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‘Should I Warn My Work Friend That She’s Going to Get Herself Fired?’

Photo-Illustration: by The Cut; Photos: Getty Images

Dear Boss,

I have worked with a very quirky soul (let’s call her Paula) for a decade now at a small company. We have a new CEO and he’s doing an excellent job. He’s respectful, careful, and thoughtful, but not afraid to make tough decisions. Recently, he fired some very problematic people who were good at their jobs with clients, but absolutely awful colleagues. Now most of us see a new, much brighter future here, and we’re really excited about making changes.

The problem is … Paula. She is considered difficult to work with by many, including me. She’s extremely negative about work, and sometimes downright venomous. She’s really good at the creative side but very protective of her work, to the point where she’s even started stamping her documents with her name in order to send a message to the rest of us. It’s just not that kind of company, and when she refuses to share helpful information it really upsets colleagues, though they tend to not confront her. She’s very passive-aggressive, but gets everything done on time; she leads teams well, but only takes them so far; etc. If she were anyone else, I might be done with her.

However, I know a lot about Paula personally. I know she’s estranged from her family … entirely estranged. She had a horrible, neglectful early life (no dad, mom was an addict), and overcame it with advanced degrees and a very committed work ethic in her own small sphere. She’s been working on herself in therapy off and on for many years (I know, because I recommended her most recent therapist, who is also mine). She’s really prickly, but sometimes when she drops her guard we can actually connect. I feel for her. She’s finally gotten to a place where she feels safe and she’s holding onto that with all her might, in her way. But the ground is shifting in our company, and she doesn’t appear to be shifting with it.

If my instincts are correct (and they have been spot-on so far, as firing and other dynamics have gone), I think she might be on the chopping block in the coming year. I have no concrete evidence, but I just wonder if I should gently say something? Point a few things out? I’ve told her point-blank twice over the years that she seems really unhappy on the job, and asked her if she’d ever thought of starting fresh somewhere, because it worked well for me (said in the kindest, most neutral way I could muster). She immediately rejected the idea.

It’s not up to me whether she stays or goes. I find her a trial to work with at times, but I’d feel terrible for her if she was let go. As a sort-of friend who cares what happens to her, is it worth it to warn her of my worries on her behalf? And if I did, what might be the best tack?

It would be kind of you to talk to Paula about this, but go in knowing that it might not yield the result you’re hoping for.

From what you’ve described of Paula, a warning that her behavior could get her fired may not be enough to get her to change. You’re talking about someone you’ve characterized as sometimes “downright venomous”! She’s negative, overly protective of work, won’t share information, and upsets her colleagues. That’s all a pretty big deal, especially taken in combination, and it can be really hard to turn that kind of mind-set around, especially since it sounds like there’s some deep-rooted stuff going on. Plus, you’ve attempted to approach her about some of this in the past only to be shut down.

That said, since you’re concerned now that her job could be in jeopardy, it would be a kindness to her to try. You just shouldn’t feel like you personally failed if it doesn’t spark a transformation in her.

It does sound like you have better rapport with Paula than most people there do, which means that you might have more credibility with her if you lay some of this out. If she has a good manager, she’ll have heard some of it before — but sometimes it can make a difference to hear it from a more trusted source and someone she might more easily see as an ally.

Speaking of which, does she have a good manager? It’s hard to imagine a competent manager letting the behavior you described continue unchecked, so I wonder if the problems are being compounded by a lack of oversight. If that’s the case, you could be doing her an even bigger favor by being the one to say, “You’ve got to fix this or it could get you fired.” That’s a message her manager should be delivering, but if they’re not, it’s possible Paula has no idea how poorly she’s perceived or what the consequences could end up being. Of course, people shouldn’t need to be told that it’s unacceptable to treat their colleagues the way she does, but if it’s gone on this long and no one has told her it needs to stop, she might truly be blindsided if and when it eventually gets her fired. (And if I can get on a soapbox for a moment: Managers, don’t do this! People deserve to hear about problems long before things get to the point where their jobs are in jeopardy. Managers who wait that long do their employees a grave disservice and, frankly, are abdicating a fundamental responsibility of their positions.)

So. Talk to Paula. You could frame it as, “We’ve worked together a long time, I consider you a friend, and I would want you to tell me this if our roles were reversed. I think the culture here is shifting and some things that were okay in the past aren’t working anymore. The new CEO has fired people who were good at their jobs but hard for others to work with — and I’m worried that some of your own habits could put you on the chopping block if you don’t change them. Can I tell you what I’ve seen that worries me?”

And then see. If Paula drops her guard and is willing to listen, who knows — you might get through. Or you might not. If she makes it clear that she’s not open to having the conversation, there’s nothing to be gained by trying to hammer in a point she doesn’t want to hear, so at that point you should back off. But it’s worth a try — and even if it seems in the moment like she’s shutting you out, it’s possible you’ll have planted a seed that she’ll think more on later, possibly even much later.

Whether or not it succeeds, you’re a good person to want to try.

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email Her advice column appears here every Tuesday.

‘Should I Warn My Friend That She’s Difficult to Work With?’