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Thoughts on Motivation and My 40-Year Career

mipsytipsy, , , , , , 27 Comments

I’ve never published an essay quite like this. I’ve written about my life before, reams of stuff actually, because that’s how I process what I think, but never for public consumption.

I’ve been pushing myself to write more lately because my co-authors and I have a whole fucking book to write between now and October. After ten years, you’d think this would be getting easier, not harder.

There’s something about putting out such memoiristic material that feels uncomfortably feminine to me. (Wow, ok.) I want to be known for my work, not for having a dramatic personal life. I love my family and don’t want to put them on display for the world to judge. And I never want the people I care about to feel like I am mining their experiences for clicks and content, whether that’s my family or my coworkers.

Many of the writing exercises I’ve been doing lately have ended up pulling on threads from my backstory, and the reason I haven’t published them is because I find myself thinking, “this won’t make any sense to people unless they know where I’m coming from.”

So hey, fuck it, let’s do this.

I went to college at the luckiest time

I left home when I was 15 years old. I left like a bottle rocket taking off – messy, explosive, a trail of destruction in my wake, and with absolutely zero targeting mechanisms.

It tells you a lot about how sheltered I was that the only place I could think of to go was university. I had never watched TV or been to a sports game or listened to popular music. I had never been to a doctor, I was quite unvaccinated.

I grew up in the backwoods of Idaho, the oldest of six, all of us homeschooled. I would go for weeks without seeing anyone other than my family. The only way to pass the time was by reading books or playing piano, so I did quite a lot of both. I called up the University of Idaho, asked for an admissions packet, hand wrote myself a transcript and gave myself all As, drove up and auditioned for the music department, and was offered a partial ride scholarship for classical piano performance.

I told my parents I was leaving, with or without their blessing or financial support. I left with neither.

My timing turned out to be flawless. I arrived on the cusp of the Internet age – they were wiring dorms for ethernet the year I enrolled. Maybe even more important, I arrived in the final, fading glory years of affordable state universities.

I worked multiple minimum wage jobs to put myself through school; day care, front desk, laundry, night audit. It was grueling, round the clock labor, but it was possible, if you were stubborn enough. I didn’t have a Social Security number (long story), I wasn’t old enough to take out loans, I couldn’t get financial aid because my parents didn’t file income taxes (again, long story). There was no help coming, I sank or I swam.

I found computers and the Internet around the same time as it dawned on me that everybody who studied music seemed to end up poor as an adult. I grew up too poor to buy canned vegetables or new underwear; we were like an 1800s family, growing our food, making our clothes, hand-me-downs til they fell apart.

Fuck being poor. Fuck it so hard. I was out.

I lost my music scholarship, but I started building websites and running systems for the university, then for local businesses. I dropped out and took a job in San Francisco. I went back, abortively; I dropped out again.

By the time I was 20 I was back in SF for good, making a salary five times what my father had made.

I grew up with a very coherent belief system that did not work for me

A lot of young people who flee their fundamentalist upbringing do so because they were abused and/or lost their faith, usually due to the hypocrisy of their leaders. Not me. I left home still believing the whole package – that evolution was a fraud, that the earth was created in seven days, that woman was created from Adam’s rib to be a submissive helpmate for their husband, that birth control was a sin, that anyone who believed differently was going to hell.

My parents loved us deeply and unshakably, and they were not hypocrites. In the places I grew up, the people who believed in God and went to church and lived a certain way were the ones who had their shit together, and the people who believed differently had broken lives. Reality seemed to confirm the truth of all we were taught, no matter how outlandish it sounds.

So I fully believed it was all true. I also knew it did not work for me. I did not want a small life. I did not want to be the support system behind some godly dude. I wanted power, money, status, fame, autonomy, success. I wanted to leave a crater in the world.

I was not a rebellious child, believe it or not. I loved my parents and wanted to make them proud. But as I entered my teens, I became severely depressed, and turned inward and hurt myself in all the ways young people do.

I left because staying there was killing me, and ultimately, I think my parents let me go because they saw it too.

Running away from things worked until it didn’t

I didn’t know what I wanted out of life other than all of it; right now, and my first decade out on my own was a hoot. It was in my mid twenties that everything started to fall apart.

I was an earnest kid who liked to study and think about the meaning of life, but when I bolted, I slammed the door to my conscience shut. I knew I was going to hell, but since I couldn’t live the other way, I made the very practical determination based on actuarial tables that I could to go my own way for a few decades, then repent and clean up my shit before I died. (Judgment Day was one variable that gave me heartburn, since it could come at any time.)

I was not living in accordance with my personal values and ethics, to put it lightly. I compartmentalized; it didn’t bother me, until it did. It started leaking into my dreams every night, and then it took over my waking life. I was hanging on by a thread; something had to give.

My way out, unexpectedly, started with politics. I started mainlining books about politics and economics during the Iraq War, which then expanded to history, biology, philosophy, other religious traditions, and everything else. (You can still find a remnant of my reading list here.)

When I was 13, I had an ecstatic religious experience; I was sitting in church, stewing over going to hell, and was suddenly filled with a glowing sense of warmth and acceptance. It lasted for nearly two weeks, and that’s how I knew I was “saved”.

In my late 20s, after a few years of intense study and research, I had a similar ecstatic experience walking up the stairs from the laundry room. I paused, I thought “maybe there is no God; maybe there is nobody out there judging me; maybe it all makes sense”, and it all clicked into place, and I felt high for days, suffused with peace and joy.

My career didn’t really take off until after that. I always had a job, but I wasn’t thinking about tech after hours. At first I was desperately avoiding my problems and self-medicating, later I became obsessed with finding answers. What did I believe about taxation, public policy, voting systems, the gender binary, health care, the whole messy arc of American history? I was an angry, angry atheist for a while. I filled notebook after notebook with handwritten notes; if I wasn’t working, I was studying.

And then, gradually, I wound down. The intensity, the high, tapered off. I started dating, realized I was poly and queer, and slowly chilled the fuck out. And that’s when I started being able to dedicate the creative, curious parts of my brain to my job in tech.

Why am I telling you all this?

Will Larson has talked a lot about how his underlying motivation is “advancing the industry”. I love that for him. He is such a structured thinker and prolific writer, and the industry needs his help, very badly.

For a while I thought that was my motivation too. And for sure, that’s a big part of it, particularly when it comes to observability and my day job. (Y’all, it does not need to be this hard. Modern observability is the cornerstone and prerequisite for high performing engineering teams, etc etc.)

But when I think about what really gets me activated on a molecular level, it’s a little bit different. It’s about living a meaningful life, and acting with integrity, and building things of enduring value instead of tearing them down.

When I say it that way, it sounds like sitting around on the mountain meditating on the meaning of life, and that is not remotely what I mean. Let me try again.

For me, work has been a source of liberation

It’s very uncool these days to love your job or talk about hard work. But work has always been a source of liberation for me. My work has brought me so much growth and development and community and friendship. It brings meaning to my life, and the joy of creation. I want this for myself. I want this for anyone else who wants it too.

I understand why this particular tide has turned. So many people have had jobs where their employers demanded total commitment, but felt no responsibility to treat them well or fairly in return. So many people have never experienced work as anything but a depersonalizing grind, or an exercise in exploitation, and that is heartbreaking.

I don’t think there’s anything morally superior about people who want their work to be a vehicle for personal growth instead of just a paycheck. I don’t think there’s anything wrong with just wanting a paycheck, or wanting to work the bare minimum to get by. But it’s not what I want for myself, and I don’t think I’m alone in this.

I feel intense satisfaction and a sense of achievement when I look back on my career. On a practical level, I’ve been able to put family members through college, help with down payments, and support artists in my community. All of this would have been virtually unimaginable to me growing up.

I worked a lot harder on the farm than I ever have in front of a keyboard, and got a hell of a lot less for my efforts.

(People who glamorize things like farming, gardening, canning and freezing, taking care of animals, cooking and caretaking, and other forms of manual labor really get under my skin. All of these things make for lovely hobbies, but subsistence labor is neither fun nor meaningful. Trust me on this one.)

My engineer/manager pendulum days

I loved working as an engineer. I loved how fast the industry changes, and how hard you have to scramble to keep up. I loved the steady supply of problems to fix, systems to design, and endless novel catastrophes to debug. The whole Silicon Valley startup ecosystem felt like it could not have been more perfectly engineered to supply steady drips of dopamine to my brain.

I liked working as an engineering manager. Eh, that might be an overstatement. But I have strong opinions and I like being in charge, and I really wanted more access to information and influence over decisions, so I pushed my way into the role more than once.

If Honeycomb hadn’t happened, I am sure I would have bounced back and forth between engineer and manager for the rest of my career. I never dreamed about climbing the ladder or starting a company. My attitude towards middle management could best be described as amiable contempt, and my interest in the business side of things was nonexistent.

I have always despised people who think they’re too good to work for other people, and that describes far too many of the founders I’ve met.

Operating a company draws on a different kind of meaning

I got the chance to start a company in 2016, so I took it, almost on a whim. Since then I have done so many things I never expected to do. I’ve been a founder, CEO, CTO, I’ve raised money, hired and fired other execs, run organizations, crafted strategy, and come to better understand and respect the critical role played by sales, marketing, HR, and other departments. No one is more astonished than I am to find me still here, still doing this.

But there is joy to be found in solving systems problems, even the ones that are less purely technical. There is joy to be found in building a company, or competing in a marketplace.

To be honest, this is not a joy that came to me swiftly or easily. I’ve been doing this for the past 9.5 years, and I’ve been happy doing it for maybe the past 2-3 years. But it has always felt like work worth doing. And ultimately, I think I’m less interested in my own happiness (whatever that means) than I am interested in doing work that feels worth doing.

Work is one of the last remaining places where we are motivated to learn from people we don’t agree with and find common pursuit with people we are ideologically opposed to. I think that’s meaningful. I think it’s worth doing.

Reality doesn’t give a shit about ideology

I am a natural born extremist. But when you’re trying to operate a business and win in the marketplace, ideological certainty crashes hard into the rocks of reality. I actually find this deeply motivating.

I spent years hammering out my own personal ontological beliefs about what is right and just, what makes a life worth living, what responsibilities we have to each another. I didn’t really draw on those beliefs very often as an engineer/manager, at least not consciously. That all changed dramatically after starting a company.

It’s one thing to stand off to the side and critique the way a company is structured and the decisions leaders make about compensation, structure, hiring/firing, etc. But creation is harder than critique (one of my favorite Jeff Gray quotes) — so, so, so much harder. And reality resists easy answers.

Being an adult, to me, has meant making peace with a multiplicity of narratives. The world I was born into had a coherent story and a set of ideals that worked really well for a lot of people, but it was killing me. Not every system works for every person, and that’s okay. That’s life. Startups aren’t for everyone, either.

The struggle is what brings your ideals to life

Almost every decision you make running a company has some ethical dimension. Yet the foremost responsibility you have to your stakeholders, from investors to employees, is to make the business succeed, to win in the marketplace. Over-rotating on ethical repercussions of every move can easily cause you to get swamped in the details and fail at your prime directive.

Sometimes you may have a strongly held belief that some mainstream business practice is awful, so you take a different path, and then you learn the hard way why it is that people don’t take that path. (This has happened to me more times than I can count. 🙈)

Ideals in a vacuum are just not that interesting. If I wrote an essay droning on and on about “leading with integrity”, no one would read it, and nor should they. That’s boring. What’s interesting is trying to win and do hard things, while honoring your ideals.

Shooting for the stars and falling short, innovating, building on the frontier of what’s possible, trying but failing, doing exciting things that exceed your hopes and dreams with a team just as ambitious and driven as you are, while also holding your ideals to heart — that’s fucking exciting. That’s what brings your ideals to life.

We have lived through the golden age of tech

I recognize that I have been profoundly lucky to be employed through the golden age of tech. It’s getting tougher out there to enter the industry, change jobs, or lead with integrity.

It’s a tough time to be alive, in general. There are macro scale political issues that I have no idea how to solve or fix. Wages used to rise in line with productivity, and now they don’t, and haven’t since the mid 70s. Capital is slurping up all the revenue and workers get an ever decreasing share, and I don’t know how to fix that, either.

But I don’t buy the argument that just because something has been touched by capitalism or finance it is therefore irreversibly tainted, or that there is no point in making capitalist institutions better. The founding arguments of capitalism were profoundly moral ones, grounded in a keen understanding of human nature. (Adam Smith’s “Wealth of Nations” gets all the attention, but his other book, “Theory of Moral Sentiments”, is even better, and you can’t read one without the other.)

As a species we are both individualistic and communal, selfish and cooperative, and the miracle of capitalism is how effectively it channels the self-interested side of our nature into the common good.

Late stage capitalism, however, along with regulatory capture, enshittification, and the rest of it, has made the modern world brutally unkind to most people. Tech was, for a shining moment in time, a path out of poverty for smart kids who were willing to work their asses off. It’s been the only reliable growth industry of my lifetime.

It remains, for my money, the best job in the world. Or it can be. It’s collaborative, creative, and fun; we get paid scads of money to sit in front of a computer and solve puzzles all day. So many people seem to be giving up on the idea that work can ever be a place of meaning and collaboration and joy. I think that sucks. It’s too soon to give up! If we prematurely abandon tech to its most exploitative elements, we guarantee its fate.

If you want to change the world, go into business

Once upon a time, if you had strongly held ideals and wanted to change the world, you went into government or nonprofit work.

For better or for worse (okay, mostly worse), we live in an age where corporate power dominates. If you want to change the world, go into business.

The world needs, desperately, people with ethics and ideals who can win at business. We can’t let all the people who care about people go into academia or medicine or low wage service jobs. We can’t leave the ranks of middle and upper management to be filled by sycophants and sociopaths.

There’s nothing sinister about wanting power; what matters is what you do with it. Power, like capitalism, is a tool, and can be bent to powerful ends both good and evil. If you care about people, you should be unashamed about wanting to amass power and climb the ladder.

There are a lot of so-called best practices in this industry that are utterly ineffective (cough, whiteboarding B-trees in an interview setting), yet they got cargo culted and copied around for years. Why? Because the company that originated the practice made a lot of money. This is stupid, but it also presents an opportunity. All you need to do is be a better company, then make a lot of money. 😉

People need institutions

I am a fundamentalist at heart, just like my father. I was born to be a bomb thrower and a contrarian, a thorn in the side of the smug moderate establishment. Unfortunately, I was born in an era where literally everyone is a fucking fundamentalist and the establishment is holding on by a thread.

I’ve come to believe that the most quietly radical, rebellious thing I can possibly do is to be an institutionalist, someone who builds instead of performatively tearing it all down.

People need institutions. We crave the feeling of belonging to something much larger than ourselves. It’s one of the most universal experiences of our species.

One of the reasons modern life feels so fragmented and hard is because so many of our institutions have broken down or betrayed the people they were supposed to serve. So many of the associations that used to frame our lives and identities — church, government, military, etc — have tolerated or covered up so much predatory behavior and corruption, it no longer surprises anyone.

We’ve spent the past few decades ripping down institutions and drifting away from them. But we haven’t stopped wanting them, or needing them.

I hope, perhaps naively, that we are entering into a new era of rebuilding, sadder but wiser. An era of building institutions with accountability and integrity, institutions with enduring value, that we can belong to and take pride in… not because we were coerced or deceived, not because they were the only option, but because they bring us joy and meaning. Because we freely choose them, because they are good for us.

The second half of your career is about purpose

It seems very normal to enter the second half of your 40 year career thinking a lot about meaning and purpose. You spend the first decade or so hoovering up skill sets, the second finding your place and what feeds you, and then, inevitably, you start to think about what it all means and what your legacy will be.

That’s definitely where I’m at, as I think about the second half of my career. I want to take risks. I want to play big and win bigger. I want to show that hard work isn’t just a scam inflicted on those who don’t know any better. If we win, I want the people I work with to earn lifechanging amounts of money, so they can buy homes and send their kids to college. I want to show that work can still be an avenue for liberation and community and personal growth, for those of us who still want that.

I care about this industry and the people in it so much, because it’s been such a gift to me. I want to do what I can to make it a better place for generations to come. I want to build institutions worth belonging to.

Thoughts on Motivation and My 40-Year Career

Corporate “DEI” is an imperfect vehicle for deeply meaningful ideals

mipsytipsy, , , , , 12 Comments

I have not thought or said much about DEI (Diversity, Equity and Inclusion) over the years. Not because I don’t care about the espoused ideals — I suppose I do, rather a lot — but because corporate DEI efforts have always struck me as ineffective and bland; bolted on at best, if not actively compensating for evil behavior.

I know how crisis PR works. The more I hear a company natter on and on about how much it cares for the environment, loves diversity, values integrity, yada yada, the more I automatically assume they must be covering their ass for some truly heinous shit behind closed doors.

My philosophy has historically been that actions speak louder than words. I would one million times rather do the work, and let my actions speak for themselves, than spend a lot of time yapping about what I’m doing or why.

I also resent being treated like an expert in “diversity stuff”, which I manifestly am not. As a result, I have always shrugged off any idea that I might have some personal responsibility to speak up or defend these programs.

Recent events (the tech backlash, the govt purge) have forced me to sit down and seriously rethink my operating philosophy. It’s one thing to be cranky and take potshots at corporate DEI efforts when they seem ascendant and powerful; it’s another when they are being stamped out and reviled in the public mind.

Actually, my work does not speak for itself

It took all of about thirty seconds to spot my first mistake, which is that no, actually, my work does not and cannot speak for itself. 🤦 No one’s does, really, but especially not when your job literally consists of setting direction and communicating priorities.

Maybe this works ok at a certain scale, when pretty much anyone can still overhear or participate in any topic they care about. But at some point, not speaking up at the company level sends its own message.

If you don’t state what you care about, how are random employees supposed to guess whether the things they value about your culture are the result of hard work and careful planning, or simply…emergent properties? Even more importantly, how are they supposed to know if your failures and shortcomings are due to trying but failing or simply not giving a shit?

These distinctions are not the most important (results will always matter most), but they are probably pretty meaningful to a lot of your employees.

The problem isn’t the fact that companies talk about their values, it’s that they treat it like a branding exercise instead of an accountability mechanism.

Fallacy #1: “DEI is the opposite of excellence or high performance”

There are two big category errors I see out there in the world. To be clear, one is a lot more harmful (and a lot more common, and increasingly ascendant) than the other, but both of these errors do harm.

The first error is what I heard someone call the “seesaw fallacy”: the notion that DEI and high performance are somehow linked in opposition to each other, like a seesaw; getting more of one means getting less of the other.

This is such absolute horseshit. 🙄 It fails basic logic, as well as not remotely comporting with my experience. You can kind of see where they’re coming from, but only by conveniently forgetting that every team and every company is a system.

Nobody is born a great engineer, or a great designer, or a great employee of any type. Great contributors are not born, they are forged — over years upon years of compounding experiences: education, labor, hard work, opportunities and more.

So-called “merit-based” hiring processes act like outputs are the only thing that matter; as though the way people show up on your doorstep is the way they were fated to be and the way they will always be. They don’t see people as inputs to the system — people with potential to grow and develop, people who may have been held back or disregarded in the past, people who will achieve a wide range of divergent outcomes based on the range of different experiences they may have in your system.

Fallacy #2: “DEI is the definition of excellence or high performance”

There is a mirror image error on the other end of the spectrum, though. You sometimes hear DEI advocates talk as though if you juuuust build the most diverse teams and the most inclusive culture, you will magically build better products and achieve overwhelming success in all of your business endeavors.

This is also false. You still have to build the fucking business! Your values and culture need to serve your business and facilitate its continued existence and success.

With the small caveat that … DEI isn’t the way you define excellence unless the way you define excellence is diversity, equity and inclusion, because “excellence” is intrinsically a values statement of what you hold most dear. This definition of excellence would not make sense for a profit-driven company, but valuing diverse teams and an inclusive culture over money and efficiency is a perfectly valid and coherent stance for a person to take, and lots of people do feel this way!

There is no such thing as the “best” or “right” values. Values are a way of navigating territory and creating alignment where there IS no one right answer. People value what they value, and that is their right.

DEI gets caricatured in the media as though the goal of DEI is diverse teams and equitable outcomes. But DEI is better seen as a toolkit. Your company values ought to help you achieve your goals, and your goals as a business usually some texture and nuance beyond just profit. At Honeycomb, for example, we talk about how we can “build a company people are proud to be part of”. DEI can help with this.

Let’s talk about MEI (Merit, Excellence and Intelligence)

Until last month I remained blissfully unaware of MEI, or “Merit, Excellence and Intelligence” (sic), and if you were too until just this moment, I apologize for ruining your party.

This idea that DEI is the opposite of MEI is particularly galling to me. I care a lot about high-performing teams and building an environment where people can do the best work of their lives. That is why I give a shit about building an inclusive culture.

An inclusive culture is one that sets as many people as possible up to soar and succeed, not just the narrow subset of folks who come pre-baked with all of life’s opportunities and advantages. When you get better at supporting folks and building a culture that foregrounds growth and learning, this both raises the bar for outcomes for everyone, and broadens the talent base you can draw from.

Honestly, I can’t think of anything less meritocratic than simply receiving and replicating all of society’s existing biases. Do you have any idea how much talent gets thrown away, in terms of unrealized potential? Let’s take a look at some of those stories from recent history.

If you actually give a shit about merit, you have to care about inclusion

Remember the Susan Fowler blog post that led to Travis Kalanick’s ouster as CEO of Uber in 2017? I suggest going back and skimming that post again, just to remind yourself what an absolutely jaw-dropping barrage of shit she went through, starting with being propositioned for sex by her very own manager on her very first day.

In “What You Do Is Who You Are”, investor Ben Horowitz wrote,”By all accounts Kalanick was furious about the incident, which he saw as a woman being judged on issues other than performance.” He believed that by treating her this way, his employees were failing to live up to their stated values around meritocracy.

I think that’s a flawed (but revealing) response to the situation at hand. Treating this like a question of “merit” suggests that they should be prioritizing the needs of whoever was most valuable to the company. And it kind of seems like that’s exactly what Kalanick’s employees were trying to do.

Susan was brilliant, yes; she was also young (25!) small, quiet, with a soft voice, in a corporate environment that valued aggression and bombast. She was early in her career and comparatively unproven; and when she reported her engineering manager’s persistent sexual advances and retaliatory actions to HR, she was told that HE was the high performer they couldn’t afford to lose.

Ask yourself this: would the manager’s behavior have been any more acceptable if Susan had been a total fuckup, instead of a certifiable genius? (NO. 😡)

Susan’s piece also noted that the percentage of women in Uber’s SRE org dropped from 25% to 3% across that same one year interval. Alarm bells were going off all over the place for an entire year, and nobody gave a shit, because an inclusive culture was nowhere on their radar as a thing that mattered.

There is no rational conversation to be had about merit that does not start with inclusion

You might know (or think you know) who your highest performers are today, but you do not know who will be on that list in six months, one year, five years. Your company is a system, and the environment you build will drive behaviors that help determine who is on that list.

Maybe you have a Susan Fowler type onboarding at your company right now. How confident are you that she will be treated fairly and equitably, that she will feel like she belongs? Do you think she might be underestimated due to her gender or presentation? Do you think she would want to stick around for the long haul? Will she be motivated to do her best work in service of your mission? Why?

Can you say the same about all your employees, not just ones you already know to be certifiable geniuses?

That’s inclusion. That’s how you build a real fucking meritocracy. You start with “do not tolerate the things that kneecap your employees in their pursuit of excellence”, and ESPECIALLY not the things that subject them to the compounding tax of being targeted for who they are. In life as in finance, it’s the compound interest that kills you, more than the occasional expensive purchase.

There’s more to merit and excellence than just inclusion, obviously, but there’s no rational adult conversation to be had about merit or meritocracy that doesn’t start there.

Susan left the tech industry, by the way. She seems to be doing great, of course, but what a loss for us.

If you give a shit about merit, tell me what you are doing to counteract bias

Anyone who talks a big game about merit, but doesn’t grapple with how to identify or counteract the effects of bias in the system, doesn’t really care about merit at all. What they actually want is what Ijeoma Oluo calls “entitlement masquerading as meritocracy” (“Mediocre”).

The “just world fallacy” is one of those cognitive biases that will be with us forever, because we have such a deep craving for narrative coherence. On a personal level, we are embodied beings awash with intrinsic biases; on a societal level, obviously, structural inequities abound. No one is saying we should aim for equality of outcomes, despite what some nutbag MEI advocates seem to think.

But anyone who truly cares about merit should feel compelled to do at least some work to try and lean against the ways our biases cause us to systematically under-value, under-reward, under-recognize, and under-promote some people (and over-value others). Because these effects add up to something cumulatively massive.

In the Amazon book “Working Backwards”, chapter 2, they briefly mention an engineering director who “wanted to increase the gender diversity of their team”, and decided to give every application with a female-gendered name a screening call. The number of women hired into that org “increased dramatically”.

That’s it — that’s the only tweak they made. They didn’t change the interview process, they didn’t “lower the bar”, they didn’t do anything except skip the step where women’s resumes were getting filtered out due to the intrinsic biases of the hiring managers.

There’s no shame in having biases — we all have them. The shame is in making other people pay the price for your unexamined life..

DEI is an imperfect vehicle for deeply meaningful ideals

I am by no means trying to muster a blanket defense of everything that gets lumped under DEI, just to be clear. Some of it is performative, ham-handed, well-intentioned but ineffective, disconnected or a distraction from real problems; diversity theater; a steam valve to vent off any real pressure for change; nitpicky and authoritarian, flirts with thought policing, or just horrendously cringe.

I don’t know how much I really care whether corporate DEI programs live or die, because I never thought they were that effective to start with. Jay Caspian Kang wrote a great piece in the New Yorker that captured my feelings on the matter:

The problem, at a grand scale, is that D.E.I.’s malleability and its ability to survive in pretty much every setting, whether it’s a nearby public school or the C.I.A., means that it has to be generic and ultimately inoffensive, which means that, in the end, D.E.I. didn’t really satisfy anyone.

What it did was provide a safety valve (I am speaking about D.E.I. in the past tense because I do think it will quickly be expunged from the private sector as well) for institutions that were dealing with racial and social-justice problems. If you had a protest on campus over any issue having to do with “diverse students” who wanted “equity,” that now became the provenance of D.E.I. officers who, if they were doing their job correctly, would defuse the situation and find some solution—oftentimes involving a task force—that made the picket line go away.

~Jay Caspian Kang, “What’s the Point of Trump’s War on DEI?”

It’s a symbolic loss of something that was only ever a symbolic gain. Corporate DEI programs as we know them sprung up in the wake of the Black Lives Matter protests of 2020, but I haven’t exactly noticed the world getting substantially more diverse or inclusive since then.

Which is not to say that tech culture has not gotten more diverse or inclusive over the longer arc of my career; it absolutely, definitely has. I began working in tech when I was just a teenager, over 20 years ago, and it is actually hard to convey just how much the world has changed since then.

And not because of corporate DEI policies. So why? Great question. 🙌

Tech culture changed because hearts and minds were changed

I think social media explains a lot about why awareness suddenly exploded in the 2010s. People who might never have intentionally clicked a link about racism or sexism were nevertheless exposed to a lot of compelling stories and arguments, via retweets and stuff ending up in their feed. I know this, because I was one of them.

The 2010s were a ferment of commentary and consciousness-raising in tech. A lot of brave people started speaking up and sharing their experiences with harassment, abuse, employer retaliation, unfair wage practices, blatant discrimination, racism, predators.. you name it. People were comparing notes with each other and realizing how common some of these experiences were, and developing new vocabulary to identify them — “missing stair”, “sandpaper feminism”, etc.

If you were in tech and you were paying attention at all, it got harder and harder to turn a blind eye. People got educated despite themselves, and in the end…many, many hearts and minds were changed.

This is what happened to me. I came from a religious and political background on the far right, but my eyes were opened. The more I looked around, the more evidence I saw in support of the moral and intellectual critiques I was reading online. I began waking up to some of the ways I had personally been complicit in doing harm to others.

The “unofficial affirmative action movement” in tech, circa 2010-2020

And I was not alone. Emily once offhandedly referred to an “unofficial affirmative action movement” in tech, and this really struck a chord with me. I know so many people whose hearts and minds were changed, who then took action.

They worked to diversify their personal networks of friends and acquaintances; to mentor, sponsor, and champion underrepresented folks in their workplaces; to recruit, promote, and refer women and people of color; to invite marginalized folks to speak at their conferences and on their panels; to support codes of conduct and unconscious bias training; and to educate themselves on how to be better allies in general.

All of this was happening for at least a decade leading up to 2020, when BLM shook up the industry and led to the creation of many corporate DEI initiatives. Kang, again:

What happened in many workplaces across the country after 2020 was that the people in charge were either genuinely moved by the Floyd protests or they were scared. Both the inspired and the terrified built out a D.E.I. infrastructure in their workplaces. These new employees would be given titles like chief diversity officer or C.D.O., which made it seem like it was part of the C-suite, and would be given a spot at every table, but much like at Stanford Law, their job was simply to absorb and handle any race stuff that happened.

The pivot from lobbying/persuading from the outside to holding the levers of formal power is a hard, hard one to execute well. History is littered with the shells of social movements that failed to make this leap.

You got here because you persuaded and earned credibility based on your stories and ideals, and now people are handing you the reins to make the rules. What do you do with them? Uh oh.

It’s easier to make rules and enforce them than it is to change hearts and minds

I think this happened to a lot of DEI advocates in the 2020-2024 era, when corporations briefly invested DEI programs and leaders with some amount of real corporate power, or at least the power to make petty rules. And I do not think it served our ideals well.

I just think…there’s only so much you can order people to do, before it backfires on you. Which doesn’t mean that laws and policies are useless; far from it. But they are limited. And they can trigger powerful backlash and resentment when they get overused as a means of policing people’s words and behaviors, especially in ways that seem petty or disconnected from actual impact.

When you lean on authority to drive compliance, you also stop giving people the opportunity to get on board and act from the heart.

MLK actually has a quote on this that I love, where he says “the law cannot make a man love me”:

“It may be true that the law cannot make a man love me, religion and education will have to do that, but it can restrain him from lynching me. And I think that’s pretty important also. And so that while legislation may not change the hearts of men, it does change the habits of men.”

~ Dr. Martin Luther King, Jr.

There are ways that the DEI movement really lost me around the time they got access to formal levers of power. It felt like there was a shift away from vulnerability and persuasion and towards mandates and speech policing.

Instead of taking the time to explain why something mattered, people were simply ordered to conform to an ever-evolving, opaque set of speech patterns as defined by social media. Worse, people sometimes got shamed or shut down for having legitimate questions.

There’s a big difference between saying that “marginalized people shouldn’t have to constantly have to defend their own existence and do the work of educating other people” (hard agree!), and saying that nobody should have to persuade or educate other folks and bring them along.

We do have to persuade, we do have to bring people along with us. We do have to fight for hearts and minds. I think we did a better job of this without the levers of formal power.

Don’t underestimate what a competitive advantage diversity can be

People have long marveled at the incredible amount of world class engineering talent we have always had at Honeycomb — long before we even had any customers, or a product to sell them. How did we manage this? The relative diversity of our teams has always been our chief recruiting asset.

There is a real hunger out there on the part of employees to work at a company that does more than the bare minimum in the realm of ethics. Especially as AI begins chewing away at historically white collar professions, people are desperate for evidence that you can be an ambitious, successful, money-making business that is unabashed about living its values and holding a humane, ethical worldview.

And increasingly, one of the main places people go to look for evidence that your company has ethical standards and takes them seriously is…the diversity of your teams.

Diversity is an imperfect proxy for corporate ethics, but it’s not a crazy one.

The diversity of your teams over the long run rests on your ability to build an inclusive culture and equitable policies. Which depends on your ability to infuse an ethical backbone throughout your entire company; to balance short-term and long-term investments, as you build a company that can win at business without losing its soul.

And I’m not actually talking about junior talent. Competition is so fierce lower on the ladder, those folks will usually take whatever they can get. (💔) I’m talking about senior folks, the kind of people who have their pick of roles, even in a weak job market. You might be shocked how many people out there will walk away from millions/year in comp at Netflix, Meta or Google, in order to work at a company where ethics are front and center, where diversity is table stakes, where their reporting chain and the executive team do not all look alike.

The longer you wait to build in equity and inclusion, the tougher it will be

Founders and execs come up to me rather often and ask what the secret is to hiring so many incredible contributors from underrepresented backgrounds. I answer: “It’s easy!…if you already have a diverse team.”

It is easier to build equitable programs and hire diverse teams early, and not drive yourself into a ditch, than it is to go full tilt with a monoculture and face years of recovery and repair. The longer you wait to do the work, the harder the work is going to be. Don’t put it off.

As I wrote a while back:

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

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

~ Pragmatism, Neutrality and Leadership

It can be a massive competitive advantage if you build a company that knows how to develop a deep bench of talent and set people up for success.

Not only the preexisting elite, the smartest and most advantaged decile of talent — for whom competition will always be cutthroat — but people from broader walks of life.

Winning at business is what earns you the right to make bigger bets and longer-term investments

As the saying goes, “Nobody ever got fired for buying IBM” — and nobody ever had the failure of their startup blamed on the fact that they hired engineers away (or followed management practices) from Google, Netflix or Facebook, regardless of how good or bad those engineers (or practices) may be.

If you want to do something different, you need to succeed. People cargo cult the culture of places that make lots of money.

If you want your values and ideals to spread throughout the industry, the most impactful thing you can possibly do is win.

It’s a reality that when you’re a startup, your resources are scarce, your time horizons are short. You have to make smart decisions about where to invest them. Perfection is the enemy of success. Make good choices, so you can live to fight another day.

But fight another day.

If you don’t give a shit, don’t try and fake it

Finally let me say this: if you don’t give a shit about diversity or inclusion, don’t pretend you give a shit. It isn’t going to fool anyone. (If you “really care” but for some reason DEI loses every single bake-off for resources, friend, you don’t care.)

And honestly, as an employee, I would rather work for a soulless corporation that is honest with itself and its employees about how decisions get made, than for someone who claims to care about the things I value, but whose actions are unpredictable or inconsistent with those values.

Listen.. There is never just one true way to win. There are many paths up the mountain. There are many ways to win. (And there are many, many, many more ways to fail.)

Nothing that got imported or bolted on to your company operating system was ever going to work, anyway. 🤷 If it doesn’t live on in the hearts and minds of the people who are building the strategy and executing on it, they are dead words.

When I look at the long list of companies who say they are rolling back mentions to DEI internally, I don’t get that depressed. I see a long list of companies who never really meant it anyway. I’m glad they decided to stop performing.

You need a set of operating practices and principles that are internally consistent and authentic to who you are. And you need to do the work to bring people along with you, hearts and minds and all.

So if we care about our ideals, let’s go fucking win.

 

 

Corporate “DEI” is an imperfect vehicle for deeply meaningful ideals

“Founder Mode” and the Art of Mythmaking

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

How might another person have told this story?

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

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

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

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

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

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

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

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

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

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

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

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

The story, in Brian Chesky’s words

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

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

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

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

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

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

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

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

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

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

Sounds like a mess, all right.

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

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

Which brings us to our first lesson on efficiency.

You should have as few employees as possible

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

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

Brooks’ Law

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

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

Your managers should be subject matter experts

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Deep breaths.

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

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

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

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

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

Great leadership is presence, not absence

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

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

A-fucking-men.

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

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

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

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

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

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

Whuf.

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

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

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

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

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

His co-author, Erin Meyer, chimes in:

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

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

There are many paths up the mountain

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

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

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

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

But wait — it gets worse. 😅

Should the CEO interview every candidate?

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

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

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

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

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

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

It keeps getting worse! Here comes the low point.

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

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

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

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

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

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

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

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

Executive hiring fails when you hire someone at the wrong stage

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

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

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

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

References are critical for building confidence in your hires

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

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

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

This trick doesn’t fool anybody.

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

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

A basket of interviewing tips and tricks

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

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

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

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

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

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

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

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

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

There is no such thing as the ‘best people’

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

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

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

Not the “best” people. 

The right people.

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

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

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

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

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

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

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

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

Hypergrowth is hazardous to your company’s health

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

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

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

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

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

The CEO-centric view of the universe

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

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

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

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

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

Yeah, bro. You do.

 

“Founder Mode” and the Art of Mythmaking

How Hard Should Your Employer Work To Retain You?

mipsytipsy, , , 6 Comments

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Some amount of employee turnover is natural and healthy

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

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

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

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

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

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

Sometimes people sit in critical roles at critical moments

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

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

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

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

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

Note that these are not necessarily the same two lists!

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

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

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

Get to know your superstars, and compensate them

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

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

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

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

Work on a plan to de-risk your SPOFs

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

A few checks and balances to consider:

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

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

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

People work at jobs for money, but not only money

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

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

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

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

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

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

 

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

How Hard Should Your Employer Work To Retain You?

Pragmatism, Neutrality and Leadership

mipsytipsy, , , , , 2 Comments

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

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

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

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

So here goes.

Caveats, challenges and cautionary tales

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

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

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

As a leader, your job is to succeed

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

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

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

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

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

Know your mission, craft a strategy, execute

And how do you do that?

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

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

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

Your culture serves the business, not the other way around

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

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

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

Companies with shitty cultures win all the time

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

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

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

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

Good culture is rooted in organizational health

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

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

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

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

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

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

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

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

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

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

And yet.

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

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

Living your values takes planning and sacrifice

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The value (and limitations) of neutrality

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

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

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

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

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

Good leaders don’t invite unnecessary controversy

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

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

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

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

Good leaders don’t make it all about them

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

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

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

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

Good leaders look for ways to de-escalate

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

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

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

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

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

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

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

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

Good leaders connect the culture to the mission

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Shit?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Pragmatism, Neutrality and Leadership

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

mipsytipsy, , , , , 18 Comments

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

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

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

— Unnecessary Overhead(?!?)

Oh boy, there’s a lot to unpack here.

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

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

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

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

Why does hierarchy exist in organizations?

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

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

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

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

Hierarchy is a property of self-organizing systems

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

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

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

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

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

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

The false binary of sociotechnical systems

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

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

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

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

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

Ehhh… 😉

Engineering managers are a useful abstraction

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

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

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

Manager calendars vs maker calendars

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

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

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

Management is a tool for accountability

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

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

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

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

Choose Boring technology Culture

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

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

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

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

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

More lines of code != more productivity

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

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

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

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

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

Are managers ever unnecessary overhead?

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

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

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

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

But yes, managers can absolutely be unnecessary overhead.

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

<3 charity

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

 

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

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

mipsytipsy, , , , , 31 Comments

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

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

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

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

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

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

Miserable managers have miserable reports

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

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

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

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

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

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

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

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

Good engineering managers are force multipliers

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

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

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

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

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

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

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

Why should you (or anyone) be a manager?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

People skills are persistent

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

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

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

One cautionary note

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

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

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

charity

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

 

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

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

mipsytipsy, , , 28 Comments

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

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

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

Tips for Careful Communication

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

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

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

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

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

Acknowledge it is hard beforehand:

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

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

… or check in afterwards.

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

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

Speak tentatively.

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

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

Try to sound friendly.

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

Take a breath.

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

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

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

“The story in my head”.

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

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

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

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

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

Communicate positive intent.

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

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

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

Give people the opening to do better.

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

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

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

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

and maybe next time it will start off like…

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

Remember the handicaps, value the effort.

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

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

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

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

 

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

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

mipsytipsy, , , , , 1 Comment

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?”

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

mipsytipsy, , , 2 Comments

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Failure is always a question of when, not if

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

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

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

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

Rituals exist to instill values and train culture

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

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

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

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

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

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

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

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

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

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

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

I can understand why people now find this story horrifying

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

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

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

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

Even:

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

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

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

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

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

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