When I wore my bright blue, silk Hawaiian shirt to a festive corporate event in Key Largo, Fla., one of the new sales guys slipped me a note that said, “Do they make that shirt for men, too?” I have to admit it was a pretty funny comment–but one more appropriate for frat-house hombres than business colleagues who barely knew one another. I knew that as general counsel I had a challenge ahead of me: coaching “Mr. Wise-Guy” on the appropriate use of humor in the workplace.

The fact is, humor isn’t always funny. One offensive comment or risqu?(C) bit of humor can trigger a lawsuit or result in disciplinary action. For example, I once defended a sexual harassment suit spawned after an executive opened his Power Point presentation to a cartoon of a topless pin-up girl leaping out of a birthday cake. The males in attendance erupted in laughter and applause. The lone woman left the room and called a lawyer.