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.”

{ 28 comments… read them below }

    1. Ann O'Nemity*

      That was my thought. The boss has acknowledged that the pay is low and the company is terrible. I’m guessing that the boss is powerless to change these bigger problems, and is trying convince the OP to stay on anyway.

      1. Laufey*

        All of the above, compounded by the fact that the manager may know the OP is job searching after only 9 months on the job (which itself may be caused by all the conversations about leaving with the boss).

        1. JM*

          That’s what I thought and he actually thinks she’s a good worker so he wants her to stick around.

    2. OP*

      From what I’ve heard without flat out asking, it doesn’t seem like anyone has stayed in this job longer than 2.5 years.

  1. thenoiseinspace*

    Another possibility is that one of the jobs OP applied for has called the manager for a reference or a background check of some kind. If so, it would have tipped him off about the job search.

  2. Just a Reader*

    I’m surprised that a boss is saying “the pay is low and the company is terrible” without selling something else really hard–growth opportunities, etc.

  3. Betsy*

    My guess is that he probably actually thinks you should look for a new job. I am putting myself in his position and imagining a really good employee in a really terrible job. From his perspective, he really needs you to stay around and keep working, but he knows that there’s really no reason why you should, given the opportunities out there for you. So he’s trying to dissuade you from making a decision that he’s just assuming you must be thinking about.

    Obviously, I don’t actually know what’s in his head, but I can absolutely see myself doing the same thing in the above situation.

  4. Brett*

    I’m in a really low pay situation; so low that I know that I am hurting my career by staying here and my only offset is doing tons of professional community work.

    Low pay makes bosses paranoid, since low pay also almost always goes with no raises, no bonuses, and no perks that cost any money (including training and paid time off). That can make employee retention a bit of a nightmare.

    1. AnonK*

      So true. It’s a boss’s worst nightmare (or at least mine). I have worked for a company that was circling the drain, and some people hadn’t received a raise for over 5 years. People become apathetic.

      Then one day, you get that amazing employee. He/she took a chance on the failing company because the commute was great. You rack your brain thinking what you can do to make sure he/she lasts. But in the back of your mind, you know that the relaxed dress code you tossed his way, the pizzas you bring in for late nights out of your pocket, and the other little motivators you try to come up with creatively are just stop gaps. He/she will eventually say, you know what? I don’t care if I add another 20 minutes to my commute and the boss at the new company requires me to dress up. They are paying 15% more AND gave a bonus last year…..

      You feel powerless.

    2. Just a Reader*

      Yep. My last job had low pay and “perks” like High Five Tuesdays. Bonuses were a joke and we had generous vacation packages that nobody ever got to use. Training was all done internally.

      1. AnonK*

        I have to ask…. what’s “High Five Tuesday”?

        If it’s anything like “Potluck Fridays” that my old company used to do, I’m so sorry….

  5. Paranoia*

    I have been in my position a bit over one year, and my immediate supervisor does this to me fairly frequently…”If you stick around a little longer you will xyz…I know you may have bigger plans, but working here has its perks…etc” It it TOTALLY unprovoked. My “group” of people in this department have decided he is completely paranoid of losing me because there have been 4 people in this position over the last 2-3 years. I have given him no reason to think I am leaving (because I’m not). In my case, it’s total paranoia. Such an uncomfortable place to be sometimes.

    1. Jen in RO*

      In my case, my former boss started saying very similar things once he learned that I was unhappy and looking to leave. I felt talked down to, since I had been waiting for the fabled changes for a year… so I still left, extra-angry at Boss.

  6. the_scientist*

    This is an interesting question, because I’m somewhat on the flip side of this situation. My boss knows that my leaving at the end of the summer is a possibility (she wrote me a genuinely lovely reference letter for a competitive professional degree), but I’m wondering if I can or should leave sooner. I am on a one-year contract and will most likely be offered a permanent position, but I’m not feeling adequately challenged in this position. It’s meant to be an entry level research position and I spend 60% of my time on admin-related tasks. I’m missing data analysis and study design more than I ever thought I would, but I also think it looks a bit ridiculous to begin job searching with only 6 months in my current role, plus the possibility of grad school. However, it took me 5+ months of searching to land this job, so I will need to start looking soon. There’s also the question of whether it’s ridiculously entitled to want to feel challenged with an entry-level position, and what the expected time to stay in one of these positions is.

  7. Artemesia*

    My spidey sense would be tingling; maybe it is a boss just worried about retention issues or maybe it is a boss that knows the place is going under and doesn’t want people bailing and making his life harder in the short term. I was once ground up and spit out in a merger — and we should have seen it coming and have all bailed long before it happened. I ended up on my feet but most of my peers who got forced out were unable to restart their careers at anything like the level they had achieved there and would have been so much better off to have taken 2 or 3 years to explore ways to make their move. No believed it could happen.

  8. Not So NewReader*

    I wonder if he knows there are changes happening and he cannot tell you. Perhaps he knows there will be an opportunity for you in six months but he is not allowed to say that.

    Definitely ask. And the way Alison framed it is perfect because it is just a question. He can answer you directly … or not. If he hems and haws you might be able to say “Is there something that you feel I should know about this company?” In other words, reframe the same question and ask again.

  9. James M*

    AAM’s advice here is spot on. Have an honest discussion with your manager. If that’s not an option, then you have a bigger can of worms to fry.

  10. Rabbex*

    This probably has nothing to do with your particular situation. But I had a coworker who would consistently ask me the same questions every time she saw me: “So, how do you like your schedule? Is it working well for you? You don’t mind the hours?” I thought she was just trying to make conversation and couldn’t think of any new topics. It turned out that about 1-2 years later she had to be let go because it became clear that she was suffering from dementia to the point where it was affecting her ability to work with our clients effectively. It was only then that I put together that she was asking me those questions over and over because she forgot she’d asked me already. Just a thought.

  11. Anonymous*

    I had a scenario #2 situation before: My former boss occasionally made similar comments, half-jokingly, to me while she was job searching. (I only found at she was job searching after she found something and gave notice). It wasn’t nearly as extreme as what’s happening here, but definitely the thought of quitting, in general, was on her mind a lot.

    If that’s the case, I doubt your boss will be completely forthright with you, but at least you will know if you appear to be unhappy or not, and it might clue your boss in that they need to keep their unhappiness a little bit more on the DL (assuming that’s the norm at your office).

  12. OP*

    Thanks for everyone’s advice. Let me start off by saying I got this job once I found out my old company was closing. When I went into this it, I knew that the company wasn’t great and there would be no growth opportunities. However, I also knew I would be learning a ton and have great experience to put on my resume(both have turned out to be true).

    I have a feeling it could be a mix of everything. The company is small (30 employees) and everyday someone is stopping my office to complain about something. The majority of the employees have also been here over 10 years. I think a lot of them feel ‘stuck’ here so even though they are frustrated with the company, they seem to just grunt and take it. It’s possible he is using the situation to internalize what he is feeling as he also has told me I shouldn’t still be here in 5 years(he has been here for 8 years). It’s really kind of sad now that I see it typed out in front of me.

    I could also be seeming more unhappy than I think. I had an issue a couple months where the company did not want to pay me for a holiday. I told him I eventually gave up fighting the issue, even though it was illegal, because it just wasn’t worth the headache. That may explain why the comments started then.

    I’m going to take AAM’s advice and just ask why he’s been mentioning it so much. Hopefully I can figure out what exactly is going on and see if I need to change either my habits or my job.

  13. Lily in NYC*

    My guess is that he thinks you are a good worker and doesn’t want to lose you – and is an anxious type of person who can’t help himself from asking because he needs reassurance that you aren’t going to quit. I had a boss like that and it was maddening! I felt like a therapist after a while.

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