I'm not sure what to make of this situation.

Over the years, my manager and I have developed a personal relationship at work. Aside from the regular communication of responsibilities, we joke with each other (and the rest of the team), talk about our lives, families, and other stuff.

Thinking back at my previous year at work, I sometimes notice a look of discontent on my boss's face whenever I describe my solution to a given problem (happened once or twice). For the first couple of times, I asked if anything is wrong, and all I got was a "no, no, just keep going at it". Even if you look at my performance reviews, you can see that there are no criticisms there. And no, I highly doubt that this is the case of the oft cited Impostor Syndrome, because I'm often very well aware of what I can improve in my work. Not to mention that I feel that this might be an impediment to me improving at what I do, which is ultimately the most important part of my work experience.

Because of this, I've become a little bit uneasy. I worry that our "closeness" (if you will) is getting in the way of him criticizing my work, even though I have repeatedly stated that I welcome this. I keep thinking to myself that next time will be the last straw, and that I will be fired out of the blue. Needless to say, I don't want this to happen, and I would like to honestly discuss this with my boss without being unnecessarily confrontational.

So, my question is: should I resign? And if not, is there a way for me to bring it up with my boss in a professional way?

  • 4
    In summary you are thinking about quitting because you are afraid you will be fired based on your boss does not give negative feedback. Your boss that you have a relationship with if going to fire you out of the blue without warning. Does that not sound a little paranoid to you? – paparazzo Dec 23 '15 at 20:43
  • @Frisbee when you put it like that, maybe – AwesomeSauce Dec 23 '15 at 20:47

I suspect you're reading way too much into the situation. Here are some reasons your boss might be frowning:

  • Your boss may be unhappy with the situation, rather than the way you've proposed handling it.
  • Your boss may not initially like your proposed solution, but then gives it a moment's thought, and realises it's a good one.
  • Your proposed solution may not be what the boss would have done in your place, but he or she is happy to let you handle it your own way. (Part of being a good boss is realising when you don't need to make a decision!)
  • Your boss might feel you're asking for approval too often.

Rather than trying to guess the reason for your boss's frown, ask! You tried asking "is anything wrong" and got a no, so try being more direct. You say you have a good relationship, so why not simply say "I've noticed sometimes you frown when I describe my solution to a problem. I'm concerned that you're unhappy with my solution, but don't want to tell me so because you think I'll be discouraged. Is that correct?"


So, my question is: should I resign? And if not, is there a way for me to bring it up with my boss in a professional way?

No you should not resign.

Instead, talk to your boss - perhaps during a regular one-on-one meeting.

This time when you ask "Is anything wrong", say something more like "I can tell by the look on your face that my solution isn't optimal. If I am to grow in my position, I need more honest feedback from you. I know this can he hard to do, but I really value your opinion, and I really need to know the truth. Can we dig into this deeper if I promise to accept all constructive criticism without being offended?"

Then, listen.

Accept all the feedback you get cheerfully, both positive and negative. If you still sense you aren't getting the full truth, stop him and say something like "There. What you just said doesn't sound like the whole story. Can we talk about it more?" And encourage him to continue.

When done, thank him for his effort. Acknowledge that this was difficult for him and that you will try hard to improve.

Then improve. But don't quit!

Bosses owe it to their employees to give honest feedback, both good and bad. But they are people - and criticism (particularly of people you like) is hard. You can help your boss out here by asking for the feedback more forcefully.


I would request a meeting with your boss to discuss your performance before thinking of quitting. Sit down and explain that you feel like you can improve your work and ask for your boss's opinion and feedback on the matter.

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