is my boss trying to tell me he’s unhappy with my work?

A reader writes:

I started at a new job about five months ago after leaving a pretty toxic work situation, and I am happy to report that I love my new job. No work environment is perfect, but when you’re able to do work you love, it makes any environment a lot better. I work for a pretty small agency and it’s all hands on deck. That said, I have more experience in one particular area and the person who handled that work left shortly after I started, so I quickly became the go-to person for that stuff.

A couple months in, my boss asked if that was what I wanted to be doing because they care a lot about making sure you’re happy in your work, and I said yes. He asked about my workload and capacity, and I said it was a heavy workload but that I thought I was handling it well.

Now we are transitioning a bit for various reasons and my boss has now asked me twice in the space of a month in two different check-in meetings if this work is what I wanted to be doing. In the area I’m in charge of right now, I have experience in four out of five aspects of the job and the only reason I’m not super versed in the fifth is because this aspect is not common in my previous industry. I’ve been very open about this gap in my experience (which my boss has some experience in) and have expressed an interest in learning more either with him or through professional development opportunities he has offered to pay for.

I’ve continued on my merry way and that missing element (we’ll call it X) hasn’t been relevant until very recently. We have been meeting to go over some of that work together and he has continued to ask me if there are other aspects of our client work that I am interested in or that I want to be doing.

First, there really is no one else working here that could do 90% of what I do and it should really be done in-house even though he has talked about using an outside contractor for that fifth element, X.

Second, my boss doesn’t seem much like someone for confrontation. He is very supportive but doesn’t strike me as someone who would be up-front if my job performance were underwhelming. (That said, I have no reason to believe it is. My coworker is very up-front and we work very closely together and she sings my praises.)

I’m starting to get nervous about why he’s asking me this. I can’t tell if it’s because I suck at what I’m doing and he wants to see if I can be valuable doing other things, or if it’s because of that lack in X experience, or if it’s just that he wants to be sure I’m happy with my work.

We get along really well, so I’m worried he’s just trying to be nice but for some reason isn’t happy with my work. This job is a new industry for me, but it’s been what I want to do since college and ever since I’ve started I’ve faced some imposter syndrome. I had convinced myself that I was hired for a reason and that my work is not falling short. But then he started asking me if I wanted to do what I was doing.

I’m not sure how to handle this. Is this just a case of imposter syndrome or could I be failing?

This is a really good example of something I try to instill in people here — that when your boss is saying or doing something that’s confusing you, you shouldn’t try to decode it on your own but instead should just ask! Guessing can cause lots of stress and angst, and you can end up guessing wrong.

So. Sit down with him and say this: “You’ve asked me a few times if X is really what I want to be doing and if there are other things I’d rather work on instead. I’m very happy doing X and hoped it was going well — but since you’ve asked me that several times, I’m wondering if you have worries about my work in that area that I should be aware of.”

See what he says. If his answer is vague, then say this: “Are you happy with the progress I’m making on X? Do you think it makes sense to keep X with me? If you had concerns about my abilities in that realm, I’d definitely want to know about them.”

I get that you’re concerned he wouldn’t be up-front with you if the message is a hard one to deliver, but even managers who shy away from delivering tough feedback usually won’t blatantly lie to you when you ask in this way. Some especially bad ones might, but most won’t when you (a)  make it as easy as possible for them to tell you what’s up and (b) flag that what they’ve been saying so far has been confusing and giving you doubts. Most people will respond to that by clarifying what’s going on.

Also, if he tells you everything is fine but then keeps asking the same questions after that, it’s okay to say right in the moment when he does it, “I’m definitely happy doing X, but you’ve asked me that a bunch so I want to make sure there’s not a piece of this I’m missing.”

As a general rule, whenever you’re confused or concerned by something your manager says or does, you can ask about it! It’s helpful to have language like this in your pocket:

* “You seemed hesitant when I brought up X last week. Do you want me to approach that differently?”
* “I realized I wasn’t sure what you meant by X – can you tell me more about that?”
* “I might be misreading this, but do you have any concerns about how I’m handling X?”
* “You said X yesterday, and it made me worried about what it means for the Y project.”

Say this stuff calmly; you want to sound genuinely inquisitive, not agitated or defensive.

But there’s no point in trying to figure out what your manager means on your own when you can ask directly.

{ 85 comments… read them below }

  1. Heidi*

    Hi OP. Your boss also could have forgotten that he asked you about doing X before. I know several people like this. Or maybe he can’t think of any other stuff to recommend for you because you’re already doing great. :) Sometimes it’s hard to come up with feedback when you truly have no complaints.

    1. pamela voorhees*

      He might also be projecting that HE doesn’t like X work very much, so he’s worried YOU don’t like X work very much, and that’s why he keeps asking.

      1. Lily Rowan*

        And especially if it was added to the position after the OP started. If the boss feels like X is terrible, and the OP graciously took it on, the boss might be worried the OP is going to be unhappy in the position if they have to keep doing X!

        1. Daniel Atter*

          Exactly. We’ve seen quite a few letters here talking about the ‘bait and switch’ where someone took a job to do A and ended up doing B. It looks from this letter that X wasn’t meant to be a part of OP’s job originally.

          So it’s good of the boss to make sure that she’s happy doing it and not resentful that it was something she didn’t like or wanted to get away from.

          Then, sure, he isn’t doing it as well as he might and the result is to worry OP. Agree fully that OP needs to sit down with him and get this cleared up.

        2. MCMonkeyBean*

          Yes, I thought that was possibly the key part as well! It sounds like much of what OP is working on now is not what they were originally hired for, and a lot of people would be unhappy in that situation which is something any good boss would want to be aware of.

      2. Threeve*

        I had a boss who did this! I was partnered with a coworker on an ongoing project, and he kept asking stuff like:
        “So how is working with Jane going? Let me know if anything ever gets to be too stressful.”
        “You and Jane are getting along? Are things good? I know you have a lot on your plate.”
        “I’m sorry we can’t have you on a solo project right now. Is collaborating with Jane okay?”

        I was paranoid for a while about how I might be coming across as annoyed or overwhelmed, but then I realized: dude just really hated Jane.

        1. NeonFireworks*

          Haha, and I WAS the boss who did this! I love my job, but there are two small occasional tasks I have to do that I dislike/resent. One of them is a long, repetitive task that I find mind-numbingly dull (say, opening all 247 automatically packed boxes of teapots to check that they haven’t been broken by the machinery). In 2019, one of my direct reports did this with me as per the requirements of her job. Afterwards she said to me in a very calm tone, “I just LOVED doing this,” and I automatically assumed she was being ironic/sarcastic and readily agreed. Then I noticed her surprise and apologized for misinterpreting. She laughed and clarified that she DID love it: she thought it was relaxing and enjoyed the responsibility of being charged with checking all the teapots even though we found no problems. To each their own!

          1. Fikly*

            My team does this! There is a task that people don’t hate, but it’s not their favorite, and it’s my favorite thing. For unimportant reasons, they get notified about the task first, and have to request assistance if they don’t have the time for it (and I almost always have more time for it than they do).

            This task has been coming up a ton lately, and in the last three days I have had two different coworkers tell me they feel guilty asking me to help, and I keep telling them it’s my favorite thing! I don’t know how to get them to believe me that I am actually excited and happy when they pass the task on to me.

            1. JessaB*

              Is it possible to just talk to the boss and say you usually have time and honestly it’s not some people’s fave but you love it so why don’t they just give it to you in the first place? If that can be said without sounding like you’re throwing the coworkers under the bus that is.

          2. Clisby*

            I can totally see that happening! Before I retired, I loved having intellectually stimulating assignments, but jeez, not everything had to be fascinating. Every once in a while, a kind of mindless (but necessary) repetitive task can be really soothing.

            1. NeonFireworks*

              And this is exactly what I overlooked. I didn’t know until my mid-twenties what I was going to aim for in terms of a career, because of that minimal boredom threshold. Everything I tried out earlier left me too often staring at the clock in moderate despair. Then there was one fall when the only thing I liked about my job was finding a way to condense my duties into a few hours a day so that I could go home early and devote extra time to my NaNoWriMo project. That’s when I realized I needed to be doing something much higher-adrenaline for a living, which was absolutely correct. Far happier now. Sometimes it leads me to project a bit, though. :D

          3. Amethyst Anne*

            My 9 coworkers and I prepare breakfast for 650 and lunch for 700 in the kitchen of a local elementary school. I like to do most everything except for one job in particular. It’s not hard but there is just something about it that bugs the heck out of me. My work partner said that it’s no big deal to her. She hates to cut cakes, brownies, and rice krispy treats that we make in 18”x26” full-size cake pans so that there are 70 square servings/pan. I love it!

            So we’ve agreed to do the job that doesn’t bother us.

      3. infopubs*

        Came here to say just this. It’s possible he can’t imagine you actually enjoying doing X and feels a bit guilty assigning it to you. That’s how my spouse feels about me doing the taxes!

      4. Gaia*

        Oooh this. I do work that a lot of people genuinely find beyond dull. I find it fascinating. So many bosses have repeatedly asked if I’m “really really sure” I want to do this work. Despite my earnest insistence that I love my work and find it fulfilling and fascinating, their own dislike just can’t understand that.

      5. Turquoisecow*

        Oh that’s totally possible. I had a boss who started out constantly asking how something was going and then transitioned later into basically apologizing for having me do that work, but I actually kind of enjoyed it. Most people didn’t, though, so it was assumed I would also.

      6. JSPA*

        Or the last person to leave angry left because they had some “X” put on their plate. He’s freaked you’re just being nice about it, you’re freaked he’s just being nice about it, and you’re locking into a double helical downward spiral for…no reason at all besides the growing sense of unacknowledged anxiety that’s in the air when the topic is raised.

  2. sigh*

    Totally go with Alison’s script, but another way to look at things is maybe your boss is just checking in, seeing if your happy. He might be aware that X is coming up soon and wants to make sure you can handle the workload.

  3. #idatherbequilting*

    As a new employee this may be his way of checking I with you to make sure you’re ok and enjoying the work.

  4. Kiwiii*

    i don’t have anything to add to this, but minus a few bigger details, I’m in a really similar boat. It’s nice to know that attempting to interpret good but nonconfrontational bosses is a skill that I need learn, rather than a failing I’m experiencing.

    1. KC Sunshine*

      The same thing happened to me about a year ago. My bosses asked me if I was happy working there (I’d been there about 6 months) and said they thought I had a negative attitude. I told them that I was very happy, apologized for what they perceived as a negative attitude and explained that it may be 1st trimester pregnancy symptoms instead (exhaustion, nausea, hormones, etc), and we discussed specific things I could do to improve my “attitude.” I did all these things, checked in weekly with them to make sure I was making good progress (I was), and documented everything. Six weeks later, I was asked to resign for not being a “good fit.” When I asked for specifics about this and cited the previous 6 weeks, they said it was “just a feeling” they had.

      Hopefully your story will end better than mine did. I’m still confused about mine.

      1. Close Bracket*

        You should probably have smiled more. /s

        I’m sorry those people were jerks. I hope you are in a better situation now.

        (ps, I was told I didn’t seem enthusiastic and was advised to act more enthusiastic. I haven’t been asked to resign yet, but it wouldn’t surprise me if I were)

      2. JSPA*

        My go-to assumption–unless there are a lot of newer people at or below your level who are pregnant or have small kids, and are thriving–is that this was pregnancy discrimination, and that you’d have every reason to get mad, rather than beating yourself up over it.

        At least…this is what pregnancy discrimination generally looks like.

        (Very few people these days will say, “we don’t hire pregnant people, and we fire them whenever we can.”)

        1. KC Sunshine*

          Yeah, that was my feeling too. I missed the deadline to fill a discrimination complaint with the EEOC (because it’s not like I had anything else going on during that time, you know?) and I don’t have the money to fight it anyway. Still looking for a job though.

        2. Nanani*

          This this this.
          Call up a friendly legal advice source in your jurisdiction, just to explore options.

      3. Mr. Tyzik*

        Ugh. I had a manager who gave me 3 projects. One was exciting and sexy. The other two were hardware upgrades that were controlled by HAL and I had no influence over how fast HAL could go.

        I loved the sexy project and threw myself into it. The other two were busywork – have a call to track HAL’s status, escalate on their slowness, latherrinserepeat.

        My manager told me I needed to show as much excitement over the upgrades as I did the sexy project, I couldn’t muster any enthusiasm at all. Shortly after, I was laid off for “reengineering”. I could connect the dots. I didn’t smile enough and wasn’t grateful for the work.

    2. TootsNYC*

      . It’s nice to know that attempting to interpret good but nonconfrontational bosses is a skill that I need learn

      Actually, Alison’s point is to NOT attempt to interpret them. But to directly ask them and to gently create an opportunity for them to give feedback that isn’t confrontational.
      If you bring it up in a framework of inquiry, they’ll have a chance to say what they mean.

      1. Product Person*

        Yes, exactly. No one should be attempting to interpret what’s behind questions from our bosses. I’ve always used Alison’s strategy, of asking in a calm manner, and then there is no risk of coming up with a story on our own that is based on speculation and unlikely to reflect reality!

        1. PABJ*

          Yes, only stress and anxiety lies down this path. Best case scenario you learn what you can fix. Worst case scenario – run away! But at least you know what you should do based on actual facts, not just your assumptions.

  5. AnotherAlison*

    Or. . .your boss wants you to do another assignment. My boss had a convo like that with someone today. We would like him to do “X” because he worked on an “X” project 5 years ago and it would be valuable to have that experience on the new project, but he wants to do “Y” because it’s a different technology and good learning experience for him. My boss wants to try to give him the career growth he wants, but we didn’t want to assume we knew what he wanted. (There is also an opportunity to step up a level from support to lead on “X”, but he doesn’t really see the value in that opp. vs. the technical learning piece.)

    1. JSPA*

      “I’m enjoying doing plenty of X, and I love that I’m getting up to speed on Y, but is there something else you’re particularly eager to have me do, instead?” is a good way to check on this sort of thing. Or even, “I love X, and I like learning Y, but you’re paying my salary, so if there’s something else you’d rather have me do, please don’t be shy about saying so.”

  6. Cobol*

    I have a manager right now who if point blank asked something that would require anything other than a positive answer would not tell you the truth. It’s a huge problem, and leads to it being hard for us to do our jobs because she won’t push back against other departments.

    While she’s the worst, I’ve worked with other people who don’t give earnest feedback, especially when tough.

  7. Alton Brown's Evil Twin*

    My first thought when reading this is that the company is shutting down the business line that OP works in, and the boss trying to hint that they should be looking for another job.

    1. Krabby*

      I wouldn’t necessarily read it that way. I had a manager who used to do this to one of her direct reports but it was because the work in that little niche the DR was working in was incredibly data driven and involved a lot of spreadsheets. In a largely creative department, this was the /worst/. No one wanted to do that piece of the job, so before DR came along, it was all falling on the manager.

      Because of that, the manager was terrified of losing DR. She would always be looking for ways to make sure DR was happy: professional development, extra time off, first stab at the most interesting projects.

      I think this is likely closer to what’s happening here since the boss has that 5% knowledge. I bet he’s incredibly worried OP will leave and he’ll need to take her work on. Or he hates that type of work and assumes most other people do as well.

    2. Artemesia*

      This is possible. Not THE most likely, but fairly likely. I worked in an organization that was headed for the dumpster (after literally hundreds of successful years) and one of the higher ups did hint several times to me that I needed to rethink my future — but he was SOOOO vague that I totally didn’t hear the subtext. So yeah, I was shocked to read on the front page of the local paper one morning that my career was about to go down in flames. So possible. Higher ups who do this may also not be able to come clean about it as this kind of information is tightly held. Just be sure you are keeping on top of information about the company in your local business press and wherever else you might find the info.

      Most likely is a boss that is poor at providing feedback and/or avoids any sort of confrontation and also believes that vague hints are information that you are taking in. So your only play is to be fairly direct about whether he is trying to focus you on some things you need to work on, wants to re-direct you, is warning you etc etc. You focus on your desire to contribute and your interest in some clear feedback – calmly and professionally as Alison suggests and keep pushing till you have some clarity.

    3. JSPA*

      That’s 1 + 1 = 11 thinking. Which is to say, there are some circumstances (if the boss is using tally marks in place of arithmetic?) where it could be true. But it’s a huge leap in most circumstances.

      And crucially, in those circumstances where it’s true (and note, this could apply to anyone, new or not, young or not, learning a new process or not), there are other signs that you can look for. Including, that other people are also getting hints about their future, and about a future outside the company. None of which are happening here, so far as we know.

      1. Captain dddd-cccc-ddWdd*

        I agree, (as someone with a huge “layoffs are in the future!!1!” radar) that it could be a possibility, but I think actually that OPs boss probably isn’t high enough on the org tree to be “in the know” about stuff like that, sorry to say!

        I get the sense that OP doesn’t really interact with many people in their company other than their boss (seems like an introvert and not really wanting to socialize or trade gossip with others in the company) so wouldn’t know if other people are getting these hints about ‘getting out while you can’ and so on. Where did you see hints about a future outside the company/organization btw?

  8. Old Cynic*

    I was in a similar situation years ago and spoke to my boss, using very a similar script to Alison’s example (more direct and less eloquent). I was told there were no problems yet the comments continued. At a subsequent meeting, my boss said my work was great but finally admitted that my execution of my duties looked so easy for me that he was concerned I was going to get bored and take off for more challenging pastures.

    1. TootsNYC*

      I would say you -eventually- had success with your questions.
      Maybe it just took longer for him to trust that he could be honest with you.

    2. That One Girl*

      I had a similar situation and it turned out my boss at the time did not think I was happy so she kept pushing it instead of leaving it alone.

  9. Seeking Second Childhood*

    One hopeful thought to keep in mind is that this might indicate that your boss has funding to hire someone new — or promote a junior employee who is ready for more responsibility.
    If either of those is the case, you may be able to customize the job even more to your liking.
    (I find having hopeful reasons make it easier for me to be curious asking questions like these, instead of fearing I sound whiny or anxious — even if I AM one of those. ;) )

    1. Aquawoman*

      I thought something similar, that if the LW took on the work of another person, the boss doesn’t want to lose the FTE in the reorg.

    2. Captain dddd-cccc-ddWdd*

      Sounds like OP was originally hired for something different than what they’re primarily working on right now (“I have more experience in one particular area and the person who handled that work left shortly after I started, so I quickly became the go-to person for that stuff. […] A couple months in, my boss asked if that was what I wanted to be doing”) so I can understand the boss wanting to clarify whether the OP wants to pursue this ‘diversion’ or continue with what their role was originally intended to be.

      I worked with someone who was in a vaguely similar situation in that they were handling the responsibilities of what should really be 2 roles. Their boss gave them the option of which “new role” they wanted to pursue (and therefore which one the boss should recruit for) based on what they primarily wanted to do. It could be something similar to that.

    3. JSPA*

      Good point! worth gaming out, “what task or tasks would I most like to give up / what other task(s), if any, would I most like to add.”

      “Why, do we have money for a temp?”
      “Is someone pressuring you to get me to do additional tasks to justify my salary? Should I worry?”
      “I understand if you can’t answer directly, but I’m getting mixed signals. Are we on the good end of a hiring opportunity? On the bad end of an efficiency drive? Or is there some other reason that you’re looking to re-align my duties?”
      “If you’re at liberty to discuss it, are you asking because there’s pressure to split two jobs into three? Or compact three jobs into two?”

      Letting the awkwardness sit just long enough is a skill (and a hard one). If you supply the “…or are you just asking,” then the boss doesn’t have to worry further. But if you ask in a way that demonstrates that a) they’re creating a situation where anxiety can set in and b) if they’re intending to hint in a direction, they need to put a whole lot more direction into those hints, then they know they need to add some actual context.

      1. MCMonkeyBean*

        I think it’s better to just ask if there are reasons behind the questions rather than suggesting some worst case scenario reasons of your own. I think if the boss is genuinely just checking in and you respond with “are you trying to justify my salary” that will come across as unnecessarily adversarial.

  10. The Man, Becky Lynch*

    Please ask him directly with the scripts provided!

    I get the feeling he’s not hinting at you that you’re doing poorly. I have had a couple bosses who are just really stuck and stunted in their general “check in” questions. So I hear a lot of the same ones and I’m like “Still the same, still the same.”

    Part of it is their idea of staying present and giving you an opening if something changes. What you said last month doesn’t necessarily mean it’s the same this month [but it gets tiresome when it’s that frequent, I totally understand.]

    So once you ask him if he has any concerns and that his line of questioning is giving you these feelings, he can have that opening to realize what his words are doing to you and either adjust or explain “no, it’s just one of my tics.”

    It’s up there with just standard check in stuff. “How are you, how are you feeling, can I do anything to make your life easier?” kind of stuff that is pretty standard for someone checking all the boxes of their scheduled check-ins.

    1. LQ*

      I totally use the same check in question every week to sort of open the floor in my one on ones. I told people I was doing it so that I could shift my brain into the thing we are talking about from whatever the last thing I was doing and to make sure that there was always a clear place for them to start. But a little bit was just I didn’t want to try to come up with something new everyweek for every person because I’m not that creative.

      This could be offering standard question all the time, or rotating (consciously or not) through a list of sort of “these are acceptable ways to kick off a conversation without the exact same words every time.”

      1. The Man, Becky Lynch*

        I would say it’s just efficient in the end, why waste the effort to mix it up? The whole point of 1:1 is to stay connected and on the same page in the end. My original comment seems cold rereading it, I shouldn’t say “stuck and stunted” but just “it works, why fix it? Check lists are a standard tool we all tell someone sometime to try out.

        I think the key is what you’ve done, let people know you’re just going through your check list. It’s harder to get into the predicament the OP is in by being that transparent.

  11. RC Rascal*

    My interpretation of this is that boss make have you in mind for something else. You might want to do X, or have experience there, but he might think you would be better at Y. When I have had these kinds of conversations with people it’s usually because they have skill potential in another area where there could be opportunity and organizational need.

  12. Red Sky*

    The repeated questioning has me wondering if the boss has been burned by employees who appeared content, but unexpectedly quit to pursue interests that may have been available at the company but were never offered or if they were, never developed. It’s like he’s overcompensating for past mismanagement.

    1. Gaia*

      This. The first six months of Current Job were filled with questions of “are you happy” and jokes of “hahaha you’re probably leaving soon right?”

      It was because their last four people were I’ll fit for the role and left within a few months. No amount of “no really, I’m happy!” could convince them that I planned on staying. Now that we’re past that stage they seem to have settled down a bit.

    2. designbot*

      Similarly, I was wondering if Boss realizes how much they are relying on keeping you in this role (nobody else there does most of what you do, etc.) , and feeling unsteady about relying on one employee for so much with no real backup plan.

  13. Anon for this one*

    Alison, I have had similar concerns with my own boss (different details, but essentially “are you happy with my work”) regarding “even managers who shy away from delivering tough feedback usually won’t blatantly lie to you when you ask in this way”. I have tried language similar to the ones you suggested, e.g. “you seemed hesistant when I proposed doing X, should I have done Y instead?” etc.

    In my case I’ve got responses like “no, that’s fine” “you’re doing fine” “there isn’t anything I want you to do differently” etc even after I probed gently in different ways.

    My boss is very conflict-avoidant though and I get the feeling would not necessarily voice concerns that I should be doing Y instead etc.

    Do you have advice in the case that OP uses wording like that and the boss does “blatantly lie” out of conflict-aversion?

    1. Anon for this one*

      I didn’t finish the thought in writing but just to make it explicit… at what point do you take the “it’s fine” at face value?

    2. Oh So Anon*

      I…would assume that you’re not necessarily getting a fulsome (or honest) answer if you’re putting a manager on the spot with a request for feedback. A lot of managers, even those who are comfortable with giving feedback, appreciate being able to prepare their delivery. “You’re doing fine” isn’t really about lying for these folk – it’s that whatever can be improved isn’t worth their energy to deal with right this second. That doesn’t necessarily mean that the area for improvement isn’t important – it could very well mean that they’re wary of dealing with your potential reaction.

      If you’re getting responses from your manager that feel kind of “meh” in the course of getting feedback for your work, wait to see what happens when you wrap up a project or during a formal performance review. A manager who doesn’t prefer to give off-the-cuff critical feedback (or one looking to identify a pattern) will probably be more forthcoming in a more formal setting.

      1. Anon for this one*

        Thanks for the response! I have assumed I’m not necessarily getting a fully honest response actually (I’m usually direct with communication myself, so I do find this difficult) but not sure I’m putting the manager “on the spot” as this is in the designated monthly “one-to-one” meeting where we are supposed to check in about goals etc.
        We don’t really have a formal performance review process, but in the meeting that has that ‘role’ the boss said they were happy (I pushed again for any negative feedback but didn’t really receive any, or just one very mild comment.)

        1. Oh So Anon*

          Sigh, that situation doesn’t sound fantastic.

          Monthly 1:1 meetings, depending on the kind of feedback you’re looking for and what else is going on, might not provide enough distance from a project or task for your manager to collect their thoughts. If this is an option with the kind of work you do, one of the things I’ve found that works is asking “if/how we could do things differently” when you do a similar task to one you feel wasn’t wrapped up with clear feedback. It gets you and your manager into the habit of post-mortem-ing work as well as gives them an opportunity to frame what would have otherwise been negative feedback as directives to move forward. The other thing that they may respond to is more of an “I wonder if XYZ is the most effective approach; what do you think about trying ABC because of PQD, etc…?” way of framing your request for feedback.

          If you’re a direct communicator and they are not, do not push for negative feedback. Do not explicitly ask for it, regardless of how open you are to it.

          1. Anon for this one*

            Thank you! you seem to understand the dilemma exactly! :D

            My instinct was I steered away from “I wonder if XYZ is the best approach..” etc because I felt that as the person doing the work ‘on the ground’ I ought to know if XYZ was the best approach so it seems a sign of weakness or lack of knowledge if I am expressing to the boss that I’m not sure if XYZ is the right thing to do or not. I did vaguely ‘wonder out loud’ that the ABC project didn’t quite go to plan because of blah blah reasons… and the boss had a lot of things to say about how it could/should have been done differently. A max of 10% things I could have changed (being generous) and 90% resentments about other people.

            1. Eliza*

              If your boss avoids direct confrontation but is happy to badmouth other people to you, it sounds like it might be worth finding out what your boss is saying to other people about you, if you can.

        2. JSPA*

          Put a loud talker and a soft talker in a room, and the loud talker will often get louder (because they’re trying to model “speaking up” for the soft talker or because the room is too dang quiet) and the soft talker will get softer (because they’re doing / feeling the opposite).

          Other times, people will take on and mirror the demeanor of those they’re talking to.

          It’s hard to distinguish “weak positive instead of weak negative, because I came in kinda negative” from “weak positive instead of strong positive, because I came in sort of negative” (or whatever permutation starts with, “weak negative” on your part). You can’t change the boss or the dynamic, but you can change your own starting point.

          Sometimes, when you’re digging for a possible negative, and you’ve tried and tried to ask for any negatives, and gotten pablum weak reassurances, it can help to come in intentionally positive.

          That way, the other person has emotional space to launch a mild negative, if that’s what they needed, to do that. And you get the info you wanted. If they instead get even more positive, then…there’s your answer. They legit think you’re solid in all ways.

    3. LQ*

      One of the things you can do in this case is talk in an indirect pattern with them. (I know I know, everything except direct is the devil, moving on.)

      You can try using a metaphor, or telling a story, or asking about someone else (hypothetical is fine), do it as a friend of a friend thing. Don’t come directly at it, and try to be more than just “asking for a friend” kind of indirect. Try to come at it more like a story you’re telling. This is helpful if your boss is actually an indirect communicator. Do they often tell stories, use metaphors, talk about one thing but are also trying to communicate several other things? If they are direct but conflict-avoidant this won’t work for this kind of boss.

      “I went to the store and the kid behind the counter was so happy and chatting with everyone and I’m sure it was great for the little old lady who was talking with him but he had a line of 10 people and no second register. It’s so frustrating when people spend all their time pleasing one person while ignoring the pile up of problems behind them.” (This story means customer service matters, but speed does too, you’re too spending too much time chatting with your coworkers and clients and not getting enough projects done.)

  14. Jennifer*

    I second Alison’s advice. Just asking in a professional way makes your life so much less stressful. If you just wonder your mind can go to some dangerous places.

  15. hbc*

    I think 90% of any success I’ve had professionally has been from pulling info from people who aren’t really saying what they mean. “Before I answer that, do you mind if I ask why you’re asking?” It’s astounding how often they’ll clarify in a way that would completely change my answer.

    If that doesn’t fit the situation for whatever reason, sometimes I’ll fill in my own options. “Are you asking because you don’t see how anyone could enjoy this, or because you’re thinking about changing my duties, or do you think that I’m doing it badly?” You probably won’t get a full straight answer, but you usually get a watered-down version of their reason for asking.

    1. Krabby*

      I really like your second paragraph if he continues to ask after the initial conversation. I think giving the boss three options will make it much harder to lie. At the very least, how he responds will give OP more clues.

      1. hbc*

        I meant to add that there’s an “etc” tone to this that’s hard to capture in writing. So I name at least a couple of things to show that I’m open to multiple possibilities, but there’s often a trailing “or….” or a receptive hand gesture or a crazy suggestion (“you’re wondering if we need an office chinchilla to increase happiness”) that show they need to jump in.

    2. Kimmy Schmidt*

      I like these ideas.

      OP, look at how many different ways the commentators have interpreted this behavior! There are so many possibilities, but you can ask what’s going on and hopefully save yourself some stress.

    3. Oh So Anon*

      I like these scripts, but not necessarily for an entry-level-ish employee. Someone in that situation may need to show a fair bit of deference so that they’re not perceived as wanting to avoid competencies they ought to develop or to call the shots regarding their job.

  16. Captain dddd-cccc-ddWdd*

    Another possibility – could it be that X by itself isn’t really a full time “contractor” role, but some of your other workload could also be offloaded to a contractor in favour of new work that you’d prefer to take on?

  17. EPLawyer*

    LP, you came from a really toxic place, which besides “use your words” that Alison always says, she says “Staying at toxic place can twist your thinking about work place norms.” You are so used to how things were at former toxic job, that you are terrified you screwed up somehow at this job and are about to be fired.

    It’s probably just the boss making sure you have everything you need and are not burning out. Bosses should use their words too.

  18. Kendra*

    You say your organization is “transitioning a bit,” which I take to mean some type of reorg or redivision of job tasks, so it’s very possible he just has that on the brain. If he’s trying to make sure he’s checked in with everyone at least once, to see if they’re ok with the way things are shaking out, he may just have forgotten that he already asked you once. I really wouldn’t read into it more than that, but definitely use Alison’s scripts if you want to set your mind at ease!

  19. TootsNYC*

    another reason to ask–maybe he’d like you to do less of that one thing in order to focus more on what it was they ACTUALLY hired your for.

    But you cannot know until you ask.

    and my script for your questions wouldn’t be “is there something about that work that I’m not doing well,” but:
    “Can I ask why this question has come up? Is there a specific concern behind it?”

    1. Captain dddd-cccc-ddWdd*

      I alluded to something similar above and now I read your comment it seems clear! Boss is typically “indirect” or “not much like someone for confrontation” [btw, from the wording of that I feel that OP is also indirect / doesn’t like confrontation]

      OP was hired for something but is now working on something else because the person working on that thing left (and it was presumably more of a priority at the time) so it became OPs responsibility, with 4/5 areas being things they already knew how to deal with (but presumably weren’t hired for as such) and area 5 (X) being something they don’t yet know too much about.

      I think boss is trying (and potentially failing due to being too circumspect) to get OP to say they want to work on the thing they were originally hired for, and so potentially for someone else to be hired to take on the existing responsibilities.

      OP needs to choose if they want to take on the leaver’s role (including X, possibly) or return to what they were recruited to do.

      It seems like they have an open choice about that, but it may be that the manager has a preference one way or the other..

      1. TootsNYC*

        OP needs to choose if they want to take on the leaver’s role (including X, possibly) or return to what they were recruited to do.

        Well, OP first needs to find out what it is her boss REALLY means. This is just one of many possible meanings.

  20. Pobody’s Nerfect*

    Ah yes, VBS (Vague Boss Syndrome). Warning signs may be heard in these phrases uttered by non-committal bosses everywhere :
    “I’m thinking maybe…”
    “Perhaps we should maybe think about…”
    “I’m wondering if there might be…”
    “I’m not sure, but I had a slight feeling…”
    “I don’t know, what does everyone else think?”
    “Let’s all think on it and maybe something will come to us…”

  21. NW Mossy*

    OP, when your boss asks you these questions, what kinds of answers do you give? Are they vague and banal (“fine” or “busy!”), or do you include specifics and commentary?

    I ask because for employees who’ve recently experienced a toxic boss, their default behavior tends to be non-committal and withholding – they don’t tell the truth, even when invited to do so. This makes total sense, because it’s a mechanism many people use to survive a situation where the boss uses anything more specific as a weapon. But with more normally-calibrated bosses, this sort of evasion looks a whole lot like disengagement and unhappiness, which they’d be rightly worried about.

    It doesn’t mean that you have to overshare with your boss, but opening up even a small fraction goes a long way here. Instead of saying “fine” or “busy,” try something like “I’m working on X and Y right now, and Lucinda was really helpful on Z last week” or “I’m glad I’m getting to spend more time on A and B this week.” By giving that little bit of extra detail, it tips your boss off that you’re mentally present and willing to have a constructive conversation about your work.

  22. Oh So Anon*

    Something that has made me good at my career (albeit overly anxious) is assuming that my manager won’t necessarily tell me if they’re moderately unhappy with my work, especially if the aspect they’re unhappy with is related to something they perceive to be a trait rather than skill. Like, for example, if you’re an introverted person who’s been tasked to do more presentations.

    It’s a nugget I hold onto even when I’m working for someone who’s generally good at giving feedback. This kind of thinking forces me to dig deep and figure out precisely what I need feedback or support on so I can communicate that to my manager or line up resources on my own.

    Can you identify where you feel your strengths and training lie in terms of doing X? Are there learning opportunities related to X that would help you feel more confident in your role? Starting from there and positioning the conversation with your manager in terms of how they can support you in delivering your best.

  23. ThisColumnMakesMeGratefulForMyBoss*

    Maybe you’re projecting unhappiness, you’re unaware of it and your boss takes that to mean you’re unhappy in your role (I have a RBF and when I concentrate at work sometimes people think I’m not happy, but it’s really just my face). Even if that’s the case, the bottom line is that you both need to stop trying to decode what the other is thinking and feeling, and have a direct and honest conversation. You don’t need to be confrontational, but just point blank ask “You’ve asked me several times if I’m happy in my role. Is there something I’m doing or saying that makes you think I’m not?” And if they answer no, but keep bringing it up, “Why aren’t you taking me at my word?”

  24. HappyToBeHere*

    Your situation almost mirrors mine. I also left a very toxic situation with my former employer about 5 months ago this past summer. In fact, it got so bad that I ended up having a mental breakdown and quitting the job on the spot. Luckily I was only unemployed for a month before finding another job. And my new job is fantastic – nothing toxic here and everyone I work with is super nice! It also came with a slight pay raise as well so I will take it.

    However, I was incessantly worried if my boss was happy about my work or not. Then I had my 3 month review – it was much more stellar than I expected and it turned out that I was worried for nothing. So I totally understand how you feel. For me, it was related to the trauma from my former employer but also that I was just being careful. Keep in mind, nobody is perfect. Mistakes happen – as long as you learn from it, you will be fine. Keep going and I hope things will further get better for you!

  25. drpuma*

    My read on this is actually that your boss thinks you would succeed in more changing or advanced roles, but doesn’t want to pressure you if you’re happy where you are. I hear this not as “Do you really think you’re doing a good job?” but “Do you want to grow at this company?” Yet another reason to ask your boss what they really think!

  26. AdAgencyChick*

    Goodness, based on the way you describe it I think you actually have one of the good bosses! Based on the fact that you were sold on one position and then quickly had to take on other duties because somebody else quit and you have the expertise to do that person’s job, my guess is this question is coming from your boss’s fear that you’ll quit and move elsewhere if he doesn’t give you work that’s more like what you were sold on to come to the company.

    If my guess is correct, then your boss is basically the boss we all should have when a company’s needs change and you’re asked to do something that’s not what you signed up for. Too often on this board we hear about OPs whose bosses completely change the job description and expect things to stay that way.

    But of course the best way to find out is by asking, as Alison says.

  27. User 483*

    Am I missing it or does the OP never actually say they do WANT to be doing this work? I see a lot about how they think they are handling it fine and that there is no one else in-house to do it. But, I don’t see where the OP actually says they enjoy the work and that they would choose to do it if there were other options.

    The boss may be picking up on that if the OP is just doing the work because they think it automatically falls to them and not because they actually want it. And, in a supportive environment, you can be upfront with your boss and say that to them and that might help address any concerns they have about you hiding your actual opinion on the task.

  28. i forget the name I usually use*

    It sounded like Boss hired LW to do 5 elements including X. Now LW is doing 4 of those and Extra Task that was inherited, but not X.

    Boss may just really want LW to do all of the elements they were hired to do and not Extra Task, or feel that Extra Task is distracting/getting in the way of learning X. But as long as LW is insisting they are fine with the workload, Boss doesn’t really have a ‘reason’ to take it away (and if they are non-confrontational they may think they need a reason?).

    But yeah LW will apparently need to prompt them to saw that… sounds really frustrating for both sides. Reminds me of “ask” “guess” and “tell” culture ideas, i.e. Boss feels they are strongly getting across that he wants this to change and just needs LW to agree to it, and LW needs something more direct rather than these subtext hints.

  29. Eccentric Smurf*

    A year ago I moved from a toxic job with a truly awful boss to a great job with a boss that sounds a lot like your current one. I had very similar concerns during conversations with new boss. I recently took the plunge and asked new boss if there is anything they would like me to improve. They made some training recommendations for long term career growth but didn’t have concerns about the work I’m currently doing. Instead of hinting around about an issue, new boss was trying to be responsive (making sure things are going well from my perspective) and trying to figure out if we are on the same page about my career trajectory. Toxic job really skewed my perception and I’m still recalibrating a year later, but it gets easier every day.

  30. V*

    Could you straight up be like, respectifully “Can I ask why you keep asking me that?”?? Or is that rude?

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