ethics

Hello World (xpost from substack)

mipsytipsy, 3 Comments

I recently posted a short note about moving from WordPress to Substack after ten years on WP. A number of people replied, commented, or DM’d me to express their dismay, along the lines of “why are you supporting Nazis?”. A few begged me to reconsider.

So I did. I paused the work I was doing on migration and setup, and I paused the post I was drafting on Substack. I read the LeaveSubstack site, and talked with its author (thank you, Sean 💜). I had a number of conversations with people I consider experts in content creation, and people I consider stakeholders (my coworkers and customers), as well as my own personal Jiminy Cricket, Liz Fong-Jones. I also slept on it.

I’ve decided to stay.

I said I would share my thinking once I made a decision, and it comes down to this: I have a job to do, and I haven’t been doing it.

I have not been doing my job 💔

I’ve gone increasingly dark on social media over the past few years, and while this has been delightful from a personal perspective, I have developed an uncomfortable conviction that I have also been abdicating a core function of my job in doing so.

The world of software is changing—fast. It’s exciting. But it is not enough to have interesting ideas and say them once, or write them down in a single book. You need to be out there mixing it up with the community every day, or at least every week. You need to be experimenting with what language works for people, what lands, what sparks a light in people’s eyes.

You (by which I mean me) also need to be listening more— reading and interacting with other people’s thoughts, volleying back and forth, polishing each other like diamonds.

How many times did we define observability or high cardinality or the sins of aggregation? Cool. How many times have we talked about the ways that AI has made the honeycomb vision technologically realizable for the first time? Uh, less, by an order of thousands.

Write more, engage with mainstream tech

My primary goal is to get back into the mainstream of technical discussion and mix it up a lot more. Unfortunately, to the extent there is a tech mainstream, it still exists on X. I am not ruling out the possibility of returning, but I would strongly prefer not to. I’m going to see if I can do my job by being much more active on LinkedIn and Substack.

My secondary goal is to remove friction and barriers to posting. WordPress just feels so heavyweight. Like I’m trying to craft a web page, not write a quick post. Substack feels more like writing an email. I’ve been trying to make myself post more all year on WP, and it hasn’t happened. I have a lot of shit backed up to talk about, and I think this will help grease the wheels.

There are platforms that are outside the pale, that exist solely to platform and support Nazis and violent extremists—your Gabs, your Parlers. Substack is very far from being one of those. All of these content platforms exist on some continuum of grey, and governance is hard, hard, hard in an era of mainstreaming right wing extremism.

Substack may not make all the decisions I would make, but I feel like it is a light dove grey, all things considered.

Some mitigations

I have received some tips and done some research on how to minimize the value of my writing to Substack. Here they are.

  • Substack makes money from paid subscriptions, so I don’t accept money. Ever.
  • I am told that if you use email or RSS, it benefits Substack less than if you use the app. RSS feed here.
  • I will set up an auto-poster from Substack to WordPress (at some point… probably whenever I find the time to fix the url rewriter and change domain pointer)

I hope these will allow conscientous objectors continue to read and engage with my work, but I also understand if not.

A vegan friend of mine once used an especially vivid metaphor to indignantly tell us why no, he could NOT just pick the meat and dairy off his plate and eat the vegetables and grains left behind (they were not cooked together). He said, “If somebody shit on your plate, would you just pick the shit off and keep eating?”

So. If Substack is the shit in your social media plate, and you feel morally obligated to reject anything that has ever so much as touched the domain, I can respect that.

Everyone has to decide which battles are theirs to fight. This one is not mine.

💜💙💚💛🧡❤️💖,
charity.

Hello World (xpost from substack)

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

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

mipsytipsy, , , , , 31 Comments

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

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

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

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

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

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

Miserable managers have miserable reports

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

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

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

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

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

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

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

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

Good engineering managers are force multipliers

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

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

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

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

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

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

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

Why should you (or anyone) be a manager?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

People skills are persistent

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

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

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

One cautionary note

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

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

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

charity

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

 

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

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

mipsytipsy, , , 28 Comments

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

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

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

Tips for Careful Communication

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

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

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

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

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

Acknowledge it is hard beforehand:

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

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

… or check in afterwards.

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

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

Speak tentatively.

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

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

Try to sound friendly.

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

Take a breath.

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

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

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

“The story in my head”.

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

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

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

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

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

Communicate positive intent.

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

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

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

Give people the opening to do better.

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

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

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

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

and maybe next time it will start off like…

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

Remember the handicaps, value the effort.

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

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

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

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

 

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

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