What I Learned from Terrible Bosses

Sometimes the worst managers teach the best lessons.

Photo by cottonbro studio

I started working when I was thirteen. I wanted something—I don’t remember what exactly—but I do remember my parents saying that if I wanted it badly enough, I should get a job. Too young for a “real” job, I found work with a landscaper. I pulled weeds, pushed wheelbarrows filled with dirt, and deadheaded plants, and even cleaned moss off flagstone patios with a caustic chemical that not only removed the moss but a layer of my skin.

I don’t remember much else about that job—and I definitely don’t remember my boss.

But as I got older and moved into jobs that paid with actual checks instead of wads of cash, I encountered my fair share of what I now think of as bad bosses. And while they were especially plentiful in the media world, I know they’re not limited to it.

Over time, I came to realize: that I learned a lot from great bosses. But I may have learned even more from the bad ones.

I’ve worked for screamers, nitpickers, ignorers, grenade-lobbers, “Mitt Romneys” (more on that another time), and a whole cast of others.

There was the editor at one newspaper who yelled at everyone—reporters, fellow editors, editorial assistants, even interns. And not just a bark. He shouted with such intensity that spit would fly from his mouth onto the glasses and faces of his victims. He believed yelling once meant you wouldn’t repeat the mistake. Maybe that worked for him. But what he failed to grasp was that compliance didn’t come from learning—it came from fear. And fear is no way to lead. If your team fears you, they won’t respect you. And the best work always comes from respect.

Then there was the CEO of a nonprofit I worked at—a nitpicker extraordinaire. She was obsessed with customer service, which in theory is admirable. But in practice? Not so much. One time, after I assembled a multi-piece mailing to thousands of members, she pulled a single envelope from the stack, opened it, and said, “You didn’t fold it right. Do it again,” before walking away. Her preferred method of folding would accordion open as you pulled it from the envelope, which… fine. But asking the team to redo everything—with overtime—felt wildly inefficient. The bigger issue? She never communicated her expectations before we started a project. It almost seemed like she enjoyed catching mistakes more than preventing them. My takeaway: communicate clearly from the start. Set expectations. Save time, resources, and morale.

And yes, I worked for a grenade-lobber. You know the type. The manager who would drop a provocative comment or vague accusation into a staff meeting, then lean back with a smirk as the room erupted into finger-pointing and chaos. I have no doubt he found it entertaining. But we weren’t monkeys. We were a team. And we deserved better.

There are more. So many more. But my goal isn’t to drag them all out—it’s to say this:

Sometimes the lessons that shape you most don’t come from inspiring mentors. They come from the leaders who left you vowing, I will never do that to someone else.

So I’m curious:

What kind of boss have you worked for—and what did you learn from them?

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