How do you tell your boss he is wrong? The short answer: very carefully. Do not get afraid.
Whether you're a senior vice president disagreeing with the chief executive, or a junior associate differing with an immediate supervisor, the key to taking opposing positions from the boss is how you package and deliver your opinions. Of course, you must have something thoughtful and
Say that’s it’s a Great idea Boss – First appreciate then you can continue pointing out the faults that you find wrong. Thank your supervisor for taking the time to discuss the project. Tell him or her you have been considering the approaches. Then state what you believe is your boss’s approach and state its merits. When he or she agrees and then say, there are just a couple of things we should do to improve upon the approach.
Suggest one thing that you think would open up the discussion and allow you to propose an alternative. If he or she is amenable, work in a second suggestion. Keep the discussion going, making it give-and-take as opposed to an argument. Keep it about the business, keep to the facts and keep calm. If you get emotional, your argument will lose its impact.
Before launching into your arguments, ask the boss if it's OK to proceed. For one thing, most people like some warning before hearing tough criticism or feedback. Then, too, sometimes the timing isn't right. The boss might be preoccupied or dealing with other issues. If you don't get permission, back off and try another time.
You shouldn't do all the talking. Try to engage the boss in a dialogue about the issue that concerns you. Make an effort to listen more than you talk. There could well be reasons or motivations for initiatives that you haven't been told about. By listening, you'll not only show your concern for the company's well being, you'll build the boss's trust. You might also gain insights into future directions for the business.
Prepare for this meeting by thinking out the key elements you want to discuss and perhaps modify. If you get to some areas where you simply can’t agree, then unless it is life threatening, dishonest or career breaking, see if there is some common ground on which you can agree. Don’t threaten, and don’t cower. Treat your boss with respect and you will get it in return.
The important thing is not to answer this in a way that shows you’re out to get the boss. The interviewer is likely going to be your boss, or one of your bosses. Everyone gets things wrong. A good boss would rather be told about a mistake in a way that doesn’t embarrass anyone.