Why It’s Good to Learn From a Bad Boss


Editor’s note: Sometimes, readers ask about past TLNT articles that they have heard about but may have missed. That’s why every Friday we’re republishing a Classic TLNT post that some of you have asked about.
Anyone who has spent much time managing knows this to be a management truism you can’t avoid: you learn more from a bad boss than you do from a good one.
I was struck by this again last weekend while reading the latest ‘Corner Office” column in The New York Times. It was a Q&A with Dawn Lepore, the chairwoman and CEO of Drugstore.com, and she had a lot to say about being a manager and building a company. It was all good, if fairly predictable, management talk, but then she said something interesting when asked if she had any bosses who were big influences:
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 probably every manager or HR professional knows in their heart – you learn the very most about managing people from dealing with those who manage people badly. And, the bad managers that have the biggest impact are those you got stuck working for yourself.
Yes, 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.
I learned from the good ones, of course, but the greatest lessons came from the really bad managers I toiled under. For example:
Bad bosses are a way of life and 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 of Drugstore.com understands this, because she said this when asked for advice to 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 kind of just take a deep breath and say, O.K., I know this is going to end and I’m willing to put up with this. But you can’t be a victim. If you let yourself become a victim, that’s the kiss of death. So you’ve got to feel, O.K., I am choosing to do this, and when I decide I can no longer do it, then I will take action. So 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 that seeps into everything you do.”
That sounds like a conversation that an HR pro 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 my HR staff say similar things. And 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.
Yes, dealing with a bad boss is one of those necessary evils you always hear about, something you need to endure and learn from, because if you ever do aspire to be a top executive or CEO, you’ll need to remember the takeaways from working with a bad manager so you can avoid doing the same.