Disagreeing with your boss is awkward, but expressing that divergent viewpoint is important in your professional growth as well as the forward progress of your company. Social scientist Joseph Grenny shares with Harvard Business Review how to express disagreement with your superior without coming across as a jackass:
Discuss intent before content. When the boss gets defensive, it’s… because she believes your dissent is a threat to her goals. Defenses are far less often provoked by actual content than they are by perceived intent. You can be far more candid about your view if you frame it in the context of a mutual purpose that the boss already cares about. If you fail to do this, the boss may believe your disagreement signals a lack of commitment to her interests.
Show respect before dissent. Most of us assume that if you want to be respectful, you have to dilute your disagreement, and if you want to be honest, you’re going to have to hurt some feelings. But this is a false dichotomy. You must find a way to assure your boss that you respect her and her position. When that sense of respect is secure, you can venture into expressing your views openly and honestly.
Basically, the trick is to frame your disparate view in the context of your team or company’s larger goals, while also conveying respect for your higher-up through the language you use and the attitude with which you use it. Disagreement can even be productive in the workplace, if and when it is communicated properly.