A Management Truism: The Very Best Lessons Usually Come From Very Bad Managers

John Hollon Business Development, Change Management, Coaching, Communication, Culture, Employee Coaching, Employee Engagement, employee experience, Harassment, Leadership, Managing People, Talent Management

Here’s a management truism to remember: You learn a lot 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 Drugstore.com, and she had a lot to say about managing and building a company.

Good advice every manager should follow

It was all 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 probably every manager and HR professional knows in their heart – you learn the 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.

The best lessons come from bad managers

I also learned things from some good ones, of course, but the greatest and most memorable 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 in 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 livelihood 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, 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 him that because he would jump down your throat 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 who was so new to the organization they didn’t know where the bathroom was – would make an off-hand observation that was wrong because they didn’t know better, but this boss would jump on that information 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 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 chide and berate you for your inability to make a strong case that would convince him you really needed the resources. You could never win with this guy no matter what you said.

Yes, bad bosses are “a necessary evil’

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, the former CEO of Drugstore.com, 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 kind of 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. If you let yourself become 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. 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 it 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.

Dealing with a bad boss is one of those necessary evils you always hear about and 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.

Bad bosses will never go away. In fact, there’s probably more now than ever before. Better get used to that fact and understand that learning how NOT to manage poorly will ultimately make you good.

And those you manage will thank you for it.

John Hollon

John Hollon is an award-winning journalist and nationally recognized expert on leadership, talent management, and smart workforce practices. He currently is Editor-at-Large at ERE Media. He also was founding Editor of the popular talent management website TLNT.com, and before that, Editor of Workforce Management magazine and workforce.com.
John also held editing positions at the Los Angeles Herald Examiner and the Orange County Register, and was top editor for Gannett at two statewide papers —Montana’s Great Falls Tribune and The Honolulu Advertiser. He also has deep experience in magazine and online publishing as editorial director at Fancy Publications, VP of Editorial at Pets.com, and Editor of the San Diego Business Journal.
In addition, John is an adjunct professor in the College of Communications at California State University, Fullerton, and a board member at the Kronos Workforce Institute. He holds an MBA from Pepperdine University’s Graziado School of Business & Management, and lives in Southern California.