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What I learned that time my boss made me cry

Spoiler: I’m still working for him today.

What I learned that time my boss made me cry
[Photo: Juan Pablo Serrano Arenas/Pexels]

When you think about the worst-case scenario at work, what comes to mind? Getting fired? Screwing up a presentation in front of the CEO? Not being able to contain yourself and crying in front of your boss?

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I’ve experienced crying in front of my boss, though he didn’t do it on purpose. We both learned from it, and he’s still my boss today (and has been for almost four years). When I started in February 2016, I was the first person he had ever managed. Today, he successfully manages a team of five, and I don’t think he’s made anyone else cry recently.

The time my manager made me cry

I remember it very distinctly, down to the very week—that’s usually how embarrassing memories go. It was the first week of January 2017, and I was nearing my one-year Lessing-Flynn (LF) anniversary as a copywriter. January is usually a very relaxed month for the team as we all return from the holidays and start to ramp up with projects for the year. This week was no different.

Let me back up. This week was no different except that Bill*, who is famously laid-back, had become a micromanaging monster. Every time he was on my side of the office, he was asking about my to-do list, my deadlines, my timesheets, and checking in on projects that he had never felt the need to follow up on before.

This behavior was unusual for our team. Before this week, we were a well-oiled machine. We were cranking out copy projects like it was nobody’s business. I realize in some work environments, frequent check-ins are necessary, but that just wasn’t how we operated as a team.

Naturally, I was on edge with stress and confusion. By Thursday, I couldn’t take it anymore. My brain was overwhelmed with negative questions. I thought, has someone complained about me? Am I doing a bad job? What have I done differently from last week? Oh no, is this weird management style one of Bill’s New Year’s resolutions? So after a sleepless night, I rolled into work Friday, ready to ask him what the hell was going on. I trudged to his desk first thing, pulled up a chair, and said, “Hey, can we talk?”

I won’t bore you with the word-for-word exchange, but I laughably remember ending my blubbering speech with something along the lines of: “I don’t need a dang gold star every day, but if something is wrong with my work or if someone complained about me missing a deadline, please just tell me, and I can work on it!”

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It turns out, nothing was wrong with my work, and no one had complained. I had not missed a deadline, and by all accounts, things were going great. The reason Bill was on my case was because our new intern was struggling to keep up with his deadlines and timesheets. Feeling guilty for talking to them so much about it, Bill started making comments to me (who sat near the intern) as an additional tactic to make them feel like they weren’t the only ones struggling. That’s all there was to it.

The lessons we learned

Since then, we’ve both attended several emotional intelligence courses with the rest of the LF team, and we’ve learned tons of skills and tools about dealing with conflict and emotional hijacking.

Bill has told me several times that this incident was a turning point in his management growth. He learned to be more direct with others when something was wrong with their work performance. For me, my growth came from the lessons in emotional hijacking, where I learned to understand the importance of speaking up if something feels off. In other words, don’t let concerns build up for days until you’re ready to explode. That’s not great for your mental health. Not to mention, the stress zapped my creativity for the week. Had I addressed it earlier in the week, I could have saved myself a lot of misery.

Most importantly, I learned not to let an embarrassing moment define who I was, and Bill didn’t either. After this weird day, we both shook it off gracefully (i.e., I said, “Sorry for crying in your office,” and then Bill said, “Sorry for being a jerk.”) Today, Bill and I have a good relationship. We can happily laugh about the situation.

Remember, everyone is human and makes mistakes. The important thing is that we learn from them. So next time you feel like your manager is out to criticize you, take a deep breath. It might have nothing to do with you.

*This name was changed to protect the identity of the manager who still feels very badly three years later.

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Rachel Wallace is a content marketing specialist at Lessing-Flynn.

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