Your worst manager was right about something


Silent treatment

I've had a lot of bad managers over my career, but none was worse than a guy we'll call Pete. Pete was technically my boss's boss, but I reported to him directly for several months while I was filling in for my manager who was on sabbatical.

From the moment Pete showed up in our organization, he wanted to be our friend. He held mandatory all-team meetings every month where weren't allowed to talk about work, only our personal lives. He was the first to comment on your new haircut. He got my AOL IM name (listen, this was Ye Olden Days) and started messaging me at night to chat about his favorite TV shows. Pete wanted to make sure that you knew that he was Not Your Boss, He Was Your Pal.

Pete was a serious golfer, like maybe could have gone pro. I know this because Pete spent 75% of all our one-on-one meetings telling me about his game. One time, some guy on the team played a prank on Pete by hiding his golf clubs for an hour. Ha ha ha, right? Pete responded by giving the four of us who knew about the prank the literal silent treatment at work for an entire week.

If you're thinking this must have been pretty awkward in a professional work environment, you're absolutely right. Pete was a mid-level executive at the time, literally ignoring work questions from us, the senior leaders on his team, for a whole week. Like just straight up stone-faced left us hanging in meetings, all because one of my coworkers hid his golf clubs for an hour.

I reported to Pete when I found out I was pregnant with my daughter. When I reached the end of my first trimester, I told him what was going on so we could plan my maternity leave. Pete congratulated me and said to let him know when I was ready to tell other teammates.

So imagine my surprise when this went down in Pete's staff meeting that same afternoon:

"That's all for today," Pete told us. "Unless you had any updates, Kieran?"

"Nope, I don't think so," I said.

"Are you sure?" Pete asked.

"Pretty sure," I replied.

"Maybe the team can guess!" Pete exclaimed. "Has anyone noticed any changes in Kieran lately? Maybe changes to her upper body?" Pete put "upper body" in air quotes.

Holy shit, did Pete just tell my peers (all male, btw!) that I was pregnant by asking them to look at my boobs? He sure did. Thanks, Pal!

Like a broken clock that is right twice a day

I know it seems like I'm exaggerating the above stories about Pete. I am not. Pete is definitely the worst manager I've ever had. So it's weird that Pete also helped me learn one of the most lasting and important lessons of my whole career.

I spent the first several years of my career, including my time working for Pete, as a product manager at a large company. I spent a lot of my time working with partners in other organizations on collaborative projects. Most of these experiences were delightful, but every so often, you'd get stuck with a real stinker of a partner. Norman was one of these stinkers.

No matter what I did, Norman was an absolute dweeb about it. He went back on agreements that had taken weeks to negotiate. He cut me off in meetings, insulted my engineering partners, and refused to look at customer feedback. In short, Norman was a nightmare.

For obvious reasons, I didn't often look to Pete for support on my actual work, but I was desperate. The project was at serious risk of failure. I told Pete what was happening and asked him what I should do.

"You have to go talk to him one on one," Pete told me.

"I can't imagine anything worse," I said. "And it's not going to accomplish anything."

"I wouldn't be so sure," he told me. "Sometimes your greatest work allies start out as rocky relationships. If you're willing to go talk to him, you never know."

I was skeptical, but I didn't have much to lose. I wrote to Norman to set up some time. To my surprise, he agreed to meet. And while I can't say that we had everything resolved at the end of the hour, it turned out to be the first step towards a much better relationship. In the end, Norman became one of my most trusted cross-team partners, and the project was a success.

The bottom line: Like a broken clock that is right twice a day, even my worst manager of all time had something to teach me. Sometimes your most trusted work allies start off as rocky relationships. I never forgot the lesson.

Who is your Pete, the terrible manager that nonetheless taught you something valuable?

Back at you next week with a fresh data story!

Kieran


If you aspire to be a better manager than Pete, I wrote down three of my tried-and-true prompts for team meetings that drive team connection and performance. No big budget required!

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nerd processor

Every week, I write a deep dive into some aspect of AI, startups, and teams. Tech exec data storyteller, former CEO @Textio.

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