12 Signs You’re Turning into a Bad Boss.

Jake Wilder
7 min readApr 20, 2021

It happens to everyone eventually.

“I don’t know if you’re as good of a boss as you used to be.”

That’s how one of my employees opened her one-on-one. I’d worked with her for years. I trusted her. If she was bringing up a concern, she felt strongly about it. And unfortunately, she was right.

I didn’t want to be a bad boss. I don’t think anyone does. I’ve had my share of bad managers. From the ineffective bureaucrat to the toxic bully, I’ve seen how these poor performers can destroy a team.

So you’d think I would have been more adept at guarding against the transition.

And yet, it happened. Times were stressful. I was trying to keep everything moving forward. My patience was short.

Slowly but surely, I stopped focusing on what made me a good leader. I started prioritizing the short-term. I put all of my focus on the work and little on the people doing it.

This happens to everyone at some point. Stress piles up. Crises distract us. We lose focus and slide into bad habits.

Whether it happens is somewhat inevitable. The difference is whether we can recognize and correct it. All of which starts with knowing what to look for.

You start saying “No,” rather than “Why not?” or “How can we make this work?”

It’s easy to be open-minded when there’s no pressure. It’s much more difficult to do so amidst looming deadlines and crises. When the work’s piling up, uncertainty’s high, and your to-do list keeps growing with no end in sight, it’s difficult to entertain new ideas that will add to it.

Yet great ideas tend to come during these times of stress. That’s when people begin to challenge existing paradigms. It’s when everyone else is trying to keep their head above water that the best opportunities arise.

Recognize that in times of stress, you’ll default to a more close-minded approach. Remind people of this and ask them to call you out on it. It shows people that you do want new ideas and you want their help developing them. And if it’s just a matter of bad timing, create a parking lot or schedule a follow-up.

Jake Wilder

I don’t know where I’m going. But at least I know how to get there.