my boss is constantly urging me to stay at my job, even though I’ve shown no signs of leaving

A reader writes:

I’ve developed a somewhat close relationship with one of my bosses, who is not my direct supervisor. I talk to him for about 15-20 minutes every day.

About once a week (sometimes more), he finds a way to turn a conversation from general work stuff to how — even though my job is far from ideal, the pay is low, and the company is terrible (his words) — I should stick it out here for a couple years. Sometimes this happens after I casually mention a small work issue, and sometimes it just happens out of nowhere. This has been going on for about 3 months now, so I’ve had this same conversation with him probably close to 15 times.

I’ve been here about 9 months, and while I agree with everything he’s said, I have begun job hunting. I’m not desperate to get out, but when I see something that feels right, I’m going for it. I’m not sure if he knows I am job hunting, but this conversation is getting awkward and really annoying. I usually just say, “I totally agree. I’m learning a lot and getting experience I wouldn’t get anywhere else,” which is true. However, I’m starting to feel like that is only encouraging the conversation to continue. Now I’ve tried simply nodding my head and smiling, but I’m running out of ways to respond. I’ve tried to avoid bringing up issues I’m having at work, but it’s pretty difficult to do in my office.

I really like this guy, so I don’t want to say something too off-putting. Is there something I can do to avoid this awkward conversation from repeating itself?

Maybe, maybe not.

Him mentioning it once or twice, I could see — but 15 times? I wonder what’s going on that makes him feel like he needs to say this all the time. Any chance it’s one of the following:

* Possibility 1: You seem more unhappy than you realize, and he’s responding to that by trying to convince you to stick it out.  You don’t say whether you agree with his assessment of your job, but nine months is a pretty short stay, and I wonder if he’s trying to point out to you that you’ll be better off staying than hopping to another job so soon. (Which might or might not be true, depending on the details.)

* Possibility 2: He’s  talking to or about himself as much as about you; he’s trying to justify (internally or to you) why he’s staying in a situation that isn’t ideal.

Both of those are just speculation though, so why not just ask him what’s up? The next time it comes up, why not  say something like, “I’m curious. You’ve mentioned this to me a lot lately. How come?”

If nothing else, the fact that you’re asking about it will probably decrease the amount he brings it up in the future — because you’ll explicitly have noted that it’s a little unusual that it comes up so much.

And in general, when you find yourself confused by what your manager is getting at by saying/doing, it’s usually fine to just ask. Frame it pleasantly, of course, but it’s usually okay to say, “Hey, I’ve noticed ___ and was wondering what’s behind it.”

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