Hard Lessons From the Worst Manager I've Ever Had

Published August 6, 2026

My first manager opened our working relationship by telling me he'd flunked out of college years earlier from drinking too much, and he told it like a redemption story — look how far I've come, look at this company that took a chance on someone like me. It wasn't an impressive story, and it didn't make me feel any better about him as my manager. Almost everything else about him followed that same pattern: he wanted the credit that comes with the title, without doing the work the title actually requires.

My first job out of college was at a big brokerage's call-center team, and I started there sometime around 2008. It had been pitched to me as a non-sales role, which mattered to me. In practice, “leads” were expected anyway. My service numbers were consistently among the strongest on the team; my numbers on leads were weaker. When I told him directly that sales wasn't where my strengths were, he didn't help me build the skill, and he didn't help make it matter less. He just held it against me.

I also tried to move within the company more than once. Each time, the interviews went quiet afterward, with no rejection and no follow-up. Based on things I heard from other people at the time, I believe he was actively working against me in those interviews, sandbagging me to keep me from moving on. I can't prove that. But I believe it.

The clearest example of who he was came in a one-on-one about Chairman's Club, an all-expenses-paid trip for top performers that he'd already won once and wanted again. Here's what I remember him saying: If you don't help me get Chairman's Club, I'm not going to help you get a new job. He wasn't talking about the team's numbers. He was talking about his own trip.

Not long after, I took a call from a customer who was swearing and irate. I stayed calm, and at one point told him something close to: If you had done it right the first time, we wouldn't be having this conversation. It worked. He calmed down, and the call ended fine. My manager had been listening in. Instead of treating it as an example of handling a hostile call well, he turned it into a performance conversation, and not a positive one.

Put those together and a pattern shows: a manager who knew the job title more than he knew how to develop people. I don't think he showed real respect to anyone the whole time I worked for him. Everything came back to him: his trip, his metrics, his comfort. And it kept getting framed as a conversation about my performance instead.

Here's what I actually took from working under him, once enough time had passed to think clearly about it. The success of the people I lead is representative of my own success — when someone on my team leaves for something better, that's a celebration for them and a celebration for me, not a threat to guard against. Lean into people's strengths instead of grinding on their weaknesses; he had years to help me build the one skill he said I lacked, and chose to punish me for not having it instead. A performance conversation should help the person walk out better than they walked in, not just make them feel small. And not knowing how to do something and being unwilling to do it are different problems. Mine was the first kind, and a good manager helps close that gap instead of holding it against you.

That's actually why I'm telling this story. The pattern matters more than the specifics. It's easy to start treating your people's growth as a threat instead of a win, or to mistake authority for respect. It's just as easy to use a performance conversation to make yourself feel better instead of making the other person better. If any of that sounds like a manager you've worked for, or a habit you're worried you've picked up yourself, it's worth sitting with. I'll admit to a cost of my own here too: how bad he made me feel about feedback probably made me slower to give it myself for years afterward. That's a hard thing to admit, and I think it's accurate.

I honestly don't know if he was a bad person. I don't think that's mine to say. I do know he was a bad manager. Some of that is on the company: they put him in charge of people without giving him the training or support to do it well, and that's a real gap in how most organizations promote. Some of it is on him too — developing yourself as a leader is also your own responsibility, and he never seemed to take it on.

I don't know if he's changed since. Maybe he's had leadership training; maybe he's better now. What I doubt is whether he has the self-awareness to look back and see any of it the way I do. My guess is he reads whatever success he's had since as proof he was doing everything right all along. It probably never occurs to him that he might be succeeding in spite of the mistakes he made with people like me.

This is one of two stories from my corporate years about what bad management taught me. The other, about a performance review that landed with zero warning, is worth reading too: Hard Lessons From the Worst Performance Review I've Ever Received.

If part of this sounds like someone you report to, or a pattern you're worried about repeating yourself, I'm glad to talk it through: https://clients.agile-ideation.com/public/fit-conversation

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