It’s difficult enough to tell your supervisor something that he or she doesn’t want to hear when the two of you have a good relationship. But what do you do when there are personality conflicts or a history of mistrust between you? How would you like unpleasant news to be conveyed to you when the faculty member giving you that information is someone you have misgivings about, little confidence in, or a troubled past with? These situations are not uncommon in higher education. We all have times when we need to tell our boss something that he or she doesn’t want to hear. Perhaps a program particularly important to your supervisor is about to be eliminated by the faculty. Maybe an unforeseeable problem is causing you to go far over budget. Or maybe you simply don’t agree with a stance that he or she has taken. When you’re in a situation like this, you don’t want to be dismissed as a failure, a mere complainer, or someone who’s bent on stirring up trouble. On the other hand, the administrator who receives these unpleasant tidings may have trouble distinguishing between discomfort with the message and distaste for the messenger.