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Make Up Your Mind: Leave Your Difficult New Boss or Keep Trying? 

How can you tell when it’s time to stop negotiating with, debating, or accommodating a new boss—in other words, when is it time to cut your losses and move on to other opportunities? 

I had trouble giving a client a conceptual answer to this tricky but common question because there are many potential reasons to go or stay, and the logic depends on the details. Instead, I gave him a specific personal example from several years ago, when I made the decision to walk away from something I “should” have wanted to keep. We drew some general guidelines from my experience, and since he found the exercise useful, I’ll share it here.

My Story: Should I Stay or Should I Go?

I once had a wonderful senior editor at a national publication who edited my pieces lightly and seemed happy with our relationship. I certainly was. When she left, I was reassigned to a junior editor who edited my work significantly, often changing its meaning or intent.

Different editors always want different things, even at the same publication. You learn to accommodate their individual styles and requirements if you want to keep writing for them. (New bosses are rarely like old bosses, but they’re the boss nonetheless.) But even after countless rewrites, I couldn’t seem to please the new editor, so I asked her how I could do a better job going forward. (It’s not helpful to defend yourself; it’s usually more effective to try first to learn what they want.)

She asked for referential links to other published works and studies as well as actual examples of the behavior I was describing—without these things, she said, I was only “giving advice” and “prognosticating.” I was confused because I’ve always included relevant research and references to published works when I’ve written for other well-known publications like the Harvard Business Review and Forbes, and I was already doing that for this publication too. (Conversely, here in my own blog, I feel quite free to share what’s only my opinion!)

For the next few pieces, the new editor and I went back and forth without much improvement. Then I wrote a piece about people-pleasing in the workplace. I couldn’t find workplace statistics about people-pleasing, but I included substantiating content and references from four other recognized publications and four real-life examples. Once again, the editor was extremely dissatisfied. After three unsuccessful rounds of revisions, I told her I didn’t want to waste her time anymore and therefore I would withdraw the piece. (When you can’t win, give in.) I asked if she could share a few pieces she liked so I could use them as examples and guides to help me figure out how to do better, but she told me it was not her responsibility to do that. (If your boss refuses to help you, take that as a real warning sign.)

She added that if I would name specific leaders and companies who demonstrated the behavior I described, it would provide “real-life flair.” It turned out that my real-life examples weren’t what she wanted because they were anonymized. “It’s not a big deal to drop some company names,” she wrote. “Just do it.” I told her I couldn’t violate my clients’ confidentiality, and she said she actually cared less about my clients than she did about “completely famous companies.” Of course there aren’t many examples in the public record of the negative impact of people-pleasing, and there are very few exposés of the hundreds of types of business people’s ineffective behaviors.  

I calculated that writing for her took two to three times longer than writing for any other publication—and caused many times more stress. So I took a stand in my next email: “You seem to have a very definitive kind of piece in mind. It’s absolutely true that many of [your publication’s] articles are about famous companies. But I’ve read numerous pieces that are completely normative or experiential and don’t provide any case examples at all. I truly don’t want to be driving you crazy. I just don’t believe I can deliver according to your parameters. And it seems too stressful for both of us if I keep producing work that is inadequate by your standards.”

Use These Questions to Make Your Determination

Here are the questions I considered before quitting:

Have I tried hard enough? In my case, I had been humble, curious, and put in significant effort and time.

Do I have enough data to make a judgment? Yes. We had gone back and forth multiple times over several months, with hard-to-get but increasing specificity. Her opinions weren’t likely to change and neither were mine.

Is the criticism valid? Whether the editor’s stance was the result of pressure from her senior editors or her own internal compass, I couldn’t know. What I did know was that my work had been carried for a long time in her publication and numerous others, usually with high regard and reasonable editing. 

Is my reaction reasonable? My frustration was understandable: The problem the editor had with my work wasn’t going to change. I wasn’t willing to violate my norms of privacy for my clients. Her growing disdain for my content and my questions made me very uncomfortable.

Do I have any leverage? The editor needed my work, but there are always many people who want to write for major publications. So she might be unhappy for a while over my leaving, but she’d get over it pretty quickly. I didn’t have anyone who could intervene on my behalf. There was no value in complaining.

What are the tradeoffs? I would lose a credential and an audience, but I would maintain my values. I would also save a tremendous amount of time and aggravation.

The Final Decision?

In the end, after answering my own questions, I exited. My client also used this same list of questions to consider his alternatives. He sought more data, adjusted some of his reactions, and applied the leverage he had with other executives. His decision? He stayed—and outlasted his new boss.

Onward and upward—
LK

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