You don’t ask this question so you can hear the answer, you ask it so your mentee can hear their answer. This is a question designed to help people understand that they should dream about their future. Isn’t it sad that we need to be encouraged to dream? Ask a six-year-old and they’ll give you a list of all the things they want to be and do. Ask a thirty-six-year old, and they’ll usually stammer and stutter. Don’t let them duck it. “I don’t know. Guess I’ve never thought much about it” can’t be an acceptable answer when a leader, acting as a coach, asks this question.

Push. Make them think about it. Make it perfectly clear that there is no right or wrong answer. They aren’t committing career suicide if they admit to a secret passion that involves writing the Great American Novel or starting their own business. You won’t take them off the promotion list if they reveal that they want your job. Let them know you’ve got five-year dreams too.