Tough Interview Questions - If your boss is wrong about something, how would you handle it?

Following is a tough interview question:

If your boss is wrong about something, how would you handle it?

Similar interview questions:
Have you ever pointed out a mistake to your manager? Have you ever corrected someone in the presence of others? Have you ever called out your boss on an error?

Why the interviewer is asking this question:
The interviewer is looking for two things: 1) your willingness (or lack thereof) to point out an error made by someone over you; and 2) how you handled the situation. Some interview books say that you should not call out your boss on an error, which shows a lack of willingness to be under authority and therefore may mark you as a potential problem. However, that is a wrong analysis of the question. Great managers want to be challenged by their team members. And if you are speaking to a manager who does not want to know about their errors (or have them pointed out), you should likely exclude that manager and/or company from your list of potential employers.

The best approach to answering this question:
Use a practical example in your work where you pointed out something wrong to your boss. Yet equally important is that you show how you handled a situation. It should always be a private one-on-one discussion with your boss, rather than in front of others. You are helping and serving your boss by showing him/her the error. The best examples are ones that directly affect you and/or your team in their deliverables by making sure your boss has the most current and accurate data. Avoid examples which might be considered small or petty (such as correcting spelling errors in a memo from your boss).

An example of how to best answer this question:
"Yes, it has happened, although not very often. Recently, we had a very important decision about pending government contracts which would be decided at the executive committee level at our company. When I first my boss' view on taking the contracts, it was in the context of a meeting with several of his peers. I could see that he was working with old and inaccurate information, which could lead others to a wrong end decision. Since I had previously worked for a government contractor, I asked to meet with my boss privately to discuss the most recent data related to the decision and how it might affect our company. There were new government rules and regulations about which he was not yet aware. I spent time before the meeting updating my own recent information with the most current sources and presented it to my boss with all of the backing details. He was surprised to learn of the recent changes in government regulation and thanked me for taking time to bring him up to speed on these changes. Because of this, he influenced his peers in a very different way in the next meeting, even using some of my research data to reinforce his newly updated position."

An example of how you should not answer this question:
"If someone is wrong about something, I call them out on it right away. It doesn't matter where or when it is, I just speak my mind. Many people tell me how refreshing it is to work with someone who speaks his mind. Sometimes, I will take a contrary position just to stir things up, so that they don't just act on their assumptions. I really like playing devil's advocate and I think it makes us all better when I am there in a meeting challenging others, whether it is my boss or my peers. Sometimes I realize that I can be a thorn in their side, but most of the time I end up being right."

Remember to answer each interview question behaviorally, whether it is a behavioral question or not. The easiest way to do this is to use an example from your background and experience. Then use the S-T-A-R approach to make the answer a STAR: talk about a Situation or Task (S-T), the Action you took (A) and the Results achieved (R). This is what makes your interview answer uniquely yours and will make your answer a star!