To ask a good question requires two things: insight and gumption. The root of all worthy questions is a desire to fill in a gap in your understanding of something. The insight in good questions comes from seeing that gap, exploring its edges, and forming a question that can serve as an invitation to others to fill. But a question can’t ask itself. You need gumption, or the courage to ask the question of someone. Many people have good questions but never find the courage to speak up and share them.

Part of the fear around questions is the worry that we will expose a truth that someone, perhaps even ourselves, doesn’t want to be brought to light. This is part of why meaningful conversations are uncommon. Most conversations in life are a kind of social grooming, a way to feel accepted and make others feel the same. We are social creatures and naturally avoid the risk of standing out, a fear that somehow asking a question will reveal our true nature, and we will be judged as stupid, wrong, or unworthy. Since the most powerful questions don’t have easy answers, we tend to play it safe and avoid asking them.

 …