Workplace Wisdom: You Can Learn More From a Bad Boss Than From a Good One

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Editor’s NoteI’ve been republishing classic (and slightly edited/updated) Skeptical Guy posts the last few months. This one is from June 2018.

HERE’S A MANAGEMENT TRUISM you just can’t avoid: You learn more from a bad boss than you do from a good one.

I was struck by this when I came across an old Corner Office” column in The New York Times. It was a Q&A with Dawn Lepore, the now-former chairwoman and CEO of, and she had a lot to say about being a manager and building a company.

Great advice for every manager to follow

It was mostly good although fairly predictable management talk, but then she said something interesting when asked if she had any bosses who were big influences in her career:

“I had a very bad boss early in my career. She was older than I was. She’d started in the financial services industry and she’d had a very hard time, so I think that probably shaped her as a leader.

She was very smart but had terrible communication skills. She did not make people feel valued or comfortable or like they were supported at all. And I remember what that felt like. And I thought, I’m never going to do that to people.”

THIS IS GREAT ADVICE that many managers and HR professionals know in their heart – you learn the most about managing people from dealing with those who manage people really badly.

There’s a lot you can learn from watching how people should NOT treat other people.

In my career, I’ve had great bosses and terrible bosses, smart bosses and dumb bosses. I’ve also had bosses who were thoughtful managers, bosses who were purposely forgetful, and bosses who were over-the-top political. There were ones I would run through a wall for but also ones I would run away from if I saw them walking down the street.

Best lessons come from bad managers

I LEARNED FROM SOME good ones, of course, but the greatest lessons came from the really bad managers I toiled under. For example:

  • There was the guy who was abusive and mean who seemed to revel his ability to bully and frighten people. I was his designated punching bag and was called on the carpet just about every day by this glowering thug who had no discernible skills except his ability to break a union – and to make you think he was ready to punch you if you said the wrong thing. He was threatened by me because I was popular with the staff, and frankly, could manage rings around him. He threatened me and my job every day until I got fed up and left.
  • Another boss was a control freak. Lots of bad managers fall into that category, and this one was an  entrepreneur who started his own company and built it into a moderate success, but was unable to let anyone else make a real decision. This stunted the company’s growth but you couldn’t tell this guy that – and he would yell at you if you even hinted at it. His worst trick was holding lunch meetings with individual departments where he interrogated the participants in the hope that someone would accidentally say something incriminating. Usually the greenest person in the room – someone so new to the organization they didn’t know which end was up – would make an off-hand comment that was wrong because they didn’t know better, and this nasty boss would jump on that info and someone would lose their job as a result.
  • Finally, there was a guy who had no appreciation at all for what it took to get work done. He thought things just magically happened, I guess, because he was constantly squeezing resources and wondering why you couldn’t do more with less. Worst yet, when you tried to bring this up during the annual budget planning discussions, he would accuse you of “not being a team player” and “not being on board” or supportive of his agenda. And if you ever brought up the lack of resources at a later date, this arrogant SOB would berate you for your inability to make a strong case that would convince him you really needed the resources anyway. It was always a no-win proposition with this guy no matter what you said.

Bad bosses are “a necessary evil’

BAD BOSSES ARE a necessary evil, because if we didn’t have bad ones, we probably wouldn’t appreciate what it takes to be a good one. Dawn Lepore, the former CEO of, understands this because she articulated it when asked for advice to give people stuck with a bad boss:

“Life is about trade-offs. And you have to be conscious of the trade-off you’re making. I felt there were enough other positives in the environment and enough opportunity that I stuck it out. But you know, I was unhappy. I had to just take a deep breath and say, ‘OK, I know this is going to end and I’m willing to put up with this’

But you can’t be a victim … that’s the kiss of death. So you’ve got to feel, ‘OK, I am choosing to do this, and when I decide I can no longer do it, then I will take action. I will not let myself be so belittled that I think I can’t do anything.’ If it starts undermining your confidence, then you have to leave, because then it seeps into everything you do.”

THAT SOUNDS LIKE a conversation that an HR professional might have with an employee stuck with a bad boss, and I know that’s the case because I have sat in on all-too-many like conversations where I heard the HR staff say similar things.

Generally in those sessions, the HR pros try to impart this bit of pragmatic advice: Just about everyone has to deal with a bad boss at some point, and how you deal with them says a lot about you.

Dealing with a bad boss is one of those necessary evils you always hear about, and something you need to endure and learn from.

That’s because if you aspire to be a top executive or CEO, you’ll need to remember the takeaways from working with bad managers so you can avoid doing the same.

Yes, live and learn, and remember the classic wisdom: what doesn’t kill you makes you stronger.

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