Apparently I can't take a joke
Q. I have a very charming, funny boss who jokes around with everyone in the office. He recruited me heavily for a few years, and I finally took a management position with the company a few months ago. My issue is that he routinely (weekly) makes comments about how lazy I am, how surprised he is that I bothered to show up for work, how he isn't sure what I actually do there. I've tried several times (over lunch, in his office, via email) to follow up with him about these comments, asking if he was serious and requesting feedback on my performance. He laughs it off and says he was just joking and that I'm too serious. Yet he never says anything positive about my work and the "jokes" continue. I am definitely not someone who needs constant praise to do my job, but his comments and lack of feedback on my performance leave me feeling unsure of what he really thinks, and I'm considering taking a new job. Any advice for getting him to tell me what he really thinks?
A: You are definitely OK to set up a meeting to get some feedback. Make sure that an "official" meeting is set up (not just a time when you catch him in his office). Make sure there is at least an hour set aside for this meeting so you know it will be taken seriously. Then, make sure you are prepared. Think about (even write down) what you have done so you can share this with him in case he has questions about your performance (assuming he does not see everything).
In the meeting, you can tell him you wanted to gain his perspective on how things are going and wanted to hear from him about things you were doing well as well as any areas for improvement. You should also use this as an opportunity to share with him that you wanted to hear his views since he sometimes makes statements that lead you to believe you are not doing what you need to be doing on the job. You did not say whether he makes these comments in front of others, but if he does, you really need to let him know that this can make your job more difficult (since it lowers your credibility).