The Most Challenging Managers to Work With (And What to Do About It)

25 Jun 2025 #career

I’ve changed my mind about what a good manager is.

At one past job, I worked on short-term projects. Every six months or so, I had new projects with a new team leader and sometimes a new team.

I worked with all kinds of managers. From those who still coded to others who hadn’t touched code in years.

The most challenging ones? The newly promoted team members.

In times of uncertainty, which is pretty much all the time, they fell back on what they know best: coding. And they forgot that as managers, they aren’t the best coders anymore.

In those situations, the best thing to do is follow the advice from Why Engineers Hate Their Managers:

If you’re an engineer frustrated with your manager, consider that they might be drowning too—sometimes the best thing you can do is have an honest conversation about what you both need to succeed.

The day before, they were just teammates who got a quick promotion, tapped on their shoulder with no training or clear expectations. Just, “You’re a manager now. Figure it out. See you at the next performance review.”

I used to think a good manager was a still-technical team member making code-level decisions. Now, a good manager is simply someone I’d like to work with again.