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I'm struggling with my boss --- not for the first time.

I'm the kind of person that likes knowing what is expected of me, learning how to do it, and then working hard to excel at it.

What I am starting to notice is that my boss has a way of criticizing me without explaining what I could be doing differently. That makes me question the nature of the criticism.

Case in point: he has taken to implying or saying in passing that I am not "smooth" or have a difficult personality to work with. For example, "Oh, well, knowing that guy, he's hard to work with, and, as we've talked about, you're not exactly a smooth character yourself so it would be tough for you to work with him." OK...?

Part of the issue here is I am very conscious of not becoming a "yes man" and I haven't been afraid to tell my boss "no" when I felt it was necessary to do so. (I am convinced more of my boss's employees need to work on setting boundaries and saying "no" for the benefit of his mental health/managing his ego --- my "issues" notwithstanding.) Moments where not playing "yes man" have gone awry are all I can remember as far as what "we've talked about."

Another case: he recently implied I would start an e-mail with "Hi Bobby" to a very high level executive at our company (as an example of something not to do) --- this was in an attempt to advise me to write the e-mail to this executive carefully. Anyone who knows me well knows that I would not do this.

This is my sixth year working for this person. First of all, I'm floored that he doesn't know me better than that. I also see this as an instance of him regarding me as a silly child --- which I'm not, but maybe it makes him feel good thinking that's what I am in comparison to him? I would have expected that by this point he and I would be on more of an equal footing in our relationship.

Generally, I am beginning to get the impression that, on some level, my boss likes finding opportunities to criticize me --- and, when this happens, again, it becomes this "Oh, you silly child, I can't leave you for five minutes" kind of moment. But I know undisciplined people who can't be trusted to take the initiative or need constant supervision to stay productive, and that's not me.

Finally, when my boss criticizes my work, I sometimes feel it's more like a putdown than helpful criticism. I often find myself thinking "Well, yeah, I see where you're coming from, but do you have suggestions about how to improve it?" Or I feel as though he's bickering with me about minutiae rather than concerning himself with the big picture. (For example, when I was writing a grant proposal, two of my mentors gave me broad comments about how to improve the entire message --- both wanted me to emphasize a certain aspect of my accomplishments --- but the criticism from my boss was literally things like where to put commas. Note the difference between "Here's how to present your work better" versus "My writing style is better than yours" style criticism.)

My theory has become my boss is insecure and quite literally does some of this stuff to "score points" --- if I'm not perfect, he will go after me because it makes him look better. (For instance, if I send him a rough draft of a project document in its early stages in order for him to see the progress on the project, he will invariably criticize typos as though I should know better --- which pushes my buttons because I want to meet my boss's expectations --- even though, at that stage, the point is the progress, not the writing.)

Does this sound plausible? Are there other things I'm missing here? If the problem lies with me, I'm happy to work on it.

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  • I would start an e-mail with "Hi Bobby" to a very high level executive at our company how else you (one) should start? I'm interested! Nov 8 '21 at 6:49
  • @SouravGhosh Just a "Mr Smith," should do the trick. Nov 8 '21 at 8:12
  • @GregoryCurrie , or maybe a "Dear Mr. Smith"? But frankly speaking, I do not see a problem with "Hello Alan" either. Do you? Nov 8 '21 at 9:33
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    @SouravGhosh It depends on the culture. I try to avoid projecting my cultural expectations on others. If the OP believes it's inappropriate, I'm inclined to accept that on face value if it is not a core part of the question. Nov 9 '21 at 1:34
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    @SouravGhosh You opinion on the matter doesn't matter. Both the OP and the boss have an expectation of a more formal manner of address. You wanted to know how you could address somebody in a more formal manner. I answered. I'm not going to sit here and pretend I understand what is or isn't suitable in the OPs situation. Nov 9 '21 at 6:49
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To answer the question in the title: We cannot know. We can speculate, but that doesn't help at all.

What we can help you with is how to deal with the situations you encounter. I would suggest you be more clear in what you expect from you boss. Don't do it during one of those feedback moments where they are criticizing minutia, but do it during a 1-on-1 (or a similar meeting). Tell your boss that while you appreciate their feedback, the criticism on typos doesn't feel useful and that you need more feedback on the contents of your work, not the details.

If they cannot provide this, you should consider if you want a new manager after six years to make sure your professional development isn't hindered.

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He did not mention himself - ok, he's not so good at his job. Did you ask him?

With my emphasis to your words:

I sometimes feel it's more like a putdown than helpful criticism. I often find myself thinking "Well, yeah, I see where you're coming from, but do you have suggestions about how to improve it?"

Next time, try asking this loud and clear.

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  • Totally agreed. Also don't forget your boss works for stakeholders who need something. It may be that ultimately that's the way they need it or they need it within some timeframe and doing "best case" is not the best idea.
    – Dan
    Nov 8 '21 at 20:42
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  1. When directly asking for feedback, try to head off stuff you're not interested ("Hi Boss, I'd really like your thoughts on this document. It's only a draft, so don't worry about spelling or grammar, but I'd like to know if you think the technical details I discuss are the best examples to use...")

  2. If your boss gives you feedback like "you're not exactly a smooth character yourself" either try to get more concrete feedback then and there, or make a note of it and ask for actions to improve it via email or a separate. Ask for specific examples of when the behaviour happened and specific examples of how your boss things you could have handled it differently. Keep doing this, as you know his feedback his pretty useless without specific ways to improve, so feel entitled to keep pushing this, in a positive way ("Thanks that's great, but I really need to understand what you would do differently...")

  3. If that doesn't work, then you may have to accept that's just how your boss is (and it's not your job to "fix" him, you have better stuff to do). I've worked for people like that, and it isn't easy, but it is do-able. The bigger question then is, can you thrive without useful feedback from them (by getting it from others) and can you put up with point-scoring.

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If the problem lies with me, I'm happy to work on it.

To me this just looks like your boss has a personality. After 6 years you should be used to it not get upset by it.

It's unlikely to change, so my strategy is just to take those things as part of working with an individual and look for what is useful to me and disregard the rest.

I am convinced more of my boss's employees need to work on setting boundaries and saying "no" for the benefit of his mental health/managing his ego

Proactively doing this is abrasive, you should expect it to be and make compensations for it's affect. You're not in charge of his therapy, nor do you seem to be qualified to make judgements like this. If you feel the need to act like this then you should consider potential repercussions and factor them in to how he is reacting rather than expecting him to conform.

Outside of cultural and societal biases, a persons perception of you is largely based on your actions. So it makes sense that he finds you troublesome and probably even mildly dislikes you on a personal level.

I would have expected that by this point he and I would be on more of an equal footing in our relationship.

You are, you give him a bit of grief over his job and he gives it back.

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I recommend taking a step back; you are too close to the issue. When you get so close that every response is micro-analyzed, it's time to take a step back. I recognize myself in what you describe and while I had negative results, I am hoping that you will not. Remember what your goal is. Is it to correct or change your manager or is your goal to afford to pay off your new house? I found my focus narrowing so much that it didn't resemble anywhere close to what it was. Take a step back, re-evaluate your focus, re-establish your goal if needed. Then, maybe, your path forward will clear a bit.

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