It’s four answers to four questions. Here we go…

1. My friend’s work problems are making me anxious

I have a friend who can’t seem to hold down a job for very long before becoming very frustrated with it. Every workplace has an issue: coworkers who are catty, management that isn’t supportive, information that isn’t clear, and demands that are unrealistic.

From my vantage point, they are similar and benign issues that most workplaces have and there are ways around them. But whenever I try to share thoughts like that, she gets mad at me for not being supportive. So I have been trying to just listen and let her vent.

However, now I notice that I am getting very anxious. I fear she is jeopardizing her jobs with her behavior but she doesn’t see it. She needs the job so it’s not like she is trying to sabotage them. She genuinely seems confused about why they aren’t going well and doesn’t see her own role in the difficulties.

How do I best help her here? Is it better to just be the friend who listens or should I try to help her understand the work world a little better?

It sounds like you’ve tried to help her understand what’s going on and she’s gotten angry at you. But that doesn’t mean you need to let her vent to you endlessly either; at some point it’s reasonable to say, “I support you and I know you’re struggling with this stuff, but when I’ve tried to share my thoughts on it, you’ve gotten angry. I’m at the limits of how I can help, so can we talk about stuff other than work instead?” Friendship does not require you to endlessly listen at the expense of your own peace of mind; you are allowed to set limits.

If she’s a very good friend, you could try saying, “I see this really differently than you do, and I think you’re causing problems for yourself that you don’t see. It’s making me worried for you. Would you like me to share my perspective?” But if you try it and she’s unmoved, then you’re back to the above.

Alternately, every time she complains about work, you can try saying, “So what do you think you’ll do about it?” … but if that gets you labeled as “unsupportive” as well, then you’re back to the above too.

2. My manager’s phrasing is driving me nuts

I think I may be overly sensitive on this one, but I need some perspective. My manager has recently starting messaging me saying, “Can we do X?” as a way to assign me tasks. It absolutely drives me crazy. I prefer direct communication, and would much rather she ask, “Can you do X?”

Using “we” makes me feel like she doesn’t respect my contributions and that anything I do is just something “we” have done together. Plus, I worry that the lack of clarity will cause issues down the road — I imagine a situation where she thinks she assigned me something and I think that she is working on it. I’ve started replying with “yes, I can do that” to try to get her to recognize what she is doing without raising it directly. I feel like I’m being too nit-picky with her language, but this is something that really bothers me. Is there something I can do to get her to stop?

I’d recommend trying to let it go since asking her to stop likely will come off as nit-picky and overly controlling. The part of this that you have the most control over is your reaction to it. Can you focus on trying to change that instead?

That said … are you seeing any other evidence that your boss doesn’t respect your contributions and/or takes credit for your work? If so, those are substantive issues and worth addressing (totally aside from the language issue). If you’re not seeing any signs of that and it’s really just her use of “we” that annoys you, that’s all the more reason to try to get past it. We all have annoying verbal tics.

(For the record: Managers shouldn’t do this! If she were writing to me, I’d tell her to stop doing it and to be clearer when she’s assigning work, and ask if she’s using “we” out of a discomfort with authority. But she’s not the one writing for advice.)

3. I got accused of trashing my former company

I left a niche industry over eight years ago. Very dysfunctional, small company, family-run business. I was there more than 10 years. The last several years, it was obvious my boss barely tolerated me. When I finally found a chance to move on and gave my two weeks, my boss barely spoke to me.

Years of gaslighting, inappropriate comments, intrusive questions about personal matters … on and on it went. So I left with minimal contact with ex-coworkers. There was one person I did like working with and I stayed in touch with for a while, meeting up for the occasional coffee.

This past weekend, my husband and I were in a retail establishment, and low and behold next to me waiting to be served was the owner’s son from that job. After a few pleasantries, he went off — demanding to know why I trashed his dad and the company when I left. Totally taken aback, I said, “What are you talking about?” He went off calling me a liar and said, “Oh, so everyone made that up?” I have no idea what I allegedly said, nor did he provide specifics. I’m totally baffled. Furthermore, I would hope that I would have been more professional than that because I know it’s professional suicide to trash ex-employers. I have been racking my brain and honestly nothing is coming to me that could have been construed as badmouthing. And the fact that they waited this long to call me out?

Any advice? I know for a fact It won’t do me any good to try to talk to him about it further.

Leave it alone. it doesn’t sound like there’s anything to be gained from trying to engage. Who knows what he’s talking about — maybe someone there misrepresented your actions after you left (it sounds like the sort of place where that could happen), maybe he misconstrued something he heard, maybe he completely mistook who you are and thought you’re someone else entirely. Regardless, this is someone who thinks it’s okay to confront someone in public eight years after they left a job. He’s not someone whose judgment you should put a lot of stock in.

You’re not in touch with that company anymore or even in the same industry. You don’t need to put energy into sorting out what the owner’s son thinks.

4. My employee is applying for an internal job but doesn’t know I’m on the hiring committee

One of my direct reports, Jane, has applied for an internal open position. This position is in my department but does not report to me.

The trouble is that I am on the hiring committee and I don’t believe Jane knows this. She hasn’t said anything to me about applying. She had a phone interview last week with the committee head (other members were not involved, which is standard) and it wasn’t discussed there either. When I learned Jane had applied, I offered to recuse myself from the search, but the committee head didn’t feel it was necessary.

How should I approach this with Jane, if at all? Mostly I want to spare her the experience of coming for an in-person interview and seeing her boss on the other side of the table.

She might have not mentioned to you because she didn’t think she needed to, but she could also be worried that you’d respond badly to hearing that she’s looking to move on. (Of course, she may or may not be actively looking to move on; it’s possible she’s just interested in this particular job.) So the key thing is to make it clear that you’re not upset that she applied for another job.

I’d say it this way: “I wanted to give you a heads-up that I’m on the hiring committee for the X position so I’ll be in the interviews next week. I didn’t want you to be blindsided by that! I’m excited to talk more about the role with you.” If you think she’s a good candidate, add something supportive — “I think it could be a great next step for you” or “I could see you being really good at this” or “I’d hate to lose you, but I’d be glad the company is keeping you” or whatever makes sense for the context.

If she doesn’t get the job and you’d ideally like to keep her, talk with her about whether there are ways she’d like her current job to evolve. Are there areas where she wants to develop/projects she wants to take on/etc. and are those things you can realistically offer?

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