So, you have a boss who likes to joke around occasionally at work. The only problem is that the things he says aren’t always that appropriate to the environment. Maybe his ‘humor’ involves inappropriate racial, sexual, religious or other elements. Maybe he publicly teases you about things you’d rather not be teased about. Maybe he just doesn’t know when to stop. Whichever it is, he often makes you uncomfortable.

Before you actually deal with the issue, there are a few things you should think about.

1. What is the purpose of his humor? Is he genuinely (but unsuccessfully) trying to lighten the mood and inject a little fun into the workplace? Or does there seem to be a darker intent or more pointed message behind the humor? There’s a big difference between a well-meaning but socially clumsy boss, and an insensitive boor.

2. How often is it happening? Is it a daily occurrence, or is it just an occasional lapse in judgment? Can you just give him a mulligan, or is it worth pursuing?

3. Do you have a bias? We each have hot buttons – topics on which we’re a little (sometimes a lot) more sensitive. Do your coworkers appear to be as troubled as you are by your boss’s behavior? If not, you may want to take a hard look in the mirror before you take any action. It would be a mistake to just unconditionally assume that you have the moral high ground.

If, after this introspection, you’ve decided it’s something that warrants action, it’s time for a conversation with your boss. Get him alone and explain to him that his jokes are making you uncomfortable. How you present this is very important. For example, don’t say, “Boss, your jokes are sexist.” Say instead “Boss, I know you mean well, but your jokes make me a little uncomfortable.” The first example is confrontational and will make your boss defensive. The second says, “If you care about me, you won’t do this any more.”

If this approach has no effect, or worse – if it just adds fuel to the fire, you may have no other alternative than to take the issue to a higher authority, or find employment elsewhere.

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