few final nuggets.

Executive hiring fails when you hire someone at the wrong stage

“Probably the number one reason executive hiring fails is because you hire somebody at the wrong stage. And they were managing instead of building, and you didn’t know that. And so you brought in a manager who is an expert or not so expert, but comfortable in a highly political bureaucracy. And now they have to do things themselves and they can’t. They also have the wrong stage instinct, right? Maybe a CMO used to run $500 million marketing budgets. Now they have a $50 million or $5 million budget, and they don’t know what to do and they can’t do anything themselves.”

Yes, execs can fail because they are managing instead of building, but they can ALSO fail because they are building instead of managing. I’ve worked with execs who operated like they were effectively the most senior IC in the room, and they had…extreme limitations as leaders, let’s put it that way.

Overall, this is a solid point. Being a CMO that takes a company from $1-10m or $10-$50m is a very, very different skill set than taking a company from $50 to $250m, or through an IPO.

We look for executives who can both scale up and scale down. Scale up: you can speak credibly to the board, at the right level of abstraction vs detail, you can craft strategy, see around corners etc. Scale down: you know what “good” looks like for work all over your organization, you can get down in the weeds to help coach a struggling IC back to victory, you can debug a flailing campaign or workflow. Both matter.

References are critical for building confidence in your hires

“I actually prioritize references over interviewing…Andreeson Horowitz would tell me, you should do 8 hours of reference checks per employee.”

Agreed. I’ve said many times that if I had to choose between interviews or references, I would pick references every time. (Fortunately, you don’t have to pick!)

“Ask them who the best people are. Say, ‘okay, separate from this topic, I just want to know who’s the best person you’ve ever worked with.’ Do they say the person’s name you just talked about?”

This trick doesn’t fool anybody.

“Then you ask questions like, okay, what do I need to watch out for? If I were to hire them? What is the one area of development you would give them?”

This is good advice. You should always probe into people’s weaknesses and areas of development. Everyone has them, there’s no shame in that. Hearing details about where they are weak can give you confidence, and set you up better to support them. It gives you richer insight into them as a person and coworker.

A basket of interviewing tips and tricks

“Interviewing. My first tip is you ask follow up questions. You ask them how to explain how they did something. And the key is to ask two followups. You never want to get the first answer, you always want the third answer.”

Asking follow-up questions is a classic technique, and a good one. But don’t let them dominate the conversation with a narrative. You want to be intentional about pulling on specific threads and making sure they answer what you asked, not pull a politician’s move and give the answer they feel like answering. Does the answer sound canned, or are they thinking on their feet?

“Often there’s too many people interviewing for too short a time, not going deep enough. Your interview panel should be as few people as possible, going as deep as possible…3 or 4 people going really deep is better than 8 or 10 people giving you their first impression…and they’re actually mostly thinking about what this means for them.”

Yeah, so this is an area where my thinking has actually changed a lot over the years. I used to cast a much wider net, like I felt like people ought to get to interview anyone who was being hired over them. I’ve come to realize that having too many veto points in the system is dangerous and doesn’t actually add more value. Yes, people like being offered the opportunity to affirmatively vet someone, but at a certain point you have to prioritize the candidate experience — and trust your team to make good choices.

It’s usually better to have a fewer number of interviewers, but make sure they are all well calibrated for the role, and that there’s a certain amount of coordination between interviewers so everyone is covering different questions/aspects of the role. If you have 8 or 10 interviewers, that is way, way too many.

“Every potential hire is guilty until proven innocent. It is the opposite of our justice system. Most people, when they interview, they look for the absence of weaknesses and that is innocence. The presumption is someone’s good. You should always presume somebody is not good. You need proof. They don’t work for you. So you need evidence to hire them, not evidence to eliminate them as a candidate and almost every company gets this wrong. And what they end up doing is hiring mediocre people with an absence of weaknesses, not people that have a preponderance of evidence of being really good and spike in a few areas.”

Again, there is a solid principle buried deep under all this repugnant bullshit about “mediocre people” and “guilty until proven innocent”. Here’s how I would put it: you want to hire people for their unique strengths, not their lack of weaknesses. If they’re strong where you need them to be strong, it’s okay if they aren’t equally superpowered at everything — that’s why we build teams, to supplement and balance each other out.

In the Honeycomb interview process, we emphasize that we want to see you at your best — please help us do that! If you don’t feel like we’ve seen your strengths, please tell us, so we can fix it. 

See, how hard was that? Same point, zero jackassery.

There is no such thing as the ‘best people’

Another way to look at it is the quality of the people. People never hire people better than them. So there might be people that are good at their job, but it’s not enough to be good at your job in most large companies. If you are the best in the world at your job, but you can’t hire really great people, then you’re not going to be the best in the world because your team isn’t really good. 

God, he does this over and over again, talking about people like they exist on some index you can stack rank or something.

Here’s one small mental hack that makes a world of difference: remember that you are trying to hire the right people to join your team/org/company.

Not the “best” people. 

The right people.

The fact that someone isn’t a superstar employee for this company, this product, this team, at this stage, doesn’t mean they might not be a superstar employee for someone else. And people who aren’t “superstar employees” are still worthy of your respect. Not wanting to work your ass off is a perfectly legitimate life choice and does not make them a lower quality human. Maybe they aren’t the right hire for you, but you don’t have to treat them — or talk about them — like shit.

People who work for big, stable companies, are not necessarily bad at their job or incapable of building things. They have a different skill set, they may work at a different tempo, but this doesn’t mean they suck. My god. So fucking condescending.

There’s such a special kind of hubris in these startup kids who are losing tens of millions of dollars a year and looking down their noses at their peers in organizations that are making tens of millions of dollars a year, believing themselves to be categorically better than them just because they can…prototype real fast? Unclear.

Building a world-class team is about more than just hiring

I wrote a piece a few years ago called “The Real 11 Reasons I Don’t Hire You”, where I discussed a few of the many variables that go into deciding who to hire. It’s complicated — it is irreducibly complicated. And it should be.

But it’s also just the beginning. The team, the culture, the sociotechnical systems you hire them into are going to exert a gravitational pull over all of the people you hire. Are you bringing them into an environment that is generative, playful, creative, experimental, intense, competitive, demoralizing, controlling, grinding, aspirational, compliant, hierarchical, passive-aggressive, or aggressive-aggressive? Are standards applied consistently? What behaviors get rewarded or punished, actively or otherwise? Who gets mentored and fast tracked to the top? Who gets the most facetime with the CEO? Is CEO facetime a prized currency? Why? Systems drive behavior.

Sociologists have a term for the cognitive bias that causes us to predictably, consistently over-emphasize individual agency and attributes and underestimate situational factors: the FAE, or Fundamental Attribution Error. This whole interview is sopping with FAE energy.

It’s not as simple as “just hire great people”. You want to hire people who share your values, want to do the job, have the right skills, are motivated, etc, and then the conditions you create for them to work under will either cause them to flourish and feed their creativity and drive, or will crush them and shut them down. The feedback loop runs both ways.

Hypergrowth is hazardous to your company’s health

“In a hypergrowth company, it could even be 50% of your time is hiring.”

Chesky mentions hypergrowth only once and briefly, towards the end, but it’s a vital piece of context if you want to understand the Airbnb story.

As he says, Airbnb was one of the O.G. unicorns — a unicorn before they coined the term ‘unicorn’. It was born in the era of hypergrowth and free money. That’s the only way to make any sense of the fact that a company could pay such comically little attention to efficiency, for so long. (Thirteen years, to be exact.)

When all you have is a hammer, everything looks like a nail. In hypergrowth mode, you solve every problem by throwing more resources at the system. The tools you learn are weird ones, which map awkwardly to the skills you need to run a normal, sustainable company that’s expected to turn a profit. Hypergrowth encourages a raft of bad habits, and attacking every problem by hiring more people is one of them.

This is not good for anyone, except perhaps venture capitalists. The externalities are dreadful. It’s impossible to scale your culture, your practices, your values, or people’s expectations at an equivalent pace. The correction is brutal, when the time finally comes to worry about efficiency — and eventually, everybody needs to worry about efficiency. The higher the ride, the harder the fall. The bill comes due.

The CEO-centric view of the universe

One of my least favorite things about YC is the way it seems to pursue extremely young and inexperienced founders. If you’ve never been a manager, director, VP, staff or principal engineer, it’s a lot easier to look down on those people and disrespect the role they play in the ecosystem.

It looks like Brian Chesky was about 26 years old when he cofounded Airbnb. He has basically been a CEO for his entire career. And this is, I think, a great example of the kind of blinkered perspective you get from someone who has no real idea what it’s like to sit anywhere else on the org chart.

After watching the first 40 minutes of this talk, one might reasonably wonder if Brian Chesky understands that being CEO of a company means being accountable for its outcomes.

What makes all of this extra frustrating is that in the final five minutes, he shows us that he does know this…at least when it comes to board interactions.

“Oftentimes if you take advice from a VC and it doesn’t work and you don’t have traction…You’re still held responsible. So the only thing that matters is you’re successful, not if you listen to them or not. People sometimes forget and they’re like, well, you shouldn’t have listened to me. They don’t say it that way, but that’s kind of the way it happens. So I would just know that, like, you own the outcome no matter what.”

Yeah, bro. You do.

 

“Founder Mode” and the Art of Mythmaking

How Hard Should Your Employer Work To Retain You?

mipsytipsy, , , 6 Comments

Recently we learned that Google spent $2.7 billion to re-hire a single AI researcher who had left to start his own company. As Charlie Brown would say: “Good grief.” 🙄

This is an (incredibly!) extreme example. But back in the halcyon days of the zero interest rate phenomenon (ZIRP), smaller versions of this tale played out daily. Many rank-and-file engineers have stories about submitting their resignation, or threatening to quit, and their managers plying them with stock or cash or promotions to stay. This happened so much that it started to seem like the normal thing to do when you wanted a raise or a promotion. Job hopping for better comp also happened, but people quickly figured out that by merely threatening to leave, you could often get the loot without the hassle of having to actually switch jobs.

Many of these stories have been embellished dramatically over time, as real anecdotes fade into legends of the “my friend knows a person who” or “I read it on Blind” varieties, but the lore is based in reality. It really did happen. The legacy of these episodes is…not great.

To be clear, I do not begrudge employees trying to maximize their wages and comp by changing jobs. It’s the gamification and brinksmanship I object to, and all the ways it ends up distorting company culture and values and outcomes. In the overheated ZIRP environment, lots of companies felt like this is what they were forced to do to compete for talent. Maybe so, maybe not. But money is not the only thing people value, which means that this is not the only way to compete for talent.

After all, the hot air of the inflationary ZIRP bidding wars is what led to the post-ZIRP job market collapse. The boom and bust cycle is stressful and counterproductive, which leads to uneven, disastrously unfair outcomes and an oppositional, extractive mindset on both sides. We can do better. We must do better. Let’s talk about how.

You should stay at your job as long as it fulfills your career priorities

How long should you stay at your job? As long as it’s the best thing you can do for your career, or at least a reasonable, smart career choice, in alignment with your own personal career goals and life priorities.

Maybe this sounds mind-numbingly obvious to you. But far too many people stay far too long at jobs where they aren’t happy, aren’t growing, and aren’t setting their future selves up for success. Hey, I’ve been there…these decisions can be brutal. 💔

Your career is an appreciating, multimillion dollar asset, probably the largest single asset you will ever own. How you define what is best or right for you will inevitably shift over the course of your 40-year career, and that’s fine. This is normal.

But you have to make these decisions based on what is right for you, your career, and your family. Not because, say, you feel responsible for protecting your team from upper management, or you’re afraid of what will happen to the product or the team if you leave, or you feel like you owe them something. Nor should you stay out of fear, whether that be fear of interviews, that this is the best you can do, etc.

Sometimes your top priority might be making the most money, so you can get out of debt. Sometimes it might be a simple, uncomplicated paycheck and low expectations so you can spend a lot of time with your family. Sometimes you may be on a hot streak and raring to go, working like crazy and making a name for yourself in the industry. When in doubt, my advice is to 1) preserve optionality, 2) follow good people and 3) lean into that which energizes you.

The company should employ you as long as it’s a good fit

There are certainly companies where people get fired too quickly or in bad faith. There are also companies where people who are not working out linger on and on and on in the role. It might be tempting to conceive of the latter situation as more worker-friendly, but in all honesty, neither situation is great.

If the wants and needs of the company and the employee are not aligned, you aren’t doing them any favors by dragging it out or keeping them around in a prolonged state of purgatory. If things are decidedly not working out, I promise, they are miserable.

If you are a manager, your number one job is to bring clarity. What are the expectations for the role, what does success look like, what support does the employee need in getting there? When things aren’t going well, your job is to work with them to figure out what is happening, and come up with a plan. Is there a shared understanding of what success looks like in this role? Is it a skills gap, are there relationships that need mending, do they need some time off to deal with personal issues? Are they still interested in the work? Is it still a good fit?

There is an extremely short list of jobs that can only be done by managers, and managing people out (which does sometimes mean firing them, but not always), is at the tippy top of that list. Making sure the right people are on the team is job number one. Figuring this shit out swiftly — we’re talking months, not years — is critical.

Also, none of this happens magically or automatically. This shit is hard. Which is why it is important to invest in these skills and set expectations for your managers.

Your manager should try to make this a great career opportunity for you, for as long as possible

It’s the job of your manager to ensure that this role is a great opportunity for you, for as long as possible. For mid-level engineers this means making sure you are learning and expanding your skill sets, that you have access to mentorship and support systems, that you get to follow your curiosity to some extent and work on things that interest you. For more senior folks, this might mean looking out for opportunities to lead projects or wear new hats.

But that won’t be forever, for anyone — not even your CEO or founders! And that’s okay. This is not a family, it’s a company, and hopefully something of a community.

Sometimes you get an opportunity you can’t refuse. Or life takes you in a different direction. It happens! It is not a tragedy when people leave for a better opportunity or something that excites them.

Real-life example: Paul Osman left Honeycomb because he and his family were moving to NYC and needed a Big Tech salary. He was a wonderful staff engineer (at a time when those were scarce), a high performer, effective across the org, beloved by all; he was even on our board of directors, our first elected employee board member! But when he let us know he was going to leave, we … wished him well. We couldn’t match the salary he needed to pull down; he knew that, we knew that. Nor would it have been fair to all the other staff engineers if we had tried.

Managers need to be actively engaging in career development and planning with their reports. The more you know about someone’s personal values and priorities, the better you can do to try and set them up with opportunities that appeal to them and the trajectory they are on.

Your manager should also be honest if you could find better opportunities elsewhere

I also believe that good managers will be honest with their employees when they feel like this may no longer be the best place for them. Not every opportunity exists at every company, at every time.

It can be hard to admit to your star employee that if you were them, you’d be looking elsewhere for opportunities. Maybe you have an incredible, ambitious senior engineering director who is hungry and chafing to move up, but you don’t expect to see any openings at the VP level over the next year or two. They deserve to know that, I think.

To be clear, you are NOT firing them. Usually, you are holding your breath and praying they will choose to stay. Often they do! Maybe they love their job enough that they’re happy to stick around for another couple years just to see if any openings do arise, or they switch into passive job search mode, taking interesting calls but not actively looking. Maybe you have a conversation about ways they could build their career in other ways, by doing more writing and speaking. Maybe they decide this is a good window of time to have another kid.

But if you can’t honestly look them in the eye and tell them this is the best place for them, given what you know of their ambitions and priorities, you have to say so. It’s on them to decide what to do with that information. But if you want them to trust you when you say this is a great opportunity for their career, you have to be truthful when the opportunity is just not there.

Some amount of employee turnover is natural and healthy

When I worked at Linden Lab in my early twenties, I remember vividly how much pride we took in the fact that people never left. I was there for 4.5 years, and I think we had a single-digit number of departures that entire time. I remember thinking to myself how incredibly special this company must be, because nobody ever wants to leave.

It was a special company. ❤️ But when I look back now, this part makes me cringe. Yep, nobody ever left. No one was ever managed out, even the people who never seemed to do anything but hang out in Second Life or work on whatever the fuck they personally felt like doing. It was a little bit … culty? There were some incredible engineers there, but also a systematic inability to row in the same direction or make a plan and execute on it. In some ways Linden felt more like a social club than a business.

I loved working there, don’t get me wrong, and I learned a lot. But in retrospect, some amount of turnover is good. It’s healthy. It means you have standards for yourselves, and someone is paying attention to whether or not we’re actually making progress and getting shit done, or whether or not the people we need are in the right seats.

Tenure functions somewhat differently at very large companies; it may take years for someone just to come up to speed and learn how to operate within the system, so they do their best to retain people for decades. When you’re a startup in growth mode, though, you become a completely different organism every few years. People who are happy as clams and supremely productive from $0-$1m or 1-50 people may or may not adjust well to the $50m or $200m environment. People who are superstars on one side of the Dunbar number are sometimes bitterly unhappy on the other side.

There’s “regrettable” and “non-regrettable” attritions, but the company should be able to go on operating even in the face of “regrettable” departures.

There are, of course, exceptions. So let’s talk about these.

Sometimes people sit in critical roles at critical moments

At any given time, there exists a subset of people who are disproportionately critical to the success of the business at the moment, people whose departure could seriously jeopardize the company’s ability to meet its goals this quarter or even this year. It sucks, but it’s a reality. This happens.

If that’s a very long list of people, however, or if it’s the same people over and over, or if the actual survival of the company would be in jeopardy and not just a subset of your goals, then your leaders are not doing their fucking job.

Part of the job of running a company is developing talent to be successors to key people. Part of their job is to replicate and distribute critical company knowledge and skills. None of us should be irreplaceable — not even the CEO, or CTO, or founders. If the company’s future depends irrevocably on the continued employment of any individual person, the company’s leaders are fucking up, full stop.

There are two types of disproportionally critical employees: superstars and SPOFs

The right time to determine who is on that critical subset is NOT when one of them resigns. You should be asking yourselves somewhat regularly — which people are our superstars, the ones we really, really want to make sure are happy and fulfilled here, and which people are single points of failure, the ones we cannot easily replace, or function in their absence?

Note that these are not necessarily the same two lists!

This doesn’t have to be a heavyweight process, but if you are large enough to have a People team or HR team, they should be ensuring that talent reviews and succession planning conversations are happening like clockwork, once per quarter or so.

Your superstars are the people who are standout performers, carrying a ton of load for the company or generating uniquely creative ideas, etc. You should identify these people proactively and make sure they are feeling challenged, supported and valued. What are their values — what lights their fire? Where are they trying to go in their career, in their life? How do they like to receive recognition? How does it manifest when they feel overwhelmed or demotivated?

Managers tend to devote most of their attention to their lowest performers. Be wary of this. Yes, give people the support they need. But the biggest bang for your buck is typically the time you spend on your highest performers. Don’t neglect your superstars just because they are doing well.

Get to know your superstars, and compensate them

And compensate your superstars. Whatever pool of money is set aside for high performers at your company, make sure they get a slice of it — a raise, a bonus, direct equity, etc.

But money isn’t the full story, it’s just the first chapter. This is where you need to dig a little deeper and get to know them better — their values, their love languages, how they like to receive recognition. Make sure other company leaders know who is kicking ass and what kind of opportunities they’d be into.

Being a superstar should earn you more than money — it earns the right to experiment, try a moonshot, be first in line for a lateral role change into another area of interest. Maybe you can line them up with a work coach or continuing education, support them writing or presenting their work at conferences…the list is endless What do they value? Find out.

It is normal and desirable for your shortlist of superstars to shift over time. If it’s always the same few names on the list, that may reflect a different problem: that you are handing out all of the opportunities to take risks and shine brightly to the same few people, over and over again. It’s your job to cultivate a deep bench of talent, not one or two lead singers with everyone else in the chorus.

Work on a plan to de-risk your SPOFs

And then there are your single points of failure, people who are the only person who knows how to do something, or the only person in a function. In the early days of any startup, you have a ton of these. As you grow, you should steadily pay down this list.

If superstars are the people you want to keep out of joy, SPOFs can be the people you need to keep out of fear. You can’t function without them, even if they’re mediocre contributors. This is bad on several levels.

This is just a risk analysis you need to work through as a leadership team. Have a plan, have a backup options, and steer a path out of this state as soon as you can afford to.

I’m not naive. The realities of business are real, and sometimes something takes you by surprise, or you need to try and do a diving save for someone who has just announced they are leaving. But that should not be common. The normal, expected reaction when someone tells you they are leaving should be, “ah, that’s too bad, we’ll miss you! I’m so happy for you and this new opportunity you’re excited about!”

Most jobs will be saved or lost by boring organizational labor, not heroic diving saves.

Here is one important reality that many employees don’t seem to grasp:

The harder your employer is affirmatively working to do right by you, the fewer heroics they will be willing or able to do to retain you. And the harder the company is working to be fair and equitable, the less they will be willing or able to make exceptions to their existing compensation framework.

Here is one good end-to-end test of the system: you should not be able to get a higher salary or a larger stock grant by quitting and getting immediately re-hired. If you can, your company is not doing the work to value the labor of its existing employees by the same yardstick as it values new hires.

A lot of companies fail this test! Because in order for this to be true, your company needs to consistently adhere to pay bands, pegged to market rates, adjusted and reconciled each year. They need to do something like boxcar stock grants. They need to periodically audit their own levels and comp and look for evidence of systematic bias. They REALLY need to not make exceptions to their own god damn rules.

As Emily Nakashima says, “Many companies hemorrhage great employees in underrepresented groups because they do all those things but they fail to bring a DEI lens to them — ‘we have salary bands! we have a fair comp system! we think about ladders and promo paths!’ and then they do zero work to make sure those things are applied equitably to all their employees, including across axes of diversity like race and gender.”

All of these things take organizational willpower, and they are hard. It means a lot of hard conversations. It means saying “no” to people. It’s much easier to give out goodies to the people who complain the loudest or threaten to quit, at least in the short term.

It’s easy to talk about fairness and equity, but it takes a lot of structural labor to walk the walk

A lot of work goes into building and maintaining a system that can pass the sniff test in terms of compensating people fairly and equitably, instead of based on their negotiating skills or how much they made at their previous job.

You need to have a job ladder and levels you believe in, ones that accurately reflect the skills, behaviors and values of your org and have broad buy-in from the team. You need a process for leveling people as new hires and at review time, and for appealing those levels when you get it wrong. You should have salary bands for each level, with compa ratios based on market rates. You should be able to show your work and explain your decisions. (For example, we target the 65th% for companies of our size and funding levels, and we pay everyone SF market rates, no matter where they are located in the world.)

This is why review-time calibrations are so important. Calibrations are not about calibrating ICs, they are about calibrating managers. Calibrations are to diminish the inequity that results when one manager has a different understanding of the level an engineer is operating at, so the engineer would receive a different level, band, or rating under a different manager.

Obviously, all of these sociotechnical systems are made and operated by human beings, so there will always be some intrinsic messiness and imprecision. This is why it matters that managers show up with humility and work to get aligned with their peers on what truly matters to the company and the org. This is why it is so important that we show our work and engage with ladders and levels as living documents.

A lot of this labor is invisible to employees, and not especially well understood. I think a critical part of making these systems work is helping employees understand the tradeoffs being made, and how having a consistent leveling system ultimately benefits them, even if they are personally frustrated about not getting promoted this half. Which means every manager needs to be equipped to have these hard conversations with their team.

It should be okay to tell your manager you’re thinking about leaving, and talk about your options

HR teams will typically bucket departures into voluntary and involuntary, aka “regrettable” and “nonregrettable”. In reality, almost any time someone leaves their job, it’s some muddled combination of the two.

In the optimal case, voluntary departures are rarely a complete surprise. Surprises suck. They’re hard to plan around, they often leave gaps in coverage or contributions, and they’re a bummer for morale. You should be able to be honest with your manager and tell them if you’re starting to look around, or if you’re finding yourself less happy and motivated these days. However, this requires a lot of trust in the relationship — that the manager won’t retaliate, won’t fire you, etc — and from what I gather, it seems to be fairly uncommon in the wild. 🙁

Employees do not owe their manager a heads up or a conversation in advance, but this is unequivocally the level of relationship trust we should aim for.

Steph Hippo says, “I love being the manager people want to work for, and it took me a while to figure out how to also be the kind of manager people wanted to have ‘fire’ them by helping them move on. I’m really proud of how many people I’ve been able to help move off my team because we found a better fit. Doing this contributes to your reputation as a leader and as an employer. I found it meaningful if someone that moved on from my team did so on good terms, came back to visit, or sent other people to check out our job listings. That’s a sign that you’re parting with folks on good terms.” 💯

Managers can prove themselves worthy of this trust by not reacting, not retaliating, not treating people any differently, not leaping to conclusions, not running ahead and making decisions or commitments ahead of what the employee has stated.

Should you ever try to change someone’s mind about leaving?

Not never…but rarely. You should always try to understand why someone is leaving. Exit interviews are a great tool here, especially in situations where there has been relationship friction. Departures are a trailing indicator, but often a very powerful signal of things managers should be paying attention to, to make things better for those who remain.

If someone has decided to leave, you’re not going to “save” them via bribery alone. I’ve never seen the tactic of throwing money and titles at someone actually get them to stick around in the long run.

However, I have seen departure announcements get turned around when they include some form of development — when you can identify real underlying sources of discontent, and meet them with action.

Another real life example: A couple years ago, Phillip Carter told us he had decided to leave and take another role in the industry. We had some intense conversations about why that was and what was missing, and realized he had been struggling to connect with the reasons behind what we were building, largely because he had never written or supported code in production during his time as a software engineer. He decided not to leave after that, and he is here to this day.

There will be times when someone has decided to leave, and you want to fight for them to stay. In those situations, you need to get really crystal clear with yourself before taking action. What are the underlying risks to the business, and how far are you prepared to go?

On extremely rare occasions, heroic measures may be the lesser of two evils

Sometimes you may have to try for a diving save. That’s just the reality of doing business, esp at startup stages where you have less redundancy, a shorter planning horizon, more overall chaos and a smaller overall operating budget.

Sometimes your goals are at risk, and you feel like you don’t have a choice. But any time you find yourself bargaining or trying to bribe people to stay after they’ve decided to leave, you should take a hard fucking look at yourself and how you got there, and whether or not you can justify your actions.

Exceptions are often the path of least resistance for the manager making the exception in the moment, but they impose a heavy, compounding cost to the business over time. Any time you make an exception to keep someone, you risk breaking your commitments to everyone else. And rumors about exceptions being made will fly fast and furious (sometimes it seems like there is a 10-20x multiplier of rumors to reality). 😣

I will not sit here and tell you no exceptions can be ever made. Systems made of people are systems that are never perfect. Once in a while, making an exception might actually the way to restore justice to a situation. Other times your ass is well and truly backed into a corner. But exceptions are SO costly to your credibility, you must at least build peer review and consequences for exceptions into the system.

A few checks and balances to consider:

  • Individual managers should not be able to make an exception without the buy-in of their director, VP, and people team
  • It should generally trigger some kind of review of the system policy in question, to see if it still serves its purpose
  • You should be able to look in each other’s eyes and explain your reasoning, and not feel ashamed of it if word gets out

Shit does happen. But if this kind of shit happens on the regular, you can’t blame people for becoming extremely cynical about the way you do business, and you can expect to get way more people trying to game the system to get the same results for themselves.

People should not use threats of leaving to try and effect change or get raises. This should not be an effective tactic — and in order for it not to be an effective tactic, we cannot reward it with results. When you make exceptions, you all but guarantee more people will try this.

People work at jobs for money, but not only money

While writing this piece, a friend told me a story about when he became an engineering manager a decade ago, and soon noticed that his two women engineers were the lowest paid and the lowest leveled people on the team, which didn’t seem to correlate with their actual skills or experience. He asked his own manager what was up with this, and the response he received was: “Well yeah, neither of them has ever been a flight risk.”

This kind of attitude is, to put it politely, a fucking cancer on our industry.

There are two radically different philosophies when it comes to corporate compensation. In the first scenario, you pay people as little as possible, and consider it your job as a manager to extract the most work out of people for the least pay. Information is power, so information asymmetry is endemic in these environments, and people are paid according to their skill at negotiation or brinksmanship. You typically blow your wad trying to compete for the “best” talent in the world.

In the second scenario, you do your best to compensate employees fairly and competitively, balancing their needs and wants against other stakeholders and the overarching mandate for the company as a whole to succeed. You practice transparency and show your work, and actively work to counter systemic biases. You understand you can’t compete for every great hire out there, but you try to equip people with the information they need to evaluate whether or not you are mutually a good fit.

Companies that operate according to the first scenario are so alienating and toxic (and almost certainly illegal, in many cases) that few will openly claim to be this kind of company. Most companies at least pay lip service to equity and fairness. But because everyone is typically mouthing the same kind of things, employees will scrutinize your actions far more than your words, especially when it comes to comp.

At the end of the day, these are jobs. People work at jobs for money, but not only money. I think we would all be better off if we could get better at articulating the tangible and intangible rewards of our labor, treating each other with dignity and honesty, and being straightforward about our needs and wants and goals on both sides, instead of treating comp like some kind of high stakes casino game.

 

Huge thanks to Steph Hippo, Paul Osman, Phillip Carter, Lesley Cordero, Emily Nakashima for their feedback, critique, and stories.

How Hard Should Your Employer Work To Retain You?

Pragmatism, Neutrality and Leadership

mipsytipsy, , , , , 2 Comments

Every year or so, some tech CEO does something massively stupid, like declaring “No politics at work!”, or “Trump voters are oppressed and live in fear!”, and we all get a good pained laugh over how out of touch and lacking in self-awareness they are.

We hear a lot about the howlers, and much less about the practical challenges leaders face in trying to create a work environment where people from vastly different backgrounds and belief systems come together in peace to focus on the mission and do good work. Or how that intersects with the deeply polarizing events that now seem to shatter our world every other week — invasions, Supreme Court rulings, elections, school shootings, and the like.

Are we supposed to speak up or stay silent? Share our own beliefs, or take a studiously neutral stance? What do we do if half of the company is numb and reeling with grief, and the other half is bursting with joy? Nothing at all? That feels inhumane. Is the reality that we live in a world where we can only live, work, and interact with people who already agree with us and our political beliefs? God, I hope not. 🙁

This has been on my mind a lot recently. We are 103 days out from a US Presidential election, and it’s going to get worse before it gets better.

So here goes.

Caveats, challenges and cautionary tales

There are some immediate challenges to things I’m trying to say here. A couple:

The term “politics”, much like the term “technical debt”, can mean way too many things. Local, regional or national electoral politics; activities associated with power distribution or resource allocation; influence peddling or status seeking behaviors, putting your needs above the good of the group, and so much more. Therefore I will use the term sparingly, and prefer more specific language where possible.

I don’t often do this, but I am explicitly addressing this piece to other founders and execs. Not because it doesn’t apply to people in other roles; it does. It just got really wordy trying to account for all the possible variations on role, scope and perspective involved.

As a leader, your job is to succeed

This might sound obvious, possibly to the point of idiocy. Yet I think it bears repeating. For all the mountains of forests of trees worth of books that get written every year on leadership, it remains the case that nobody knows what the fuck they’re doing.

“I think great leaders treat money like oxygen: they make sure there is plenty of it, and understand that if you’re talking about it all of the time you’re in deep shit and better take drastic actions to make sure you have enough.” ~ Mark Ferlatte

As a founder or leader of a venture-backed startup or public company, your #1 job is to make the business succeed. Success comes first. It’s Maslow’s hierarchy of needs all over again; you must ensure your company’s continued existence before you earn the right to tinker.

Success in business is what earns you the right to devote more time, attention, and resources to cultural issues, and to experiment with things that matter to you.

One of the most common ways that leaders fail is that they get so bogged down in the daily chaos of running the company, managing a team, raising money, responding to crises and scoring OKRs is that they struggle to keep the focus zeroed in on the most important thing: succeeding at your mission.

Know your mission, craft a strategy, execute

And how do you do that?

Know your mission, craft a strategy, and execute. It’s as simple and straightforward as it is unbelievably difficult and devastatingly complicated.

The system exists to fulfill the mission. I’ve written before about systems thinking in organizations, how hierarchy emerges to benefit the workers, how we look up for purpose and down for function.

Your mission is what brings people together to collectively build something that they could not do as individuals. The more crisp and well articulated your mission, the more employees can tie the work they do back to the mission, the more meaningful their daily work is likely to feel.

Your culture serves the business, not the other way around

A great culture can’t compensate for a weak product that users don’t want. If people want to work at your company more than they want to use your product, that’s a bad sign.

A company culture with tremendous energy, ownership and transparency can be an accelerant to your business, it can grant you unique advantages, and it can help mitigate risks. But it is not why you exist. Your mission is why you exist.

It would be nice to believe that having a warm, supportive culture, with friendly people and four day work weeks, could guarantee success, or at least give you a reliable advantage. Wouldn’t it?

Companies with shitty cultures win all the time

We’ve all watched companies become wildly successful under assholes, while waves of employees leave broken and burned out. I wish this wasn’t true, but it is. People’s lives and careers are just another externality as far as the corporate books are concerned.

Many live through this nightmare and emerge dead set on doing things differently. And so, when they become founders or leaders, they put culture ahead of the business. And then they lose.

Most companies fail, and if you aren’t hungry and zeroed in on the success of your business, your slim chances become even slimmer.

I don’t believe this has to be either/or, cultural success or business success. I think it’s a false dichotomy. I believe that healthy companies can be more successful than shitty ones, all else being equal. Which is why I believe that leaders who care about building a workplace culture rooted in dignity and respect have a responsibility to care even more about success in business. Let’s show these motherfuckers how it’s done. Nothing succeeds like success.

Good culture is rooted in organizational health

Six questions for organizational health, from “The Advantage” by Patrick Lencioni

I feel like a big reason so many leaders get twisted up here is by trying to make employees happy instead of driving organizational health. This is a huge topic, and I won’t go deep on it here, but my understanding of organizational health owes a lot to “The Advantage: Why Organizational Health Trumps Everything Else In Business”, by Patrick Lencioni, with honorable mention going to “ Good Strategy/Bad Strategy”, by Richard Rumelt.

A terrific company culture begins with organizational health: a competent, experienced leadership team that trusts each other, a mission, and a strategy, clarity and good communication. If everyone in the company knows what the most important thing is, and their actions align with that, your company is probably pretty healthy.

People’s feelings matter, and you should treat them with dignity and respect, but you can’t be driven by them. You have to let go of underperformers, deliver hard feedback, set high standards and hold people accountable. A lot of this does not feel good.

You will make mistakes. Things will fail. You will have to spin down teams, or entire orgs. People are going to have huge emotional reactions about your decisions and take things personally. They’ll be angry with you and disagree with your decisions. They will blame you, and maybe they should.

If you do your job well, with some luck, many people will be happy, much of the time. But if your goal is to make people happy, you will fail, and then everyone will be unhappy. Feelings are a trailing indicator and only roughly, occasionally a sign that you are doing a good job.

Survive in the short term, but live your values in the longer term

Most companies have seen times where all of the options seem like bad ones, even a betrayal of their values. There are times that hurt your conscience, or rouse up anger and cynicism in the ranks. Some hypothetical examples:

  • When you’re doing layoffs to save the company, and realize the list is disproportionately made up of marginalized groups 💔
  • When you have an all-male exec team, and desperately need a new engineering leader, but all of the qualified candidates in your pipeline are men
  • When you had to let someone go for cause, and they’re going around publicly lying about what happened but you can’t respond

These things happen. And when they do, you have a legal and ethical responsibility to make the decision that is right for the company, every time.

And yet.

You must remind yourself as you do, uneasily, queasily, how easily “I didn’t have a choice” can slip from reason to excuse. How quickly “this isn’t the right time” turns into “never the right time”. You know this, I know this, and I guarantee you every one of your employees knows this.

Don’t expect them to give you the benefit of the doubt. Why should they? They’ve heard this shit a million times. Don’t get mad, just do your job.

Living your values takes planning and sacrifice

No halfway decent leader spends ALL their time reacting to the burning bushes in front of their faces. Being a leader means planning for the future, so you can do better next time.

So you had to make a tough decision, and the optics (and maybe the reality) of it are terrible. Okay. It happens. Don’t just wince and put it behind you. If you don’t take steps to change things, you’re going to face the same bad choices next time.

  • What will you do differently?
  • Why were there no good alternatives?
  • What will the right time look like? How will you know?
  • How will you do a better job of recruiting, retaining, or setting them up for success?

If you don’t spend time, money, attention, or political capital on it, you don’t care about it, by definition. And it is a thousand times worse to claim you value something, and then demonstrate with your actions that you don’t care, than to never claim it in the first place.

Your resources are limited, and you must spend them with purpose

As an exec, you get a very limited amount of people’s time and attention — maybe a few minutes per week, or per month. Don’t waste them.

Jess Mink, our director of platform engineering, has a lovely story about this. They work with local search and rescue teams, which are staffed by people all over the political spectrum. The mission is crystal clear; all of them know why they’re there, and they don’t talk about things that aren’t tied to the mission. Yet Jess is giving a talk about pronouns at their next training. Why?

”Because there’s a really crisp, clear mission, I can say, I don’t care what your politics are. I’m not asking you to change your beliefs, but this is the impact of what you’re doing on these people that you’ve said you’re here to help.” ~ Jess Mink

There are a million things in the world you could say or do that would have intrinsic value. Why this thing? You should have a reason, and it should connect to your mission or your strategy for achieving it, or you are just muddying the waters.

Should political speech at work be a free-for-all?

Many leaders have opted to ban political speech at work. What’s the alternative, a free-for-all? Trump gifs and Biden Harris banners and a heated debate on the border in #general?

Please. Nobody wants that. Most folks seem to understand that work Slack is not the place for proselytizing or stirring up shit. There’s an element of good judgment here that extends well beyond political speech to include other disruptive actions such as criticizing religious beliefs, oversharing extremely personal info, posting sexy selfies, or good old verbal diarrhea. These are all, shall we say, “good coaching opportunities”. You don’t have to ban all political speech just to enforce reasonable norms.

In general, people want to work in an environment that is relatively peaceful and neutral-feeling, where people can focus on their work and our shared mission. But people also need spaces to talk about what’s going on in their lives and process their reactions.

At Honeycomb, we prefix all non-work slack channels with #misc. We have #misc-bible-reading-group, #misc-politics, #misc-book-club, #misc-shoes-and-fashion, #misc-so-fuzzy (for pictures of people’s pets).

People don’t join those channels automatically upon being hired — you have to seek them out, and you can leave them just as easily. Nobody has to worry about missing out on critical work conversations co-mingling with off putting political speech. And it’s easy to redirect non-work chatter out of work channels.

The value (and limitations) of neutrality

Neutral spaces are a good thing — a societal necessity. However, it becomes a problem when it fails to honor the paradox of tolerance — that if we tolerate the intolerant, intolerance will ultimately dominate. We cannot be equally tolerant of gay people and people who hate gay people, in other words.

At their worst, statements of neutrality punish the victimized and protect the victimizers. As Yonatan Zunger puts it, in one of my favorite essays of all time, “Tolerance is not a moral absolute; it is a peace treaty.”

But even peace treaties have their limits. Some problems are just fucking hard . As Emily put it,

“What does it mean to feel silence from the majority of your coworkers on a topic that feels like life and death to you? In normal times, silence can seem like a lack of political speech; in extraordinary times, silence speaks volumes. This creates division, even if your coworkers have landed there through ignorance or low awareness.” ~ Emily Nakashima

The hard thing about hard things is that they’re really fucking hard. There is no playbook. I can’t solve them for you here. Every situation is unique, and the details matter — details really matter, in fact. You can only take each situation as it comes with humility, sensitivity, and a willingness to listen.

Good leaders don’t invite unnecessary controversy

If you are a CEO or founder, especially, the things you say will be heard as representing the views of your company. Period. Keep this in mind, and try to be extra respectful and responsible. You don’t want your big mouth to accidentally create a wave of distraction and drama for people throughout your company to have to deal with. Your opinions are more than just your opinions.

If you’re thinking that I’m an odd person to be delivering this particular message, I sheepishly acknowledge the truth of this.

If you work at a company where the CEO and leadership openly espouse a particular set of partisan beliefs, you are inevitably going to feel somewhat othered. You wonder uncomfortably whether or not they are aware you hold different beliefs. If so, will you be promoted, will you be given equal opportunities? Would your leaders like you as much as they like employees who share their political convictions? Would they be as willing to chat with you or hang out with you? Does it matter?

People aren’t wrong to be concerned. There’s scads of research that shows how much we automatically prefer people who are more like us. It’s automatic — it’s natural. That doesn’t mean it’s right. Nor is it inevitable. We have to work harder to give an equal shot to those who aren’t like us, and we should do that.

Good leaders don’t make it all about them

One of the hardest parts about being a good leader is managing your ego, and keeping it from taking center stage or making things worse.

I have done and said a lot of dumb things online, but the worst of them was probably during the Black Lives Matter protests of 2020. I was trying to express my support, so I tweeted something about how actions matter more than words, and that we were trying to help by building a workplace where Black employees could thrive, or something like that. I don’t remember exactly (and the tweets are gone), but it was awful. I made it about us; it was super tone deaf. And I got whaled on, in a way that really threw me for a loop. I tried to apologize and made it worse. Friends blocked me.

It took me a long time to process the experience and come to terms with my mistakes: first, by framing my comments almost like a promo for how great honeycomb was, and second, by reacting so defensively when called out over it.

You don’t need to have a take on everything. And the more you have a track record of taking stances on issues, the more it’s expected of you, and the more dicey it becomes, because even not taking a stance is taking a stance.

Good leaders look for ways to de-escalate

Any time the conversation sails into the terrain of morals and ethics, it’s an automatic escalation. It raises the stakes, it exacerbates differences. It can transform an ordinary, practical matter into the forces of good versus evil in the blink of an eye.

There are bright lines and moral dilemmas in business. (Should you pay women less than men for the same work? No.) But most of our everyday work doesn’t need to be so emotionally fraught.

An example may help here. When you have a geographically distributed company, you have two basic choices when it comes to comp philosophy:

  1. have a single set of comp bands, which apply no matter where you live
  2. peg their salary to their local cost of living

When this question first came up, back in 2019, I came out swinging for the fences on option 1). I treated it like a moral question, a matter of basic human equity. “What kind of company would dare pay you less money based on where you live? What business is it of theirs where you live?” — that sort of thing.

In this, I was hardly alone. A lot of people have really strong feelings about this (I still have some pretty strong feelings about it 😬). But there are also some pretty reasonable arguments for and circumstances in which geo wage arbitrage makes a lot of sense, and can offer more opportunities to more people than you could otherwise afford. It’s not as simple as I made it out to be.

Having taken such a strong stance though, I have definitely made it extremely difficult for our finance team to change that policy, should we ever decide to.

Good leaders turn the volume down. They dampen drama, they don’t amplify it. They don’t ratchet up the stakes or the rhetoric, they look for practical solutions where possible.

Good leaders connect the culture to the mission

I started off as one of those leaders who cared more about culture than the business. In honesty, I assumed we’d fail. I never planned to start a company, it was an impulse decision. I really didn’t think I’d have to be the CEO. I wasn’t equipped for the job; I didn’t even know the difference between sales and marketing. I did however have MANY strong opinions on company culture.

The first few years of Honeycomb, any time I thought of some neat thing to try, I did it. Put an employee on the board? Yes! Run regular ethics discussions? Hell yes! Put together cross-functional teams to discuss company values? Cool!

I don’t regret it, precisely; I think it played a role in instilling a culture of curiosity and ownership. I think it helped us figure out who we were.

But as we grow past 200 people, and as the pace of growth accelerates, I am increasingly aware of the opportunity cost of these experiments. It doesn’t mean we don’t do things like this anymore, but there needs to be a much better reason than “Charity thinks it would be cool.” It needs to add up to something bigger.

Good leaders have conviction, and don’t pretend to give a shit when they don’t

I appreciate it when leaders do real talk about their values and how they make decisions. Too many leaders hide behind the bland slogans of corporate piety, in ways that tell you nothing about how they make decisions or where their priorities lie when the chips are down.

Honestly, I would rather work for someone who holds different values than I do, but who seems honest and consistent and fair-minded in their decision-making, than someone who holds the same values but whose decisions seem impulsive and subjective.

This is a business, not a family. If I believe in the mission, and the leaders and I align on the facts, and I respect their integrity and the way they make decisions, that matters more.

As it turns out, all of this has been said before…by my antagonists?!? Oh dear…

As I was wrapping up this article, I went back and read a few of the pieces written by and about the companies who banned political speech, and my mouth literally dropped open.

You could copy-paste entire sections between my article and theirs, without anyone knowing the difference.

Companies exist for the sake of their mission, check. They don’t have to have a take on everything, check. Your work day shouldn’t consist of arguments over abortion and other hot button topics, check. It IS distracting. It’s NOT why you’re here. Uh…

How can I have written the same fucking article as theirs, and come to such a radically different conclusion?

Or is it that radically different? After all, I’m not out here advocating a free-for-all, or that companies should take a stand on every social issue of the day. I actually pretty much agree with most of the sentiments these founders wrote in their official posts on the matter.

Shit?

I was sitting here having a legit internal crisis, and then I stumbled into some other pieces, where rank-and-file employees were talking about the changes and what led up to them.

Employees say the founders’ memos unfairly depicted their workplace as being riven by partisan politics, when in fact the main source of the discussion had always been Basecamp itself.

“At least in my experience, it has always been centered on what is happening at Basecamp,” said one employee. “What is being done at Basecamp? What is being said at Basecamp? And how it is affecting individuals? It has never been big political discussions, like ‘the postal service should be disbanded,’ or ‘I don’t like Amy Klobuchar.’

The whole article is required reading. It goes on to detail a hair-raising amount of hypocrisy and high-handed behaviors by the Basecamp founders; a bunch of workers who self-organized to improve internal hiring practices and culture, and how they got shut down.

“There’s always been this kind of unwritten rule at Basecamp that the company basically exists for David and Jason’s enjoyment,” one employee told me. “At the end of the day, they are not interested in seeing things in their work timeline that make them uncomfortable, or distracts them from what they’re interested in. And this is the culmination of that.”

Then there was this damning piece from the NYTimes about the appalling way Black employees were treated at Coinbase, and this one, which closes with an anecdote about the Coinbase CEO tweeting out his own (noxious) political views in direct contradiction of his own policies. Oopsie-daisy. 🌼

Are these policies designed to protect the mission, or the CEO?

All of this paints a very different picture. These bans on political speech seem to be less about protecting the commons from wayward employees who won’t stop distracting everyone with hot button political arguments, and more about employees doing their level best to grapple with real tensions and systemic problems at work — problems that their leaders got sick of hearing about and decided to shut down.

There’s a real stench of “politics for me, but not for thee!” in a lot of these cases, which makes it extra galling. At the beginning of this piece, I noted that “politics” is an obscenely broad category — it can mean almost anything. So when the CEO arrogates to himself the right to define it and silence it, it generates a lot of confusion and uncertainty. That’s bad for the mission!

The fact is, this shit is hard. It’s hard to craft a strategy and execute. It’s hard to train managers to have hard conversations with their employees, or gently de-escalate when things get emotionally fraught. It’s hard to reset expectations on how much of a voice employees can expect to have in a given area. It’s hard to know when to take a stand on principle, and back it with your time and treasure, and when to settle or compromise.

But you signed up for this, bro. It’s part of the job, and you’re getting paid a lot of money to do it. You don’t get to just nope out when the going gets rough.

Just because you made a rule that people can’t talk about the hard stuff, doesn’t mean the hard stuff goes away. It mostly just serves to reinforce whatever power structures and inequities already exist in your company. Which means a lot of people will go on doing just fine, while some are totally fucked. You’ve also shut down all of the reasonable routes for people to advocate for change, so good job, you.

You don’t have to agree with them, but you do have to be respectful to your employees

Look, none of us are perfect. That’s why systems need mechanisms for change. Resiliency isn’t about never breaking the system, it’s about knowing your systems will break, and equipping them with the tools to repair.

If you want to lead a company, you have to deal with the people. It comes with the job.

If you want your people to care as much about the mission as you do, to feel personally invested in its success, to devote whole long stretches of their brilliant, creative, busy lives to helping you make that mission come true…you owe them in return.

If a bunch of your employees are waving a flag and urgently saying “we have a problem”, they are very likely doing you a favor. Either way, they deserve to be heard.

You don’t have to do what they want. But you ought to listen to them, and reserve judgment. Open your eyes. Look around. Do some reading. Talk to people. Consider whether you might be missing something. Then make a decision and give an honest answer. They may or may not agree, and they may or may not choose to stay, but that’s what treating them with respect looks like, just like you ask them to treat you, and each other.

To instead say “Sorry, your feedback is a distraction from the mission and will no longer be tolerated” is so unbelievably disrespectful, and wrapping your decision in the noble flag of the mission is dishonest. It’s hard to tell sometime whether people are deluding themselves or only trying to delude other people, but holy shit, what a doozy.

Good leaders know they will make mistakes, and when they do, they own them, apologize properly, and fix them. They do not use their power to silence people and then swagger around like they own the moral high ground.

Pragmatism, Neutrality and Leadership

Questionable Advice: “My boss says we don’t need any engineering managers. Is he right?”

mipsytipsy, , , , , 18 Comments

I recently joined a startup to run an engineering org of about 40 engineers. My title is VP Engineering. However, I have been having lots of ongoing conflict with the CEO (a former engineer) around whether or not I am allowed to have or hire any dedicated engineering managers. Right now, the engineers are clustered into small teams of 3-4, each of which has a lead engineer — someone who leads the group, but whose primary responsibility is still writing code and shipping product.

I have headcount to hire more engineers in the coming year, but no managers. My boss says we are a startup and can’t afford such luxuries. It seems obvious to me that we need engineering managers, but to him, it seems just as obvious that managers are unnecessary overhead and that all hands should be on deck writing code at our stage.

I don’t know how to make that argument. It seems so obvious to me that I actually struggle to put it into words or make the case for why we should hire EMs. Help?

— Unnecessary Overhead(?!?)

Oh boy, there’s a lot to unpack here.

It is unsurprising to me that your CEO does not understand why managers exist, given that he does not seem to understand why organizational structures exist. 🙈 Why is he micromanaging how you are structuring your org or what roles you are allowed to fill? He hired you to do a job, and he’s not letting you do it. He can’t even explain why he isn’t letting you do it. This does not bode well.

But I do think it’s an interesting question. So let’s pretend he isn’t holding your ability to do your damn job hostage until you defend yourself to his satisfaction. 😒

I can think of two ways to make the case for engineering managers: one is rather complicated, from first principles, and the other very simple, but perhaps unsatisfying.

I personally have a … vigorous … knee-jerk response to authority; I hate being told what to do. It’s only recently that I’ve found my way to an understanding of hierarchy that feels healthy and practical, and that was by looking at it through the lens of systems theory.

Why does hierarchy exist in organizations?

It makes sense that hierarchy comes with a lot of baggage. Many of us have had bad experience with managers — indeed, entire organizations — where hierarchy was used as a tool of oppression, where people rose up the leadership ranks by hoarding information and playing dominance games, and decisions got made by pulling rank.

Working at a place like that fucking sucks. Who wants to invest their creativity and life force into a place that feels like a Dilbert cartoon, knowing how little it will be valued or reciprocated, and that it will slowly but surely get crushed out of you?

But hierarchy is not intrinsically authoritarian. Hierarchy did not originate as a political structure that humans invented for controlling and dominating one another, it is in fact a property of self-organizing systems, and it emerges for the benefit of the subsystems. In fact, hierarchy is absolutely critical to the adaptability, resiliency, and scalability of complex systems.

Let’s start with few basic facts about systems, for anyone that may be unfamiliar.

Hierarchy is a property of self-organizing systems

A system is “a network of interdependent components that work together to try to accomplish a common aim” (W. Edward Deming). A pile of sand is not a system, but a car is a system; if you take out its gas tank, the car cannot achieve its aim.

A subsystem is a collection of elements with a smaller aim inside a larger system. There can be many levels of subsystems that operate interdependently. The subsystems always work to support the needs of the larger system; if the subsystem instead optimizes for its own best interests, the whole system can fail (this is where the term “suboptimize” comes from 😄).

A system is self-organizing if it has the ability to make itself more complex, by diversifying, adapting, and improving itself. As systems self-organize and their complexity increases, they tend to generate hierarchy — an arrangement of systems and subsystems. In a stable, resilient and efficient system, subsystems can largely take care of themselves, regulate themselves, and serve the needs of the larger system, while the larger system coordinates between subsystems and helps them perform better.

Hierarchy minimizes the costs of coordination and reduces the amount of information that any given part of the system has to keep track of, preventing information overload. Information transfer and relationships within a subsystem are much more dense and have fewer delays than information transfer or relationships between subsystems.

(This should all sound pretty familiar to any software engineer. Modularization, amirite?? 😍)

Applying this definition, we can say that a manager’s job is to coordinate between teams and help their team perform better.

The false binary of sociotechnical systems

You’ve probably heard this canard: “Engineers do the technical work, managers do the people work.” I hate it. ☺️ I think it misconstrues the fundamental nature of sociotechnical systems. The “socio” and “technical” of sociotechnical systems are not neatly separable, they are interwoven and interdependent. There is actually precious little that is purely technical work or purely people work; there is a metric shitload of glue work that draws upon both skill sets.

Consider a very partial list of tasks done by any functional engineering org, besides writing code:

  • Recruiting, networking, interviewing, training interviewers, synthesizing feedback, writing job descriptions and career ladders
  • Project management for each project or commitment, prioritizing backlog, managing stakeholders and resolving conflicts, estimating size and scope, running retrospectives
  • Running team meetings, having 1x1s, giving continuous growth feedback, writing reviews, representing the team’s needs
  • Architecture, code review, refactoring; capturing DORA and productivity metrics, managing alert volume to prevent burnout

A lot of this work can be done by engineers, and often is. Every company distributes the load somewhat differently. This is a good thing! You don’t WANT an org where this work is only done by managers. You want individual contributors to help co-create the org and have a stake in how it gets run. Almost all of this work would be done more effectively by someone with an engineering background.

So you can understand why someone might hesitate to spend valuable headcount on engineering managers. Why wouldn’t you want everyone in engineering to be writing and shipping code as their primary job? Isn’t that by definition the best way to maximize productivity?

Ehhh… 😉

Engineering managers are a useful abstraction

In theory, you could make a list of all the tasks that need to be done to coordinate with other teams and have each item be picked up by a different person. In practice, this is impractical because then everybody would need to know about everything. One of the primary benefits of hierarchy, remember, is to reduce information overload. Intra-team communication should be high-bandwidth and fast, inter-team communication should be more sparse.

As the company scales, you can’t expect everybody to know everyone else; we need abstractions in order to function. A manager is the point of contact and representative for their team, and they serve as routers for important information.

I sometimes imagine managers as the nervous system of the company body, carrying around messages from one limb to another to coordinate actions. Centralizing many or most of these functions into one person lets you take advantage of specialization, as a manager builds relationships and context and improves at their role, and this massively reduces context switching for everyone else.

Manager calendars vs maker calendars

Engineering labor takes concentration and focus. Context switching is expensive, and too many interrupts can be fatal. Management labor consists of context switching every hour or so, and being available for interruptions throughout the day. These are two very different modes of being, headspaces, and calendar schedules, and do not coexist well.

In general, you want people to be able to spend most of their time working on things that contribute to the success of the outcomes they are directly responsible for. Engineers can only do so much glue work before their calendar turns into Swiss cheese and they can no longer deliver on their commitments. Since managers’ calendars are already Swiss cheese, it’s typically less disruptive for them to take on a larger share of glue labor.

It isn’t up to managers to do all the glue work, but it is a manager’s job to make sure that everything that needs to get done, does gets done. It is a manager’s job to try to line up every engineer with work that is interesting and challenging, but not overwhelming, and to ensure that unpleasant labor gets equitably distributed. It’s also a manager’s job to make sure that if we are asking someone to do a job, they are equipped with the resources they need to succeed at that job. Including time to focus.

Management is a tool for accountability

When you’re an engineer, you are responsible for the software you develop, deploy, and maintain. When you’re a manager, you are responsible for your team and the organization as a whole.

Management is one way of holding people accountable for specific outcomes (building teams with the right skills, relationships, and processes to make good decisions and build value for the company), and equipping them with the resources (budget, tools, headcount) to achieve those outcomes. If you aren’t making building the organization someone’s number one job, it won’t be anyone’s number one job, which means it probably won’t get done very well. And whose responsibility will that be, Mr. CEO?

There’s a real upper limit to what you can reasonably expect tech leads, or engineers, or anyone whose actual job is shipping software to do in their “spare time”. If you’re trying to hold your tech leads responsible for building healthy engineering teams, tools, and processes, you are asking them to do two calendarily incompatible jobs with only one calendar. The likeliest scenario is that they will focus on the outcomes they feel comfortable owning (the technical ones), while you pile up organizational debt in the background.

In natural hierarchies, we look up for purpose and down for function. That, in a nutshell, is the more complicated argument for why we need engineering managers.

Choose Boring technology Culture

The simpler argument is this: most engineering orgs have engineering managers. That’s the default. Lots of people much smarter than you or me have spent lots of time thinking and tinkering with org structures over the years, and this is what we’ve got.

As Dan McKinley famously said, we should “choose boring technology“. Boring doesn’t mean bad, it means the capabilities and failure conditions are well understood. You only ever get a few innovation tokens, so you should spend those wisely on core differentiators that could make or break your business. The same goes for culture. Do you really want to spend one of your tokens on org structure? Why??

For better or for worse, the hierarchical org structure is well understood. There are plenty of people on the job market who are proficient at managing or working with managers, and you can hire them. You can get training, coaching, or read a lot of self-help books. There are various management philosophies you can coalesce around or use to rule people out. On the other hand, the manager-free experiments I’m aware of (e.g. holacracy at Medium and GitHub, or “Choose Your Own Work” at Linden Lab) have all been quietly abandoned or outgrown. Not, in my experience, because leaders went mad for power, but due to chaos, lack of focus, and poor execution.

When there is no explicit structure or hierarchy, the result is not freedom and egalitarianism, it’s “informal, unacknowledged, and unaccountable leadership”, as famously detailed in “The Tyranny of Structureless“. In reality, sadly, these teams tend to be chaotic, fragile, and frustrating. I know! I’m pissed too! 😭

This argument doesn’t necessarily prove your CEO is wrong, but I should think his bar for proof is much higher than yours. “I don’t want any of my engineers to stop writing code” is not an argument. But I’m also feeling like I haven’t quite addressed the core question of productivity, so let’s pick that up again once more.

More lines of code != more productivity

To briefly recap: we were talking about an org with ~40 engineers, broken up into 10 small clusters of 3-4 engineers, each with a tech lead. Your CEO is arguing that you can’t afford to lose any velocity, which he thinks is what would happen if anyone stops writing code full time.

Maybe. But everything I have ever experienced leads me to believe that a fewer number of larger teams, each helmed by an experienced engineering manager, should way outperform this gaggle of tiny groups. It’s not even close. And they can do so in a way that’s more efficient, sustainable, and humane than this scrappy death march.

And systems thinking shows us why! With fewer groups, but larger ones, you have less overall management overhead, and much less of the slow and costly intra-group coordination. You unlock rich, dense knowledge transfer within groups, which gives you more shared coverage of the surface area. With 7-9 engineers per group you can build a real on call rotation, which means fewer heroics and less burnout. The coordination that you do need to do can be more strategic, less tactical, and much more forward-looking.

Would five big teams ship as many lines of code as 10 small teams, even if five engineers become managers and stop writing code? Probably, but who cares? Your customers give zero fucks how many lines of code you write. They care about whether you are building the right things and solving problems that matter to them. What matters is moving the business forward, not churning out code. Don’t forget, the act of churning out code creates costs and externalities in and of itself.

What defines your velocity is that you spend your time on the right things. Learning to make good decisions about what to build is something every organization has to work out for itself, and it is always an ongoing work in progress. Engineering managers don’t do all the work or make all the decisions, but they are absolutely fucking vital, in my experience, to ensuring that work happens and is done well. As I wrote in my last piece, engineering managers are the embodiment of the feedback loops that systems use to learn and improve.

Are managers ever unnecessary overhead?

Sure, absolutely. Management is about coordinating between teams and helping teams run more optimally, so anything that decreases your need for coordination also decreases your need for management. If you are a small company, or if you have really senior folks who are used to working together, you need a lot less coordination. The next most relevant factor is probably the rate of change; if you’re growing fast or have a lot of turnover, or if there’s a lot of time pressure or frequent shifts in strategy, your need for managers goes up. But there are plenty of smaller orgs out there that are doing just fine without a lot of formal management.

Look, I’m not a fan of the word “overhead”, because a) it’s kind of rude and b) people who call managers “overhead” are typically people who disrespect or do not value the craft of management.

But management is, in fact, overhead. 😅 So is a lot of other glue work! By which I mean the work is important, but does not itself move the business forward; we should do as much of it as absolutely necessary and no more. The nature of glue work is such that it too-easily expands to consume all available time and space (and then some). Constraints are good. Feeling a bit underresourced is good, and should be the norm. It is incredibly easy for management to get a bit bloated, and managers can be very loath to acknowledge this, because it’s not like they ever feel any less stressed or stretched.[*]

Management is also very much like operations work in that when it’s being done well, it’s invisible. Evaluating managers can be very hard, especially in the near term, and making decisions about when it’s time to create or pay down organizational debt is a whole nother ball of wax, and way outside the scope of this post.

But yes, managers can absolutely be unnecessary overhead.

However, if you have 40 engineers all reporting to one VP, and nobody else whose number one job is the outcomes related to people, teams and org, I feel pretty safe in saying this is not a risk for you at this time.

<3 charity

[*] In fact, the reverse can be true; bloated management can create MORE work for managers, and they may counterintuitively feel LESS stretched or stressed with a leaner org chart. Bureaucracies do tend to pick up a momentum all their own. Especially when management gets all wrapped up in promotions and egos. Which is yet another good reason to ensure that management is not a promotion or a form of domination.

 

Questionable Advice: “My boss says we don’t need any engineering managers. Is he right?”

Becoming An Engineering Manager Can Make You Better At Life And Relationships

mipsytipsy, , , , , 31 Comments

Original title: “Why Should You (Or Anyone) Become An Engineering Manager?”

The first piece I ever wrote about engineering management, The Engineer/Manager Pendulum, was written as a love letter to a friend of mine who was unhappy at work. He was an engineering director at a large and fast-growing startup, where he had substantially built out the entire infrastructure org, but he really missed being an engineer and building things. He wasn’t getting a lot of satisfaction out of his work, and he felt like there were other people who might relish the challenge and do it better than he could.

At the same time, it felt like a lot to walk away from! He had spent years building up not only the teams, but also his influence and reputation. He had grown accustomed to being in the room where decisions get made, and didn’t want to give that up or take a big step back in his career. He agonized over this for a long time (and I listened over many whiskeys). 🙂

To me it seemed obvious that his power and influence would only increase if he went back to engineering. You bring your credibility and your relationships along with you, and enthusiasm is contagious. So I wrote the piece with him in mind, but it definitely struck a nerve; it is still the most-read piece I have ever written.

That was in 2017. I’ve written a lot over the years since then about teams and management. For a long time, everything I wrote seemed to come out with a pretty noticeable bias against management, towards engineering:

I go back and read some of those pieces now, and the pervasive anti-manager slant actually makes me a bit uncomfortable, because the environment has changed quite a lot since then.

Miserable managers have miserable reports

When I started writing about engineering management, it seemed like there were a lot of unhappy, resentful, poorly trained managers, lots of whom would prefer to be writing code. Most people made the choice to switch to management for reasons that had nothing to do with the work itself.

  • Becoming a manager was seen as a promotion
  • It was the only form of career progression available at many places
  • Managers made a lot more money
  • It was the only way to get a seat at the table, or be in the loop
  • They were tired of taking orders from someone else

But a lot has changed. The emergence of staff+ engineering has been huge (two new books published in the last five years, and at least one conference!). The industry has broadly coalesced around engineering levels and career progression; a parallel technical leadership track is now commonplace.

We’ve become more aware of how fragile command-and-control systems are, and that you want to engage people’s agency and critical thinking skills. You want them to feel ownership over their labor. You can’t build great software on autopilot, or by picking up jira tasks. Our systems are becoming so complex that you need people to be emotionally and mentally engaged, curious, and continuously learning and improving, both as individuals and as teams.

At the same time, our expectations for managers have gone up dramatically. We’ve become more aware of the damage done by shoddy managers, and we increasingly expect managers to be empathetic, supportive, as well as deeply technical. All of this has made the job of engineering manager more challenging.

Ambitious engineers had already begun to drift away from management and towards the role of staff or principal engineer. And then came the pandemic, which caused managers (poorly supported, overwhelmed, squeezed between unrealistic expectations on both sides) to flee the profession in droves.

It’s getting harder to find people who are willing to be managers. On the one hand, it is fucking fantastic that people aren’t being driven into management out of greed, rage, or a lust for power. It is WONDERFUL that people are finding engineering roles where they have autonomy, ownership, and career progression, and where they are recognized and rewarded for their contributions.

On the other hand, engineering managers are incredibly important and we need them. Desperately.

Good engineering managers are force multipliers

A team with a good engineering manager will build circles around a team without one. The larger or more complex the org or the product, and the faster you want to move, the more true this is. Everybody understands the emotional component, that it feels nice to have a competent manager you trust. But these aren’t just squishy feels. This shit translates directly into velocity and quality. The biggest obstacles to engineering productivity are not writing lines of code too slowly or not working long hours, they are:

  • Working on the wrong thing
  • Getting bogged down in arguments, or being endlessly indecisive
  • Waiting on other teams to do their work, waiting on code review
  • Ramping new engineers, or trying to support unfamiliar code
  • When people are upset, distracted, or unmotivated
  • Unfinished migrations, migrations in flight, or having to support multiple systems indefinitely
  • When production systems are poorly understood and opaque, quality suffers, and firefighting skyrockets
  • Terrible processes, tools, or calendars that don’t support focus time
  • People who refuse to talk to each other
  • Letting bad hires and chronic underperformers stick around indefinitely

Engineers are responsible for delivering products and outcomes, but managers are responsible for the systems and structural support that enables this to happen.

Managers don’t make all the decisions, but they do ensure the decisions get made. They make sure that workstreams are are staffed and resourced sufficiently, that engineers are trained and improving at their craft. They pay attention to the contracts and commitments you have made with other teams, companies or orgs. They advocate for your needs at all levels of the organization. They connect dots and nudge and suggest ideas or solutions, they connect strategy with execution.

Breaking down a complex business problem into a software project that involves the collaboration of multiple teams, and ensuring that every single contributor has work to do that is challenging and pushes their boundaries while not being overwhelming or impossible… is really fucking hard. Even the best leaders don’t get it right every time.

In systems theory, hierarchy emerges for the benefit of the subsystems. Hierarchy exists to coordinate between the subsystems and help them improve their function; it is how systems create resiliency to unknown stressors. Which means that managers are, in a very real way, the embodiment of the feedback loops and meta loops that a system depends on to align itself and all of its parts around a goal, and for the system itself to improve over time.

For some people, that is motivation enough to try being a manager. But not for all (and that’s okay!!). What are some other reasons for going into management?

Why should you (or anyone) be a manager?

I can think of a few good reasons off the top of my head, like…

  • It gets you closer to how the business operates, and gives you a view into how and why decisions get made that translate eventually into the work you do as an engineer
  • Which makes the work feel more meaningful and less arbitrary, I think. It connects you to the real value you are creating in the world.
  • Many people reach a point where they feel a gravitational pull towards mentorship. It’s almost like a biological imperative to replicate yourself and pass on what you have learned to the next generation.
  • Many people also get to a point where they develop strong convictions about what not to do as a manager. They may feel compelled to use what they’ve learned to build happy teams and propagate better practices through the industry
  • One way to develop a great staff engineer is to take a great senior engineer and put them through 2-3 years of management experience.

But the main reason I would encourage you to try engineering management is a reason that I’m not sure I’ve ever heard someone articulate up front, which is that…it can make you better at life and relationships, in a huge and meaningful way.

Work is always about two things: what you put out into the world, and who you become while doing it.

I want to stop short of proclaiming that “being a manager will make you a better person!” — because skills are skills, and they can be used for good or ill. But it can.

It’s a lot like choosing to become a parent. You don’t decide to have kids because it sounds like a hoot (I hope); you go into it knowing it will be hard work, but meaningful work. It’s a way of processing and passing on the experiences that have shaped you and who you are. You also take up the mantle understanding that this will change you — it changes who you are as a person, and the relationships you have with others.

From the outside, management looks like making decisions and calling the shots. From the inside, management looks more like becoming intimately acquainted with your own limitations and motivations and those of others, plus a lot of systems thinking.

Yes, management absolutely draws on higher-level skills like strategy and planning, writing reviews, mediating conflict, designing org charts, etc. But being a good manager — showing up for other people and supporting them consistently, day after day — rests on a bedrock of some much more foundational skills.

The kind of skills you learn in therapy, not in classes

Self-regulation. Can you take care of yourself consistently — sleep, eat, leave the house, socialize, balance your moods, moderate your impulses? As an engineer, you can run your tank dry on occasion, but as a manager, that’s malpractice. You always need to have fuel left in the tank, because you don’t know when it will be called upon.

Self-awareness. Identifying your feelings in the heat of the moment, unpacking where they came from, and deciding how to act on them. It’s not about clamping down on your feelings and denying you have them. It’s definitely not about making your feelings into other people’s problems, or letting your reactions create even bigger problems for your future self. It’s about acting in ways that are fueled by your authentic emotional responses, but not ruled by them.

Understanding other people. You learn to read people and their reactions, starting with your direct reports. You build up a mental model for what motivates someone, what moves them, what bothers them, and what will be extremely challenging for them. You must develop a complex topographical map of how much you can trust each person’s judgment, on which aspect, in any given situation.

Setting good boundaries. Where is the line between supporting someone, advocating for them, encouraging them, pushing them … but not propping them up at all costs, or taking responsibility for their success? How is the manager/report relationship different from the coworker relationship, or the friend relationship? How do you navigate the times when you have to hold someone accountable because their work is falling short?

Sensitivity to power dynamics. Do people treat you differently as a manager than they did as a peer? Are there things that used to be okay for you to say or do that now come across as inappropriate or coercive? How does interacting with your reports inform the way you interact with your own manager, or how you understand what they say?

Hard conversations. Telling people things that you know they don’t want to hear, or things that will make them feel afraid, angry, or upset; and then sitting with their reactions, resisting the urge to take it all back and make everything okay.

The art of being on the same side. When you’re giving someone feedback, especially constructive feedback, it’s easy to trigger a defensive response. It’s SO easy for people to feel like you are judging them or criticizing them. But the dynamic you want to foster is one where you are both side by side, shoulder to shoulder, facing the same way, working together. You are giving them feedback because you care; feedback that could help them be even better, if they choose to accept it. You are on their side. They always have agency.

Did you learn these skills growing up? I sure as hell did not.

I grew up in a family that was very nice. It was very kind and loving and peaceful, but we did not tell each other hard things. When I went off to college and started dating, I had no idea how to speak up when something bothered me. There were sentences that lingered on the tip of my tongue for years but were never spoken out loud, over the ebb and fall of entire relationships. And if somebody raises their voice to me in anger, to this day, I crumble.

I also came painfully late to developing a so-called growth mindset. This is super common among “smart kids”, who get so used to perfect scores and praise for high achievements that any feedback or critique feels like failure…and failure feels like the end of the world.

It was only after I became a manager that I began to consciously practice skills like giving feedback, or receiving constructive criticism, or initiating hard conversations. I had to. But once I did, I started getting better.

Turns out, work is actually kind of an ideal sandbox for life skills, because the social contract is more explicit. These are structured relationships, with rules and conventions and expectations, and your purpose for coming together is clear: to succeed at business, to finish a project, to pull a paycheck. Even the element of depersonalization can be useful: it’s not you-you, it’s the professional version of you, performing a professional role. The stakes are lower than they would be with your mother, your partner, or your child.

You don’t have to be a manager to build these skills, of course. But it’s a great opportunity to do so! And there are tools — books and classes, mentors and review cycles. You can ask for feedback from others. Growth and development is expected in this role.

People skills are persistent

The last thing I will say is this — technical skills do decay and become obsolete, particularly language fluency, but people skills do not. Once you have built these muscles, you will carry them with you for life. They will enhance your ability to connect with people and build trust, to listen perceptively and communicate clearly, in both personal and professional relationships.

Whatever you decide to do with your life, these skills increase your optionality and make you more effective.

And that is the reason I think you should consider being an engineering manager. Like I said, I’ve never heard someone cite this as their reason for wanting to become a manager. But if you ask managers why they do it five or ten years later, you hear a version of this over and over again.

One cautionary note

As an engineer, you can work for a company whose leadership team you don’t particularly respect, whose product you don’t especially love, or whose goals you aren’t super aligned with, and it can be “okay.” Not terrific, but not terrible.

As a manager, you can’t. Or you shouldn’t. The conflicts will eat you up inside and/or prevent you from doing excellent work.

Your job consists of representing the leadership team and their decisions, pulling people into alignment with the company’s goals, and thinking about how to better achieve the mission. As far as your team goes, you are the face of The Man. If you can’t do that, you can’t do your job. You don’t get to stand apart from the org and throw rocks, e.g. “they told me I have to tell you this, but I don’t agree with it”. That does nothing but undermine your own position and the company’s. If you’re going to be a manager, choose your company wisely.

charity

P.S. My friend (from the start of the article) went back to being an engineer, despite his trepidation, and never regretted it once. His career has been up and to the right ever since; he went on to start a company. The skills he built as a manager were a huge boost to an already stellar career. 📈

 

Becoming An Engineering Manager Can Make You Better At Life And Relationships

How to Communicate When Trust Is Low (Without Digging Yourself Into A Deeper Hole)

mipsytipsy, , , 28 Comments

This is based on an internal quip doc I wrote up about careful communication in the context of rebuilding trust. I got a couple requests to turn it into a blog post for sharing purposes; here you go.🌈✨🥂

In this doc I mention Christine, my wonderful, brilliant cofounder and CEO, and the time (years ago) when our relationship had broken down completely, forcing us to rebuild our trust from the ground up.

(Cofounder relationships can be hard. They are a lot like marriages; in their difficulty and intensity, yes, but also in that when you’re doing it with the right person, it’s all worth it. 💜)

Tips for Careful Communication

When a relationship has very little trust, you tend to interpret everything someone says in the worst possible light, or you may hear hostility, contempt, or dismissiveness where none exists. On the other side of the exchange, the conversation becomes a minefield, where it feels like everything you say gets misinterpreted or turned against you no matter how careful you are trying to be. This can turn into a death spiral of trust where every interaction ends up with each of you hardening against each other a little more and filing away ever more wounds and slights. 💔

Yet you HAVE to communicate in order to work together! You have to be able to ask for things and give feedback.

The way trust gets rebuilt is by ✨small, positive interactions✨. If you’re in a trust hole, you can’t hear them clearly, and they can’t hear you (or your intent) clearly. So you have to bend over backwards to overcommunicate and overcompensate.

There are lots of books out there on how to talk about hard topics. (We actually include a copy of “Crucial Conversations” in every new employee packet.) They are all pretty darn cheesy, but it’s worth reading at least one of them.

I’m not going to try and cover all of that territory. What follows is a very subjective list of tactics that worked for Christine and me when we were digging our way out of a massive trust deficit. Power dynamics can admittedly make things more difficult, but the mechanics are the same.

Acknowledge it is hard beforehand:

“I want to say something, but I am having a hard time with it.”
“I have something to say, but I don’t know how you’ll take it.”
“I need to tell you something and I am anxious about your reaction.”

What this does: forces you to slow down and be intentional about the words you’re going to use. It gives the other person a heads up that this was hard for you to say. Most of all, it shows that you do care about their feelings, and are trying to do your best for them (even if you whiff the landing).

… or check in afterwards.

“I’m not sure how that came across. Is there a better way I could have phrased it?”
“In my head that sounded like a compliment…how did you hear it?”
“Did that sound overly critical? I’m not trying to dwell on the past, but I could use your help in figuring out a better way.”

It’s okay if it’s minutes or hours or days later; if it’s still eating at you, ✨clear the fucking air.✨

Speak tentatively.

“Speak tentatively” is the exact opposite of the advice that people (especially women) tend to get in business. But it’s actually super helpful when the relationship is frayed because you are explicitly allowing that they may have a different perception, and making it safer to share it.

“From my perspective, it looks like these results might be missing some data… do you see the same thing?” opens the door for a friendly conversation based on concrete outcomes, whereas “You’re missing data” might sound accusatory and trigger fear and defensiveness.

Try to sound friendly.

Say “please” and “thank you” a lot. Add buffer words like “Hey there”, or “Good morning!” or “lol”. Even just using 🌱emojis🍃 will soften your response to an almost unsettling degree. This may seem almost insultingly simple, but it works. When trust is low, the lack of frills can easily be read as brusque or rude.

Take a breath.

If you are experiencing a physical panic response (sweating, heart racing, etc), announce that you need a few minutes before responding. Compose yourself. Firing off a reply while you are in fight-or-flight mode reliably leads to unintentional escalations.

If you need to take a few beats to read and process, take the time. But empty silence can also generate anxiety 🙂 so maybe say something to indicate “I’m listening, but I need a minute to absorb what you said”, or “I’m still processing”. (We often use “whoa…” as shorthand for this.)

(Alternately, if you find yourself really pissed, “whoa” becomes a great placeholder for yourself to get yourself under control 😬 before saying something you’ll regret having to deal with later.)

“The story in my head”.

When you are in a state where you are assuming the worst of someone and reading hostile intent into their words or actions, try to check yourself on those assumptions.

Repeat the words or behaviors back to them along with your interpretation, like: “The story in my head is that you asked me to send that status email because you don’t trust me to have done the work, or maybe even gathering evidence that I am not performing for a PIP.” This gives them the opportunity to reply and clarify what they actually meant.

Engineer positive interactions, even if you have to invent them.

Relationship experts say that there’s a magic ratio for happy, healthy relationships, which is at least five positive interactions for every one negative interaction. If you only interact with the people you have difficult relationships when you have something difficult to say, you are always going to dread it. Forever.

It might seem artificial at first, but look for chances to have any sort of positive interactions, and seize them.

Communicate positive intent.

In a low trust environment, you can assume everything you say will be read with a voice that is menacing, dismissive or sneering. It behooves you to pay extra attention to tone and voice, and to add extra words that overcommunicate your intended meaning. A neutral statement like “That number seems low”, or “Why is that number low?” will come out sounding brusque and accusatory, e.g. why isn’t that number growing? it’s your fault, you should know this, I blame you, you’re bad at your job. Not might: it will. Try to immunize your communication from distortion by saying things like,

“Hey, I know this just got dropped in your lap, but do you have any idea why this number is so low?”
“This number seems lower than usual. I’m wondering if it’s due to this other thing we tried. Do you have any better ideas?”
“I know it isn’t exactly in your wheel house, but can you help me understand this?”
“I’m new to this system and still trying to figure out how it works. Should this number be going down like this?”

It may seem excessive and time consuming, but it will save you time and effort overall because you will have fewer miscommunications to debug. ☺️

Give people the opening to do better.

We tend to make up our minds about people very quickly, and see them through that lens from then on. It takes work to open our selves up again.

“Assume positive intent” is a laudable goal, but in practice falls short. If every word someone says sounds accusatory or patronizing to you, what are you supposed to do with that advice? Just pretend you don’t hear it, or tell yourself they mean well? That’s not sustainable; your anger will only build up.

But if you can hold just enough space for the idea that they might mean well, then you can give them the opportunity to clarify (and hopefully use different words next time). Like,

Person A: “Why is that number low?”
Person B: “I’m not sure.”
(pause)
Person B: “…. Hey, sorry to interrupt, but the story in my head is that you think owning that number is part of my job, and now you’re upset with me, or you think I’m incompetent at my job.”
Person A: “OMG no, not at all. I’m just trying to figure out who understands this part of the system, since it seems like none of us do! 😃 Sorry for stressing you out!”

and maybe next time it will start off like…

Person A: “Hey, do you have any idea why this number is low? It’s a mystery … nobody I’ve talked to yet seems to know.” 🙂

Remember the handicaps, value the effort.

Ever meet someone you didn’t like online, and realize they’re terrific in person? Online communication loses sooooo much in transit. Christine and I know each other extremely well, and still sometimes we realize we’re reading way too much into each other’s written words. That’s when we try to remember to move it to “mouth words”, aka zoom or phone. Not as good as in person, but eons better than text.

Once you’ve met someone in person, it’s usually easier to read their written words in their voice, too.

Some people just aren’t great at written communication. Some people have neurodiversities that make it difficult for them to hear tone. Some people have English as a second language. And so on. Do give points for effort; if they’re trying, obviously, they care about your experience.

To the best of your ability, try to resist reading layers of meaning into textual communication; keep it simple, overcommunicate intent, and ask for clarity. And if someone is asking you for clarity, help them do a better job for you.

 

How to Communicate When Trust Is Low (Without Digging Yourself Into A Deeper Hole)

Helicopter Management and Other Mistakes

mipsytipsy, , , 4 Comments

You are a freshly minted manager. You come full of rage and frustration at the poor management you’ve endured and witnessed in tech, and you are god damn determined not to repeat all of those mistakes.

You are tired of reporting to a manager who isn’t transparent with you, who hoards critical information and isn’t forthcoming about changes that impact you. You are tired of not being listened to or treated like a cog, so you swear to really listen and take your reports seriously.

You have seen sooooo many managers who failed to develop their people or sponsor them for growth opportunities, who blamed their team and hung them out to dry instead of having their back behind closed doors. Managers who didn’t seem to care about you as people, or who never made it feel safe to say, “I need a mental health day”. Managers who dangled the promise of a promotion, but even though you are doing the work, the recognition never comes.

Fuck that shit. You aren’t going to do ANY of it.

And … you don’t! 🎉

🌸🍃 You make time in your 1x1s to ask about their personal lives and hobbies — you are careful not to pry or be intrusive, just showing that you care. You urge them to take vacation, often. You remind them, firmly, not to be a hero. You model the behavior of taking mental health days to show that not only is it safe, but managers need them too.

🌸🍃 You ask them about their career goals and aspirations. You make it your personal mission to get them promoted, so you frequently check in with them to make sure they’re on the right path. You keep an eye out for things they do that are above and beyond, and for strengths that make them special. They always know you are on their side.

🌸🍃 If you hear about a clash or a conflict between them and another team member, you quickly jump in to figure out what’s going on and make sure it gets resolved, with each person feeling heard before the conflict has time to marinate or fester.

🌸🍃 When reviews comes around, you write warm, passionate essays for each of your direct reports, listing all the things they have done and all the ways they have grown. You go in to manager calibrations fully prepped to advocate for each of your people to get the promotions and rewards they so richly deserve.

🌸🍃 If someone on your team ends up needing more help, whether that’s keeping them productive and on track or helping with prioritization or conflicts… whatever it is, you are there to help turn the situation around. This person was struggling under their old manager, maybe even close to being let go, but under your care they are thriving.

🌸🍃 Nobody ever leaves your team. This is a point of quiet pride for you. People want to transfer to your team, but never from. There may have been a couple close calls, but you are always able to save the day by talking it out with the person and figuring out what they need in order to stay.

🌸🍃 You take pride in your transparency and the democratized ethos of your team, where you collectively determine your priorities and no one feels pressured into doing something they don’t want to do.

Bottom line: you are a GREAT manager.

Right???

After all, your team ranks sky high on every company survey on employee happiness, manager trust, and autonomy and sense of purpose. Your team fucking LOVES YOU. You’re pretty sure they would follow you to your next job, if you left. So maybe you ARE the world’s greatest manager.

Or maybe…you are heavily optimizing for one aspect of the management role, the part where you interface with your direct reports as an ally and coach. You might even be optimizing to the extent that you are neglecting or outright harming other aspects of the job.

Rookie Mistake #1: Only Managing Down

But management means coaching and supporting the people on your team, right? What else is there?

Well.. a lot, actually. Like, the business needs to succeed, for starters. ☺️ And there are a bunch of other relationships that matter besides your own direct reports. A good, strong manager needs to care about:

  • Goals and planning. Managers are generally responsible for crafting a team roadmap out of the impossible mess of company strategy requirements, requests from other teams, product roadmap commitments, and KTLO (keep the lights on) work. Some companies also use OKRs.
  • Right-sizing workloads. There is always at least 10x as much work to be done as cycles to do work, which means estimating how much your team can deliver, planning that work, and dealing with the inevitable surprises that come up during execution. How do you balance urgency vs importance? It is YOUR job to make sure your team isn’t overcommitted.
  • Stakeholder management. Does your team have a reputation for delivering quality work when they say they will, more or less on schedule? Are you a good neighbor to other teams, or do they feel like anything they ask for goes into a black hole? This is largely determined by you.
  • Managing up. Your manager relies on you to provide enough visibility into your team that they can (at minimum) make good decisions where your team is involved, and help head off any problems or conflicts before they escalate.
  • Managing up (another sort) is the relationships you build and impressions you leave with your skip-level and other adjacent leaders. You are your team’s representative and ambassador. Leaders form a view of the org based on scraps of data. For the sake of your team: give good scraps.
  • Managing out horizontally. Building great relationships and a web of mutual support with your peers. Sharing context with each other. Managers are like the nervous system, carrying signal from point to point.
  • Contributing to the organization your team sits in, and its standards, policies, and structural integrity. This is the one most likely to suffer if a manager is laser focused on their own team. This means things like…applying the job ladder fairly and consistently, without playing favorites. Engaging in a dialogue with the ladder rather than bending the rules or making an exception.

As a manager, you have been granted certain formal powers by the org, to be used for the benefit of the org. This means you have a responsibility to care for the organization, and your team within that context.

You shouldn’t be advocating for the benefit of your team members, you have a greater responsibility to the rules and categories of the system, which you collectively maintain and agree upon. The system can’t survive if every manager is gaming the rules on behalf of their team. The system only works if every manager is playing fair.

As a line manager, the work you do interfacing with your team will likely be 50-75% of your time and energy … and impact. But this ratio changes as you go up the org chart. As a VP? Maybe 10-20% of your energy and time can go to your direct reports.

The higher up the ladder you go, the less important your bedside manner becomes and the more important your strategic direction becomes. You are first and foremost responsible for the company’s success, not for your reports’ feelings and career development.

Rookie mistake #2: Helicopter management

If rookie manager mistake number one is thinking that management consists of coaching and interfacing with your team, mistake number two is closely related. Mistake number two is … overmanaging the team, coddling people, and basically never allowing anyone to fail. I think of it as “helicopter managing”.

Helicopter management consists of overly identifying with your team and their needs and wants, instead of taking a step back and considering them in the full context of the organization, or letting them take risks and stand on their own two feet. You’re their manager, not their babysitter.

I have a personal story to illustrate this.

Once upon a time, many years ago, I had a team member who was energetic, highly talented, and a little high strung. I ended up spending a lot of time managing their relationships with other team members, keeping them on track with their projects, and helping them manage their emotional state in general. They nearly left in a dudgeon one time, and I think most managers would have let them go, but I saved the day and they stayed. I was actually really proud of the fact that I had retained them and kept them high-functioning for years. If you asked me, I would have shelved this under my successes, maybe even “proudest manager moments”.

Years later, though, I look back on this situation through very different eyes. Yes, I retained them at the company / on the team, with decent relationships, and they did a lot of good work! But should I have?

At what cost?

Most weeks, I probably spent 50-75% of my total emotional bandwidth on this one person’s needs. For years. Is this the best thing I could have done for the company with all that time and energy? Probably not!

Was this the best thing I could have done for them? I don’t even think it was that either! All that my coddling ultimately did was teach them the wrong lessons, and prevent them from learning the right ones. It delayed those lessons by a few years, and made learning them all the more painful when they finally came.

There are no clear bright lines here. But it’s worth checking in with yourself from time to time, and asking hard questions.

  • You spent all that time coaching and doing a diving save to retain that person …. but should you have? Is this really the best place for them to be at this point in their career?
  • Or let’s say you managed to turn around someone’s performance from failing to succeeding. Great!! But are you confident they are set up to excel, or are they always going to be hovering on the lower bound of acceptable performance? Are you going to be having this same discussion again next quarter?
  • Consider all that time you spent intimately entwined with every detail of every technical project your entire team was working on, reading every PR and design doc. Should you have? Or did you unintentionally deprive them of some agency, while cheating yourself out of time you should have spent becoming a better leader, strengthening your org, or understanding next year’s challenges?
  • Are you giving people only positive feedback? This is a common rookie manager mistake, and it often comes from a place of kindness, or overcompensating for overly negative environments. But you are not only cheating your people of opportunities for growth, you are teaching them that growth is something to be feared and avoided.
  • Or are you cheerleading people so intensely that they come away with a lopsided view of how valuable or advanced their skills are? Are you promoting fast and loose, so they grow to equate promotions with career development? Have you been spoon feeding them growth, or are they developing autonomy over time?

This can be especially unfortunate at higher levels, where autonomy is part of the definition of being a senior+ engineer. You might be stifling them and not allowing them to exercise that agency, or even develop that skill. For senior contributors, autonomy is what they bring. You gotta let them do it.

This shit is challenging. There are no simple answers. The “right” answer is often only obvious in retrospect, months or years later. Everyone needs help sometime, some of us more than others, and that’s okay.

But is it sustainable? What price will you pay?

What I do know is that if you haul someone over the finish line, that is not a success. If you’re going to be having the same hard conversations with them again in one month, three months, six months…that is not success. If they are going to have a rough landing the next time they change teams, that is not success, nor is it in their best interest. And if your team is overly dependent on you, you aren’t actually doing your job.

And honestly? People really WANT to be challenged. They crave it! Or at least the people you want to work with do.

Rookie Mistake #3: Your view of the system is incomplete

I’m only going to touch on this one very briefly; it’s long and complicated, and probably deserves a post of its own.

Systems thinking is a core skill for both managers and engineers. It’s not a skill we are born with; it takes a lot of practice and failure to develop good instincts for debugging complex systems. As an engineering manager, you may have spent 10+ years writing software and learning how computers work, but you have hardly begun to understand how business and organizational systems work.

This explains a lot when it comes to the empathy gap between engineers and management, I believe. 🙃

We spend a lot of time talking about empathy these days — empathy between teams, people, neurotypes; holding space for the fact that nobody is always at their best, etc. Yet engineers can still be incredibly dismissive and judgey towards management actions and organizational decisions.

We see a decision that doesn’t make sense to us, or that we wouldn’t have made, and we write it off as being selfish, uninformed, incompetent, stupid, money-grubbing, bureaucratic, untrustworthy, craven, selling out. Or — maybe worst of all — we shrug and say something cynical about how this kind of thing always happens in business. Or they’re out to get us, or they never listen to us, or it shows how much they don’t give a shit about us..

Far be it to me to excuse corporate venality, or to try and blow smoke up your ass about your leaders’ motives. But in many, many of these situations, this actually represents a failure of systems thinking when it comes to imagining the complex business, corporate, and people systems your leaders are operating in.

When you find yourself thinking things like:

  • “Why am I hearing this feedback so late, in such a roundabout way? Why didn’t they just come to me right away and tell me directly, and I could have fixed it so much sooner!”
  • “Why would they hire someone external to fill that role, instead of promoting the person who has been doing the work just fine in the meantime? Typical exec move; they never see the potential in the people they have, they always want to get someone who has already done the job before.”
  • “Why is our roadmap changing yet again? Why is this getting dropped in our lap? Our director doesn’t seem to know anything about building good software.”
  • “Why didn’t I get invited to that meeting, when it was about MY budget and MY workload? You can’t even get a seat at the table around here unless you have a director title or report to the CEO.”
  • “Why is that person being given ANOTHER chance? If they weren’t a straight white guy, they would have been fired a year ago.”

… or anything else that boils down to “other managers are stupid, hypocritical, or bad at their jobs”, stop yourself, and first try to understand “under what circumstances might their action be a reasonable one, or even the right one?”

Approaching people systems problems with curiosity, empathy, and the full awareness that you may never know the entire story (and there may be good reasons for this!) will make you a better coworker and a much more effective leader.

And if you are working as a manager at a company where you have enough evidence to prove that you cannot, should not take such a generous view of your peers, then maybe don’t. Like, if you have a professional responsibility to represent an organization you can not ethically represent… I would suggest not doing that. ¯\_(ツ)_/¯ If you can.

Your View of Your Manager Is Incomplete

One of the most challenging things to deal with, in my (limited) experience as an exec, is when you have a manager who is well-liked by their team but fundamentally ineffective in the role, so you have to replace them. Then you are left with a team left feeling bereft and confused, and you can’t just give them a list of all the ways their manager was actually dropping the ball and not doing their job well, because people deserve some privacy and dignity. You pretty much just have to suck it up, and hope that you have enough trust banked for them not to quit.

It’s entirely possible for a manager to be beloved by their entire team, while having a corrosive effect on the system around them. Sometimes it’s their very willingness to bend the system for their people’s benefit that generates that loyalty.

An unwary manager may create a sort of island within the company, where the team does not feel part of — may even feel separate from, superior to, or suspicious of — the broader org or the company. Team members may feel like “this is the only team I would ever want to belong to at this company”, or “my manager is great, they protect us from all the big company bullshit”, or “it’s us against the world”, or “nobody understands us, except our manager”. These are seductive dynamics to slip into because tribalism is so powerful. The more apart you feel from the company, the more tightly you may bond with each other.

I’m not judging you. I was that manager at Parse, to some extent, after the Facebook acquisition. I did not give a shit about the org, I only cared about my team. So…I get it. I still wouldn’t want me as a manager in my org.

What would you do?

The system is what the system does.

Put yourself in your senior leadership’s shoes. What would YOU do if you had to choose between a good, reliable manager who gets the job done for the org and isn’t particularly beloved by their reports (she’s not awful, the team thinks she’s “fine”), vs a manager who is beloved by their reports and cares about their career growth deeply, but is weak at everything else? What will manager #2 cost the rest of the org, and who will bear those costs?

Don’t make your leadership make that choice. Be a manager who is good to your team, and good to the organization too.

Honestly, it is healthy for a manager to not identify too closely with their team. You should stand with them, but a step or two apart. After all, your job is to be pushing or pulling them in a direction, not just standing still and … marinating.

If you identify with them too closely, it can get very hard to tell your reports hard things. You may empathize with them so much that you put their feelings above the need to get shit done. You can be friends with your team, just like parents can be friends with their children, but the friendship doesn’t come first. Your formal role comes first.

On being a new manager who cares a lot

There’s something really beautiful about the energy and dedication that brand new managers bring to the role. Some of the most spectacular results I’ve ever seen for individual team members have come from teams with first time managers, who are determined and idealistic and pouring their whole heart and soul into the people reporting to them. They haven’t yet learned to pace themselves or to be more well-rounded with their time and energy, and sometimes a person can soak up that attention and turn a failing situation around into a thriving one.

I would never tell a manager that they should care less. Caring for people is the beating heart of this job. It doesn’t matter how efficient and effective you are at delivering feedback, managing people out, and planning roadmaps if you don’t truly give a shit about the people you serve. Even as you rise in the ranks and people-interfacing becomes a smaller % of what makes you good at your job, caring is still absolutely essential.

So I hope the message of this post doesn’t come across as “you think you’re a good manager, but here’s why you actually suck”. ☺️ You got into this role because you cared, and this is valuable. Never lose touch with it.

The message is simply that it took me years and years to learn that there is more to being a great manager than caring about my team. I hope you can learn it faster than I did.

 

Helicopter Management and Other Mistakes

Ritual Brilliance: How a pair of Shrek ears shaped Linden Lab culture by making failure funny — and safe

mipsytipsy, , , 2 Comments

[Originally posted on the now-defunct “Roadmap: A Magazine About Work” website, on May 30th, 2023. A pretty, nicely-formatted PDF version of this article can be downloaded here. Thanks to Molly McArdle for editing!]

If you talk to former Lindens about the company’s culture—and be careful, because we will do so at length—you will eventually hear about the Shrek ears.

When you saw a new person wearing the Shrek ears, a matted green-felt headband with ogre ears on it, you introduced yourself, congratulated them warmly, and begged to hear the story of how they came to be wearing them. Then you welcomed the new person to the team (“You’re truly one of us now!”) and shared a story about a time when you did something even dumber than they did.

My first job after (dropping out of) college was at Linden Lab, the home of Second Life. I joined in 2004 and stayed for nearly six years, during which the company grew from around 25 nerds in a room to around 400 employees who worked out of offices in Brighton, San Francisco, Menlo Park, and Singapore, or their own homes—wherever they were.

When I think back on that time now, almost two decades later, I’m puzzled by the Shrek ears phenomenon. I wasn’t exactly powerful then, at barely 20 years old. Not only was this my first real job, I was also the first woman engineer, and I made tons of mistakes. Shouldn’t I have found the practice of being systematically singled out and spotlighted for my errors humiliating, shaming, and traumatic?

Yet I remember loving the tradition and participating with joy and vigor. Everyone else seemed to love it, too. The practice spread beyond engineering and out into the rest of the company, not by fiat but because individual people would voluntarily track down the Shrek ears and put them on their own head. (I’m not imagining this, right?)

Step 1, break production; Step 2, put on Shrek ears

Here’s how it worked: The first time an engineer broke production or caused major outage, they would seek out the ears and put them on for the day. The ears weren’t a mark of shame—they were a badge of honor! Everyone breaks production eventually, if they’re working on something meaningful.

If people saw you wearing the ears, they would eagerly ask, “What happened? How did you find the problem? What was the fix?” Then they would regale you with their own stories of breaking production or tell you about the first outage they caused. If the person was self-flagellating or being too hard on themselves, the Shrek ears gave their colleagues an excuse to kindly but firmly correct it on the spot. It was Linden’s way of saying, Hey, we don’t do that here: “You did the reasonable thing! How can we make the system better, so the next person doesn’t stumble into the same trap?”

In those days, Linden was running a massively distributed system across multiple data centers on three continents, and doing so without the help of DevOps, CI/CD, GitHub, virtualization, the cloud, or infrastructure as code. We had an incredibly high-performing operations team, with a thousand-to-one server-to-ops engineer ratio, which was a real achievement in the days when the role required doing everything from racking and stacking boxes in the colocation center to developing your own automation software.

Failures were just fucking inevitable. In a world like that, devoid of the entire toolchain ecosystem we’ve come to rely on, you just had to learn to roll with it, absorb the hits, and keep moving fast. You could only test so much in staging; it was more important to get it out into production and watch it—understand it—there. It was better to invest in swift recovery, graceful degradation, and decoupling services than to focus on trying to prevent anything from going wrong. (Still is, as a matter of fact.)

This might all sound a little overwrought to you—maybe even dangerous or irresponsible. Didn’t we care about quality? Were we bad engineers?

The Shrek ears were “blameless retros” before there were blameless retros

I assure you, we cared. The engineers I worked with at Linden were of at least as high a caliber as the engineers I later worked with at Facebook (and a whole lot more diverse). In this specific place and time, the Shrek ears were what we needed to alleviate paralysis and fear of production, and to encourage the sharing of knowledge—even if anecdotal—about our systems.

In retrospect, the Shrek ears were a brilliant piece of social jujitsu. There was an element of shock value or contrarianism in celebrating outages instead of getting all worked up about them. But the larger purpose of the ears was to reset people’s expectations (especially in the case of new hires) and reprogram them with a different set of values: Linden’s values.

In the years since those early days at Linden, the industry has developed an entire language and set of practices around dealing with the aftermath of incidents: blameless post mortems, retrospectives, and so on. But those tools weren’t available to us at the time. What we did have was the Shrek ears. A couple of times a month something would break, the ears would be claimed, and we would all go around reminding one another that failure is both inevitable and ridiculous, and that no one is going to get mad at you or fire you when it happens.

Failure is always a question of when, not if

It’s important to note that you never saw anyone get teased or shamed for wearing the ears or for breaking production. There was a script to follow, and we all knew it. We learned it from watching others put on the ears, or by donning them ourselves. On a day when the Shrek ears had appeared, people would gather around at lunch or at the bar after work and swap war stories, one-upping one another and laughing uproariously.

Every new engineer was told, “If you never break production, you probably aren’t
doing anything that really matters or taking enough risks.”

It’s also important to emphasize that the ears were opt-in, not opt-out. You didn’t have to do it. And if you did take them, you could expect a wave of sympathy, good humor, and support. It affirmed that you deserved to be here, that you were part of the team.

And though the Shrek ears started in engineering, people in sales, marketing, accounting, and other departments picked them up over the years. It was a process of voluntary adoption, not a top-down policy. Someone would announce in IRC that they were wearing the ears today, and why. The camaraderie and laughter that ensued were infectious—and made it easier and easier over time for people to be transparent about what wasn’t working.

Rituals exist to instill values and train culture

In Rituals for Work, Kursat Ozenc defines rituals as “actions that a person or group does repeatedly, following a similar pattern or script, in which they’ve imbued symbolism and meaning.” Ritual exists to instill a value, create a mindset, or train a reflex.

And this particular ritual was extremely effective at taking lots of scared engineers and teaching them, very quickly:

✨ It is safe to fail✨
✨ Failure is constant✨
✨ Failure is fucking hilarious✨

At Linden, failure was not something to be ashamed of or to hide from your teammates. We understood that it’s not something that happens only to careless or inexperienced people. In fact, the senior people have the funniest fuckups—because what they are trying to do is insanely hard. The Shrek ears taught us that you fail, you laugh, you drink whiskey, you move on.

Other companies had similar rituals around the same time—Etsy famously had the “three-armed sweater,” which they would pass around to whoever had last broken production. But I’ve never again worked at a place where mistakes were discussed as freely and easily across the entire company as they were at Linden Lab. And I think the Shrek ears had a lot to do with that.

Their point was never to single out the person who had made a mistake and humiliate them, but the exact opposite. By putting on the ears, you said not just “Hi, I made a mistake” but also “I’m going to be brave about it, so we can all collectively learn and improve.” It was a ritualized act of bravery rewarded by affirmation, empathy, and acceptance. At Linden, the Shrek ears weren’t just a terrific tool for promoting team coherence and creating a sense of belonging. They also provided structure to help individuals and teams recover from scary events, and even traumas.

In so many ways, Linden Lab was ahead of its time

Linden was an extremely strange workplace when I was there, and it inspired unusually strong devotion, which we self-deprecatingly referred to as “the Kool-Aid.” It can be difficult to convey just how radical and weird it was at the time because the world has changed so much since then, and so many of the company’s “weird” philosophies have since gone mainstream. (Though not all: using “Kool-Aid” as a casual phrase to denote “excessive enthusiasm” or “cult-like devotion” is now recognized by many as being in poor taste. After all, people actually died at the Jonestown massacre.)

In a lot of ways, Linden culture (and Second Life technology) was profoundly, recognizably modern, and similar to the best workplaces of today, 20+ years later.

Philip Rosedale, Linden’s founder and CEO, is an inventor and technologist who believed it was every inch as interesting and important to experiment with company culture as with the virtual worlds we built. Except we did it all from scratch: building the technology and the culture together. And this led us down some weird rabbit holes, such as a cron job that rsynced the entire file system down over thousands of live servers every night. And the Shrek ears.

There was a period when “Choose your own work” was a company core value, and there were effectively no managers. (Not every experiment worked!) We went all-in on a fully distributed company culture at a time when practically no one else had. We ran a massively distributed, high-concurrency virtual world at a time before microservices, sharded databases, config management virtualization, AWS, or SRE and DevOps.

I can understand why people now find this story horrifying

With the distance of time, I get why the Shrek ears might make you recoil. If you think “That sounds awful! What kind of monsters would do that to each other?”—you are far from alone. Any time I mention the story in public, a sizable minority of people are aghast and appalled. Representative quotes include:

“I hope you realize how many people you traumatized by doing this to them.”

“I wonder how many introverted people found this excruciating but were too
afraid to say so.”

“Office bullying is fucked up even with cute Shrek ears.”

Even:

“We heard about the Shrek ears from an engineer we interviewed. He was telling us how great they were, but we were all so horrified that we declined to hire him because of it.”

And they’re right. It sounds awful to us now. It really does! It sounds like we were singling people out for their failures, like a dunce cap. I wouldn’t be surprised to someday learn that, in fact, a small number of people did felt pressured into using the ears, or hated them and were too afraid to say something. But how do we account for the fact that this tradition was so deeply beloved by so many—and that we are still fondly reminiscing about it more than 15 years later? It had a purpose.

Linden Lab was an incredibly progressive company for its time: very anti-hierarchical, very much about empowering people to be creative and independent. It also was by far the most diverse company I’ve ever worked in (other than Honeycomb, which I cofounded and where I’m CTO), with lots of women and genderqueer and trans people and people of color. We were way out on the sensitive branch relative to tech at that time. It’s tough to square this knowledge of what Linden was like as a place with the reactions some people outside the organization have to the Shrek ears.

I think this is, above all, a sign of progress. So many questionable practices that were ordinary back then—like referring to everyone as “guys,” using terms like “master/slave” for replication, or throwing alcohol-sloshed parties—are now rightfully frowned upon. We have become more sensitive to people’s differences and more clued into the power dynamics of the workplace. It’s far from perfect, but it is a lot better.

As a ritual, the Shrek ears were powerful and did the job. They were also fun—proving once again that making something goofy is the best way to make it stick. But I can’t imagine plopping Shrek ears on a new hire who has just broken production in 2023. And honestly, I think that’s probably a good thing. It’s time for new rituals.

Ritual Brilliance: How a pair of Shrek ears shaped Linden Lab culture by making failure funny — and safe

Choose Boring Technology Culture

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Honeycomb recently announced our $50M Series D funding round. We aren’t the type to hype this a lot; Emily summed it up crisply as, “Living another day on someone else’s money isn’t business success, even though it is a lovely vote of confidence.”

Agreed. The vote of confidence does mean more than usual, given the dire state of VC funding these days, but…raising money is not success. Building a viable, sustainable company is success.

Whenever we are talking to investors, something that inevitably comes up is what a bomb ass team 🌈 we have. They have always been impressed by our ability to recruit and retain marquee names, people we “shouldn’t have been able to get” at our stage; honestly it’s even better than they realize, because we have heavy hitters all up and down the company, most of whom simply aren’t as well known. 😉 (Fame, and this may shock you, is not a function of talent.)

People join Honeycomb for many reasons, but “culture” is one of the most commonly cited. We have never been shy about talking about the ways we think tech culture sucks, or the experiments we are running. But this has given rise to the occasional impression that we are primarily cultural innovators who occasionally write software. We really aren’t.

In fact, I’d say the opposite is true. We try to choose boring culture.

What The Fuck Does “Culture” Even Mean?

Ok, so this is where the problem starts. This is why it grates on my nerves any time someone starts making pronouncements about how “your culture is bad”, “culture is the problem”, “fix your broken culture”… AUUGGGHHH. Those sentences are MEANINGLESS.

What does “culture” even mean?? Let’s consult the interwebs:

  • Culture: “An umbrella term which encompasses the social behavior, institutions and norms for a group; knowledge, beliefs, arts, laws, customs, capabilities, and habits of those individuals”
  • Culture: “The shared values, goals, attitudes and practices that characterize an organization; working environment, company policies and employee behavior”
  • Culture: “Maintain tissue cells, bacteria, etc in conditions suitable for growth”

Well, at least that last one makes sense. 😛 But if culture means everything, then culture means nothing. That’s just not helpful!

Instead, let’s disambiguate company culture into two categories. There is the formal culture of the organization (meetings, mission/vision, management, job ladders, hiring practices, strategy, organizational structure, team dynamics, and so on), and there is the informal culture of the people, the ways that humor, playfulness, and practices manifest in groups and individuals.

Organizational culture is professional, formal, structural, institutional. Managerial responsibilities, promotions, compensation plans, and fiduciary duties are just a few of the .many aspects of organizational culture.

Informal culture is chaotic, joyful, free-spirited, and fun, individualized, inherently anarchic and bottoms-up. It’s things like writing release notes in limerick form, bringing banana bread to work after an outage, long pun threads, slack channels dedicated to pets, competing on the number of employees named “Jess”* vs “Chris”*.

Organizational culture is the cake; informal culture is the frosting. Organizational culture is what leaders are hired to build, informal culture is what bubbles up irrepressibly in the gaps. (I wish I had better names for these!) And when it comes to formal, organizational culture, you don’t want to be in the business of innovating.

Culture Serves The Business

As a leader, you should absolutely care about your culture, but your primary responsibility is the health of the business. The purpose of your culture is to make your business succeed. It does not serve you, and it does not serve the people you care about, to be unclear on this front.

I don’t mean to make it sound like this is simple or easy. It is not. You are dealing with people’s lives and livelihoods, and it is all about tradeoffs. What might be best for an individual in the long run (for example, leaving your company to pursue another opportunity) might harm your business in the near term. Yet you might decide to celebrate them in leaving and not pressure them to stay, because you believe that what’s best for your business in the longer term is for employees to be able to trust their managers when they say, “I believe that working here is the best thing you can do for your career right now.”

The transactional nature of work relationships is how they differ from e.g. family relationships. You can form intense bonds and deep friendships with the people you work with — you may even form bonds that transcend your work relationship — but your relationship at work comes with terms and conditions.

Your company culture can’t be everything to everyone. Nor should you try.

You HAVE to care more about the health of the business than about culture for culture’s own sake. Even if — especially if — you have lots of strong opinions about culture, and there are lots of ways you want to deviate from common wisdom. Doing well at business is what earns you more innovation tokens to invest.

“Choose Boring Technology Culture”

Dan McKinley coined the phrase “choose boring technology” and the concept of innovation tokens nearly a decade ago.

“Boring” should not be conflated with “bad.” There is technology out there that is both boring and bad [2]. You should not use any of that. But there are many choices of technology that are boring and good, or at least good enough….The nice thing about boringness (so constrained) is that the capabilities of these things are well understood. But more importantly, their failure modes are well understood. — @mcfunley

The moral of the story is that innovation is costly, so you should choose standard, well-understood, rock-solid technologies insofar as you possibly can. You only get a few innovation tokens to spend, so you should spend them on technologies that can give you a true competitive advantage — not on, like, reinventing memcache for the hell of it.

The same goes for running a business, and the same goes for organizational culture. We have collectively inherited a set of default practices that work pretty well, like the 40 hour work week and having 1x1s with your manager. You CAN choose to do something different, but you should probably have a good reason. To the extent that you can learn from other people’s experience, you probably should, whether in business or in tech; innovation is expensive, and you only get so many tokens. Do you really want to spend one on a radical reinvention of your PTO policy? How does that serve you?

Innovation gets all the headlines, but I would posit that what most companies need is actually much simpler: organizational health.

Great Culture begins with Organizational Health

There’s this book by Patrick Lencione called “The Advantage: How Organizational Health Trumps Everything Else in Business.” (He is best known for writing “Five Dysfunctions of a Team“.) This guy is to organizational health what James Madison was to constitutional government: a very specific kind of genius.

I picked up “The Advantage” in 2020, around the time Honeycomb stopped teetering on the brink of failure, once it became clear we were likely to be around for a while. It made a huge impression on me. He makes the case that most businesses spend a ton of energy on trying to be “smart”, and relatively little on being “healthy”.

Healthy orgs are characterized by minimal politics, minimal confusion, high morale, high productivity, and low turnover. Health begets — and trumps — intelligence.

As Lencione says, an organization that is healthy will inevitably get smarter over time. People in a healthy organization will learn from each other, identify problems, and recover quickly from mistakes. Without politics and confusion, they will cycle through problems and rally much faster than dysfunctional rivals will. And they create an environment in which everyone else can do the same, which creates a multiplier effect.

The healthier an org is, the more of its collective intelligence it is able to tap into and use. Most orgs exploit only a fraction of the knowledge, experience, and intellectual capital available to them, but the healthy ones can tap into almost all of it.

Organizational Health Is Too Boring

No one would disagree with any of this, in principle. ☺️ EVERYBODY wants to work at a place where the mission, vision, and values are clear, meaningful and inspiring; where everyone is rallied around the same winning strategy; and where it’s crystal clear how your role specifically will contribute to that success. Everybody agrees that a healthy organizational culture leads to better outcomes.

So why isn’t every company like that?

Well, it is much easier said than done. ¯\_(ツ)_/¯ It is unglamorous work, difficult to measure, and at the end of the day we are always making risky decisions between conflicting tradeoffs based on partial information. We are imperfect meat sacks who lack self awareness, struggle to understand each other, and get hangry and snap. And the job is never done. You never “get there”, any more than you are ever perfectly healthy with perfect relationships.

But that doesn’t mean we shouldn’t try. We don’t have to be perfect to be a meaningfully better presence in people’s lives. We just have to be healthy enough to achieve our goals.

Nobody Wants An “Exciting” Company Culture

When you tell your partner you had an exciting day at work, do they respond with “uh oh 😬🔥🧯”?

All too often, excitement at work comes from strategic swerves, projects getting canceled, lack of focus, missteps or conflicts, anxiety and passive aggression, outages or downtime, outrageous demands coming from out of left field, or getting information at the last minute that you should have had ages ago. Living on the edge of your seat can be very stimulating! Firefighting is a huge rush, and if you’re part of the essential glue holding this creaky vessel together, you can get hooked on feeling desperately needed.

But this isn’t good for your cortisol levels, and it doesn’t move the company forward. When so much of your energy goes to bailing water and staying afloat, you don’t have much left over for rowing the oars. You want energy going to the oars.

Should work be exciting? ¯\_(ツ)_/¯ It’s not the adjective I would reach for. Emotional rollercoaster rides don’t provide the kind of circumstances that tend to unlock great design or engineering, or collaboration or focus. I would rather reach for words like achievement, fulfillment, pride, comradeship, or the joy of being part of something greater than yourself, not “exciting” or “fun”.

Leaders Worry Too Much About Making Work Fun

As a leader, your job is not to “make work fun”. You are not here to entertain your employees. Your responsibility is to build a formal culture that works, that supports the success of the business.

So what, am I dooming you to a life of bureaucratic beige and meetings without puns? Fuck no.

If formal organizational culture is like the architecture, then informal culture is furnishings, light displays, murals and banners — whatever you do on the inside. You don’t want someone getting overly creative with the load-bearing beams. Save that for when it’s time to paint “Frozen” murals on the walls and hang the matching icicle curtains.

You want formal culture to be boring, stable, reliable, load-bearing…because this creates a safe structure for people to bring the humor, the fun, the joy, the delight, without any fear of building collapse. The company doesn’t have to bring the fun; people bring the fun. Have you met people? People are fucking weirdos. 🥰 If you create an emotionally safe zone and the conditions for success, informal culture will thrive. 🪅People bring the fun🪅 — they always do.

The best informal culture is almost always bottoms up. But managers, execs, HR/People teams, etc can encourage informal culture. One of the most powerful things you can do is just participate. Show up for drinks, play the board games, keep the puns rolling, get silly with your team! Your participation gives people permission and shows that you value their creative cultural labor at work.

Of course there are no bright lines — companies can throw great parties! — but that’s not the job; building a healthy org is the job. Doing that right frees people up to have joy at work. It makes the celebrations that much bigger, the fun that much funnier.

Success Is Rocket Fuel For Fun

Think back to the most corporate fun you’ve ever had at work — the biggest parties, celebrations, blowouts, etc. Were they holiday parties and random occasions, or were they actually linked to great achievements? I bet they were the latter.

You don’t gather at work for the fun of it, you come together to do great things. It stands to reason the peak moments of joy and bonding are fueled by a sense of accomplishment.

Even on a smaller scale, levity and joy are inextricably linked to doing great work and making customers happy. For example, ops/SRE teams are notorious for their gallows humor around outages (ops is ALWAYS the funniest engineering team, in my experience ☺️). But dark humor is only funny when you are also taking your work seriously. Joking about the inevitability of data loss stops being funny real fast if you are actually playing fast and loose with customer backups.

In the absence of success, progress, and high performance, the kind of “frosting” behaviors that bring so much hilarity to work — joking and teasing, puns and stories — actually stop being fun and start making people feel distracted, irritated and on edge. You don’t want to hear a steady stream of jokes from somebody who keeps letting you down.

Side note: unhealthy orgs may have pockets of humor, but it often comes at the expense of other, less prestigious teams. Lots of people may feel too anxious, powerless or threatened to participate. Your experience of whether those companies are “fun” or not is likely to depend heavily on where you sit in the hierarchy. But a healthy org creates the level conditions for humor, playfulness and creativity throughout the org.

Investing Your Innovation Tokens

So yeah. Despite our reputation for cultural innovation, I’d say we’re actually pretty conservative when it comes to operating a company.

Not only are we not revolutionaries, we are actually trying to do as little differently as possible, because innovation is costly!! Instead, we (as a leadership team) are more focused on trying to execute well and improve upon our organizational health. For the past year, we have been laboring especially hard over strategy — the diagnosis, guiding policy, and set of coherent actions we need to win. Our first responsibility is to make the business succeed, after all.

Which brings us back to the topic of innovation tokens.

I started writing down some of the innovation tokens I feel like we’ve spent. But it dawned on me that when I look at most of the cultural experiments we run, and the things we talk about and write about publicly — stuff like the dangers of hierarchy, hiring, interviewing, high-leverage teams, engineering levels, rituals for engineering teams, etc — it doesn’t feel like innovation at all. It’s all just about trying to have a healthier organization. Hierarchy sucks because visible hierarchy has been shown to dampen people’s creativity, motivation and problem-solving skills. Engineering levels are important because they bring clarity. And so on.

What makes something rise to the level of an innovation token is the amount of time we end up asking other people to invest lots of their time into.

  • Like, we are 1.5 years into a 4 year experiment having an employee on our board of directors. We are about to spin up an internal Advisory Panel to more broadly distribute the impact of our employee board member around the company.
  • In the past, we have experimented with regular ethics discussion groups.
  • Last year we did a deep dive into company values with small breakout groups.
  • Some internal decisions around things like values are handled, not by estaff, but by a group of six people; one employee representative of each org, nominated by their VP; who do a deep dive into the material together and come back with a decision or recommendation.
  • We are about to start the process of developing our own leadership curriculum. We know that we need to equip our managers with better tools, and culturally indoctrinate new employees, so I am excited to build something with our cultural fingerprints all over it.

We run a lot of experiments around transparency, like, the agenda for exec staff meetings can be viewed by the whole company. After every board meeting, we present the same thing we showed to the board to the whole company during all-hands. We are transparent on salary bands. Stuff like that.

We are far from perfect; we have a long ways to go, and when I look around the org it’s hard not to only see all the work left to be done. But we are a lot healthier and better off than we were a year ago, which was better off than we were two years ago, let alone three.

The Experience Of Making This Will Be With Us Forever

A few months ago I was reading this lengthy profile of Sarah Polley in the New Yorker, as she was doing a bunch of press for her new movie, “Women Talking”. (The movie itself sounds incredibly intense; I am still trying to find time and emotional energy to watch it. Someday!)

One thing she said got lodged in my brain, and I’ve been unable to forget it ever since. She’s talking about the experience of having been a child actor, and how intensely it informs the experience she strives to create for everybody working on the set of one of her movies; where parents get to go home and have dinner with their kids, etc.

[He] told her, “If this film is everything we want it to be, maybe, if we are very lucky, it will affect a few people for a little while, in a way that is out of our control. The only thing that’s certain is that the experience of making it will be with all of us—it will become part of us—forever. So we must try our best to make it a good experience.”

Making a movie that lots of people want to see, one that was a good financial return on investment, buys you the ability to make even more movies, employ more people, take even bigger creative risks. If all you want to do is be a niche indie player, working on a shoestring budget, more power to you. But if you really believe in your ideas, and you want to see them go mainstream … you need mainstream success.

Sarah Polley makes movies. We make developer tools. ☺️ But the same thing is true of working at Honeycomb.

If we are very lucky, and work very hard, our work may help teams build better software and spend fewer, more meaningful hours at work, for a long time to come. I love our mission. But the only certain thing is that the experience of making it will be with all of us, become part of us, forever.

So we should try our best to make it a good experience. ☺️

charity.

Footnotes

(1) Inherited Defaults

How to access these inherited defaults can be a bit more complicated than I make it sound. Working as a manager at Facebook for two years taught me more about these defaults than anything else I’ve ever done in my career. Big companies have had to figure a lot of shit out in order to function at scale, which is why I often advise anyone who plans on starting a company or being a director/VP to do a stint at one. Will Larson’s book “An Elegant Puzzle” does a great job of laying out defaults and best practices for engineering orgs, and his blog has even more useful bits.. Otherwise, you might wanna get yourself an advisor or two with a lot of operator experience, and get used to asking questions like “how does this normally get done?”

(2) Corporate Fun

There’s plenty of stuff in the grey area between formal, organizational culture and informal, individual culture. Companies often stray into fun-like adjacencies like holiday parties, offsites, etc. Fostering a sense of “play” and informality is actually really important for making teams click with each other, and obviously the company should foot the bill if it’s a work function. Just be mindful of what you’re doing and what your goals are when you veer into the rocky shoals of Forced Corporate Fun. 😆

Choose Boring Technology Culture

Questionable Advice: “People Used To Take Me Seriously. Then I Became A Software Vendor”

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I recently got a plaintive text message from my magnificent friend Abby Bangser, asking about a conversation we had several years ago:

“Hey, I’ve got a question for you. A long time ago I remember you talking about what an adjustment it was becoming a vendor, how all of a sudden people would just discard your opinion and your expertise without even listening. And that it was SUPER ANNOYING.

I’m now experiencing something similar. Did you ever find any good reading/listening/watching to help you adjust to being on the vendor side without being either a terrible human or constantly disregarded?”

Oh my.. This brings back memories. ☺️🙈

Like Abby, I’ve spent most of my career as an engineer in the trenches. I have also spent a lot of time cheerfully talking smack about software. I’ve never really had anyone question my experience[1] or my authority as an expert, hardened as I was in the flames of a thousand tire fires.

Then I started a software company. And all of a sudden this bullshit starts popping up. Someone brushing me off because I was “selling something”, or dismissing my work like I was fatally compromised. I shrugged it off, but if I stopped to think, it really bothered me. Sometimes I felt like yelling “HEY FUCKERS, I am one of your kind! I’m trying to HELP YOU. Stop making this so hard!” 😡 (And sometimes I actually did yell, lol.)

That’s what I remember complaining to Abby about, five or six years ago. It was all very fresh and raw at the time.

We’ll get to that. First let’s dial the clock back a few more years, so you can fully appreciate the rich irony of my situation. (Or skip the story and jump straight to “Five easy ways to make yourself a vendor worth listening to“.)

The first time I encountered “software for sale”

My earliest interaction with software vendors was at Linden Lab. Like most infrastructure teams, most of the software we used was open source. But somewhere around 2009? 2010? Linden’s data engineering team began auditioning vendors like Splunk, Greenplum, Vertica[2], etc for our data warehouse solution, and I tagged along as the sysinfra/ops delegate.

For two full days we sat around this enormous table as vendor after vendor came by to demo and plump their wares, then opened the floor for questions.

One of the very first sales guys did something that pissed me off me. I don’t remember exactly what happened — maybe he was ignoring my questions or talking down to me. (I’m certain I didn’t come across like a seasoned engineering professional; in my mid twenties, face buried in my laptop, probably wearing pajamas and/or pigtails.) But I do remember becoming very irritated, then settling in to a stance of, shall we say, oppositional defiance.

I peppered every sales team aggressively with questions about the operational burden of running their software, their architectural decisions, and how canned or cherry-picked their demos were. Any time they let slip a sign of weakness or betrayed uncertainty, I bore down harder and twisted the knife. I was a ✨royal asshole✨. My coworkers on the data team found this extremely entertaining, which only egged me on.

What the fuck?? 🫢😧🫠 I’m not usually an asshole to strangers.. where did that come from?

What open source culture taught me about sales

I came from open source, where contempt for software vendors was apparently de rigueur. (is it still this way?? seems like it might have gotten better? 😦) It is fascinating now to look back and realize how much attitude I soaked up before coming face to face with my first software vendor. According to my worldview at the time,

  1. Vendors are liars
  2. They will say anything to get you to buy
  3. Open source software is always the safest and best code
  4. Software written for profit is inherently inferior, and will ultimately be replaced by the inevitable rise of better, faster, more democratic open source solutions
  5. Sales exists to create needs that ought never to have existed, then take you to the cleaners
  6. Engineers who go work for software vendors have either sold out, or they aren’t good enough to hack it writing real (consumer facing) software.

I’m remembering Richard Stallman trailing around behind me, up and down the rows of vendor booths at USENIX in his St IGNUcious robes, silver disk platter halo atop his head, offering (begging?) to lay his hands on my laptop and bless it, to “free it from the demons of proprietary software.” Huh. (Remember THIS song? 🎶 😱)

Given all that, it’s not hugely surprising that my first encounter with software vendors devolved into hostile questioning.

(It’s fun to speculate on the origin of some of these beliefs. Like, I bet 3) and 4) came from working on databases, particularly Oracle and MySQL/Postgres. As for 5) that sounds an awful lot like the beauty industry and other products sold to women. 🤭)

Behind every software vendor lies a recovering open source zealot(???)

I’ve had many, many experiences since then that slowly helped me dismantle this worldview, brick by brick. Working at Facebook made me realize that open source successes like Apache, Haproxy, Nginx etc are exceptions, not the norm; that this model is only viable for certain types of general-purpose infrastructure software; that governance and roadmaps are a huge issue for open source projects too; and that if steady progress is being made, at the end of the day, somewhere somebody is probably paying those developers.

I learned that the overwhelming majority of production-caliber code is written by somebody who was paid to write it — not by volunteers. I learned about coordination costs and overhead, how expensive it is to organize an army of volunteers, and the pains of decentralized quality control. I learned that you really really want the person who wrote the code to stick around and own it for a long time, and not just on alternate weekends when they don’t have the kids (and/or they happen to feel like it).

I learned about game theory, and I learned that sales is about relationships. Yes, there are unscrupulous sellers out there, just like there are shady developers, but good sales people don’t want you to walk away feeling tricked or disappointed any more than you want to be tricked or disappointed. They want to exceed your expectations and deliver more value than expected, so you’ll keep coming back. In game theory terms, it’s a “repeated game”.

I learned SO MUCH from interviewing sales candidates at Honeycomb.[3] Early on, when nobody knew who we were, I began to notice how much our sales candidates were obsessed with value. They were constantly trying to puzzle out out how much value Honeycomb actually brought to the companies we were selling to. I was not used to talking or thinking about software in terms of “value”, and initially I found this incredibly offputting (can you believe it?? 😳).

Sell unto others as you would have them sell unto you

Ultimately, this was the biggest (if dumbest) lesson of all: I learned that good software has tremendous value. It unlocks value and creates value, it pays enormous ongoing dividends in dollars and productivity, and the people who build it, support it, and bring it to market fully deserve to recoup a slice of the value they created for others.

There was a time when I would have bristled indignantly and said, “we didn’t start honeycomb to make money!” I would have said that the reason we built honeycomb because we knew as engineers what a radical shift it had wrought in how we built and understood software, and we didn’t want to live without it, ever again.

But that’s not quite true. Right from the start, Christine and I were intent on building not just great software, but a great software business. It wasn’t personal wealth we were chasing, it was independence and autonomy — the freedom to build and run a company the way we thought it should be run, building software to radically empower other engineers like ourselves.

Guess what you have to do if you care about freedom and autonomy?

Make money. 🙄☺️

I also realized, belatedly, that most people who start software companies do so for the same damn reasons Christine and I did… to solve hard problems, share solutions, and help other engineers like ourselves. If all you want to do is get rich, this is actually a pretty stupid way to do that. Over 90% of startups fail, and even the so-called “success stories” aren’t as predictably lucrative as RSUs. And then there’s the wear and tear on relationships, the loss of social life, the vicissitudes of the financial system, the ever-looming spectre of failure … 👻☠️🪦 Startups are brutal, my friend.

Karma is a bitch

None of these are particularly novel insights, but there was a time when they were definitely news to me. ☺️ It was a pretty big shock to my system when I first became a software vendor and found myself sitting on the other side of the table, the freshly minted target of hostile questioning.

These days I am far less likely to be cited as an objective expert than I used to be. I see people on Hacker News dismissing me with the same scornful wave of the hand as I used to dismiss other vendors. Karma’s a bitch, as they say. What goes around comes around. 🥰

I used to get very bent out of shape by this. “You act like I only care because I’m trying to sell you something,” I would hotly protest, “but it’s exactly the opposite. I built something because I cared.” That may be true, but it doesn’t change the fact that vested interests can create blind spots, ones I might not even be aware of.

And that’s ok! My arguments/my solutions should be sturdy enough to withstand any disclosure of personal interest. ☺️

Some people are jerks; I can’t control that. But there are a few things I can do to acknowledge my biases up front, play fair, and just generally be the kind of vendor that I personally would be happy to work with.

Five easy ways to make yourself a vendor worth listening to

So I gave Abby a short list of a few things I do to try and signal that I am a trustworthy voice, a vendor worth listening to. (What do you think, did I miss anything?)

🌸 Lead with your bias.🌸
I always try to disclose my own vested interest up front, and sometimes I exaggerate for effect: “As a vendor, I’m contractually obligated to say this”, or “Take it for what you will, obviously I have religious convictions here”. Everyone has biases; I prefer to talk to people who are aware of theirs.

🌸 Avoid cheap shots.🌸
Try to engage with the most powerful arguments for your competitors’ solutions. Don’t waste your time against straw men or slam dunks; go up against whatever ideal scenarios or “steel man” arguments they would muster in their own favor. Comparing your strengths vs  their strengths results in a way more interesting, relevant and USEFUL discussion for all involved.

🌸 Be your own biggest critic.🌸
Be forthcoming about the flaws of your own solution. People love it when you are unafraid to list your own product’s shortcomings or where the competition shines, or describe the scenarios where other tools are genuinely superior or more cost-effective. It makes you look strong and confident, not weak.

What would you say about your own product as an engineer, or a customer? Say that.

🌸 You can still talk shit about software, just not your competitors‘ software. 🌸
I try not to gratuitously snipe at our competitors. It’s fine to speak at length about technical problems, differentiation and tradeoffs, and to address how specifically your product compares with theirs. But confine your shit talking to categories of software where you don’t have a personal conflict of interest.

Like, I’m not going to get on twitter and take a swipe at a monitoring vendor (anymore 😇), but I might say rude things about a language, a framework, or a database I have no stake in, if I’m feeling punchy. ☺️ (This particular gem of advice comes by way of Adam Jacob.)

🌸 Be generous with your expertise.🌸
If you have spent years going deep on one gnarly problem, you might very well know that problem and its solution space more thoroughly than almost anyone else in the world. Do you know how many people you can help with that kind of mastery?! A few minutes from you could potentially spare someone days or weeks of floundering. This is a gift few can give.

It feels good, and it’s a nice break from battering your head against unsolvable problems. Don’t restrict your help to paying customers, and, obviously, don’t give self-serving advice. Maybe they can’t buy/don’t need your solution today, but maybe someday they will.

In conclusion

There’s a time and place for being oppositional. Sometimes a vendor gets all high on their own supply, or starts making claims that aren’t just an “optimistic” spin on the facts but are provably untrue. If any vendor is operating in poor faith they deserve to to be corrected.

But it’s a shitty, self-limiting stance to take as a default. We are all here to build things, not tear things down. No one builds software alone. The code you write that defines your business is just the wee tippy top of a colossal iceberg of code written by other people — device drivers, libraries, databases, graphics cards, routers, emacs. All of this value was created by other people, yet we collectively benefit.

Think of how many gazillion lines of code are required for you to run just one AWS Lambda function! Think of how much cooperation and trust that represents. And think of all the deals that brokered that trust and established that value, compensating the makers and allowing them to keep building and improving the software we all rely on.

We build software together. Vendors exist to help you. We do what we do best, so you can spend your engineering cycles doing what you do best, working on your core product. Good sales deals don’t leave anyone feeling robbed or cheated, they leave both sides feeling happy and excited to collaborate.[4]

🐝💜Charity.

[1] Yes, I know this experience is far from universal; LOTS of people in tech have not felt like their voices are heard or their expertise acknowledged. This happens disproportionately to women and other under-represented groups, but it also happens to plenty of members of the dominant groups. It’s just a really common thing! However that has not really been my experience — or if it has, I haven’t noticed — nor Abby’s, as far as I’m aware.

[2] My first brush with columnar storage systems! Which is what makes Honeycomb possible today.

[3] I have learned SO MUCH from watching the world class sales professionals we have at Honeycomb. Sales is a tough gig, and doing it well involves many disciplines — empathy, creativity, business acumen, technical expertise, and so much more. Selling to software engineers in particular means you are often dealing with cocky little shits who think they could do your job with a few lines of code. On behalf of my fellow little shits engineers, I am sorry. 🙈

[4] Like our sales team says: “Never do a deal unless you’d do both sides of the deal.” I fucking love that.

Questionable Advice: “People Used To Take Me Seriously. Then I Became A Software Vendor”

Every Achievement Has A Denominator

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One of the classic failure modes of management is the empire-builder — the managers who measure their own status, rank or value by the number of teams and people “under” them.

Everyone knows you aren’t supposed to do this, but most of us secretly, sheepishly do it anyway to some extent. After all, it’s not untrue — the more teams and people that roll up to you, the wider your influence and the more impact you have on more people, by definition.

The other reason is, well, it’s what we’ve got. How else are we supposed to gauge our influence and impact, or our skill as a leader? We don’t really have any other language, metrics or metaphors readily available to us. 😖

Well… Here’s one:

✨Every achievement has a denominator✨

Organization size can be a liability

Let’s say you have 1,000 people in your org and you collectively achieve something remarkable. Good for you!

What if you achieved the same thing with 10,000 people, instead? What would that say about your leadership?

What if you achieved the same thing with 100 people?

Or even 10 people?

Lots of people take pride in their ability to manage large organizations. And with thousands of people in your org, you kinda better do something fucking great. But what if you instead took pride in your ability to deliver outsize results with a small denominator?

What if comp didn’t automatically bloat with the size of your org, but rather the impact of your work divided by the number of contributors — rewarding leaders for leaner teams, not larger ones?

Bigness itself is costly. There’s the cost of the engineers, managers, product and designers etc, of course. But the bigger it gets, the more coordination costs are incurred, which are the worst costs of all because they do not accrue to any user benefit — and often lead to lack of focus and product surface sprawl.

Constraints fuel creativity. Having “enough” engineers for a project is usually a terrible idea; you want to be constrained, you want to have to make hard decisions about where to spend your time and where to invest development cycles.

More often than not, scope is the enemy

As Ben Darfler wrote earlier this year about our approach to engineering levels at Honeycomb:

There are times when broad scope may be unavoidable, but at Honeycomb, we try to cultivate a healthy skepticism toward scope. More often than not, scope is the enemy. We would rather reward engineers who find clever ways to limit scope by decomposing problems in both time and size. We also want to reward engineers who work on the most important problems for the business, regardless of the size of the project. We don’t want to reward people for gaming out their work based on what will get them promoted.

The same is true for engineering managers, directors and VPs. We would rather reward them for getting things done with small, nimble teams, not for empire building and team sprawl. We want to reward them for working on the most important problems for the business, regardless of what size their teams are.

What was the denominator of the last big project you landed? Could you have done it with fewer people? How will you apply those learnings to the next big initiative?

Can we find more language and ways to talk about, or take pride in how efficiently we do big things? At the very least, perhaps we can start paying attention to the denominator of our achievements, and factor that into how we level and reward our leaders.

charity.

P.S. I did not invent this phrase, but I am unfortunately unable to credit the person I heard it from (a senior Googler). I simply think it’s brilliant, and so helpful.

Every Achievement Has A Denominator

The Future of Ops is Platform Engineering

mipsytipsy, , , , , , , Leave a comment

First published on 2022-09-30 at https://www.honeycomb.io/blog/future-ops-platform-engineering.

Two years ago I wrote a piece in The New Stack about the Future of Ops Careers. Towards the end, I wrote:

The reality is that jack-of-all-trades systems infrastructure jobs are slowly vanishing: the world doesn’t need thousands of people who can expertly tune postfix, SpamAssassin, and ClamAV—the world has Gmail. (…)

Building infrastructure and operational expertise used to be bundled together into a single role. But the industry is now bifurcating along an infrastructure fault line, and the overlap between infrastructure-oriented engineers and operationally-minded engineers is swiftly eroding. Engineers who love this work increasingly have a choice to make. Either you can 1) go deep on infrastructure by joining a company that does infrastructure as a service, or 2) go broad on operability by joining a company to help them do as little infrastructure as possible.

I described the second category as “operations engineering minus the infrastructure,” dedicated to evaluating and assembling a production stack of third-party platform providers, enabling software engineers to self-serve their services and own their own code in production. I said:

  • Your job will be to aggressively minimize the cycles your org devotes to infrastructure by finding effective ways to outsource or minimize infra labor. Your job is to NOT go deep if there is any workable alternative.
  • Your job will be to work cross-functionally with all the other software engineering teams, looking for ways to speed up their time to value and helping them own their own code in production.
  • Your job will be to move past the kludgey old models of “outsourcing” to sophisticated understandings of how and where to leverage abstractions that can radically accelerate development.

That second category I was describing now has a name. We call those teams “platform engineering.”

The fifty-year arc of software careers

In the beginning, there were people who wrote and ran software. At some point, we spun away ops skills from dev skills into two different professions, but that turned out to be a ginormous mistake, so along came DevOps to reunify them. Nowadays, ops as an independent profession is in the process of fading out. Companies are spinning down their ops teams left and right. Engineers who formerly identified as sysadmins or operations have turned into DevOps engineers, and soon there will just be “software people” again. This is the way of things.

Please note that this is NOT the same thing as saying “ops is dead,” or “ops skills are no longer valuable or needed1.” Our systems are only getting more complex, more difficult to operate, and simultaneously more critical to life on earth, which means that operational excellence has never been more desperately needed (and if you don’t respect that, 🌈 you deserve to suffer 🌈).

The industry story of the past three to five years has been us trying to figure out how to help software engineers own their own code in production2, phasing out dedicated ops teams, and aggressively outsourcing as much infrastructure as possible.

As we should. Developer cycles are the scarcest resource in your company, and you want to spend as many of those as possible on your core product: the crown jewel, the code that makes you a business. Money is cheaper than engineering cycles, and teams that are focused on their core business will always outperform teams whose focus is spread across dozens of non-revenue-generating projects. Let someone else build and run all the dependencies and adjacencies.

Before: some engineers wrote code, and some engineers ran code.

Now: all engineers write code, and all engineers run the code they write.

Platform engineering is what stands between you and darkness

When you start talking about putting software engineers on call for their own code, and generally being more involved in production, some percentage of the time you will hear back a guttural wail of despair: “You can’t expect me to know EVERYTHING about EVERYTHING!”

Quite right; we can’t. Platform engineering teams are part of the answer to this perfectly reasonable complaint. It’s not that you’re being asked to do or understand more in toto, but the distribution of labor and responsibility is shifting:

Before: some engineers wrote code, and some engineers ran code.

Now: all engineers write code, and all engineers run the code they write—but we divide the areas of responsibility by layer or function.

The emergence of a minimum viable self-serve tier

In the earliest days of a company, your first few engineers end up bootstrapping an infrastructure by reading AWS docs or blog posts, or asking a friend for recommendations to get started. They might start by setting up a managed container service, or configuring Terraform, and for a while everybody deploys and owns their own code, just as god intended.

But cognitive limits kick in pretty quickly. The maze of APIs and SDKs and components out there is simply bewildering, even for an experienced ops hand. Before long, it becomes someone’s job to make good decisions, pick a suite of compute and storage options that serve the team’s needs, and write some tooling that pulls everything into a coherent whole—which, at a minimum, lets you:

  1. Run tests and generate new artifacts
  2. Deploy artifacts, version them, and roll back
  3. Instrument, monitor, and debug
  4. Store data somewhere, manage schemas and migrations
  5. Adjust capacity as needed
  6. Define and commit all components (and their relationships) as code

Once these are built, it should be trivial for an engineer to come along and spin up a new service using templates and components from existing services. It should be much simpler and easier to use the blessed paths than anything else, and there should be friction if you go off the beaten path.

Congratulations! You’ve just been platformed 🎉. One of the key principles of any developer platform is that it should be easy to do the right things, and hard to do the wrong things.

The differences between platform engineering and traditional ops

Platform teams are typically staffed by engineers who are comfortable writing software. Not just scripting and automation, but writing tests and doing code reviews. Platform teams also operate much more like product development teams do, with product managers (and occasionally, designers, developer advocates, or UX researchers).

This doesn’t mean that everybody on a platform team has to have originally been a software engineer; in fact, a super common failure condition for platform teams is simply thinking all they need to do is hire software engineers to build developer tools. A strong platform team has an equally deep grounding in operations experience and software development. Individuals who are experts in both areas are fairly rare, but you can pull together a strong, well-rounded team by assembling a mix of SWEs (with some ops experience) and ops or DevOps engineers (with some software experience) and having them learn and grow from each other.

Platform teams are decidedly cloud-native; they actually mostly involve platforms built atop the cloud itself—PaaS, IaaS, everything-aaS, serverless, and so forth.

Ops/DevOps teams are oriented around managing infrastructure, often several generations of infrastructure. Their turf is everything from data centers and bare metal up through virtualization, containers, and the cloud (they aren’t so much cloud-native as cloud-enabled). They measure themselves on things like SLOs and the DORA metrics. You know they’re doing a good job if the system is up/available and users are happy.

Platform teams are oriented around providing a good experience for developers to self-serve and self-manage their code. The more swiftly and easily developers can move, the better your platform team. Operational excellence, in the platform model, is actually more the responsibility of the other engineering teams (and/or an adjacent SRE team) than that of the platform team.

Platform teams typically work higher up the stack than operations, DevOps, or SRE teams do, and they involve a great deal less infrastructure. On the contrary, platform teams are bent on paying other people to run as much shit as possible, preserving their own scarce development cycles for their core product.

Here is a somewhat tongue-in-cheek table of the similarities and differences between the archetypes.

Platform engineers vs. DevOps engineers

Platform Engineer Ops (or DevOps) Engineer
% of job spent writing code > 50% < 50%
Rest of time spent Gathering product requirements, doing user research, architecture discussions, optimizing internal workflows, researching new tools and developer productivity ideas, reviewing other teams’ diffs for impact, performance tuning, helping other engineers own & scale their code, fixing CI/CD pipelines. Fixing cron jobs, automating old setup docs, converting PXE/rsync to Chef/Puppet, converting Chef/Puppet to Terraform, converting VMs to containers, deploying software, debugging broken deploys, writing monitoring checks, doing retros, building out new services, pairing with software engineers to understand and debug their code, investigating weird shit, documentation, etc.
Responsible for Enabling internal teams to self-serve their ability to run and own their code in production. Creating standard, reusable components and processes. Defining golden paths. Infrastructure capacity planning, scaling, performance tuning, upgrading. Reliability and resiliency, SLOs and monitoring/alerting. Delivering quality experience to customers.
Builds for Internal developer teams Customers
Development style Infrastructure as a product Infrastructure as code
Works with product managers Yes No
Works with UX researchers or designers Sometimes No
Dashboards & graphs Uses APM, observability, tracing. Cares a lot about instrumentation and OpenTelemetry. Uses metrics, logs, dashboards; monitoring, alerting, and agent/sidecar/blackbox telemetry.
What ‘coding’ means to them Developing new features & services, writing tests. These are (primarily) software people who do systems. Automation, configuration, DSLs, extending and debugging existing code. These are systems people who do software.
Preferred language Go, Rust Python, Ruby
Time spent in Linux Hardly any A lot
Succeeds when Developers can easily choose good defaults, self-serve their infra, and own their own code in production. Infrastructure is scalable, secure, cost-effective, reliable, and customers are happy.
Native terrain Serverless, *aaS, APIs for everything (cloud-native and above). Instances, VMs, containers, regions, multi-cloud (everything “below,” but up to and including the cloud).
Databases Uses hosted DBs Runs their own, blending automation & DBA expertise
SSH No Yes
Shell REPL bash/zsh
Mantra “Run Less Software” “Cattle, Not Pets”

What about DevOps vs. SRE?

Countless words have been spilled on the difference between DevOps and SRE3, which I won’t rehash.

Here’s what I’ll say: DevOps, to me, feels like a relevant concept for companies that have a lot of infrastructure to wrangle. Companies that do in fact have dev teams and ops teams, or dev teams and DevOps teams (🙄), tend to have a lot of operational shit to automate, test, and run. They use config management, virtualization, and containers, often managing several generations worth of technology, possibly even down to data centers and bare metal. DevOps is for companies that have some combination of bare metal, VMs, regions, AZs, multi-cloud, networking devices, self-managed databases, etc.

DevOps is capacious. It contains multitudes. DevOps writes code, and DevOps has a fuckload of code to manage.

It is also on its way to becoming irrelevant. We are swiftly entering a post-DevOps world.

SRE, to me, feels different. I associate SRE with very large companies, where they mostly have software engineers owning their own code in production, but maybe still struggle with it a bit. SREs are often embedded within software engineering teams or product groups, and they focus a lot on, well, reliability, as the name suggests.

This means they do less infrastructure jockeying or automating (although they still do some coding). They typically have a lot to say about instrumentation, monitoring and observability, and cross-functional coordination. They run incident response and do blameless retros, and they tend to be experts at scaling.

If a company has both a DevOps team and SRE, typically I expect to see the SRE team more on the frontlines, involved with incidents, telemetry, etc., and DevOps teams more on the backburner, slinging pipes and plumbing.

Observability engineering as a case study

In the same piece I referenced earlier, I also wrote about the role of observability teams. I said they should largely no longer be running their own monitoring and graphing software in-house. Yet there is still a place for observability teams to exist: they remain a critical link between outsourced solutions and internal developer needs.

That team should write libraries, generate examples, and drive standardization; ushering in consistency, predictability, and usability. They should partner with internal teams to evaluate use cases. They should partner with your vendors as roadmap stakeholders. They might also write glue code and helper modules to connect disparate data sources and create cohesive visualizations. Basically, that team becomes an integration point between your organization and the outsourced work.

I originally wrote this about observability, but it could just as easily be used to describe platform engineering as a whole. This is the role—being the bridge between other vendors and your own core software. It’s a very high-leverage place to sit.

Ops is dead, long live ops

I’ve spent a lot of time thinking about this because we’ve had such a hard time nailing down exactly who the Honeycomb customer is. Sometimes our buyer is an ops team buying it for their SWEs, sometimes it’s SREs in the midst of an outage, sometimes it’s a VP or director of engineering, or an architect, or a CTO, or a “full stack” engineering team, or even a product manager. It is hard to form a snappy answer out of that list.

The first couple questions every new go-to-market candidate asks us are “who is your buyer?” and “how do we help them?” To which I respond with a five minute ramble where I list every above persona and each of their pain points. Hardly the concrete answer they would like to receive.

As it goes, sociotechnical trends come and go. A year ago, Christine and I were speculating that platform engineering might be on the verge of consolidating the necessary ingredients that makes up our ideal buyer:

  1. Writing and shipping code, and needing to understand their own code
  2. Positioned to help other teams with their instrumentation patterns and tooling
  3. Firmly cloud-native+ and untethered to hardware or traditional infrastructure

To my delight, since that conversation, these trends have only accelerated—and I, for one, welcome our new platform engineering overlords to the observability table. ☺️

If you’d like to learn more about platform engineering, we’ll be running a Twitter space on ✨ October 20th ✨ at 12:00 p.m. PT. Come join us! I’ll be there along with two colleagues and we’ll be answering your questions and shedding more light on the topic.

1  I do hear people saying that, and it used to make me fucking furious, but now I just smugly remind myself how much self-inflicted suffering they are in for. Disrespecting operational expertise is the shortest path to never again sleeping through the night.

2 It is rather incredible how rapidly this idea has taken off. When we started talking about putting developers on call for their code in 2016, people got seriously angry with us. Before that, the only twitter mention I could find of putting devs on call was one by (of course) Adrian Cockcroft, but by 2019-2020 it had stopped being controversial and soon became common wisdom.

3 I actually wrote one of those myself: DevOps vs SRE: Delayed Coverage of the Dumbest War). LMAO. I think Liz had the final word on this back in … 2017? 2018? … when she said something like class SRE implements DevOps. And yes, DevOps is a philosophy or a methodology and not a job title, etc.

The Future of Ops is Platform Engineering

The Hierarchy Is Bullshit (And Bad For Business)

mipsytipsy, , 16 Comments

My friend Molly has had an impressive career. She got a job as a software engineer after graduating from college, and after kicking ass for a year or so she was offered a promotion to management, which she accepted with relish. Molly was smart, driven, and fiercely ambitious, so she swiftly clambered up the ranks to hold director, VP, and other shiny leadership roles. It took two decades, an IPO and a vicious case of burnout before she allowed herself to admit how much she hated her work, and how desperately she envied (guess who??) the software engineers she worked alongside. Turns out, all she ever really wanted to do was write code every day. And now, to her dismay, it felt too late.

Why did it take Molly so long to realize what made her happy? I personally blame the fucking hierarchy.

The Hierarchy Lie

The “Big Lie” of hierarchy is that your organizational structure is a vertical tree from the CEO on down, where higher up is always better.

Of course any new grad is going to feel that way, on the heels of 15-20 years spent going through school year by year, grade by grade, measuring success via good grades and teacher approval. The early years of professional life are a similar blend of hard work, leveling up and basic skills acquisition. (They got Molly hopped on the leveling treadmill before she even had a chance to become a real adult, in other words. 😍)

But by the time you are fully baked as a senior contributor, maybe 7-8 years in, your relationship to levels and ladders should undergo a dramatic shift. At some point you have to learn to tune in to your own inner compass. What draws you in to your work? What fuels your growth and success?

Being an adult means not measuring yourself entirely on other people’s definition of success. Personal growth might come in the guise of a big promotion, but it also might look like a new job, a different role, a swing to management or back, becoming well-known as a subject matter expert, mentoring others, running an affinity group, picking up new skill sets, starting a company, trying your hand at consulting, speaking at conferences, taking a sabbatical, having a family, working part time, etc. No one gets to define that but you.

You have a thirty- or forty-year adult life and career in front of you. What the hell are you going to do with all that time and space??

Your career is not one mad sprint to the finish line

Literally nobody’s career looks like a straight line, going up, up up and to the right, from intern to CEO (to a coffin).

One of the most exhausting things about working at Facebook was the way engineering levels feltLiterally no one's career, ever. like a hamster wheel, where every single quarter you were expected to go go go go go, do more do more, scrape up ever more of your mortal soul to pour in more than you could last quarter — and the quarter before that, and before that, in ever-escalating intensity.

It was fucking exhausting, yo. Life does not work that way. Shit gets hilly.

The strategy for a fulfilling, lifelong career in tech is not to up the ante every interval. Nor is it to amass more and more power over others until you explode. Instead:

  1. Train yourself to love the feeling of constantly learning and pushing your boundaries. Feeling comfortable is the system blinking orange, and it should make you uneasy.
  2. Follow your nose into work that lights you up in the morning, work you can’t stop thinking about. If you’re bored, do something else.
  3. Say yes to opportunities!! Intensity is nothing to be afraid of. Instead of trying to cap your speed or your growth, learn to alternate it with recovery periods.
  4. If you aren’t sure what to do, make the choice that preserves or expands future optionality. Remember: Most startups fail. Will you be okay with your choices if (& when) this one does too?

Why do people climb the ladder? “Because it’s there.” And when they don’t have any other animating goals, the ladder fills a vacuum.

But if you never make the leap from externally-motivated to intrinsically-motivated, this will eventually becomes a serious risk factor for your career. Without an inner compass (and a renewable source of joy), you will struggle to locate and connect with the work that gives your life meaning. You will risk burnout, apathy and a serious lack of fucks given..

The times I have come closest to burnout or flaming out have never been when I was working the hardest, but when I cared the least. Or when I felt the least needed.📈📉💔

A disturbing number of companies would rather feel in control than unclench and perform better

But hey! Lack of inner drive isn’t the ONLY thing that drives people to climb the ladder. Plenty of companies fuck this up too, all on their lonesome. Let’s talk about more of the ways that companies mess up the workplace! Like by disempowering the people doing the work and giving all the power to managers, thereby forcing anyone who wants a say in their own job become one.

The way we talk about work is riddled with hierarchical, authoritarian phrases: “She was my superior”, “My boss made me do it”, “I got promoted into management”, and so on.

There are plenty of industries where line workers are still disempowered cogs and power structures are hierarchical and absolute (like flipping burgers at McDonalds, or factory line work). There are even software companies still trying to make it work in command-and-control mode, to whom engineers are interchangeable monkeys that ship story points and close JIRA tasks.

But if there’s one thing we know, it’s that for industries that are fueled by creativity and innovation, command-and-control leadership is poison. It stifles innovation, it saps initiative, it siphons away creativity and motivation and caring.

Studies also show that the more visible someone’s power is, the less likely anyone is to give them honest feedback.[2]

Companies that don’t learn this lesson are unlikely to win over the long run. Engineering is a deeply creative occupation, and authoritarian environments are toxic for creativity and people’s willingness to share information.

Hierarchy is just a data structure

The basic function of a hierarchy is to help us make sense of the world, simplify information, and make decisions. Hierarchy lets us break down enormous projects — like “let’s build a rocket!”, or “let’s invade the moon!” — into millions of bite size decisions and tasks, and this is how progress gets made.

A certain amount of authority is invested into the hierarchy model. If you are responsible for delivering a unit of work, the company needs to make sure you have enough resources and decision-making ability to do so. This is what we think of as the formal power structure [1], and there is nothing wrong with that. It’s what makes the system work.

The problem starts when we stop thinking of hierarchy as a neutral data structure — a utilitarian device for organizing groups and making decisions — and start projecting all kinds of social status and dominance onto it.

A sensitivity to social dominance is wired deep, deep into our little monkey brains. It’s what tells us we deserve more power, leverage, pride, influence, and autonomy — and simply have more value — than those below us. It’s what tells us those above us are better, stronger and more deserving than we are, and that we owe them our respect and deference.

It also tells us “if you lose status, YOU MIGHT DIE” 😱😱😱 which is why we may react to a perceived loss of status with a sting that seems astonishingly extreme and overwrought, even to ourselves, yet somehow impossible to shrug off.

hierarchies tend to get mixed up with social dominance

In general, it is better to pursue roles and growth based on the affirmative (what it is you want to learn, grow or do more of) than the negative (what you want to avoid, evade or stop doing). Your motivation systems don’t kick in to gear when you are feeling “lack of pain” — the system doesn’t work that way. They kick in when you get interested.

And if you are sick of doing something or being treated a certain way, chances are everyone else will hate it, too. Who wants to work at a company where all the shit rolls downhill?

Hierarchies have stuck around for one very good reason: because they work. Hierarchies are simple, intuitive, and allow large numbers to collaborate with low cognitive overhead. Unfortunately, most hierarchies become entwined with status and dominance markers, which can bring enormous downsides. At their worst, they can suck the literal life out of work, reducing us all to glum little cogs obeying orders.

We aren’t getting rid of hierarchy anytime soon. But we can use culture and ritual to gently untangle them from dominance, and we can choose to interpret formal power as a service function instead of a dictatorship. This frees people up to choose their work based on what makes them feel fulfilled, instead of their perceived status. (Also helpful? Flatter pay bands. 😛)

Good managers do not dictate and demand, they nurture, develop, and inspire. The most important roles in the company aren’t held by managers; they are all the little leaf nodes  busily building the product, supporting users, identifying markets, writing copy, etc. The people doing the work are why we exist as a company; all the rest is, with considerable due respect, overhead.

How to drain your hierarchy of social dominance

When it comes to hierarchy and team structure, there are the functional, organizational aspects (mostly good) and the social dominance parts (mostly bad). With that in mind, there are plenty of smaller things we can do as a team to remind people that we are equal colleagues, simply with different roles.

  • Be conscious of the language you use. Does it reinforce dominance and hierarchy? (Step one: stop calling management “a promotion”🥰)
  • De-emphasize trappings of power. The more you refer to someone’s formal power, the less likely anyone is to give them critical feedback or question them.
  • Push back against common but unhelpful practices, like “a manager should always make more money than the people who report to them.” Really? Why??
  • Are there opportunities for career advancement as an IC, or only as a manager? Everyone should have the ability to advance in their career.
  • Do your own dishes, everyone.
  • Practice visualizing the org chart upside down, where managers and execs support their teams from below rather than topping them from above. (I was going to write a whole post about this, then discovered other people have been doing that for the past decade. 🤣)

And then there is the big(ger) thing we can (and must!) do, in order to 1) make people go into management for the right reasons, 2) help senior IC roles remain attractive to highly skilled creative and technical contributors, and 3) encourage everybody to make career decisions based on curiosity, growth, and what’s best for the business, instead of turf and power grabs. Which is:

Practice transparency, from top to bottom

Share authority, decision-making and power

Technical contributors own technical decisions

Most people who go in to management don’t do it out of a burning desire to write performance reviews. They do it because they are fed the fuck up with being out of the loop, or not having a say in decisions over their own work. All they want is to be in the room where it happens, and management tends to be the only way you get an invite.

EVERY company says they believe in transparency, but hardly any of them are, by my count. Transparency doesn’t mean flooding people with every trivial detail, or freaking them out with constant fire drills. It does mean being actively forthcoming about important questions and matters which are happening or on the horizon…often before you are fully comfortable with it. Honestly, if you never feel any discomfort about your level of transparency, you probably aren’t transparent enough.

People do better work with more context! You’re equipping them with information to better understand the business problems and technical objectives, and thereby unleashing them and their creativity to help solve them. You’re also opening yourself up to questioning and sanity checks — which may feel uncomfortable, but 🌞sunlight is sanitizing🌞 — it is worth it.

Some practical tips for transparency

At Honeycomb, we present the full board deck after every board meeting in our all hands, and take questions. When we’re facing financial uncertainty, we say so, along with our working plan for dealing with it. We also do org-level updates in all hands, once per quarter per org. Each org presents a snapshot to the company of how they are doing, but we ask that no more than 2/3 of the presentation be about their successes and triumphs, and 1/3 of their material be about their failures and misses. Normalize talking about failure.

Being transparent isn’t about putting everyone on blast; it’s about cultivating a habit of awareness about what might be relevant to other people. It’s about building systems of feedback, updates and open questioning into your culture. This can be scary, so it’s also about training yourselves as a team to handle hard news without overreacting or shooting the messenger. If you always tell people what they want to hear, they’ll never trust you. You can’t trust someone’s ‘yes’ until you hear their ‘no’.

Transparency is always a balance between information and distraction, but I think these are healthy internal rules of thumb for management:

  1. If anyone has further questions or wants to know more details than what was shared, they are free to ask any manager or exec, who will willingly answer more fully, up to the boundaries of privacy or legal reasons. As employees, they have a right to know about the business they are part of. A right — not a privilege, which can be revoked on a whim.
  2. When making internal decisions about e.g. salary bands, individual exceptions to formal policy, etc, ask each other … if this decision were to leak, could we justify our reasoning with head held high? If you would feel ashamed, or if you really don’t want people to find out about it, it’s probably the wrong decision.

Some practical tips for distributing power

Power flows to managers by default, just like water flows downhill. Managers have to actively push back on this tendency by explicitly allocating powers and responsibilities to tech leads and engineers. Don’t hoard information, share context generously, and make sure you know when they would want to tap in to a discussion. Your job is not to “shield” them from the rest of the org; your job is to help them determine where they can add outsize value, and include them. Only if they trust you to loop them in will they feel free to go heads down and focus.

Wrap your senior ICs into planning and other leadership activities. Decisions about sociotechnical processes (code reviews, escalation points, SLI/SLOs, ownership etc) are usually better owned by staff+ engineers than anyone on the management track. Invite a couple of your seniormost engineers to join calibrations — they bring a valuable perspective to performance discussions that managers lack.

Demystify management. Blur the lines between people managers and engineers; delegate ownership and accountability for some important projects to ICs. Ask every engineer about their career interests, and if management is on the list, find opportunities for them to practice and improve at managerial skills — mentoring, interviewing, onboarding, etc.

Adults don’t like being told what to do

People do phenomenal work when they want to do it, when they are creatively and emotionally engaged at the level of optimum challenge, and when they know their work matters. That’s where you’ll find your state of flow. That is where you’ll do your best work, which is also the best way to get promoted and make durable advances in your career.

Not, ironically, by chasing levels and titles for their own sake. ☺️

People want to be challenged. They want you to ask them to step up and take responsibility for something hard. They want to be needed, and they want to have agency in the doing of it. Just like you do.

Oh yeah, back to Molly …

Molly, who I mentioned at the beginning, joined Honeycomb five years ago as a customer success exec. After realizing she wanted to go back to engineering, she switched to working our support desk to build up her technical chops while she practiced writing code on the side. She has now been working as a software engineer on the product team for over two years, and she is ✨rocking it.✨ It is NEVER too late. 🙌

<3 charity

p.s. Molly also says, “don’t waste time at bad companies, whether you’re climbing the ladder or not!” 🥂

 

[1] Formal power is only one kind of power, and in some ways it is the weakest, because it doesn’t belong to you. It belongs to the company and is only loaned out for you to wield on its behalf. (You don’t carry the innate ability to fire people along with you after you stop being an engineering manager, for example.) Formal powers are limited, enumerated, and functional. You don’t get to use them for any reason other than furthering the goals of the org, or else it is literally an abuse of power.

Formal power is fascinating in another way, too: which is that your formal power is seen as legitimate only if you ~basically always wield it in the ways everyone already expects you to. You can make a surprising call only so often; you can straight up overrule the wishes of your constituents extremely rarely. If you use your formal power to do things that people disagree with or don’t support, without taking the time to persuade them or create real consensus, you will squander your credibility and good faith unbelievably fast.

[2] I am not going to bother rustling up lots of links and citations, because I expect most of this falls into the voluminous category of “shit you already knew”. But if any of it sounds surprising to you, here are some classic reference works:

Flow, by Mihaly Csikszentmihalyi
Drive, by Dan Pink
The Culture Code: Secrets of Successful Groups, by Daniel Coyle
A Lapsed Anarchist’s Guide to Being a Better Leader, by Ari Weinzweig

[3] The scientific literature suggests that dominating instincts tend to emerge in more overtly hostile environments. Make of that what you will, I guess.

 

Some other writing I have done on this topic, or topics adjacent …

The Engineer/Manager Pendulum
The Pendulum or the Ladder
If Management Isn’t a Promotion, then Engineering isn’t a Demotion
Twin Anxieties of the Engineer Manager Pendulum
Things to Know About Engineering Levels
Advice for Engineering Managers who want to Climb the Ladder
On Engineers and Influence
Is There a Path Back from CTO to Engineer?

The Hierarchy Is Bullshit (And Bad For Business)