Questions about organizational culture

3/29/2021 in code
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The following is extracted from my Hire me page - basically all the stuff there that doesn't pertain to my personal employment.

I promised myself I'd 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.

To figure out whether an organization is a healthy work environment 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.


  • 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?

Further reading

Further reading that has informed my views and opinions:

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