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My boss keeps bad talking her boss to me. She seems to expect that I should join in, but I was raised to believe if you can't say anything nice, don't say anything. I'm really not comfortable, but I'm new on the job and don't want to seem like somebody who can't fit in. What should I do?

It's always challenging when a supervisor puts unreasonable expectations on behavior or interpersonal relationships. You are right not to want to engage in negativity like that. It can be tremendously demoralizing for all who participate or are subjected to it.

While it's understandable that you would want to fit in with your supervisor or peers, it's more important that you be able to fit in as a professional than as a friend or confidant. Whenever your supervisor starts taking the conversation into areas with which you aren't comfortable, try to politely bring the conversation back to work-related topics. After a few times, your supervisor should get the message that you can be relied on for work, but not gossip.

If for some reason your supervisor doesn't get the hint, then you may need to schedule some private time where you can explain your discomfort with those topics of conversation. Make sure to emphasize how you feel and avoid accusations or statements directed against your supervisor. If after that, it continues to be a problem, or if you feel that your supervisor is retaliating against you, then you will want to escalate your concerns above your supervisor. Normally we might suggest going to your supervisor's immediate superior, but since that person is a target of the gossip, you will probably want to address your concerns with somebody in your HR department, if there is one.