tech culture

Thoughts on Motivation and My 40-Year Career

mipsytipsy, , , , , , 28 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

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

How “Engineering-Driven” Leads to “Engineering-Supremacy”

mipsytipsy, , , , , 11 Comments

Honeycomb has a reputation for being a very engineering-driven company. No surprise there, since it was founded by two engineers and our mission involves building an engineering product for other engineers.

We are never going to stop being engineering-driven in the sense that we are building for engineers and we always want engineers to have a seat at the table when it comes to what we build, and how, and why. But I am increasingly uncomfortable with the term “engineering-driven” and the asymmetry it implies.

We are less and less engineering-driven nowadays, for entirely good reasons — we want this to be just as much of a design-driven company and a product-driven company, and I would never want sales or marketing to feel like anything other than equal partners in our journey towards revolutionizing the way the world builds and runs code in production.

It is true that most honeycomb employees were engineers for the first few years, and our culture felt very engineer-centric. Other orgs were maybe comprised of a person or two, or had engineers trying to play them on TV, or just felt highly experimental.

But if there is one thing Christine and I were crystal clear on from the beginning, it’s this:

✨WE ARE HERE TO BUILD A BUSINESS✨

Not just the shiniest, most hardcore tech, not just the happiest, most diverse teams. These things matter to us — they matter a lot! But succeeding at business is what gives us the power to change the world in all of these other ways we care about changing it.

If business is booming and people are thirsty for more of whatever it is you’re serving, you pretty much get a blank check for radical experiments in sociotechnical transformation, be that libertarian or communitarian or anything in between.

If you don’t have the business to back it up, you get fuck-all.

Not only do you not get shit, you risk being pointed out as a Cautionary Tale of “what happens if $(thing you deeply care about) comes true.” Sit on THAT for a hot second. 😕

So yes, we cared. Which is not to say we knew how to build a great business. We most certainly did not. But both of us had been through too many startups (Linden Lab, Aardvark, Parse, etc) where the tech was amazing, the people were amazing, the product was amazing … and the business side just did not keep up. Which always leads to the same thing: heartbreak and devastation.

✨IF you can’t make it profitable✨
✨your destiny will inevitably be✨
✨taken out of your hands✨
✨and given to someone else.✨

So Christine and I have been repeating these twin facts back and forth to each other for over six years now:

  1. Honeycomb must succeed as a revenue-generating, eventually profitable business.
  2. We are not business experts. Therefore we have to make Honeycomb a place that explicitly values business expertise, that places it on the same level as engineering expertise.

We have worked hard to get better at understanding the business side (her more than me 🙃) but ultimately, we cannot be the domain experts in marketing or sales (or customer success, support, etc).

What we could do is demonstrate respect for those functions, bake that respect into our culture, and hire and support amazing business talent to run them with us.

On being “engineering-driven”

Self-described “engineering-driven” companies tend to fall into one of two traps. Either they alienate the business side by pinching their nose and holding business development at arm’s length (“aaahhh, i’m just an engineer! I have no interest in or capacity for participating in developing our marketing voice or sales pitch decks, get off me!”), or they act like engineering is a sort of super-skillset that makes you capable of doing everybody else’s job better than they possibly could. As though those other disciplines and skill sets aren’t every bit as deep and creative and challenging in their own right as developing software can be.

For the first few years we really did use engineers for all of those functions. We were trying to figure out how to build and explain and sell something new, which meant working out these things on the ground every day with our users. Engineer to engineer. What resonated? What clicked? What worked?

So we hired just a few engineers who were interested in how the business worked, and who were willing to work like Swiss Army knives across the org. We didn’t yet have a workable plan in place, which is what you need in order to bring domain experts on board, point them in a direction, and trust them to do what they do best in executing that plan.

Like I said, we didn’t know what to do or how to do it. But at least we knew that. Which kept us humble. And translated into a hard, fast rule which we set early on in our hiring process:

We DO NOT hire engineers who talk shit about sales and marketing.

If I was interviewing an engineer and they made any alienating sort of comment whatsoever about their counterparts on the business side, it was an automatic no. Easy out. We had a zero tolerance policy for talking down down about other functions, or joking, even for being unwilling to perform other business functions.

In retrospect, I think this is one of the best decisions we ever made.

Hiring engineers who respected other functions

We leaned hard into hiring engineers who asked curious questions about our business strategy and execution. We pursued engineers who talked about wanting to spend time directly with users, who were intrigued by the idea of writing marketing copy to help explain concepts to engineers, and who were ready, willing and able to go along on sales calls.

Once we finally found product-market fit, about 2-3 years ago, we stopped using engineers to play other roles and started hiring actual professionals in product, design, marketing, sales, customer success, etc to build and staff out their organizations. That was when we first started building the business for the longer term; until we found PMF, our event horizon was never more than 1-3 months ahead of “right now”.

(I’ll never forget going out to coffee with one of our earlier VPs of marketing, shortly after she was hired, and having her ask, in bemusement: “Why are all these engineers just sitting around in the #marketing channel? I’ve never had so many people giving opinions on my work!” 🙃)

Those early Swiss Army knife engineers have since stepped back, gratefully, into roles more centered around engineering. But that early knee-jerk reaction of ours established an important company norm that pays dividends to this day.

Every function of the business is equally challenging, creative, and worthy of respect. None of us are here to peacock; our skill sets serve the primary business goals. We all do our jobs better when we know more about how each other’s functions work.

These days, it’s not just about making sure we hire engineers who treat business counterparts like equals. It’s more about finding ways to stimulate the flow of information cross-functionally, creating a hunger for this information.

Caring about the big picture is a ✨learnable skill✨

You can try to hire people who care about the overall business outcomes, not just their own corner of reality, and we do select for this to  some degree — for all roles, not just engineers.

But you can also foster this curiosity and teach people to seek it out. Curiosity begets curiosity, and every single person at Honeycomb is doing something interesting. We all want to succeed and win together, and there’s something infectious and exciting about connecting all the dots that lead to success and reflecting that story back to the rest of the company.

For example,

    1. Every time we close a deal, a post gets written up and dropped into the announcements slack by the sales team. Not just who did we close and how much money did we make, but the full story of that customer’s interaction with honeycomb. How did they hear of us? Whose blog posts, training sessions, or office hours did they engage with? Did someone on the telemetry pull a record-fast turnaround on an integration they needed to get going? What pains did we solve effectively for them as a tool, and where were the rough edges that we can improve on in the future?

      The story is often half a page long or more, and tags a dozen or more people throughout all parts of the company, showing how everyone’s hard work added up and materially contributed to the final result.

    2. We have orgs take turn presenting in all hands — where they’re at, what they’ve built, and the impact of their contributions, week after week. Whether that’s the design team talking about how they’ve rolled out our new design system and how it is going to help everyone in the company experiment more and move more quickly, or it’s the people team showing how they’ve improved our recruiting, interviewing, and hiring processes to make people feel more seen, welcomed, and appreciated throughout the process.

      We expect people to be curious about the rest of the company. We expect honeybees to be interested in, excited about and celebratory of each other’s hard work. And it’s easy to be excited when you see people showing off work that they were excited to do.

    3. We have a weekly Friday “demo day” where people come and show off something they’ve built this week, rapid-fire. Whether it’s connecting to a mysql shell in the terminal to show off our newly consistent permissioning scheme, or product marketing showing off new work on the website. Everybody’s work counts. Everybody wants to see it.

    4. We have a #love channel in slack where you can drop in and tag someone when you’re feeling thankful for how much they just made your day better. We also have a “Gratefuls” section during all hands, where people speak up and give verbal props to coworkers who have really made a difference in their lives at work.

We have always attracted engineers who care about the business, not just the technology and the culture. As a result, we have consistently recruited and retained business leaders who are well above our weight class — our investors still sometimes marvel at the caliber of the business talent we have been able to attract. It is way above the norm for developer tools companies like ours.

“Engineering-driven” can be a mask for “engineering-supremacy”

Because the sad truth is that so many companies who pride themselves on being “engineering-driven” are actually what I would call more “engineering-supremacist”. Ask any top-tier sales or marketing leader out there about their experiences in the tech industry and you’ll hear a painful, rage-inducing list of times they were talked down to by technical founders, had their counsel blown off or overridden, had their plans scrapped and their budgets cut, and every other sort of disrespectful act you can imagine.

(I am aware that the opposite also exists; that there are companies and cultures out there that valorize and glorify sales or marketing while treating engineers like code monkeys and button pushers, but it’s less common around here. In neither direction is this okay.)

This isn’t good for business, and it isn’t good for people.

It is still true that engineering is the most mature and developed organization at the company, because it has been around the longest. But our other orgs are starting to catch up and figure out what it means to “be honeycomby” for them, on their own terms. How do our core values apply to the sales team, the developer evangelists, the marketing folks, the product people? We are starting to see this play out in real time, and it’s fascinating. It is better than forcing all teams to be “engineering-driven”.

Business success is what makes all things possible

We are known for the caliber of our engineering today. But none of that matters a whit if you never hear about us, or can’t buy us in a way that makes sense for you and your team, or if you can’t use the product, or if we don’t keep building the right things, the things you need to modernize your engineering teams and move into the future together.

When looking towards that future, I still want us to be known for our great engineering. But I also want us to be a magnet for great designers who trust that they can come here and be respected, for great product people who know they can come here and do the best work of their life. That won’t happen if we see ourselves as being “driven” by one third of the triad.

Supremacy destroys balance. Always.

And none of this, none of this works unless we have a surging, thriving business to keep the wind in our sails.

~charity

How “Engineering-Driven” Leads to “Engineering-Supremacy”

Things to know about engineering levels

mipsytipsy, , , , 11 Comments

This twitter thread seemed to strike a chord with people, rather astonishingly so. I am transcribing parts of it for the sake of longevity and findability.

I keep talking to engineers who are frustrated that they aren’t leveling up faster, aren’t reaching senior levels as quickly as other people they know, feel stuck and don’t know how to get to the next level, etc. And I’ve begun to notice a common blind spot around leveling —

✨ not every opportunity exists ✨
✨ at every company ✨
✨ at every time.✨

Sure, if you’re a junior engineer, you should be able to level up to intermediate pretty much anywhere. But it gets progressively trickier after that. Even the path from intermediate to senior can depend on a number of situational variables:

Is there oxygen?

  • How many other senior engineers do you work with? how many other intermediate engineers around your level? All of these people will be pulling from the same bin of work, looking for promo-worthy, solidly-senior projects.
  • Does your ladder explicitly call for mentorship or leading small teams of lower-leveled engineers? Are there enough of those folks to go around?
  • Have you sufficiently wrapped up your last project well enough to move on? Was it actually completed in a way that demonstrated clear mastery and readiness for bigger and harder work, ordid you leave a mess behind you? That may limit people’s appetite to take a risk on you with mission-critical projects.
  • What are the biggest needs of the business right now? Any process that generates projects ought to begin with this question before proceeding on to carve out a chunk that fits your promo desires, not the other way around. 🙃
  • Do you happen to work in a niche or specialty area of engineering, particularly one crammed with super-senior, world-famous highly leveled people? This can be fantastic when it comes to your ability to soak up knowledge from the world’s best, but it may simultaneously delay your ability to level up.

In short, is there oxygen at the next level? Does the company need more of the type of engineer you want to be, vs more of the type of engineer you are now? If they need more people pounding out code and fewer architects, they’re unlikely to want to promote you to a role that involves mostly architecture..

Literally no company can possibly make use of a top-heavy eng org stuffed with senior+ engineers, if all of them are expected to demonstrate company-wide impact or global impact every review period. There’s only so much high-level work to go around for every fifty engineers writing code and features and executing on those systems.

There is only so much oxygen at each level.

Inflation.

Of course, this is all assuming that your company takes leveling seriously. Most … really … don’t.

It’s tough. It’s tough to hold your ground when a valued engineer is complaining and dropping hints they may leave if they don’t get that promotion soon. It’s much easier to give in, make an exception, argue for rounding up.

This may sound good, but it is not ultimately in your best interests as that engineer. Seriously. </3

There is sooo much title inflation in this industry already. People are given the title “senior engineer” in just 3-5 years, need I say more??

If you let a little inflation into your system by making exceptions, it causes more trouble than it’s worth. Always. The only leverage you have when people try to get you to make exceptions is if you can honestly say, “no exceptions.” Give in just once, and your moral authority evaporates.

Leveling up.

I would urge you not to make most, if any, career decisions based on levels or titles that are offered you. But I do understand how frustrating and infuriating it can be to be in a situation that is clearly unfair (usually because a manager got pressured into making an exception… tsk tsk), or if you don’t understand how to move your career forward.

So, here are a few strategic tips for leveling up.

  1. Generalists level up faster than specialists.
  2. When evaluating roles, choose ones where your specialty is part of their mission, or at least key to its execution. It has a far lower likelihood of getting outsourced, deprioritized, lacking investment in, or just forgotten about if what you do is core to what they do.
  3. Always ask to see the job ladder when interviewing. If they hedge or fumble, don’t take that job.
  4. Talk to your manager about the job ladder. Talk to your skip level about levels too! Managers love this shit. They can talk on and on and on about levels, long past your exhaustion point. It can be annoying, but it’s actually a sign of a good manager who cares and thinks about the edge cases in processes, and their impacts on people and teams.
  5. That said, don’t take the ladder as a checklist to memorize or thing to be pored over and obsessed over. It’s an incomplete attempt at both shaping and reflecting relative impact. Focus on impact.
  6. Is it easier to level up as a manager than as an engineer? Sorta-kinda, I guess so? There are at least two real phenomena at play here.
    1. There are simply more roles to go around in the management track. You need like, what, 1-2 E7/E8 (or principal, or architect?) level engineers per 100-500 engineers, but several managers/directors/etc
    2. Manager effectiveness is grounded in their relationships. It takes managers longer to have impact after they start a new role, but their potential impact grows and grows as their tenure gets longer. So yes, there’s a bit more of an escalator effect if you stay on the manager track at a company for several years. There is no similar escalator on the eng side; you have to be truly exceptional or truly lucky.
    3. But it really depends on the organization.
  7. It is much easier to level up quickly at fast-growing companies. When there is far more work than workers, and everyone is getting dropped in the deep end to sink or swim, you level up fast. Don’t underestimate what a stressful and awful experience this can be, though.
  8. Many engineers get stuck on the bubble getting to senior because they are impatient and want a map. They just want someone to *tell them what to do*. Which is the very opposite of what a senior engineer does. 🙃  Develop your judgment around what needs to be done, and do it.
  9. Your relationship with your manager matters. So does your ability to communicate about the work you are doing, its difficulty, its unexpected challenges and triumphs, etc. This is called “managing up”, and it is an actual skill which I am *terrible* at. So are most of you. 😉
  10. TLDR, if leveling matters to you (and it should matter to everyone, to some extent!), then look curiously and critically around for opportunities, and seek to maximize them. Want to become an E6/E7? Probably don’t join a startup that doesn’t have any very high-level work to do, or already has more than enough people functioning at those levels and many more nipping their heels looking for the same opportunity.This sort of thing is very obvious to us with the manager track (if you want to go from M->Dir, don’t join a startup that already HAS directors and managers who want to level up), but seems less obvious with engineering.

Most reasonable, non-desperate companies with options won’t hire you directly into the next level up which you haven’t done before, on either the manager or the engineer track. (Yellow flag if they do.)

But it is perfectly reasonable to express your career objectives in the interview, and make sure you’re on the same wavelength and seeing the same opportunities. Do you want to become a manager or a tech lead in a few months? Say so.

If it doesn’t exist now, do they think this opportunity may soon open up? Can they see a path forward for you there, if all goes well? Would they be interested in helping you get there? How many people may already be eyeing that same path? Is there enough opportunity for more than one? On what timeframe? Who will decide who gets the role, and how?

Engineers tend to find these conversations uncomfortable, and so they tend to avoid them because they don’t want to make the hiring manager uncomfortable by being pushy.

Relax. Managers don’t find this uncomfortable at all, it’s their bread and butter. (And even fi they do find it uncomfortable, tough beans.. it’s their job.) Ask away. ☺️

Misc notes on leveling.

P.S. Engineers seem to have a very sparse mental model of how leveling works, so here are a few more notes on how levels work at Honeycomb, which is adapted from conventions at Facebook/Google.

  • Each level after senior engineer (E5 for us) gets approx an order of magnitude harder to achieve, and an order of magnitude fewer engineers hold that title.
  • E5 is considered a “terminal level”, which sounds scary, but just means “you do not have to advance beyond this level.” If you never get promoted again, you won’t get fired either.
  • Whereas if you do not advance from E3-> E4 within 2 years, and E4->E5 within 3 years, you are automatically put on a performance improvement plan (at Facebook, I mean, not Honeycomb).
  • We (Honeycomb) hire into E5 as our highest level to start at, both because a) our interview process is not designed to let us parse differences between senior vs super-senior or super-duper senior, and b) we figure nobody is really able to come in the door with >E5 impact for the first 6 months anyway. So we can level them up quickly after they join and we get a feel for their work.

<3 charity.

Things to know about engineering levels

The Official, Authorized List Of Legitimate Reasons For Deciding to Become a Manager

mipsytipsy, , , 17 Comments

“Why did you decide to become a manager?”

It’s a question that gets asked a lot, in job interviews, 1x1s, and plain old casual conversation. I ask this question a lot, and I am often frustrated (or bored) by the answers I hear back.

Most of them can be bucketed in one of three ways:

  1. The pious. “I just really, really love helping other people achieve their goals.”
  2. The pleasers. the ones who answer, then pause uncertainly: “Is that what you’re looking for?”
  3. The sheepish. “I probably shouldn’t say this, but..” (followed by something very close to real honesty)

People are rarely inclined to divulge the range and depth of their reasons for going into management. And why should they? We are constantly being lectured about what the RIGHT reasons for going into management are, with aspersions cast upon anyone who dares enter the profession for any reasons that are not completely selfless.

“I LOVE mentoring.” “I wanted to protect my team.” “I’m motivated by people problems.” “I just really love helping people grow.”

Okay.

I’m not saying that everybody who says these words is lying, but I would be surprised if it was the entire story. People make career moves for a complex mix of altruism and self-interest.

It’s socially acceptable to cop to the selfless reasons. But what about the rest? Like “I wanted more money”? “I wanted career progression and couldn’t get any as an IC”? What about “I couldn’t get a seat at the table as an engineer”, “I was tired of being left out of important decisions”, or “My reporting chain was opaque and kept fucking up, and I figured I couldn’t do any worse than those bozos”?

Now we’re talking.

Most people become managers to compensate for org fuckery.

In my experience, most engineers become managers primarily due to organizational dysfunction. When you become a manager you acquire certain institutional powers, and you can use those powers to change the thing that makes you miserable.

It’s a hack. A gnarly one. And like most hacks, it kinda works.

For example, say it pisses you off to be left out of decisions. So you become a manager, and then you can either a) use your power and access to push for including engineers in the decision-making process, or at very least b) you personally will no longer left out.

In a healthy org, I would argue that most of these reasons should not exist. You should not have to become a manager to have career progression, pay equity, access to information, to be included in the decision-making process, even to set company strategy (to an extent congruent with your level, impact, role, tenure, etc)..

Everybody can’t weigh in on everything, obviously, but technical leaders are the best people to make technical decisions, not managers. In healthy orgs, managers work to push those powers outwards to the people closest to the work rather than hoarding it for themselves.

Legitimate reasons for being interested in management.

If you claw away all the org fuckery that forces so many people who care deeply about their work and coworkers into management, there is only one honest reason left for why anyone should try management.

✨Because you feel like it.✨

Because you’re curious. Because there’s an opportunity, maybe, or it seems interesting. Because why not? It’s as good a reason as any. Why do you learn a new framework, a new language, why do you write about your work, why do you pick up any new skill or new role? Why do any of it?

We are not rational beings. First comes emotional urge (“I want that”), then comes rationalization (“because, uh, I love people?”). That’s just how our brains work. You don’t really have to defend or justify it any further.

In reality …

I have observed that many people (especially early-career) are semi-obsessed with getting in to management.

There are many reasons for this. In most places, it is still regarded as a promotion, not a support role / change of career. With high achievers, all you have to do is plunk a ladder next to them to make them want to climb it. Many people feel a lack of agency and lack of autonomy in their role, and they think becoming a manager will solve all their problems.

The swiftest cure for this delusion is  … actually becoming a manager.

Management is a role where you are granted certain institutional powers, at the expense of other powers, freedoms and benefits. Many people who try management figure out pretty quickly that it’s not for them. Formal powers are, in many ways, the weakest powers of them all.

Which is why I think anybody who is interested in management should get a shot at it. Let’s demystify the role, strip it of its mystique and glamour, and make it what it should be: a role of service to others not dominance over others; staffed by people who genuinely take joy in that people side of sociotechnical problem solving.

 

charity

 

 

The Official, Authorized List Of Legitimate Reasons For Deciding to Become a Manager

Questionable Advice: Can Engineering Productivity Be Measured?

mipsytipsy, , , , , , 17 Comments

I follow you on Twitter and read your blog.  I particularly enjoy this post: https://charity.wtf/2019/05/01/friday-deploy-freezes-are-exactly-like-murdering-puppies/ I’m reaching out looking for some guidance.

I work as an engineering manager for a company whose non-technology leadership insists there has to be a way to measure the individual productivity of a software engineer. I have the opposite belief. I don’t believe you can measure the productivity of “professional” careers, or thought workers (ex: how do measure productivity of a doctor, lawyer, or chemist?).

For software engineering in particular, I feel that metrics can be gamed, don’t tell the whole story, or in some cases, are completely arbitrary. Do you measure individual developer productivity? If so, what do you measure, and why do you feel it’s valuable? If you don’t and share similar feelings as mine, how would you recommend I justify that position to non-technology leadership?

Thanks for your time.

Anonymous Engineering Manager

Dear Anon,

Once upon a time I had a job as a sysadmin, 100% remote, where all work was tracked using RT tasks. I soon realized that the owner didn’t have a lot of independent technical judgment, and his main barometer for the caliber of our contributions was the number of tasks we closed each day.

I became a ticket-closing machine. I’d snap up the quick and easy tasks within seconds. I’d pattern match and close in bulk when I found a solution for a group of tasks. I dove deep into the list of stale tickets looking for ones I could close as “did not respond” or “waiting for response”, especially once I realized there was no penalty for closing the same ticket over and over.

My boss worshiped me. I was bored as fuck. Sigh.

I guess what I’m trying to say is, I am fully in your camp. I don’t think you can measure the “productivity” of a creative professional by assigning metrics to their behaviors or process markers, and I think that attempting to derive or inflict such metrics can inflict a lot of damage.

In fact, I would say that to the extent you can reduce a job to a set of metrics, that job can be automated away. Metrics are for easy problems — discrete, self-contained, well-understood problems. The more challenging and novel a problem, the less reliable these metrics will be.

Your execs should fucking well know this: how would THEY like to be evaluated based on, like, how many emails they send in a day? Do they believe that would be good for the business? Or would they object that they are tasked with the holistic success of the org, and that their roles are too complex to reduce to a set of metrics without context?

This actually makes my blood boil. It is condescending as fuck for leadership to treat engineers like task-crunching interchangeable cogs. It reveals a deep misunderstanding of how sociotechnical systems are developed and sustained (plus authoritarian tendencies, and usually a big dollop of personal insecurity).

But what is the alternative?

In my experience, the “right” answer, i.e. the best way to run consistently high-performing teams, involves some combination of the following:

  • Outcome-based management that practices focusing on impact, plus
  • Team level health metrics, combined with
  • Engineering ladder and regular lightweight reviews, and
  • Managers who are well calibrated across the org, and encouraged to interrogate their own biases openly & with curiosity.

The right way to look at performance is at the team level. Individual engineers don’t own or maintain code; teams do. The team is the irreducible unit of ownership. So you need to incentivize people to think about work and spending their time cooperatively, optimizing for what is best for the team.

Some of the hardest and most impactful engineering work will be all but invisible on any set of individual metrics. You want people to trust that their manager will have their backs and value their contributions appropriately at review time, if they simply act in the team’s best interest. You do not want them to waste time gaming the metrics or courting personal political favor.

This is one of the reasons that managers need to be technical — so they can cultivate their own independent judgment, instead of basing reviews on hearsay. Because some resources (i.e. your budget for individual bonuses) are unfortunately zero-sum, and you are always going to rely on the good judgment of your engineering leaders when it comes to evaluating the relative impact of individual contributions.

“I would say that Joe’s contribution this quarter had greater impact than Jane’s. But is that really true? Jane did a LOT of mentoring and other “glue” work, which tends to be under-acknowledged as leadership work, so I just want to make sure I am evaluating this fairly … Does anyone else have a perspective on this? What might I be missing?” — a manager keeping themselves honest in calibrations

I do think every team should be tracking the 4 DORA metrics — time elapsed between merge and deploy, frequency of deploy, time to recover from outages, duration of outages — as well as how often someone is paged outside of business hours. These track pretty closely to engineering productivity and efficiency.

But leadership should do its best to be outcome oriented. The harder the problem, the more senior the contributor, the less business anyone has dictating the details of how or why. Make your agreements, then focus on impact.

This is harder on managers, for sure — it’s easier to count the hours someone spends at their desk or how many lines of code they commit than to develop a nuanced understanding of the quality and timbre of an engineer’s contributions to the product, team and the company over time. It is easier to micromanage the details than to negotiate a mutual understanding of what actually matters, commit to doing your part … and then step away, trusting them to fill in the gaps.

But we should expect this; it’s worth it. It is in those gaps where we feel trusted to act that we find joy and autonomy in our labor, where we do our best work as skilled artisans.

Questionable Advice: Can Engineering Productivity Be Measured?

Trolley Problems as a Service

mipsytipsy, , , , 6 Comments

Consider:

  • Is it ethical to discriminate in whom you will sell to as a business?  What would you do if you found out that the work you do every day was being used to target and kill migrants at the border? 
  • Is it ethical or defensible to pay two people doing the same job different salaries if they live in different locations and have a different cost of living?  What if paying everyone the same rate means you are outcompeted by those who peg salaries to local rates, because they can vastly out-hire you?
  • You’re at the crowded hotel bar after a company-sponsored event, and one of your most valued customers begins loudly venting opinions about minorities in tech that you find alarming and abhorrent.  What responsibility do you have, if any?  How should you react?
  • If we were close to running out of money in the hypothetical future, should we do layoffs or offer pay cuts?

It’s not getting any simpler to live in this world, is it?  💔

Ethical problems are hard.  Even the ones that seem straightforward on the face of them get stickier the closer you look at them.  There are more stakeholders, more caveats, more cautionary tales, more unintended consequences than you can generally see at face value. It’s like fractal hardness, and anyone who thinks it’s easy is fooling themselves.

We’ve been running an experiment at Honeycomb for the past 6 months, where we talk through hypothetical ethical questions like these once a month. Sometimes they are ripped from the headlines, sometimes they are whatever I can invent the night before. I try to send them around in advance. The entire company is invited.**

Honeycomb is not a democracy, nor do I think that would be an effective way to run a company, any more than I think we should design our SDKs by committee or give everyone an equal vote on design mocks.

But I do think that we have a responsibility to act in the best interests of our stakeholders, to the best of our abilities, and to represent our employees. And that means we need to know where the team stands.

That’s one reason. Another is that people make the worst possible decisions when they’re taken off guard, when they are in an unfamiliar situation (and often panicking). Talking through a bunch of nightmare scenarios is a way for us to exercise these decision-making muscles while the stakes are low. We all get to experience what it’s like to hear a problem, have a kneejerk reaction .. then peeling back the onion to reveal layer after layer of dismaying complexities that muddy our snap certainties.

Honeycomb is a pretty transparent company; we believe that companies are created every day by the people who show up to labor together, so those people have a right to know most things. But it’s not always possible or ethically desirable to share all the gritty details that factor into a decision. My hope is that these practice runs help amplify employees’ voices, help them understand the way we approach big decisions, and help everyone make better decisions — and trust each other’s decisions — when things move fast and times get hard.

(Plus, these ethical puzzles are astonishingly fun to work through together. I highly recommend you borrow this idea and try it out at your own company.)

cheers, and please let me know if you do try it ☺️

charity

** We used to limit attendance to the first 6 people to show up, to try and keep the discussion more authentic and less performative. We recently relaxed this rule since it doesn’t seem to matter, peacocking hasn’t really been an issue.

Trolley Problems as a Service

17 Reasons NOT To Be A Manager

mipsytipsy, , , , 40 Comments

Yesterday we had a super fun meetup here at Intercom in Dublin.  We split up into small discussion groups and talked about things related to managing teams and being a senior individual contributor (IC), and going back and forth throughout your career.

One interesting question that came up repeatedly was: “what are some reasons that someone might not want to be a manager?”

Fascinatingly, I heard it asked over the full range of tones from extremely positive (“what kind of nutter wouldn’t want to manage a team?!”) to extremely negative (“who would ever want to manage a team?!”).  So I said I would write a piece and list some reasons.

Point of order: I am going to focus on intrinsic reasons, not external ones.  There are lots of toxic orgs where you wouldn’t want to be a manager for many reasons — but that list is too long and overwhelming, and I would argue you probably don’t want to work there in ANY capacity.  Please assume the surroundings of a functional, healthy org (I know, I know — whopping assumption).

https://twitter.com/jetpack/status/1169675819716763649

1. You love what you do.

Never underestimate this one, and never take it for granted.  If you look forward to work and even miss it on vacation; if you occasionally leave work whistling with delight and/or triumph; if your brain has figured out how to wring out regular doses of dopamine and serotonin while delivering ever-increasing value; if you look back with pride at what you have learned and built and achieved, if you regularly tap into your creative happy place … hell, your life is already better than 99.99% of all the humans who have ever labored and lived.  Don’t underestimate the magnitude of your achievement, and don’t assume it will always be there waiting for you to just pick it right back up again.

https://twitter.com/jetpack/status/1169780841532276736

2. It is easy to get a new engineering job.  Really, really easy.

Getting your first gig as an engineer can be a challenge, but after that?  It is possibly easier for an experienced engineer to find a new job than anyone else on the planet. There is so much demand this skill set that we actually complain about how annoying it is being constantly recruited!  Amazing.

It is typically harder to find a new job as a manager.  If you think interview processes for engineers are terrible (and they are, honey), they are even weirder and less predictable (and more prone to implicit bias) for managers.  So much of manager hiring is about intangibles like “culture fit” and “do I like you” — things you can’t practice or study or know if you’ve answered correctly.  And soooo much of your skill set is inevitably bound up in navigating the personalities and bureaucracies of particular teams and a particular company.  A manager’s effectiveness is grounded in trust and relationships, which makes it much less transferrable than engineering skills.

3. There are fewer management jobs.

I am not claiming it is equally trivial for everyone to get a new job; it can be hard if you live in an out-of-the-way place, or have an unusual skill, etc.  But in almost every case, it becomes harder if you’re a manager.  Besides — given that the ratio of engineers to line managers is roughly 7 to one — there will be almost an order of magnitude fewer eng manager jobs than engineering jobs.

4. Manager jobs are the first to get cut.

Engineers (in theory) add value directly to the bottom line.  Management is, to be brutally frank, overhead.  Middle management is often the first to be cut during layoffs

Remember how I said that creation is the engineering superpower?  That’s a nicer way of saying that managers don’t directly create any value.  They may indirectly contribute to increased value over time — the good ones do — but only by working through other people as a force multiplier, mentor etc.  When times get tough, you don’t cut the people who build the product, you cut the ones whose value-added is contingent or harder to measure.

Another way this plays out is when companies are getting acquired.  As a baseline for acquihires, the acquiring company will estimate a value of $1 million per engineer, then deduct $500k for every other role being acquired.  Ouch.

5. Managers can’t really job hop.

Where it’s completely normal for an engineer to hop jobs every 1-3 years, a manager who does this will not get points for learning a wide range of skills, they’ll be seen as “probably difficult to work with”.  I have no data to support this, but I suspect the job tenure of a successful manager is at least 2-3x as long as that of a successful IC.  It takes a year or two just to gain the trust of everyone on your team and the adjacent teams, and to learn the personalities involved in navigating the organization.  At a large company, it may take a few times that long.  I was a manager at Facebook for 2.5 years and I still learned some critical new detail about managing teams there on a weekly basis.  Your value to the org really kicks in after a few years have gone by, once a significant part of the way things get done resides in your cranium.

https://twitter.com/jetpack/status/1169698084240031744

6. Engineers can be little shits.

You know the type.  Sneering about how managers don’t do any “real work”, looking down on them for being “less technical”.  Basically everyone who utters the question “.. but how technical are they?” in that particular tone of voice is a shitbird.  Hilariously, we had a great conversation about whether a great manager needs to be technical or not — many people sheepishly admitted that the best managers they had ever had knew absolutely nothing about technology, and yet they gave managers coding interviews and expected them to be technical.  Why?  Mostly because the engineers wouldn’t respect them otherwise.

https://twitter.com/jetpack/status/1169685458340573184

7.  As a manager, you will need to have some hard conversations.  Really, really hard ones.

Do you shy away from confrontation?  Does it seriously stress you out to give people feedback they don’t want to hear?  Manager life may not be for you.  There hopefully won’t be too many of these moments, but when they do happen, they are likely to be of outsized importance.  Having a manager who avoids giving critical feedback can be  really damaging, because it deprives you of the information you need to make course corrections before the problem becomes really big and hard.

8.  A manager’s toolset is smaller than you think.

As an engineer, if you really feel strongly about something, you just go off and do it yourself.  As a manager, you have to lead through influence and persuasion and inspiring other people to do things.  It can be quite frustrating.  “But can’t I just tell people what to do?” you might be thinking.  And the answer is no.  Any time you have to tell someone what to do using your formal authority, you have failed in some way and your actual influence and power will decrease.  Formal authority is a blunt, fragile instrument.

9. You will get none of the credit, and all of the blame.

When something goes well, it’s your job to push all the credit off onto the people who did the work.  But if you failed to ship, or and, or hire, or whatever?  The responsibility is all on you, honey.

https://twitter.com/jetpack/status/1169828158566125569

10.  Use your position as an IC to bring balance to the Force.

I LOVE working in orgs where ICs have power and use their voices.  I love having senior ICs around who model that, who walk around confidently assuming that their voice is wanted and needed in the decision-making process.  If your org is not like that, do you know who is best positioned to shift the balance of power back?  Senior ICs, with some behind-the-scenes support from managers.  For this reason, I am always a little sad when a vocal, powerful IC who models this behavior transitions to management.  If ALL of the ICs who act this way become managers, it sends a very dismaying message to the ranks — that you only speak up if you’re in the process of converting to management.

11.  Management is just a collection of skills, and you should be able to do all the fun ones as an IC.

Do you love mentoring?  Interviewing, constructing hiring loops, defining the career ladder?  Do you love technical leadership and teaching other people, or running meetings and running projects?  Any reasonably healthy org should encourage all senior ICs to participate and have leadership roles in these areas.  Management can be unbundled into a lot of different skills and roles, and the only ones that are necessarily confined to management are the shitty ones, like performance reviews and firing people.  I LOVE it when an engineer expresses the desire to start learning more management skills, and will happily brainstorm with them on next steps — get an intern? run team meetings?  there are so many things to choose from!  When I say that all engineers should try management at some point in their career, what I really mean is these are skills that every senior engineer should develop.  Or as Jill says:

12. Joy is much harder to come by.

That dopamine drip in your brain from fixing problems and learning things goes away, and it’s … real tough.  This is why I say you need to commit to a two year stint if you’re going to try management: that, plus it takes that long to start to get your feet under you and is hard on your team if they’re switching managers all the time.  It usually takes a year or two to rewire your brain to look for the longer timeline, less intense rewards you get from coaching other people to do great things.  For some of us, it never does kick in.  It’s genuinely hard to know whether you’ve done anything worth doing.

https://twitter.com/jetpack/status/1169826158751338497

13. It will take up emotional space at the expense of your personal life.

When I was an IC, I would work late and then go out and see friends or meet up at the pub almost every night.  It was great for my dating life and social life in general.  As a manager, I feel like curling up in a fetal position and rolling home around 4 pm.  I’m an introvert, and while my capacity has increased a LOT over the past several years, I am still sapped every single day by the emotional needs of my team.

14. Your time doesn’t belong to you.

It’s hard to describe just how much your life becomes not your own.

https://twitter.com/jetpack/status/1169804763933753345

15. Meetings.

16. If technical leadership is what your heart loves most, you should NOT be a manager.

If you are a strong tech lead and you convert to management, it is your job to begin slowly taking yourself out of the loop as tech lead and promoting others in your place.  Your technical skills will stop growing at the point that you switch careers, and will slowly decay after that.  Moreover, if you stay on as tech lead/manager you will slowly suck all the oxygen from the room.  It is your job to train up and hand over to your replacements and gradually step out of the way, period.

17. It will always be there for you later.

In conclusion

Given all this, why should ANYONE ever be a manager?  Shrug.  I don’t think there’s any one good or bad answer.  I used to think a bad answer would be “to gain power and influence” or “to route around shitty communication systems”, but in retrospect those were my reasons and I think things turned out fine.  It’s a complex calculation.  If you want to try it and the opportunity arises, try it!  Just commit to the full two year experiment, and pour yourself into learning it like you’re learning a new career — since, you know, you are.

https://twitter.com/jetpack/status/1169641930713645057

But please do be honest with yourself.  One thing I hate is when someone wants to be a manager, and I ask why, and they rattle off a list of reasons they’ve heard that people SHOULD want to become managers (“to have a greater impact than I can with just myself, because I love helping other people learn and grow, etc”) but I am damn sure they are lying to themselves and/or me.

Introspection and self-knowledge are absolutely key to being a decent manager, and lord knows we need more of those.  So don’t kick off your grand experiment by lying to yourself, ok?

 

17 Reasons NOT To Be A Manager

Software Sprawl, The Golden Path, and Scaling Teams With Agency

mipsytipsy, , , , , , , , , 28 Comments

gplanis

Stop me if you’ve heard this one before.

The company is growing like crazy, your engineering team keeps rising to the challenge, and you are ferociously proud of them. But some cracks are beginning to show, and frankly you’re a little worried. You have always advocated for engineers to have broad latitude in technical decisions, including choosing languages and tools. This autonomy and culture of ownership is part of how you have successfully hired and retained top talent despite the siren song of the Faceboogles.

But recently you saw something terrifying that you cannot unsee: your company is using all the languages, all the environments, all the databases, all the build tools. Shit!!! Your ops team is in full revolt and you can’t really blame them. It’s grown into an unsupportable nightmare and something MUST be done, but you don’t know what or how — let alone how to solve it while retaining the autonomy and personal agency that you all value so highly.

I hear a version of this everywhere I’ve gone for the past year or two. It’s crazy how often I’ve seen it. I’ve been meaning to write my answer up for ages, and here it (finally) is.

First of all: you aren’t alone. This is extremely common among high-performing teams, so congratulations. Really!

There actually seems to be a direct link between teams that give engineers lots of leeway to own their technical decisions and that team’s ability to hire and retain top-tier talent, particularly senior talent. Everything is a tradeoff, obviously, but accepting somewhat more chaos in exchange for a stronger sense of individual ownership is usually the right one, and leads to higher-performing teams in the long run.

Second, there is actually already a well-trod path out of this hole to a better place, and it doesn’t involve sacrificing developer agency. It’s fairly simple! Just five short steps, which I will describe to you now.

How to build a golden path and reverse software sprawl

  1. Assemble a small council of trusted senior engineers.
  2. Task them with creating a recommended list of default components for developers to use when building out new services. This will be your Golden Path, the path of convergence (and the path of least resistance).
  3. Tell all your engineers that going forward, the Golden Path will be fully supported by the org. Upgrades, patches, security fixes; backups, monitoring, build pipeline; deploy tooling, artifact versioning, development environment, even tier 1 on call support. Pave the path with gold. Nobody HAS to use these components … but if they don’t, they’re on their own. They will have to support it themselves.
  4. Work with team leads to draw up an umbrella plan for adopting the Golden Path for their current projects as well as older production services, as much as is reasonable or possible or desirable. Come up with a timeline for the whole eng org to deprecate as many other tools as possible. Allocate real engineering time to the effort. Hell, make a party out of it!
  5. After the cutoff date (and once things have stabilized), establish a regular process for reviewing and incorporating feedback about the blessed Path and considering any proposed changes, additions or removals.

There you go. That’s it. Easy, right??

(It’s not easy. I never said it was easy, I said it was simple. 👼🏼)

Your engineers are currently used to picking the best tool for the job by optimizing locally. gpjonWhat data store has a data model that is easiest for them to fit to their needs? Which language is fastest for I/O throughput? What are they already proficient in? What you need to do is start building your muscles for optimizing globally. Not in isolation of other considerations, but in conjunction with them. It will always be a balancing act between optimizing locally for the problem at hand and optimizing globally for operability and general sanity.

(Oh, incidentally, requiring an engineer to write up a proposal any time they want to use a non-standard component, and then defend their case while the council grills them in person — this will be nothing but good for them, guaran-fucking-teed.)

Let’s go into a bit more detail on each of the five points. But quick disclaimer: this is not a prescription. I don’t know your system, your team, your cultural land mines or technical interdependencies or anything else about your situation. I am just telling stories here.

1. Assemble your council

Three is a good number for a council. More than that gets unwieldy, and may have trouble reaching consensus. Less than three and you run into SPOFs. You never want to have a single person making unilateral decisions because a) the decision-making process will be weaker, b) it sets that person up for too much interpersonal friction, and c) it denies your other engineers the opportunity to practice making these kinds of decisions.

  • Your council members need technical breadth more than depth, and should be widely respected by engineers.
  • At least one member should have a long history with the company so they know lots of stupid little details about what’s been tried before and why it failed.
  • At least one member should be deeply versed in practical data and operability concerns.
  • They should all have enough patience and political skill to drive consensus for their decisions. Absolutely no bombthrowers.

If you’re super lucky, you just tap the three senior technologists who immediately come to mind … your mind and everyone else’s. If you don’t have this kind of automatic consensus, you may want to let teams or orgs nominate their own representative so they feel they have some say.

 

2. Task the council with defining a Golden Path

Your council cannot vanish for a week and then descend from the mountain lugging lists engraved on stone tablets. The process of discovery and consensus is what validates the result.

The process must include talking to and gathering feedback from your engineers, talking to experts outside the company, talking to teams at other companies who are farther along using that technology, coming up with detailed pro/con lists and reasons for their choices. Maybe sometimes it includes prototyping something or investigating the technical depths … but yeah no mostly it’s just the talking.

You need your council members to have enough political skill to handle these conversations deftly, building support and driving consensus through the process. Everybody doesn’t have to love the outcome, but it shouldn’t be a *surprise* to anyone by the end.

3. Know where you’re going

Your council should create a detailed written plan describing which technologies are going to be supported … and a stab at what “supported” means. (Ask the experts in each component what the best practices are for backups, versioning, dependency management, etc.)

You might start with something like this:

* Backend lang: Go 1.11           ## we will no longer be supporting
backend scripting languages
* Frontend lang: ReactJS v 16.5
* Primary db: Aurora v 2.0        ## Yes, we know postgres is "better", 
but we have many mysql experts and 0 pg experts except the one guy 
who is going to complain about this.  You know who you are.
* Deploy pipeline: github -> jenkins + docker -> S3 -> custom k8s 
deploy tooling
* Message broker: kafka v 2.10, confluent build
* Mail: SES
* .... etc

Circulate the draft regularly for feedback, especially with eng managers. Some team reorganization will probably be necessary to bear the new weight of your support specifications, and managers will need some lead time to wrangle this.

This is also a great time to reconceive of the way on call works at your company. But I am not going to go into all that here.

4. Set a date, draft a plan: go!

Get approval from leadership to devote a certain amount of time to consolidating your stack and paying down a lump sum of tech debt. It depends on your stage of decay, but a reasonable amount of time might be “25% of engineering time for three months“. Whatever you agree to, make sure it’s enough to make the world demonstrably better for the humans who run it; you don’t want to leave them with a tire fire or you’ll blow your credibility.

The council and team leads should come up with a rough outer estimate for how long itgpjava would take to rewrite everything and move the whole stack on to the Golden Stack. (It’s probably impossible and/or would take years, but that’s okay.) Next, look for the quick wins or swollen, inflamed pain points.

  • If you are running two pieces of functionally similar software, like postgres and mysql, can you eliminate one?
  • If you are managing something yourself that AWS could manage for you (e.g. postfix instead of SES, or kafka instead of kinesis), can you migrate that?
  • If you are managing anything yourself that is not core to your business value, in fact, you should try to not manage it.
  • If you are running any services by hand on an AWS instance somewhere, could you try using a service?
  • If you are running your own monitoring software, etc … can you not?
  • If you have multiple versions of a piece of software, can you upgrade or consolidate on one version?

The hardest parts are always going to be the ones around migrating data or rewriting components. Not everything is worth doing or can afford to be done in the time span of your project time, and that’s okay.

Next, brainstorm up some carrots. Can you write templates so that anybody who writes a service using your approved library, magically gets monitoring checks without having to configure anything? Can you write a wrapper so they get a bunch of end-to-end tests for free? Anything you can do to delight people or save them time and effort by using your preferred components is worth considering.

(By the way, if you don’t have any engineers devoted to internal tooling, you’re probably way overdue at this point.)

Pay down as much debt as you can, but be pragmatic: it’s better to get rid of five small things than one large thing, from a support perspective. Your main goal is to shrink the number of types of software your team has to support, particularly databases.

Do look for ways to make it fun, like … running a competition to see who can move the most tools to AWS in a week, or throwing a hack week party, or giving dorky prizes like trophies that entitle you to put your manager on call instead of you for a day, etc.

gpcersei

5. Make the process sustainable

After your target date has come and gone, you probably want to hold a post mortem retrospective and do lots of listening. (Well — first might I recommend a bubble bath and a bottle of champagne? But then a post mortem.)

Nothing is ever fixed forever. The company’s needs are going to expand and contract, gpdiedand people will come and go, because change is the only constant. So you need to bake some flex into your system. How are you going to handle the need for changes to the Golden Path? Monthly discussions? An email list? Quarterly meetings with a formal agenda? I’ve seen people do all of these and more, it doesn’t really matter afaict.

Nobody likes a cabal, though, so the original council should gradually rotate out. I recommend replacing one person at a time, one per quarter, and rotating in another senior engineer in their place. This provides continuity while giving others a chance to learn these technical and political skills.

In the end, engineers are still free to use any tool or component at any time, just like before, only now they are solely responsible for it, which puts pressure on them not to do it unless REALLY necessary. So if someone wants to propose adding a new tool to the default golden path, they can always add it themselves and gain some experience in it before bringing it to the council to discuss a formal place for it.

That’s all folks

See, wasn’t that simple?

(It’s never simple.)

I dearly wish more people would write up their experiences with this sort of thing in detail. I think engineering teams are too reluctant to show their warts and struggles to the world — or maybe it’s their executives who are afraid? Dunno.

Regardless, I think it’s actually a highly effective recruiting tool when teams aren’t afraid to share their struggles. The companies that brag about how awesome they are are the ones who come off looking weak and fragile. Whereas you can always trust the ones who are willing to laugh about all the ways they screwed up. Right?

In conclusion, don’t feel like an asshole for insisting on some process here. There should be friction around adding new components to your stack. (Add in haste, repent at leisure, as they say.) Anybody who argues with you probably needs to be exposed to way, way more of the support load for that software. That’s my professional opinion.

Anyway. You win or you die. Good luck with your sprawl.

charity

 

 

Software Sprawl, The Golden Path, and Scaling Teams With Agency