So I've been employed at a "real job" for approximately three months, and have come to the conclusion I don't communicate well with my employer. It's not that we're not civil, or don't like each other (most of the time) it's just that my productivity at this place is severely hampered by my lack of ability to communicate with my boss.

A quick example - He asked me take an envelope of checks to the bank for deposit. I asked him if the deposit slips were filled out already and he said yes. I only heard from him later he felt I was trying to subordinate and second guess him (I was just checking if I needed to do anything other than hand the nice bank lady the envelope).

This unfortunately wasn't an isolated incident, and we just don't communicate our thoughts and intentions to each other very well. I've never had this problem with any of my part time employers, and he's never really had this problem with any of his previous employees, so I'm led to believe it's just something between us that doesn't work.

I'd like to go looking for a job where I don't feel like I'm walking on eggshells with my boss 100% of the time, and am free to ask questions when I need further info, however I feel if I go job hunting now, the first thing a recruiter is gonna see is my first job after college lasted three months and throw my resume in the trash. If I do get lucky enough to get an interview, how can I explain this in a way that doesn't make me look like a hot-headed upstart?

Additionally, I don't want to leave this job unprofessionally, I work well with my other regular coworker, and enjoy the work. How can I tell my boss I feel our communication issues are getting in the way of my job satisfaction and his bottom line?

  • You mention co-workers, so it seems safe to assume there are other employees. How do they communicate with your boss? Have you asked them if they have similar difficulties and, if so, how they deal with it? Maybe you can learn other ways to work with the boss through them. It may seem weird, but another solution may be to ask to have another person serve as a buffer between you and the boss, maybe even as your supervisor. Also, I wonder if it's a generational thing ... are you the only recent college grad there? Maybe the boss feels you are not properly respectful for your experience level.
    – GreenMatt
    Aug 7, 2014 at 16:22
  • I'm the only (relatively) recent college grad. My coworker has been here two years and got hired straight after, but he's a bit more bull headed than I am and I think that may be what works with My Boss. I do think you're right, it is a generational thing, as my boss is 2.5-3X my age, and I've seen similar attitudes from other people in that age group.
    – Anonibon
    Aug 7, 2014 at 16:52
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    Do you really want to leave just because of one person? Sure he's your boss, but we all have to work with people we don't "get along with" sometimes. Don't take it the wrong way but I think an employer, knowing this, would be right to think twice of bringing you on board. Especially if your first idea is to bail rather than smooth things out. Not the answer you wanted but I say its better to try to work things out. Even if it doesn't work in the end then you are stronger for the effort.
    – Brandin
    Aug 8, 2014 at 18:00
  • I'll echo Brandin's comment and I'd even suggest that you may want to rephrase your question to something like "How do I improve the communication with my manager?". Any answer to "how do I explain this" will probably boil down to "you can't without torpedoing your candidacy". You should also realise that if you do end up switching jobs, you'll be stuck in the new one for at least 2 years to avoid being branded as a job hopper, even if that new job makes you miserable.
    – Lilienthal
    Aug 6, 2015 at 7:50

3 Answers 3


It looks like the communications style you expect from your boss is different from what you're getting.

Whenever any of my bosses told me to do something, the first thing I'd check is whether all the pieces are in place. Sometimes, I have to depend on the boss's assurance that the key pieces are in place, and I explicitly seek this assurance, as I could be in for a significant waste of time if they weren't. They never took my due diligence questions as an affront because they understood that I was doing my job.

For whatever reason, your questions automatically come to him as casting doubt on his competence and judgment, which I am pretty sure is not your intent. I am getting the feeling that his definition of you doing your job is much narrower than you expect, because he is treating each of your questions as some kind of breach of boundary.

  1. I'd say try prefacing your due diligence question with "Due diligence question from me: did you sign the slips?" That way, you're also telling him the context of the question, which is that you are making sure.

  2. If you have a question because you don't know, preface it with "I am asking this question because I don't know"

  3. Since your boss is apt to think the worst of your questions, review why you would ask a question like "Why do we go with X?" before you say anything. If you are curious, say "I am curious, why do we do with X?" If you are baffled, say that you are baffled. If you are asking the question because you have a suggestion, say that you have a suggestion, then make the suggestion.

  4. Apparently, your boss is defensive about how he runs his business and he keeps things close to the vest. If my perception is correct, try limiting your questions to an as-you-need-to-know-to-do-your-job basis. Don't ask questions that might sound like you're prying. If you do, he'll come flying at you like a bat out of hell.

It is unfortunate but you will occasionally run into similar individuals throughout your career. You might as well learn now how to manage communication with them.

@DavidK adds: "Another way to change how you word questions is to shift the focus to you. Instead of asking "Did you fill out the slips?" ask "Do I need to fill out the slips?" or "Do you need me to fill out the slips?" I think that this is less likely to come across as second-guessing him than just needing to understand your job."

It's a great suggestion, but I'll add that tone and body language are very important. If you ask "Do I need to fill out the slips" while raising an eyebrow and looking at him quizzically, all hell will break lose :) In this particular case, given how close the boss keeps things to the vest, I am doubtful that the OP has enough info to fill them.

  • Thank you, I hadn't considered the fact that he might not think I needed to know the info as it's a small company and I was hired with the impression everyone knows basically everything (excepting finances which he handles directly). I'll try and be less pushy about what I'm asking, and preface questions with why I'm asking them.
    – Anonibon
    Aug 7, 2014 at 16:54
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    Another way to change how you word questions is to shift the focus to you. Instead of asking "Did you fill out the slips?" ask "Do I need to fill out the slips?" or "Do you need me to fill out the slips?" I think that this is less likely to come across as second-guessing him than just needing to understand your job.
    – David K
    Aug 8, 2014 at 17:09
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    @DavidK I incorporated your comment into my answer, giving you full credit, of course. Aug 8, 2014 at 17:20

Have you tried discussing this with your boss? It sounds like you could repair this relationship rather than abandoning it, and even if it doesn't work it will look better that you tried.

You've expressed the issue very well when you say "I feel our communication issues are getting in the way of my job satisfaction and his bottom line" - this would be a good starting point for a conversation. Don't get me wrong, it won't be easy to broach this subject but once you do you will either have a fruitful conversation, or know it can't be fixed. Either way, you're better off.

I would start by having a chat, in a conference room or somewhere else private. I'd say something like "I'm concerned that my communication style isn't meshing with yours, and I'd like to know how I can improve to make things easier for both of us". Be prepared for the conversation, by having 4 or 5 examples of when communication could have been better, and how you feel things might be improved.

  • Unfortunately, I've tried this with little success. We still don't communicate very well (getting clear task assignments from my perspective is a bear, and I can only guess at how he feels trying to explain it in what I feel is a sane way). On the whole question/insubordination part of it, I've tried to tone down the questions I ask, but It's pretty obvious it still riles him up and he feels I'm trying to run his business for him. (Questions usually of the format "Why do we go with X" are usually interpreted as "Why aren't we going with Y, it's so much better")
    – Anonibon
    Aug 7, 2014 at 16:03
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    I understand. Have you addressed this issue specifically, or just tried to work around it? In general, 3 months is not a long time in a job, particularly a first full-time job, and I would feel that a new start like that is only finding his feet about now.
    – TrueDub
    Aug 7, 2014 at 16:09
  • So you're saying I should stick it out for a while longer and see if it doesn't get better? I've always been a bit of a pansy about workplace conflict, and have made extensive efforts to make sure I'm not the subject of it, so this is new territory for me. Perhaps I'll give it a shot.
    – Anonibon
    Aug 7, 2014 at 16:50
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    @Anonibon Wherever you go, there is likely to be conflict. You're probably best served by treating this as a learning experience rather than running from it. You may very well find that things get better over time - three months really isn't very long at all.
    – logophobe
    Aug 8, 2014 at 17:17

Just from your description of the deposit-slip question, I expect that your boss is the problem. His reaction to your innocuous question is bizarre, and it has nothing to do with the age difference. The age difference only matters because he feels secure in his position above you.

I doubt that you are not the only one who can't communicate with him. You should discreetly talk to a trustworthy colleague about this incident. I expect that everyone finds him difficult. If you want to stay in this company, you need to cultivate friendships outside his organization.

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