How to Tell Your Boss He's Wrong

In the heartbreaking and heartwarming 1987 romantic comedy Broadcast News, Holly Hunter plays Jane Craig, a television producer with an unshakeable commitment to being right. In a heated exchange during layoffs, network executive Paul Moore remarks to her: "It must be nice to always believe you know better, to always think you're the smartest person in the room." Jane replies, with utmost sincerity: "No. It's awful."

I must admit, I can't relate to Jane. I love thinking that I know best, and I resent it when someone proves to me that I don't. (I'm working on it -- I swear!). And whether or not you're like me, chances are, you've worked with or for someone who also loves to be right. The very idea of confronting them with a perspective or data that shows that they may be wrong can be enough to make you call in sick. Nevertheless, for those of us who care about our personal and professional integrity, the quality of the work, and the impact of our organizations, standing up for what we believe in is a critical part of work -- and life.

Austrian philosopher Ivan Illich once remarked, "Leadership does not depend on being right." That may be true, but for many of us, keeping a good relationship with the boss may depend on us pretending that he or she is right, even when we think otherwise. So whether you have an inkling or a pounding sensation that the boss is wrong, here are six strategies to help you win your boss' respect without losing your job:

1) Pick your timing wisely. If you are going to have any kind of difficult conversation, let the other person choose the time that works best for them. Approach your manager by letting him or her know that you have something to discuss for 10 minutes, and ask what the best time would be for his or her FULL attention. Once you're in the meeting, if you notice that your boss is distracted or being interrupted, ask to reschedule. Nobody wants to be called out with the risk of someone overhearing, and nobody wants to do the calling out if they have to start and re-start a tricky conversation after every distraction.

2) Name the fact that you are sharing YOUR perspective only, and be open to your boss' perspective, too. In other words, approaching anyone with black/white, right/wrong choices sets them up for win/lose. Begin the conversation by saying, "I want to share my perspective on what's been happening/what I observed/what I think, and then I'd like to hear yours, too." Your perspective, of course, is that your boss is wrong. But keep in mind that you may have something to learn and maybe even reconsider when you hear another way of looking at this right/wrong issue.

3) Use the word "wrong" cautiously and very specifically. If you are going to use the word "wrong" when speaking to your boss about his or her actions, behaviors or conclusions, identify exactly what you are naming as incorrect or inappropriate. You want to make your focus the specific element that you think is wrong, rather than making your boss wrong as a person. It also helps to first name what you think is right. So for example, you might say, "I appreciate how much time you took to gather our insights for your report -- and, upon reading it, I think that three of your conclusions may be wrong." Notice: "may be wrong." Once you toss the word wrong out there, you can't really take it back without feeling embarrassed, regretful, and, well...wrong.

4) Name the agreed-upon standard (if there is one), how you boss' behavior differs from that standard, and then get curious rather than judgmental. This makes it less personal. Let's say that your boss sent an email out to a list of people that you and s/he agreed wouldn't be informed about the status of a current project. Try: "When we spoke about this, we agreed that you wouldn't email Marketing until we had firm numbers. I noticed that you emailed Marketing. Can you tell me about that decision?" Try to avoid "why" questions, which can put people on the defensive.

5) Know when to escalate. When what you think that you boss is wrong about has potential legal, fiscal, moral or safety implications, it's time to take your concerns up the food chain. You may want to check with HR (who will likely keep your inquiry confidential) before you go to your boss' boss to see if there's merit to your issue. Better to wonder in private, whether it turns out that you were right or wrong.

6) Be willing to admit to your boss (and to yourself) when you were wrong about thinking you were right. As J.K. Rowling wrote, "The best of us must sometimes eat our words."