Disagreeing with a stubborn boss

Q. My boss is a strong-willed guy. You can’t win an argument; he has an answer for everything. After a few years working for him, I’m afraid to state an opinion or point out his errors. I’ll never advance by acting like this. How do I change?

A. Don’t assume your career is dead because you don’t contradict your boss. If you make him look good and you exceed his expectations, then you’re primed to advance. Still, it’s wise to express your disagreement occasionally in private, especially if you can alert him that he’s basing a decision on faulty information. If you genuinely differ with him on a strategic issue, speak up with confidence. Don’t worry about convincing him as much as presenting a cogent, well-documented case. Even if you “lose,” you can impress him with your logic.