You know, I had this one manager who was a real puzzle. On the surface, she was always pleasant and encouraging. But there was this one ongoing thing she did that slowly chipped away at my confidence and my work. I started thinking of her as “The Saboteur.”

The specific scenario that drove me crazy revolved around deadlines. It became a predictable pattern. She would give me a project and we’d agree on a clear, reasonable due date. I’d be super organized, breaking the project down into steps and making great progress.

Then, like clockwork, two days before the deadline, she would swoop in. She’d call me into her office, looking very concerned.

“I’ve been thinking,” she’d say in a friendly, almost conspiratorial tone. “This project is so important, I think we need to add a whole new section to it. It shouldn’t take you too long, but it’s crucial.”

The new section was never small. It was always something that required a complete rethinking of my original approach. Suddenly, my well-planned schedule was in shambles. I’d have to work late, rush the new part, and the quality of the entire project would suffer because of this last-minute “improvement.”

The friendly tone made it so confusing! It felt like she was trying to help me make the project better, but the timing was sabotage. It was as if she couldn’t stand to see a project run smoothly from start to finish. She had to create a crisis.

After this happened a few times, I decided I needed to change my approach. The next time she gave me a project, I was ready. After we discussed the initial plan, I said, “This sounds great! To make sure we’re aligned, let’s map out all the key milestones together right now. That way, we can spot any potential new directions early and plan for them.”

She seemed a little surprised, but she agreed. By getting her to buy into the timeline upfront, it became *our* plan, not just *my* deadline. When she later tried to introduce a big change, I was able to gently refer back to our shared plan. I’d say, “I’d love to incorporate that idea! Given our timeline, what part of our original scope would you like to adjust to make room for it?”

It didn’t completely stop her from trying, but it gave me a friendly and professional way to push back. It turned the sabotage into a collaborative conversation. I learned that sometimes, you have to gently guide your manager into being a better manager for you. It made all the difference.

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By Emily

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