A Question

16/365²: Sin ideas
Credit: Flickr / Andrés Nieto Porras

There’s a question that I have found myself asking a lot over the last two years: “do you know what a good environment looks like, though?”

I ask it when a friend comes to me with anxiety about performance reviews. I ask it to the friend who left a bad environment only to end up in another bad environment. I ask it to the friend who is job hunting.

Most of all, I ask myself.

“Do you know what a good environment looks like, though?”

Coping Skills Considered Harmful

When you consider that it’s possible that you don’t in fact know what a good, or healthy, environment looks like you might also consider what bad environments may have done to you. What coping mechanisms did you learn? And do you need to unlearn them? So far my conversations around this have been focused on communication, but no doubt there are more.

The other thing to consider is disengagement, an early stage of burnout. Connecting the causes of burnout (other than overwork) to common themes arising from poor inclusivity was eye-opening to me.

Good Problems vs Bad Problems

Nowhere is perfect and healthy environments have problems too. In a bad environment we tell ourselves that problems are normal as a way to make whatever it happening seem not that bad whilst our friends look on in horror¹. When faced with the potential of a new environment we work to dig out the problems and worry it is no better because look! We found some.

But when we think about technology we know, intuitively, that there are Good Problems and there are Bad Problems. Scaling, for example, is a good problem to have! Because it means you have users.

Wait a moment. Actually that depends on the scaling problem. Scaling proportional to users, solvable by a new or improved tech stack is a good problem to have. Scaling proportional to some exponent of number of users that has no technical solution may contribute to killing your business².

Nowhere is without problems, but there is a world of difference between conflict arising in an environment of mutual respect and conflict arising from competition in a zero-sum game.

Personal and Systemic Brokenness

I always read lots of business books, but since escaping The Terrible Manager these have formed a kind of self-therapy, where I find the concepts and research that articulate the Bad Feelings³.

There are a lot of things that we do where we in effect conduct experiments on other people’s careers. I’m not a big fan of this, which is in part where my drive to be a good interviewer comes from. Some advice I got recently contained this gem, “managers are like doctors; the important thing is that they do no harm”, and I’ve been meditating on it ever since.

Here’s where I’m at. Managers exist in a system. A “neutral” manager is like a conduit, they channel whatever is in the system onto the people they manage. Good is good. Bad is bad. A terrible manager will make good bad, and bad terrible. Then would a good manager make good great, and bad… good? That seems like an almost sociopathic skill – a disconnect from reality like that usually has consequences. I suspect a good manager makes good great, and bad constructive.

Whenever someone complains about a woman manager, I ask about the context. Often it’s something like oh she inherited a really shitty situation X months ago and hasn’t entirely fixed things yet? I suspect that is what the glass cliff looks like up close.

The consequence of this is that you can’t evaluate how someone is doing independent of the system they are in. A terrible manager is clear, sure, but a neutral manager is a noop that doesn’t really matter if the situation they are in is good. A good manager in a bad situation will still have to make difficult choices.

Back to that Question

This question has thus far only begot more questions, but I feel like the questions themselves are getting better… and so I get closer to finding some kind of answer.


  1. I remember when I finally accepted how bad my worst manager was, my friend exclaimed to me “Cate, I’ve been trying to tell you that for MONTHS!”
  2. Think Secret, and the harassment problem that was largely dealt with manually by workers in the Philippines.
  3. The one book he recommended me seemed largely about Having Good Intentions illustrated with a number of sexist stories.

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