management

Helicopter Management and Other Mistakes

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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

Questionable Advice: “How can I drive change and influence teams…without power?”

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Last month I got to attend GOTO Chicago and give a talk about continuous deployment and high-performing teams. Honestly I did a terrible job, and I’m not being modest. I had just rolled off a delayed redeye flight; I realized partway through that I had the wrong slides loaded, and my laptop screen was flashing throughout the talk, which was horribly distracting and means I couldn’t read the speaker notes or see which slide was next. 😵 Argh!

Anyway, shit happens. BUT! I got to meet some longstanding online friends and acquaintances (hi JJ, Avdi, Matt!) and got to eat some of Hillel Wayne’s homemade chocolates, and the Q&A session afterwards was actually super fun.

My talk was about what high performing teams look like and why it’s so important to be on one (spoiler: because this is the #1 way to become a radically better engineer!!). Most of the Q&A topics therefore came down to some version of “okay, so how can I help my team get there?” These are GREAT questions, so I thought I’d capture a few of them for posterity.

But first… just a reminder that the actual best way to persuade people to listen to you is to make good decisions and display good judgment. Each of us has an implicit reputation score, which formal power can only overcome to an extent. Even the most junior engineer can work up a respectable reputation over time, and even principal engineers can fritter theirs away by shooting off at the mouth. 🥰

“how can I drive change when I have no power or influence?”

This first question came from someone who had just landed their first real software engineering job (congrats!!!):

“This is my first real job as a software engineer. One other junior person and myself just formed a new team with one super-senior guy who has been there forever. He built the system from scratch and knows everything about it. We keep trying to suggest ideas like the things you talked about in your talk, but he always shoots us down. How can we convince him to give it a shot?”

Well, you probably can’t. ☺️ Which isn’t the end of the world.

If you’re just starting to write software every day, you are facing a healthy learning curve for the next 3-5 years. Your one and only job is to learn and practice as much you possibly can. Pour your heart and soul into basic skills acquisition, because there really are no shortcuts. (Please don’t get hooked on chatGPT!!)

I know that I came down hard in my talk on the idea that great engineers are made by great teams, and that the best thing most people can do for their career is to join a high-performing, fast-moving team. There will come a time where this is true for you too, but by then you will have skills and experience, and it will be much easier for you to find a new job, one with a better culture of learning.

It is hard to land your first job as a software engineer. Few can afford to be picky. But as long as you are a) writing code every day, b) debugging code every day, and c) getting good feedback via code reviews, this job will get you where you need to go. When you’re fluent and starting to mentor others, or getting into higher level architecture work, or when you’re starting to get bored … then it’s time to start looking for roles with better teachers and a more collaborative team, so your growth doesn’t stall. (Please don’t fall into the Trap of the Premature Senior.)

This is an apprenticeship industry. You’re like a med student right now, who is just starting to do rounds under the supervision of an attending physician (your super-senior engineer). You can kinda understand why he isn’t inclined to listen to your opinions on his choice of stethoscope or how he fills out a patient chart. A better teacher would take time to listen and explain, but you already know he isn’t one. 🤷

I only have one piece of advice. If there’s something you want to try, and it involves doing engineering work, consider tinkering around and building it after hours. It’s real hard to say no to someone who cares enough to invest their own time into something.

“how can I drive change when I am a tech lead on a new team?”

“I have the same question! — except I’m a tech lead, so in theory I DO have some power and influence. But I just joined a new team, and I’m wondering what the best way is to introduce changes or roll them out, given that there are soooo many changes I’d like to make.”

(I wrote a somewhat scattered post a few years ago on engineers and influence, or influence without authority, which covers some related territory.)

As a tech lead who is new to a team, busting at the seams with changes I want to make, here’s where I’d start:

  1. Understand why things are the way they are and get to know the personalities on your team a bit before you start pitching changes. (UNLESS they are coming to you with arms outstretched, pleading desperately for changes ~fast~ because everything is on fire and they know they need help. This does happen!)
  2. Spend some time working with the old systems, even if you think you already understand. It’s not enough for you to know; you need to take the team on this journey with you. If you expect your changes to be at all controversial, you need to show that you respect their work and are giving it a chance.
  3. Change one thing at a time, and go for the developer experience wins first. Address things that will visibly pay off for your team in terms of shipping faster, saving time, less frustration. You have no credibility in the beginning, so you want to start racking up wins before you take on the really hard stuff.
  4. Roll up your sleeves. Nothing buys a leader more goodwill than being willing to do the scut work. Got a flaky test suite that everybody has been dreading trying to fix? I smell opportunity…
  5. Pitch it as an experiment. If people aren’t sold on your idea for e.g. code review SLAs, ask if they’d be willing to try it out for three weeks just as an experiment.
  6. Strategically shop it around to the rest of the team, if you sense there will be resistance…

At this point in my answer 👆 I outlined a technique for persuading a team and building support for a plan or an idea, especially when you already know it’s gonna be an uphill battle. Hillel Wayne said I should write it up in a blog post, so here it is! (I’ll do anything for free chocolate 😍)

“How can I get people on board with my controversial plan?”

So you have a great idea, and you’re eager to get started. Awesome!!! You believe it’s going to make people’s lives better, even though you know you are going to have to fight tooth and nail to make it happen.

What NOT to do:

Walk into the team meeting and drop your bomb idea on everyone cold:

“Hey, I think we should stop shipping product changes until we fix our build pipeline to the point where we can auto-deploy each merge set to production, one at a time, in under an hour.” ~ (for example)

…. then spend the rest of the hour grappling with everybody’s thoughts, feelings, and intense emotional reactions, before getting discouraged and slinking away, vowing to never have another idea, ever again.

What to do instead:

Suss out your audience. Who will be there? How are they likely to react? Are any of them likely to feel especially invested in the existing solution, maybe because they built it? Are any of them known for their strong opinions or being combative?

Great!!! Your first move is to have a conversation with each of them. Approach them in the spirit of curiosity, and ask what they think of your idea. Talking with them will also help you hash out the details and figure out if it is actually a good idea or not.

Your goal is to make the rounds, ask for advice, identify any allies, and talk your idea through with anybody who is likely to oppose you…before the meeting where you intend to unveil your plan. So that when that happens, you have:

  1. given people the chance to process their reactions and ask questions in private
  2. ensured that key people will not feel surprised, threatened, or out of the loop
  3. already heard and discussed any objections
  4. ideally, you have earned their support!

Even if you didn’t manage to convince every person, this was still a valuable exercise. By approaching people in advance, you are signaling that you respect them and their voice matters. You are always going to get people’s absolute worst reactions when you spring something on them in a group setting; any anxiety or dismay will be amplified tenfold. By letting them reflect and ask questions in private, you’re giving time for their better selves to emerge.

What to do instead…if you’re a manager:

As an engineer or a tech lead, you sometimes end up out front and visible as the owner of a change you are trying to drive. This is normal. But as a manager, there are far more times when you need to influence the group but not be the leader of the change, or when you need to be wary of sounding like you are telling people what to do. These are just a few of the many reasons it can be highly effective to have other people arguing on your behalf.

In the ideal scenario, particularly on technical topics, you don’t have to push for anything. All you do is pose the question, then sit back and listen as vigorous debate ensues, with key stakeholders and influential engineers arguing for your intended outcome. That’s a good sign that not only are they convinced, they feel ownership over the decision and its execution. This is the goal! 🌈

It’s not just about persuading people to agree with you, either. Instead of having a shitty dynamic where engineers are attached to the old way of doing things and you are “dragging them” into the newer ways against their will, you are inviting them to partner with you. You are offering them the opportunity to lead the team into the brave new world, by getting on board early.

(It probably goes without saying, but always start with the smallest relevant group of stakeholders, and not, say, all of engineering, or a group that has no ownership over the given area. 🙃 And … even this strategy will stop working rather quickly, if your controversial ideas all turn out to be disastrous. 😉)

“How do I know where to even start?!? 😱”

Before I wrap up, I want to circle back to the question from the tech lead about how to drive change on a team when you do have some influence or power. He went on to say (or maybe this was from a third questioner?*):

“There is SO MUCH I’d like to do or change with our culture and our tech stack. Where can I even start??”

Yeah, it can be pretty overwhelming. And there are no universal answers… as you know perfectly well, the answer is always “it depends.” ☺️ But in most cases you can reduce the solution space substantially to one of the two following starting points.

1. Can you understand what’s going on in your systems? If not, start with observability.

It doesn’t have to be elegant or beautiful; grepping through shitty text logs is fine, if it does the trick. But do any of the following make you shudder in recognition?:

  • If I get paged, I might lose the rest of the afternoon trying to figure out what happened
  • Our biggest problem is performance and we don’t know where the time is going
  • We have a lot of flaky, flappy alerts, and unexplained outages that simply resolve themselves without our ever truly understanding what happened.

If you can’t understand what’s going on in your system, you have to start with instrumentation and observability. It’s just too deadly, and too risky, not to. You’re going to waste a ton of time stabbing around in the dark trying to do anything else without visibility. Put your glasses on before you start driving down the freeway, please.

2. Can you build, test and deploy software in under an hour? If not, start with your deploy pipeline.

Specifically, the interval of time between when the code is written and when it’s being used in production. Make it shorter, less flaky, more reliable, more automated. This is the feedback loop at the heart of software engineering, which means that it’s upstream from a whole pile of pathologies and bullshit that creep in as a consequence of long, painful, batched-up deploys.

Here’s a talk I’ve given a few times on why this matters so much:

You pretty much can’t fail with one of those two; your lives will materially improve as you make progress. And the iterative process of doing them will uncover a great deal of shit you should probably know about.

Cheers! 🥂

charity.

* My apologies if I remembered anyone’s question inaccurately!

Questionable Advice: “How can I drive change and influence teams…without power?”

Architects, Anti-Patterns, and Organizational Fuckery

mipsytipsy, , , , 6 Comments

I recently wrote a twitter thread on the proper role of architects, or as I put it, tongue-in-cheek-ily, whether or not architect is a “bullshit role”.

It got a LOT of reactions (2.5 weeks later, the thread is still going!!), which I would sort into roughly three camps:

  1. “OMG this resonates; this matches my experiences working with architects SO MUCH”,
  2. “I’m an architect, and you’re not wrong”, and
  3. “I’m an architect and I hate you.”

Some of your responses (in all three categories!) were truly excellent and thought-provoking. THANK YOU — I learned a ton. I figured I should write up a longer, more readable, somewhat less bombastic version of my original thread, featuring some of my favorite responses.

Where I’m Coming From

Just to be clear, I don’t hate architects! Many of the most brilliant engineers I have ever met are architects.

Nor do I categorically believe that architects should not exist, especially after reading all of your replies. I received some interesting and compelling arguments for the architect role at larger enterprises, and I have no reason to believe they are not true.

Also, please note that I personally have never worked at a company with “architect” as a role. I have also never worked anywhere but Silicon Valley, or at any company larger than Facebook. My experiences are far from universal. I know this.

Let me get suuuuuper specific here about what I’m reacting to:

  • When I meet a new “architect”, they tend toward the extremes: either world class and amazing or useless and out of touch, with precious little middle ground.
  • When I am interviewing someone whose last job title was “architect”, they often come from long tenured positions, and their engineering skills are usually very, very rusty. They often have a lot of detailed expertise about how their last company worked, but not a lot of relevant, up-to-date experience.
  • Because of 👆, when I see “architect” on a job ladder, I tend to feel dubious about that org in a way I do not when I see “staff engineer” or “principal engineer” on the ladder.

What I have observed is that the architect role tends to be the locus of a whole mess of antipatterns and organizational fuckery. The role itself can also be one that does not set up the people who hold it for a successful career in the long run, if they are not careful. It can be a one-way street to being obsolete.

I think that a lot of companies are using some of their best, most brilliant senior engineers as glorified project manager/politicians to paper over a huge amount of organizational dysfunction, while bribing them with money and prestige, and that honestly makes me pretty angry. 😡

But title is not destiny. And if you are feeling mad because none of what I’ve written applies to you, then I’m not writing about you! Live long and prosper. 🖖

Architect Anti-patterns and fuckery

There is no one right way to structure your org and configure your titles, any more than there is any one right way to architect your systems and deploy your services. And there is an eternal tension between centralization and specialization, in roles as well as in systems.

Most of the pathologies associated with architects seem to flow from one of two originating causes:

  1. unbundling decision-making authority from responsibility for results, and
  2. design becoming too untethered from execution (the “Frank Gehry” syndrome)

But it’s only when being an architect brings more money and prestige than engineering that these problems really tend to solidify and become entrenched.

Skin In The Game

When that happens, you often run into the same fucking problem with architects and devs as we have traditionally seen with devs and ops. Only instead of “No, I can’t be on call or get woken up, my time is far too valuable, too busy writing important software”, the refrain is, “No, I can’t write software or review code, my time is far too valuable, I’m much too busy telling other people how to do their jobs.”

This is also why I think calling the role “architect” instead of “staff engineer” or “principal engineer” may itself be kind of an anti-pattern. A completely different title implies that it’s a completely different job, when what you really want, at least most of the time, is an engineer performing a slightly different (but substantially overlapping) set of functions as a senior engineer.

My core principle here is simple: only the people responsible for building software systems get to make decisions about how those systems get built. I can opine all I want on your architecture or ours, but if I’m not carrying a pager for you, you should probably just smile politely and move along.

Technical decisions should be ultimately be made by the people who have to live with the consequences. But good architects will listen to those people, and help co-create architectural decisions that take into account local, domain, and enterprise perspectives (a Katy Allred quote).

Architecture is a core engineering skill

When you make architecture “someone else’s problem” and scrap the expectation that it is a core skill, you get weaker engineers and worse systems.

Learning to see the forest as well as the trees, and factor in security, maintainability, data integrity and scale, performance, etc is a *critical* part of growing up as an engineer into senior roles.

The story of QA is relevant here. Once upon a time, every technical company had a QA department to test their code and ensure quality. Software engineers weren’t expected to write tests for their code — that was QA’s job. Eventually we realized that we wrote better software when engineers were held responsible for writing their own tests and testing their own code.

Developers howled and complained: they didn’t have time! they would never get anything built! But it gradually became clear that while it may take more time up front to write and test code, it saved immensely more time and pain in the longer run because the code got so much better and problems got found so much earlier.

It’s not like we got rid of QA  — QA departments still exist, especially in some industries, but they are more like consulting experts. They write test suites and test software, but more importantly they are a resource to make sure that everybody is writing good tests and shipping quality software.

This was long enough ago that most people writing code today probably don’t remember this. (It was mostly before my own time as well.) But you hear echoes of the same arguments today when engineers are complaining about having to be on call for their code, or write instrumentation and operate their code in production.

The point is not that every engineer has to do everything. It’s that there are elements of testing, operations, and architecture that every software engineer needs to know in order to write quality code — in order to not make mistakes that will cost you dearly down the line.

Specialists are not here to do the job for you, they’re to help you do the job better.

“Architect” Done Right

If you must have architects at all, I suggest:

  1. Grow your architects from within. The best high-level thinkers are the ones with a thorough grounding in the context and the particulars.
  2. Be clear about who gets to have opinions vs who gets to make decisions. Having architects who consult, educate, and support is terrific. Having “pigeon architects” who “swoop and poop” — er, make technical decisions for engineers to implement — is a recipe for resentment and weak architectures.
  3. Pay them the same as your staff or principal engineers, not dramatically more. Create an org structure that encourages pendulum swings between (eng, mgr, arch) roles, not one with major barriers in form of pay or level disparities.
  4. Consider adopting one of the following patterns, which do a decent job of evading the two main traps we described above.

If your architects don’t have the technical skills, street cred, or time to spend growing baby engineers into great engineers, or mentoring senior engineers in architecture, they are probably also crappy architects. (another Katy Allred quote)

The “Embedded Architect” (aka Staff+ Engineer)

The most reliable way I know to align architecture and engineering goals is for them to be done by the same team. When one team is responsible for designing, developing, maintaining, and operating a service, you tend to have short, tight, feedback loops that let you ship products and iterate swiftly.

Here is one useful measure of your system’s complexity and the overhead involved in making changes:

“How long does it take you to ship a one-character fix?”

There are many other measures, of course, but this is one of the most important. It gets to the heart of why so many engineers get fed up with working at big companies, where the overhead for change is SO high, and the threshold for having an impact is SO long and laborious.

The more teams have to be involved in designing, reviewing, and making changes, the slower you will grind. People seem to accept this as an inevitability of working in large and complex systems far more than I think they should.

Embedding architecture and operations expertise in every engineering team is a good way to show that these are skills and responsibilities we expect every engineer to develop.

This is the model that Facebook had. It is often paired with,

The “Architecture Group” of Practicing Engineers

Every company eventually needs a certain amount of standardization and coordination work. Sometimes this means building out a “Golden Path” of supported software for the organization. Sometimes this looks like a platform engineering team. Sometimes it looks like capacity planning years worth of hardware requirements across hundreds of teams.

I’ve seen this function fulfilled by super-senior engineers who come together informally to discuss upcoming projects at a very high level. I’ve seen it fulfilled by teams that are spun up by leadership to address a specific problem, then spun down again. I’ve seen it fulfilled by guilds and other formal meetings.

These conversations need to happen, absolutely no question about it. The question is whether it’s some people’s full time job, or one of many part-time roles played by your most senior engineers.

I’m more accustomed to the latter. Pro: it keeps the conversations grounded in reality. Con: engineers don’t have a lot of time to spend interfacing with other groups and doing “project management” or “stakeholder management”, which may be a sizable amount of work at some companies.

The “architect-engineer” pendulum

The architect-to-engineer pendulum seems like the only strategy short of embedded architects / shared ownership that seems likely to yield consistently good results, in my opinion.

The reasoning behind this is similar to the reasons for saying that engineering managers should probably spend some time doing hands-on work every few years. You need to be a pretty good engineer before you can be a good engineering manager or a good architect, and 5+ years after doing any hands-on work, you probably aren’t one anymore.

If you’re the type of architect that is part of an engineering team, partly responsible for a product, shipping code for that product, or on call for that product, this may not apply to you. But if you’re the type of architect that spends little if any time debugging/understanding or building the systems you architect, you should probably make a point of swinging back and forth every few years.

The “Time-Share Architect”

This one has aspects of both the “Architecture Working Group” and the “Architect-Engineer Pendulum”. It treats architecture is a job to be done, not a role to be occupied. Thinking of it like a “really extended pager rotation” is an interesting idea.

Somewhat relatedly — at Honeycomb, “lead engineer” is a title attached to a particular project, and refers to a set of actions and responsibilities for that project. It isn’t a title that’s attached to a particular person. Every engineer gets the opportunity to lead projects (if they want to), and everybody gets a break from doing the project management stuff from time to time. The beautiful thing about this is that everybody develops key leadership skills, instead of embodying them in a single person.

The important thing is that someone is performing the coordination activities, but the people building the system have final say on architecture decisions.

The “Advisor Architect”

I honestly have no problem with architects who are not seen as senior to, and do not have opinions overriding those of, the senior engineers who are building and maintaining the system.

Engineers who are making architectural decisions should consult lots of sources and get lots of opinions. If architects provide educated opinions and a high level view of the systems, and the engineers make use of their expertise, well  that’s fan fucking tastic.

If architects are handing them assignments, or overriding their technical decisions and walking off, leaving a mess behind … fuck that shit. That’s the opposite of empowerment and ownership.

The “skin in the game” rule of thumb still holds, though. The less an architect is exposed to the maintenance and operational consequences of decisions, the less sway their opinion should hold with the group. It doesn’t mean it doesn’t bring value. But the limitations of opinions at a distance should be made clear.

The Threat to Architects’ Careers

It’s super flattering to be told you are just too important, your time is too valuable for you to fritter it away on the mundane acts of debugging and reviewing PRs. (I know! It feels great!!!) But I don’t think it serves you well. Not you, or your team, your company, customers, or the tech itself.

And not *every* architect role falls into this trap. But there’s a definite correlation between orgs that stop calling you “engineers” and orgs that encourage (or outright expect) you to stop engineering at that level. In my experience.

But your credibility, your expertise, your moral authority to impose costs on the team are all grounded in your fluency and expertise with this codebase and this production system — and your willingness to shoulder those costs alongside them. (All the baby engineers want to grow up to be a principal engineer like this.)

But if you aren’t grounded in the tech, if you don’t share the burden, your direction is going to be received with some (or a LOT of) cynicism and resentment. Your technical work will also be lower quality.

Furthermore, you’re only hurting yourself in the long run. Some of the most useless people I’ve ever met were engineers who were “promoted” to architect many, many years ago, and have barely touched an editor or production shell since. They can’t get a job anywhere else, certainly not with comparable status or pay, and they know it. 🤒

They may know EVERYTHING about the company where they work, but those aren’t transferable skills. They have become a super highly paid project manager.

And as a result … they often become the single biggest obstacle to progress. They are just plain terrified of being automated out of a job. It is frustrating to work with, and heartbreaking to watch. 💔

Don’t become that sad architect. Be an engineer. Own your own code in production. This is the way.

Coda: On “Solutions Architects”

You might note that I didn’t include solutions architects in this thread. There is absolutely a real and vibrant use for architects who advise. The distinction in my mind is: who has the last word, the engineers or the architect? Good engineering teams will seek advice from all kinds of expert sources, be they managers or architects or vendors.

My complaint is only with “architects” who are perceived to be superior to, and are capable of overruling the judgments of, the engineering team.

Exceptions abound; the title is not the person. My observations do not obviate your existence as a skilled technologist.  You obviously know your own role better than I do. 🙃

charity

Architects, Anti-Patterns, and Organizational Fuckery

Every Achievement Has A Denominator

mipsytipsy, , , 5 Comments

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 Hierarchy Is Bullshit (And Bad For Business)

mipsytipsy, , 15 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)

Rituals for Engineering Teams

mipsytipsy, , , , , 13 Comments

Last weekend I happened to pick up a book called “Rituals For Work: 50 Ways To Create Engagement, Shared Purpose, And A Culture That Can Adapt To Change.” It’s a super quick read, more comic book than textbook, but I liked it.

It got me thinking about the many rituals I have initiated and/or participated in over the course of my career. Of course, I never thought of them as such — I thought of them as “having fun at work” 🙃 — but now I realize these rituals disproportionately contribute to my favorite moments and the most precious memories of my career.

Rituals (a definition): Actions that a person or group does repeatedly, following a similar pattern or script, in which they’ve imbued symbolism and meaning.

I think it is extremely worth reading the first 27 pages of the book — the Introduction and Part One. To briefly sum up the first couple chapters: the power of creative rituals comes from their ability to link the physical with the psychological and emotional, all with the benefit of “regulation” and intentionality. Physically going through the process of a ritual helps people feel satisfied and in control, with better emotional regulation and the ability to act in a steadier and more focused way. Rituals also powerfully increase people’s sense of belonging, giving them a stable feeling of social connection. (p. 5-6)

The thing that grabbed me here is that rituals create a sense of belonging. You show that you belong to the group by participating in the ritual. You feel like you belong to the group by participating in the ritual. This is powerful shit!

It seems especially relevant these days when so many of us are atomized and physically separated from our teammates. That ineffable sense of belonging can make all the difference between a job that you do and a role that feeds your soul. Rituals are a way to create that sense of belonging. Hot damn.

So I thought I’d write up some of the rituals for engineering teams I remember from jobs past. I would love to hear about your favorite rituals, or your experience with them (good or bad). Tell me your stories at @mipsytipsy. 🙃

Rituals at Linden Lab

Feature Fish Freeze

At Linden Lab, in the ancient era of SVN, we had something called the “Feature Fish”. It was a rubber fish that we kept in the freezer, frozen in a block of ice. We would periodically cut a branch for testing and deployment and call a feature freeze. Merging code into the branch was painful and time consuming, so If you wanted to get a feature in after the code freeze, you had to first take the fish out of the freezer and unfreeze it.

This took a while, so you would have to sit there and consider your sins as it slowly thawed. Subtext: Do you really need to break code freeze?

Stuffy the Code Reviewer

You were supposed to pair with another engineer for code review. In your commit message, you had to include the name of your reviewer or your merge would be rejected. But the template would also accept the name “Stuffy”, to confess that your only reviewer had been…Stuffy, the stuffed animal.

However if your review partner was Stuffy, you would have to narrate the full explanation of Stuffy’s code review (i.e., what questions Stuffy asked, what changes he suggested and what he thought of your code) at the next engineering meeting. Out loud.

Shrek Ears

We had a matted green felt headband with ogre ears on it, called the Shrek Ears. The first time an engineer broke production, they would put on the Ears for a day. This might sound unpleasant, like a dunce cap, but no — it was a rite of passage. It was a badge of honor! Everyone breaks production eventually, if they’re working on something meaningful.

If you were wearing the Shrek Ears, people would stop you throughout the day and excitedly ask what happened, and reminisce about the first time they broke production. It became a way for 1) new engineers to meet lots of their teammates, 2) to socialize lots of production wisdom and risk factors, and 3) to normalize the fact that yes, things break sometimes, and it’s okay — nobody is going to yell at you. ☺️

This is probably the number one ritual that everybody remembers about Linden Lab. “Congratulations on breaking production — you’re really one of us now!”

Vorpal Bunny

vorpal bunny

We had a stuffed Vorpal Bunny, duct taped to a 3″ high speaker stand, and the operations engineer on call would put the bunny on their desk so people knew who it was safe to interrupt with questions or problems.

At some point we lost the bunny (and added more offices), but it lingered on in company lore since the engineers kept on changing their IRC nick to “$name-bunny” when they went on call.

There was also a monstrous, 4-foot-long stuffed rainbow trout that was the source of endless IRC bot humor… I am just now noticing what a large number of Linden memories involve stuffed animals. Perhaps not surprising, given how many furries were on our platform ☺️

Rituals at Parse

The Tiara of Technical Debt

Whenever an engineer really took one for the team and dove headfirst into a spaghetti mess of tech debt, we would award them the “Tiara of Technical Debt” at the weekly all hands. (It was a very sparkly rhinestone wedding tiara, and every engineer looked simply gorgeous in it.)

Examples included refactoring our golang rewrite code to support injection, converting our entire jenkins fleet from AWS instances to containers, and writing a new log parser for the gnarliest logs anyone had ever seen (for the MongoDB pluggable storage engine update).

Bonfire of the Unicorns

We spent nearly 2.5 years rewriting our entire ruby/rails API codebase to golang. Then there was an extremely long tail of getting rid of everything that used the ruby unicorn HTTP server, endpoint by endpoint, site by site, service by service.

When we finally spun down the last unicorn workers, I brought in a bunch of rainbow unicorn paper sculptures and a jug of lighter fluid, and we ceremonially set fire to them in the Facebook courtyard, while many of the engineers in attendance gave their own (short but profane) eulogies.

Mission Accomplished

This one requires a bit of backstory.

For two solid years after the acquisiton, Facebook leadership kept pressuring us to move off of AWS and on to FB infra. We kept saying “no, this is a bad idea; you have a flat network, and we allow developers all over the world to upload and execute random snippets of javascript,” and “no, this isn’t cost effective, because we run large multi-terabyte MongoDB replica sets by RAIDing together multiple EBS volumes, and you only have 2.5TB FusionIO (for extremely high-perf mysql/RocksDB) and 40 TB spinning rust volumes (for Hadoop), and also it’s impossible to shrink or slice up replsets”, and so forth. But they were adamant. “You don’t understand. We’re Facebook. We can do anything.” (Literal quote)

Finally we caved and got on board. We were excited! I announced the migration and started providing biweekly updates to the infra leadership groups. Four months later, when the  migration was half done, I get a ping from the same exact members of Facebook leadership:

“What are you doing?!?”
“Migrating!”
“You can’t do that, there are security issues!”
“No it’s fine, we have a fix for it.”
“There are hardware issues!”
“No it’s cool, we got it.”
“You can’t do this!!!”

ANYWAY. To make an EXTREMELY long and infuriating story short, they pulled the plug and canned the whole project. So I printed up a ten foot long “Mission Accomplished” banner (courtesy of George W Bush on the aircraft carrier), used Zuck’s credit card to buy $800 of top-shelf whiskey delivered straight to my desk (and cupcakes), and we threw an angry, ranty party until we all got it out of our systems.

Blue Hair

I honestly don’t remember what this one was about, but I have extensive photographic evidence to prove that I shaved the heads of and/or dyed the hair blue of at least seven members of engineering. I wish I could remember why! but all I remember is that it was fucking hilarious.

In Conclusion

Coincidentally (or not), I have no memories of participating in any rituals at the jobs I didn’t like, only the jobs I loved. Huh.

One thing that stands out in my mind is that all the fun rituals tend to come bottoms-up. A ritual that comes from your VP can run the risk of feeling like forced fun, in a way it doesn’t if it’s coming from your peer or even your manager. I actually had the MOST fun with this shit as a line manager, because 1) I had budget and 2) it was my job to care about teaminess.

There are other rituals that it does make sense for executives to create, but they are less about hilarious fun and more about reinforcing values. Like Amazon’s infamous door desks are basically just a ritual to remind people to be frugal.

Rituals tend to accrue mutations and layers of meaning as time goes on. Great rituals often make no sense to anybody who isn’t in the know — that’s part of the magic of belonging. 🥰

Now, go tell me about yours!

charity

Rituals for Engineering Teams

Giving Good Feedback: Consider the Ratio

mipsytipsy, , , , 2 Comments

Consider the ratio.

You work with someone great. If someone asked, you’d say they are brilliant, inspired and dedicated. They care deeply about their work, they are timely and reliable (for the most part), and their emojis and dry sense of humor brighten your day. Your work depends on theirs, and you are working together on a neat project which is generating lots of excitement at demo days. You would miss them terribly if they left.

But today you are annoyed. They either didn’t hear or forgot your feedback from the last design review, which means you have to redo some components you thought were finished. It’s a considerable amount of work, and this isn’t the first (or second) time, either. You want to tell them so and try to debug this so it doesn’t keep happening.

So far, so good. Giving feedback like this can be hard, especially if they are senior to you. But do they understand the totality of how you see them? Or was the last time they heard from you the last time they fucked up? Out of the last ten times you gave them feedback, how many were complaining or asking for changes? Does that feedback ratio accurately represent your perception of their value?

This doesn’t mean you have to run around saying “you’re amazing!” all the time, but do be mindful of how other people think you perceive them. I can pretty much guarantee that none of the people you love working with realize just how much you value them, but they are acutely aware of all the ways they fall short or fail you. Here are some ways to correct that imbalance a bit

  • Don’t be vague. Do be specific. If you just run around saying “You’re awesome!” to people, they will tune you out. Do try to notice and reflect some of the things that making working with them a joy. Like, “I learned so much about mysql indexes pairing with you today, thank you”, or “Last week in our practice session you suggested approaching it this way, and it was so helpful in my situation”, or “I really admire the way you can talk extemporaneously about $topic, and I LOVE knowing I can rely on you with zero prep”. This is harder, and it absolutely takes more work on your part, but it lands. And sticks.
  • Use the Situation, Behavior, Impact framework…but for praise. The SBI framework is designed for delivering hard feedback, but it works just as well for delivering kudos. Use it to give great praise that isn’t generic and does let people know what they’re doing right/what they mean to you. “In the last team meeting, your overview of the messaging framework was super eye-opening for me. I learned more than ever before about not just our pyramid, but how messaging frameworks in general are used. I understand its impact on my role better now than I have in seven years of product marketing!”
  • Ground critique in your overall reaction. Let’s say someone just presented an idea that you think is super interesting and potentially very high value, but you have questions about its impact on marginalized groups. Do they know you think it is interesting and high value, when you launch into your critique? No they do not. If all they hear is several rounds of criticism, they may very well give up and cancel altogether, thinking everyone hated it. Something as simple as starting with “I LOVE this idea. Have you thought about —”, or “This is really interesting, but I’m curious…” can be enough to convey a less discouraging, more accurate sense of your perspective.
  • Don’t hold out for the “wow” moments. Sometimes even sharing what you see as a neutral description of someone’s work can be mind-blowing and affirming. Most people don’t realize how much they are just noticed, full stop. It is flattering to be noticed or have the things you said remembered. Being seen can be enough. (h/t @eanakashima)
  • Don’t contribute to a pile-on. Feedback is asymmetric — you can only give feedback as one person at a time (you!), but the recipient might be grappling with negative feedback from many, many people. In that context, anything critical you say is likely to feel like one more rock in a public stoning. Or (somewhat less dramatically), if someone asks for feedback and receives a wave of criticism, they may feel deflated and defeated and drop the entire idea. If that isn’t the outcome you want, try to bring some positive balance to the discussion instead of piling on.
  • Give feedback to grow on. Pure positivity can sound cloying and be easy to discount. If you’re just praising me, I’m learning nothing from it. We’re not talking about a shit sandwich here, but the best compliments are the ones you learn something from. “That was GREAT. It might be even better if…” Relatedly, some people find it hard to believe purely positive feedback, but if you give feedback that shows you understand their work and what they did less well, you gain credibility and they will believe the praise. (h/t @inert_wall).

Hard conversations and corrective feedback are absolutely necessary at times. But even poorly-delivered critiques can be dealt with in the context of a good relationship, when the person knows how much you value them, and even the most delicately delivered criticism can be hard to hear from someone when all you ever seem to hear from them is how much you suck.

Engineers can be the worst at this, because we tend to show our interest by eagerly engaging with an idea or piece of work … by picking it apart, and chattering about all the ways it could be better. 🙃 I generally think this is an awesome way to show love, but we could stand to be clearer about the affection part, and not let the perfect be the enemy of the good. So please consider the ratio of critique vs affirmation when giving feedback.

And there’s no reason to save all the nice words and praise and gratitude for someone’s funeral (or when they leave the company ☺️).

Giving Good Feedback: Consider the Ratio

Advice for Engineering Managers Who Want to Climb the Ladder

mipsytipsy, , , 11 Comments

We have been interviewing and hiring a pile of engineering directors at Honeycomb lately. In so doing, I’ve had some fascinating conversations with engineering managers who have been trying unsuccessfully to make the leap to director.

Here is a roundup of some of the ideas and advice I shared with them, and the original twitter thread that spawned this post.

What is an engineering director?

Given all the title inflation and general inconsistency out there, it seems worth describing what I have in mind when I say or hear “Engineering Director.”

In a traditional org chart, an engineering manager usually manages about 5-8 engineers, an engineering director manages 2-5 engineering managers, and a VP of engineering manages the directors. (At big companies, you may see managers and directors reporting to other managers and directors, and/or you may find a bunch of ‘title padding’ roles like Senior Manager, Senior Director etc.)

In smaller companies, it’s common to have a “Head of Engineering” (this is an appropriately weaselly title that commands just the right amount of respect while leaving plenty of space to hire additional people below or above them). Or all of engineering might roll up to a director or VP or CTO. It varies a lot.

When it comes to the work a director is expected to do, though, there’s a fair bit of consistency: we expect managers to manage ICs, and directors to manage managers.  Directors sit between the line managers and the strategic leadership roles. (More on this later.)

So if you’re an engineering manager, and you want to try being a director, the first thing you’ll want to understand is this: it is generally better to get there by being promoted than by getting offered a director title at a different company.

How to level up

Lots of engineers get tapped by their management to become managers, but not many become directors without a conversation and some intentional growth first. This means that for many of you, trying to become a director may be the first time you have ever consciously solicited a role outside the interview process. This can bring up feelings of awkwardness, even shamefulness or inappropriateness. You’ll just have to push through those.

If you ever want a job in upper leadership, you are going to have to learn how to shamelessly state your career goals. We want people in senior leadership who want to be there and are honing their skills in anticipation of an opportunity. Not “oops, I accidentally a VP.”

It is better to get promoted than hired up a level

There are a few reasons for this. It’s usually easier to get promoted than to get hired straight into a job you’ve never held before (at a org with high standards), and it also tends to be more sustainable/more likely to succeed if you get promoted in as well. Being a director is NOT just being a super-duper manager, it’s a different role and function entirely.

A lot of your ability to be successful as a director (or any kind of manager) comes from knowing the landscape, the product and the people, and having good relationships internally. When you are internally promoted, you already know the company and the people, so you get a leg up towards being successful. Whereas if you’ve just joined the company and are trying to learn the tech, the people, the relationships, and how the company works all at once, on top of trying to perform a new role for the first time.. well, that is a lot to take on at once.

There are exceptions, sure! Oodles of them[1]. But I would frankly look sideways at a place that wanted to hire me as a director if I haven’t been one, or hadn’t at least managed managers before. It’s at least a yellow flag. It tells me they are probably either a) very desperate or b) very sloppy with handing out titles.

If you want a promotion…

The obvious first step involves asking your manager, “what is the skill gap for me between the job I am doing right now and a director role?” Unlike in the movies, promotions don’t usually get surprise-dropped on people’s heads; people are usually cultivated for them. Registering your interest makes it more likely they will consider you, or help you develop skills in that direction as time moves on.

If you have a good manager who believes in you, and the opportunities exist at your company, that might even be all you have to do.(!)

And if so, lucky you. But as for the remaining ~80-90% of us (ha!) … well, we’ll need a bit more hustle.

Take inventory of your opportunities

Lots of companies aren’t large enough to need directors, or growing fast enough to create new opportunities. This can actually be the most challenging part of the equation, because there are generally a lot more managers who want to be directors than there are available openings.

If you do need to find a new job to reach your career goals, I would target fast-growing companies with at least 100 engineers. If you’re evaluating prospective employers based on your chance of advancement, consider the following::

  • Ask about their policies on internal vs external hires. Do they give preference to existing employees? How do they decide when to recruit vs grow from within?
  • Ask about the last time that someone was promoted into a similar role.
  • Tell the recruiter and hiring manager about your career goals. Don’t be shy. “My next career goal is to gain some experience managing managers” is fine. (That shouldn’t be the only reason you’re interested, of course.)
  • Size up the playing field. Is there oxygen at that level? Or are there a dozen other managers senior to you lined up for the same shot?

There are no sure bets. But you can do a lot to put yourself in the right place at the right time, signal your interest, and be prepared for the opportunity when it strikes.

a director is not a ‘super-senior manager’

A director is not just a manager on steroids: it is an entirely different job. It helps to have been a good manager before becoming a director, because many management skills will translate, but others will be entirely new to you. Expect this.

How being a good director is different from being a good manager

Let’s look at some of the ways that being a good engineering manager is different than being a good director.

  1. You can be a great EM, beloved by your team, without giving much thought to managing out or up. Directors cannot. If anything, it’s the opposite. You may get away with not coddling your EMs, but you must pull your weight for your peers and upper management.
  2. You can have a bit of a reputation for being stubborn or difficult as an EM, and that can be just fine. But having such a rep will probably sabotage your attempt at being promoted to director.
  3. You can be a powerful technical EM who sometimes jumps in to train engineers, be on call, or course correct technical and architectural decisions. This can even burnish your value and reputation as an EM. But this would all be a solid knock against you as a director.

Managers can get away with being opinionated and attached to technology, to some extent, while directors absolutely must balance lots of different stakeholders to achieve healthy business outcomes.

This difference of perspective is why managers will sometimes sniff about directors having sold out, or being “all about politics.”

(Blaming something on “politics” is usually a way of accidentally confessing that you don’t actually understand the constraints someone is operating under, IMO.)

A director’s job is running the business

Here’s the key fact: ✨directors run the business✨.

Managers should be focused on high-performing engineering teams. VPs should be focused on strategy and the longer term. Directors are the execution machines that knit technology with business objectives. (I like this piece, although the lede is a little buried. Key graf:)

managers, directors, VPs

Directors run the business. They are accountable for results. You can’t be bopping in and writing or reviewing code, or tossing off technical opinions. That’s not your job anymore.

Managing managers is a whole new skill set

The distance between managing engineers and managing managers is nearly as vast as the gulf between being an engineer and being a manager.

But it’s sneakier, because you don’t feel out of your depth as much as you did when you became a manager. 😁

As a manager, each of us instinctively draws on our own unique blend of strength and charisma — whatever it is that makes people look up to you and willing to accept your influence. Most of us can’t explain how we do it, because we run on instinct.

But as a director, you have to figure it out. Because you need to be able to debug it when the magic breaks down. You need to help your managers influence and lead using *their* unique strengths. What works for you won’t work for them. You have to learn how to unpack different leadership styles and support them in the way they need.

If you’re working towards a director role:

There are lots of areas where you can improve your director skills and increase your chances of being viewed as director material without any help whatsoever from your manager.

You ✨can not✨ be a blocker

Directors run the business … so you CANNOT be seen as a blocker. People must come to you of their own accord to get shit done and break through the blockers.

If they are going to other people for advice on how to break through YOU, you are not a good candidate for director. Figure out how to fix this before you do anything else.

Demonstrate impact beyond your team(s)

Another way to make yourself an attractive prospect for director is to work on systemic problems, driving impact at the org or company level. You could:

  • work to substantially increase the diversity of your teams or your candidate pipeline, and offer to work with recruiting and other managers to help them do the same (becoming BFFs with recruiting is often a canny move)
  • drive some cross-platform initiative to consolidate dozens of snowflake deploy processes and significantly reduce CI/CD build/deploy times, set an internal SLO for artifact build times, or successfully champion auto-deployment
  • champion an internal tools team with a mandate to increase developer productivity, and quantify the hell out of it
  • lead a revamp of the new hire onboarding process. Or add training and structure to the interview process and set an SLO of responding to every candidate within one week

I dunno — it all depends on what’s broken at your company. 🙃 Identify something causing widespread pain and frustration at the organizational level and fix it. 

Managing ‘up’ is not a ‘nice-to-have’…

If there’s a problem, make sure you are the one to bring it to your manager (and swiftly), along with “Here is the context, here’s where I went wrong, and this is what I’m planning to do about it.” No surprises.

At this point in your career, you should have mastered the art of not being a giant pain in the ass to your manager. Nobody wants a high-maintenance director. Do you reliably make problems go away, or do they boomerang back five times worse after you “fix” them?

…Neither is managing ‘out’

Managing “out” is important too. (Not “managing out”, which means terminating people from the company, but managing “out” as in horizontally, meaning your relationship with your peers.)

What do your peers think of you? Do you invest in those relationships? Do they see you as an ally and a source of wise counsel, or a source of chaos, gossip and instability, or a competitor with turf to protect? If you’re the manager that other managers seek out for a peer check, you might be a good candidate for director.

psst.. People are watching you

One of the most uncomfortable things to internalize if you climb the ladder is how much people will make snap judgments about you based on the tiniest fragments of information about you, and how those judgments may forever color the way they think of you or interact with you.

First impressions might be made by ten minutes together on the same zoom call…a few overheard fragments of people talking about you…even the expressions on your face as they pass you in the hallway. People will extrapolate a lot from a very little, and changing their impression of you later is hard work.

(Yes it’s frustrating, but you can’t really get upset about it, because you and I do it too. It’s part of being human. )

Because of that, you really do have to guard against being too cranky, too tired, or out of spoons. People WILL take it personally. It WILL come back to hurt you.

Remember, you don’t hear most feedback. If you visibly disagree with someone, assume 10x as many silently agree with them. If one person gives you a piece of hard feedback, assume 10x as many will never tell you. Be grateful. The more power you are perceived to have, the less feedback you will ever hear.

Pro tip

You can infer a surprising amount about how good a director candidate may be at their job, simply by listening closely to how they talk about their colleagues. Do they complain about being misunderstood or mistreated, do they minimize the difficulty or quality of others’ work, do they humblebrag, or do they take full responsibility for outcomes? And does their empathy fully extend to their peers in other departments, like sales and marketing?

Does it sound like they enjoy their work, and look forward to beginning it every day? Does it sound like they are all in the same little tugboat, all pulling in the same direction, or is there a baseline disconnect and lack of trust?

In conclusion…

Be approachable, be a drama dampener, project warmth. Control your calendar and carve out regular focus time. Guard your energy — never run your engine under 30%, and always leave something in the tank.

There are a lot more great responses and advice in the replies to my thread, btw. Go check them out if you’re interested.. and if you have something to say, contribute!.☺️

charity

Footnotes:

[1] Occasionally, it may work out to your benefit to jump into a new, higher title at a new company. This can happen when someone is already well qualified for the higher role, but is finding it difficult to get promoted (possibly due to insufficient opportunity or systemic biases). Just be aware that the job you were hired into is likely to be one where the titles are meaningless and/or the roles are chaotic. You may want to stay just long enough to get the title, then bounce to a healthier org.

Advice for Engineering Managers Who Want to Climb the Ladder

Twin Anxieties of the Engineer/Manager Pendulum

mipsytipsy, , , , , 7 Comments

I have written a lot about the pendulum swing between engineering and management, so I often hear from people who are angsting about the transition.

A quick recap of the relevant posts:

There are two anxieties I hear people express above all the rest.

The first one is something I hear over and over again, particularly from first-time managers as they contemplate the possibility of leaving management and returning to IC (individual contributor) work as an engineer:

“What if I never get another shot at people management?”
“Maybe this is the only chance I’ll ever get … and I’m about to give it up??”
“Am I going to regret this?”

“Will I ever get another shot at management?”

People decide to go back to engineering for lots of reasons. Maybe they’re burned out, or they work someplace with a poisonous management culture, or they’re having a kid and want to return to a role that feels more comfortable for a while. Or maybe they’ve been managing teams for a few years now, and have decided it’s time to go back to the well and refresh their technical skills in the interest of their long-term employability.

Regardless, these are not typically people who disliked being a manager. Rather they tend to be engineers who really enjoyed people management, and find it bittersweet to give up. Maybe they will miss the strategic elements and roadmap work, but they’re excited to clear their calendar and spend time in flow again, or they will miss having 1x1s but can’t wait to have time to mentor people. Whatever. They want to manage teams again someday, and worry they won’t get another chance.

Their anxiety is understandable! Lots of people feel like they waited a long time to be tapped for management, or like they were passed over again and again. Our cultural scripts about management definitely contribute to this sense of scarcity and diminution of agency (i.e. that management is a promotion, it is bestowed on you by your “superiors” as a reward for your performance, and it is pushy or improper to openly seek the role for yourself).

This anxiety is also, in my experience, ridiculously misplaced. ☺️

Once a manager, marked for life as a manager

You may have struggled to get your first opportunity to manage a team. But it’s a whole different story once you’ve done the job. Now you have the skills and the experience, and people can smell it on you.

I’m not joking. If you’re a good manager it’s actually nearly impossible to hide that you have the skills, because of the way it infuses your work and everything that you do as an IC. You get better at prioritization, more attuned to the needs of the business, and restless about work that doesn’t materially move the business forward. You get better at asking questions about why things need to be done and at communicating with stakeholders. You get better at motivating the people you work with, understanding their motivations and your own, and mediating conflicts or putting a damper on drama between peers. People come to you for advice and may seem to just do what you say, or go where you point.

Senior engineers with management experience are worth their weight in gold. They are valuable contributors and influential teammates. It’s a palpable shift! And every experienced manager in their vicinity will sense it.

So yes, you will be tapped for management again. And again and again and again. You are more likely to spend the rest of your career fending off management “opportunities” with a baseball bat than you are to wither away, pining for another shot.

There is a chronic shortage of good engineering managers, just like there is a chronic shortage of good, empathetic managers in every line of work. The challenge you will face from now on will not be about getting the chance to manage a team, but about being intentional and firm in carving out the time you need to recover and recharge your skills as an engineer.

“Am I too rusty to go back to engineering?”

The second anxiety is in some ways a mirror of the first:

“Can I still perform as an engineer?”
“Will anyone hire me for an engineering role?”
“Has it been too long, am I too rusty, will I be able to pull my weight?”

This is a more materially valid concern than the first one, in my opinion. Your engineering skills do wither and erode as time goes on. It will take longer and longer to refresh your skills the longer you go without using them. Management skills don’t decay in the same way that technical ones do, nor do they go out of date every few years as languages, frameworks and technologies tend to do.

If you aren’t interested in climbing the ladder and becoming a director or VP — or rather, if you aren’t actively, successfully climbing the ladder — you should have a strategy for keeping your hands-on skills sharp, because your ability to be a strong line manager is grounded in your own engineering skills.

Never, ever accept a managerial role until you are already solidly senior as an engineer. To me this means at least seven years or more writing and shipping code; definitely, absolutely no less than five. It may feel like a compliment when someone offers you the job of manager — hell, take the compliment 🙃 — but they are not doing you any favors when it comes to your career or your ability to be effective.

When you accept your first manager job, I think you should make a commitment to yourself to stick it out for two years. That’s how long it takes to rewire your instincts and synapses, to learn enough that you can tell whether you’re doing a good job or not.

After two or three years of management, it’s still pretty easy to go back to engineering. After five years, it gets progressively harder. But it can be done. And it should be worth it to your employer to invest in keeping you while you refresh your skills over the six months or whatever it may take. Insist on it, if you must. It’s better to refresh your skills while employed, on a system and codebase you’re familiar with, than to find yourself struggling to brush up enough to pass a coding interview.

Engineering fluency == job security

There is one more reason to refresh your engineering skills from time to time, one I don’t often see mentioned, and that is job security and optionality.

The higher you go up the ladder, the more money you will get paid…but the fewer jobs there be, and the fewer still that match your profile.

As a senior software engineer, there are fifteen bajillion job openings for you. Everyone wants to hire you. You can get a new job in a matter of days, no matter how picky you want to be about location, flexibility, technologies, product types, whatever. You’ve reached Peak Hire.

If you are looking for management roles, there will be an order of magnitude fewer opportunities (and more idiosyncratic hiring criteria), but still plenty for the most part. But for every step up the ladder you go, the opportunities drop by another order of magnitude, and the scrutiny becomes much more intense and particular. If you’re looking for VP roles, it may take months to find a place you want to work at, and then they might not choose you. ¯\_(ツ)_/¯

Maintaining your technical chops is a stellar way to hedge against uncertainties and maintain your optionality.

 

Twin Anxieties of the Engineer/Manager Pendulum

How can you tell if the company you’re interviewing with is rotten on the inside?

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How can you tell the companies who are earnestly trying to improve apart from the ones who sound all polished and healthy from the outside, whilst rotting on the inside?

This seems to be on a lot of minds right now, what with the Great Resignation and all. There are no perfect companies, just like there are no perfect relationships; but there are many questions and techniques you can use to increase your confidence that a particular company is decent and self-aware, one whose quirks and foibles you are compatible with.

Interviews are designed to make you feel like you are under inspection, like the interviewer holds all the power. This is an illusion. Your labor is valuable — it is vital — and you should be scrutinizing them every bit as closely as they you. In fact, here is Tip #1:

  • If they allow you plenty of time to converse with your interviewers throughout the process, great. If they tack on a cursory “any questions for us?” while wrapping up, they don’t think it matters what you think of them. Pull the ripcord.

Collect and practice good interview questions for you to ask potential employers. Write them down — your mind is likely to go blank under stress, and you don’t want to let them off the hook. There is a LOT of signal to be gained by probing down below the surface answers.

Backchanneling

  1. Whisper networks and backchannels are incredibly important. It can be especially valuable to talk to someone who has recently left the company: why did they leave? Would they go there again?
  2. Alternately, do you know anyone who has worked for or with their leadership, even if not at that company?
  3. If you know any women or under-represented minorities (URM) who work there, buy them lunch and ask for the unvarnished truth. That’s where you usually turn up the real dirt. 🥂

Diversity, equity and inclusion

Just because a company has a diverse workforce doesn’t necessarily mean it is a healthy place to work. (But it’s fair to give some points up front, because that doesn’t usually happen by accident.)

  1. Do they have a diverse leadership team? A diverse board?
  2. Is their company diverse overall, or are minorities concentrated in a few (lower-paying, high-turnover) departments?
  3. You might not want to write off all the companies that don’t meet points one and two, if for no other reason than it dramatically shrinks your available option pool. If they don’t have a particularly diverse team, and this is something that matters to you, that’s your cue to dig deeper:
    • Are they bothered by their lack of diversity? What’s the plan? Do they just feel generically sad about it, or have they set specific goals to improve by specific dates? What investments are they making?
    • Who works on DEI stuff currently? (Answers like “HR and recruiting”, or “we have a woman who’s really good at it” are bad answers.)
    • Who is accountable for making sure those goals are hit? (The only right answer is “our execs”. Having a “chief diversity officer” is an anti-pattern in my book.)
    • If the team is all guys, for example, ask if they’ve ever had any women on the team in the past. Did she/they leave? Do they know why?
  4. This is a GREAT one: “As a white man, I’d ask what they’ve done to find qualified women and minorities for the role I’m interviewing for.” (via David Daly) 🔥🔥

Company stuff

  1. What are their values? Do they feel bloodless and ripped from the pages of HBR, or are they unique, lived-in, and give you a glimpse of what the people there care about? Are they mentioned over the course of your interview?
  2. Ask tough questions about the business and try to ascertain whether they are hitting their quarterly goals, how much funding they have in the bank, what the growth curve looks like, what users really think about their product, and what the biggest obstacles to success are.
    • Companies that are floundering are going to be really stressful places to work, and even if the leadership is decent, they may find themselves backed into making some really tough decisions.
    • You want to work at a company on a strong growth trajectory for lots of reasons, but a big one is your own growth potential. You will learn the most the fastest at places that are growing fast, and have way more openings for promotions and leadership roles than a slower-growing company.
  3. Are people willing to speak freely about things they’ve tried that have failed, and things that don’t work well currently? Being self-aware and comfortable with visible failure are two of the most important self-correcting mechanisms a company can cultivate.
  4. EVERYBODY thinks they value transparency, so I wouldn’t even bother asking. Instead, ask for specific examples of leadership being forthcoming with bad news to the team, and team members delivering hard feedback or bad news to upper leadership. Transparency shouldn’t be something they’re especially proud of, so much as it is taken for granted. It’s in the air that you breathe.

Planning and the unplanned

  1. Ask about how decisions get made. A chestnut is, “how does work end up on my plate?” — meaning is there a business strategy (owned by whom?), a technical strategy, a product strategy, quarterly KPIs, customer requests, manager delegation, JIRA tickets…? (The most important part may be how similar the answers you get are. 🙃)
  2. How often does work get pre-empted and why? It’s a good thing if product development has to get put on ice once in a while so the team can focus on reliability and maintenance work. It’s a bad thing if they’re expected to stuff reliability work in the cracks around their product development, or if they’re incapable of sticking to a plan.
  3. What does “crunch time” look like? Nearly every company has one from time to time (it might even be a bad sign if it never happens), but this is when you find out your leadership’s true colors.
    • Do they praise people or call them out to thank them for pulling all nighters and other extremist behaviors? 🚨BZZT🚨
    • Is it voluntary? Are you trusted to set your own pace, your own limits, or are you pressured to do more? Are people expected to participate to the extent that they are able, and not expected to justify how hard or how much (so long as they communicate their capacity, of course)?
    • How long did it last, and how often does it happen, and why? It should be rare (1-2x/year at most), involve the whole company, and move the business forward meaningfully
    • Did they follow through by making sure people took time off afterwards to recover? Not just give permission, but actually make sure the human beings had a chance to refresh themselves? Did leaders set a good example by taking a breather themselves?

Believe it or not, crunch time done correctly can be an enormously exciting, intense, bonding time for a group of people who love what they do, culminating in a surge of collective triumph and celebration, followed by recovery time. If it was done correctly, and you ask about it afterwards, people will 💡light up💡.

Team stuff

  1. Unfortunately, culture can vary widely from function to function, even from manager to manager. Make sure you get a real interview slot with your actual manager — not just a screener or wrap-up call — and as much of the team as possible, too.
  2. Ask your potential manager about the last person they had to let go. Why? What was the process? What was the impact on the team? How did the person feel afterwards?
  3. Who is on call? How often do people get paged outside of hours, and how frequently do they work an incident? (Do managers track this?) Are you expected to keep shipping product during on call weeks, or devote your time to making the system better?
  4. If you had to ship a single line of code to production using the deploy pipeline, how long would that take? Remember, the lower the deploy interval, the happier and more productive you are likely to be as an engineer there. Under 15 minutes is great. Under an hour is tolerable. More than that, proceed with great caution.

The interview itself

  1. Was your interview well-organized and conducted in a timely fashion? Were you given detailed information about what to expect, and were your interviewers well-prepared, and conversational? Were the questions fair, open-ended, and relevant to the job in question?
  2. If they asked you to perform any kind of take-home labor of more than an hour or so, did they compensate you for your time?
  3. Did they get back to you swiftly at each step of the way to let you know where you stand and what comes next?
  4. Did you find the questions interesting and challenging? Do they have a clear idea of what success looks like for you in this role? Did you leave excited and buzzing with ideas about the work you could do together?
    • This is 👆 definitely more of a “how good is this job” question than “is this a shithole” question, but one of our honeycombers brought it up as an example of how a great interview can make you decide to leave a job , even one you’re perfectly happy with.
  5. The questions they ask you while interviewing you are the questions they ask everyone else. So…did they ask you about your views on diversity and team dynamics while interviewing you? Or is that not part of their filters, only their advertised persona?

Three more

  1. Do their employees seem to speak freely on twitter? If you are an agitator of sorts, are there others who agitate about similar issues — either with company support, or at least lack of censorship?
  2. How does the company respond to criticism and feedback? For that matter, how do they treat their competitors? Being competitive is fine, being mean is not.
  3. Get clear on your own expectations. What’s on your wishlist, and what’s make-or-break for you? If something is very important to you, consider telling the hiring manager up front. For example, “These are my expectations for how women are treated. How do you think your company matches up?” Their answers will speak volumes, and so will their comfort level with the question.

In closing

If you a join a new company, and two or three weeks in you’re just not feeling it, you’re wondering if you made a mistake — leave. You do not owe them a year of your life. Trust your instincts. Just leave it off your resume entirely and roll the dice again.

Employers are all too accustomed to feeling (and acting) like they hold all the power. They do not. Every tech company is a talent business, which rises and falls on the caliber of the people they can convince to stay. They aren’t doing you a favor by employing you; you are doing THEM a favor by lending them your creativity, labor, and a third of the hours in your day.

Do they deserve it? Will their success make the world a better place? If not, stop supporting them with your work and lend your muscle to a company that deserves it.

In the hottest job market of my lifetime, with millions of opportunities newly open to people who live literally anywhere, you owe it to yourself, your future self, and your family to take a good hard look at where you sit. 🍄 Are you happy? 🍄 Are you compensated well, is your time valued? 🍄 Are you still learning new things and improving your skills every day? 🍄 Is your company still on a growth trajectory? 🍄 Do you trust your leadership and your team, 🍄 do still you believe in the mission, and 🍄 do you think your labor contributes meaningfully to making the world a better place?

If not, consider joining the Great Resignation. I hear they have cookies.

Huge thanks to Amy Davis, Phillip Carter, Ian Smith, Sarah Voegeli, Kent Quirk, Liz Fong-Jones, Amanda Shapiro, Nick Rycar, Fred Hebert and David Daly, all of whom contributed to this post!

How can you tell if the company you’re interviewing with is rotten on the inside?