Empathetic management mistakes

It’s not me, it’s you

When I started my first company, I had never managed anyone before. I have always considered myself a “people person,” so I really didn’t think that much of it. I just assumed that if you are fair and honest, clear and communicative, everything else would fall into place[1].

Clearly I was a bit wet behind the ears.

One big mistake I made was assuming that my employees were just like me.

I’m a typical entrepreneur. I hate people breathing down my neck. I find it distrustful and demoralizing. I prefer minimal structure, self learning, and maximum autonomy.

As such, when I became the boss, I made sure to set the objectives and stay out of the way. Everyone could take care of their shit however they saw best, exactly how I wished to be managed. I was so proud of myself.

Empathize, don’t project

At first, I didn’t even notice there was a problem. When my teammates asked me for confirmation on how they should do things or wanted my feedback on their rationale for decisions they were considering, I assumed that they were doing it for me. “Don’t worry, I trust you,” I would say before turning back to my work.

It wasn’t until my very bright junior product manager almost had a breakdown that I realized I wasn’t doing MY job. I had no idea why she updated me on her every move, but I just assumed it was this “millennial” thing everyone was talking about. After the fifth update on a long day, I was a bit sharp and told her I didn’t want to hear from her again until the roadmap was done. She snapped right back and told me that she had no idea whether anything she was doing was worthwhile. I was making her incredibly anxious.

I had no idea.

Needless to say, the golden rule doesn’t always apply to management. This is probably obvious for everyone but entrepreneurs and criminals, but lots of people WANT to be told EXACTLY what to do. The more direction, the more rules, the less leeway, the better.

Some people like it formal, some like to Bro it out. Some need to lock in and tune out, others need to talk it over. Your job as bosswoman is to figure out and speak your team’s language, not make them learn yours.


Solid update and definition from my friend Grant Rafter:

What you discuss in your piece is called mirror-image attribution error and it’s an main analytic fallacy. Even empathy (seeing from another’s perspective) falls victim to this if you “place yourself in their shoes.” It’s not what you do in their shoes, but what they do in their shoes.

[1]All of these characteristics ARE critically important, and for small tight knit teams, they will get get you surprisingly far. But they are far from the whole enchilada.