One reader writes:

I’ve been working with a very headstrong soul (let’s call her Paula) in a small company for a decade. We have a new CEO and he’s doing an excellent job. He is respectful, careful, and thoughtful, but not afraid of making difficult decisions. He recently fired some very problematic people who did their jobs with clients but absolutely terrible colleagues. Now most of us see a new, much better future here, and we are really excited to make changes.

The problem is … Paula. It is seen as difficult by many, including me. It’s extremely negative about work and sometimes downright toxic. She’s really good on the creative side, but very protective of her job, to the point where she’s even started stamping her name on her documents to send a message to the rest of us. It’s just not that type of company, and when they refuse to provide helpful information, it really annoys colleagues even though they don’t confront them. She is very passive-aggressive, but does everything on time; she leads teams well but only takes them so far; etc. If she was someone else I could be done with her.

However, I know Paula very well personally. I know she is alienated from her family … completely alienated. She had a terrible, sloppy early life (no dad, mom was addicted) and outwardly overcame it with advanced degrees and a very dedicated work ethic in her own small area. She has been working on herself for many years in therapy (I know because I recommended her last therapist, who is also mine). She is really prickly, but sometimes when she loses her vigilance we can actually bond. I feel for her. She has finally reached a place where she feels safe and she holds on to it with all her might. But the ground is changing in our company and it doesn’t seem to move with it.

If my instincts are right (and they’ve been spot on so far with the shooting and other dynamics gone), I think she might be on the chopping block in the coming year. I don’t have any specific evidence, but I just wonder if I should gently … say something? Point out a few things? I’ve told her twice over the years that she seems really unhappy at work, and I asked her if she’d ever thought of starting somewhere because it worked well for me (in the kindest , most neutral kind that I could muster). She immediately rejected the idea.

It’s not up to me whether she stays or goes. I find her challenging to work with at times, but I would feel terrible for her if she were released. Is it worth warning her of my worries as some kind of friend who cares what happens to her? And if so, what would be the best way?

You can read my reply to that letter in New York Magazine today. Go there to read it.

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