I hate it when employees seem to think it's their job to second-guess what the boss really wants or whether the boss is right in what they are telling them. I hear fairly often from either a frustrated manager who's dealing with someone like that, or an employee who thinks that have to check with me constantly to make sure their manager knows what he or she is talking about. Usually they are fairly subtle when they ask me but I remember one who actually asked me if their manager could tell them to do things a certain way or if they were just "throwing their weight around".