I promised myself to get better at identifying and contributing to healthy work environments.

I believe the thoughts and feelings presented here aren’t singular or disruptive but I am publishing them because I think they are at least underrepresented in the tech sector and I want to do my small part to help change that.

What excites me

Having taken some time away from tech work, I’ve had the chance to observe my brain respond to problems in construction, kitchen and restaurant work, music production, and parenting, to name a few.

I’ve learned that my brain’s response to a problem invariably unfolds in this order:

  1. Here’s how technology could help!
  2. But technology so often just makes things worse.
  3. Can we figure out what people really need and solve it with only the right amount of technology?

I believe we more often need to stop, think, and feel for others in order to get to the right solution.

  • Stop yourself from feeling like your preferred way of solving problems is always the right way to solve other people’s problems.
    • I can’t deny my instincts to solve problems with tech, but I sure can try to channel them with care and consideration.
  • Recognize that genuinely making people’s lives better is not universally glamorous.
    • The labor of making your product resilient and friendly in face of error conditions is not commonly considered sexy.
  • Invest the time to understand not only the right solution but also its implications - ethical, economic, and technical.
    • Don’t build things just because we can or because it’s cool.

And curiously enough, this all excites me.

This way of thinking and feeling makes for a hard and daunting road, but it’s a road that I believe helps us genuinely make other people better and happier. I’ll take a hard road towards that over an easy road towards crap any day. I prefer work that’s rewarding over work that’s fun any day.

There’s a lot of emotional labor in this and I’ve found that that’s something I really enjoy.

Building, supporting, and rewarding teams that excel at applying emotional labor to genuinely make other people better and happier - that excites me.

What doesn’t excite me

Competition doesn’t excite me; mostly it’s just a turn-off. I don’t care to beat anyone or have my success imply or require the loss of another. I recognize there are many who find competition exciting. I’m just not one of them, and if you are, we may or may not get along and that’s okay. I do want to be better than the me of yesterday. I want to learn and grow, but I also have enough empathy for myself not to force that on me every day so as to compete with myself.

What sort of work I’m looking for

I’m pretty convinced that I’m onto something with this empathy and emotions thing so I care a lot about how I work. As a shorthand, let’s call this culture.

  • Is your culture already awesome? Great - let’s work together to sustain that and see what more we can do.
  • Is your culture in need of help? Great - give me real power to change it and let’s work together to improve it.

Most importantly, though, I care that you care.

If you don’t have the time or energy to actually care about culture, empathy, or diversity - we’re just not right for one another at this time and that’s okay.

To figure out whether we might have a good time together I thought of some questions as conversation starters.

Questions I find interesting

What does success look like to you?

How some of my previous bosses have or might have answered this:

  • Tell me you’ll do seven things, then deliver five with sparks flying.
  • Follow all the rules. No sparks.
  • Be fast and agile while making it beautiful and reliable.
  • Minimize process.

Obviously some of these worked out better than others but just about none are inherently wrong.

Follow-up questions:

  • How does your boss define success?
    • How do you know?
    • How do successes and failures play out?
  • How do your peers define success?
    • (same)
  • How does your customer define success?
    • (same)

The answers don’t need to be ideal, if there even is such a thing, nor do they need to be perfectly aligned (perfect alignment can well be a bad thing).

It’s great if you have a cohesive view on this and if you’re actively managing discrepancies in others’ definitions of success.

How do you fire people?

There’s a lot to unpack about organizational culture and I think this is a good, pointed question to get started with.

Why?

  • If you don’t part ways with people with any sort of frequency, in my experience that’s a bad sign.
  • If you aren’t respectful and supportive in parting ways with people, that’s a bad sign.
    • I believe in the Netflix approach - provide generous severance and make parting ways easy and comfortable for those leaving and those remaining.
  • If you don’t have a good decision-making system for parting ways with people, you may not have one for hiring and growing people either, so let’s just start with the touchiest end and work our way back from there.

How do you say no?

Specific examples would be awesome.

I believe that healthy organizations consist of people who complement one another. Nobody can be everything to everyone in every situation.

By extension, your group — up/down/sideways — would ideally have complementing and thus conflicting points of view and those should require y’all to say no to one another from time to time. If you don’t, something’s off. If you can’t do that with ease, respect, and care (i.e. empathy), something’s off.

Follow-up question: You may well have come across ideas that are technically or economically sound but have some ethical implications worth exploring. What happens then?

And if your culture is based on “how do we get to yes?”, how do you get past bad ideas once you’ve identified them to be bad? In other words, how do you learn?

How do you learn?

There’s a lot to unpack here in part because good learning requires some dissonance.

  • How do you reward people when they succeed without mistakes vs. when they make and then learn from mistakes?
  • How do you prioritize short-term business success against long-term growth of people/teams/products?

Again, the answers don’t need to be ideal, if there even is such a thing.

This is also a good time for a conversation about psychological safety, consent, and agency.

What’s your approach to diversity?

Whichever way you slice it, diversity is hugely important.

The more we as a group think, feel, and operate differently from one another, the more likely we are to come up with better and broader solutions that better the lives of more people.

  • As an employee and creator of tools/products, I feel a duty to help as broad and varied a customer base as I can.
  • As an employer and creator of jobs, I feel a duty to sponsor and grow as broad and varied an employee base as I can.

Of course I’m curious about your diversity stats; I’m more curious about how readily we could do even better.

My previous conversation starter questions don’t directly ask about diversity in terms of race/ethnicity/preferences/etc.; instead they try to determine whether we have what I consider to be prerequisites for a diverse organization.

Prereq: What does success look like to you?

If you don’t know what success looks like, how do we value how much closer to success a more diverse team will get us?

In my experience, because it’s the right thing to do lasts until the next hiring frenzy or the next round of budget cuts — either can be just as bad.

Prereq: How do you fire people?

If you don’t know how to part ways with people, how will we take greater chances in hiring to improve our chances of diverse hiring?

  • I’ve seen far better diversity stats in the second career (e.g. coding academies) talent pool than in the traditional college pipeline pool.
    • Let’s posit that there’s a risk tradeoff in hiring somebody with one year of coding experience and (e.g.) ten years of professional/adulting experience compared to a candidate with four years’ coding experience and zero years of professional/adulting experience.
    • How do we make everyone comfortable in navigating that risk trade-off with/without a respectful parting-of-ways process?
  • Much the same goes for cross-functional hiring from within the same company.

No one in tech ever got fired for hiring a college kid, and yet that hiring strategy hasn’t gotten our industry to where we want to be. So let’s not just “blame the pool”. Let’s correct for structural inequities by expanding our notion of pools, writing better job ads, and taking some chances.

Prereq: How do you say no?

If you don’t know how to intentionally identify and resolve conflict with empathy, how can we maintain a safe and supportive environment for people with diverse approaches to conflict?

Prereq: How do you learn?

If you don’t know how to foster learning, how will we grow people from diverse points of origin?

When I might be the wrong person for the job

If you don’t want to talk about the things I care about as described above, you will find me difficult and we will not have a good time.

If you don’t want to sit down and talk with me at least once every fortnight, you will find me difficult and we will not have a good time.

Empathy is a form of emotional labor. Emotional labor involves emotions. If talking about emotions (mine or others’) makes you uncomfortable, you may find me difficult and we may not have a good time.

I want to do my best, at my best. Labor — emotional, intellectual, or physical — draws upon reserves that I need to recharge every week after 35-40 hours if I am to be at my best. If you believe in late nights, long hours, and the hustle, you will be disappointed in me and we will not have a good time. (And that’s before we talk about the deleterious impact of the hustle on diversity that I’ve observed.)

I like doing things right. That’s not the right approach for every problem (e.g. the v1 of a startup). Others love minimum-viable-v1 stuff and that’s great, it’s just not me. Need something complex/expensive/high-cost-of-failure done well and with discipline? That’s my jam.

If your company is all about open space, we’ll have words. I’m not saying it’s a deal breaker, but open space as practiced by most tech firms is quantifiably bad and scientifically as well as empirically (by my own A/B experiences) worse than individual workspaces. If nothing else, let’s at least talk about how this is a bad idea and then move on.

When I might be the right person for the job

If you care about the things I described above as much as I do, we may have a great time together.

If you need somebody who cares about all these things and also has a proven track record of shipping software to a billion users and writing kernel code that currently executes trillions of times a day, let’s talk. Just because I care doesn’t mean I’m not also deeply technical.

Further reading

Further reading that has informed my views and opinions: