Good Questions

Last updated: January 16, 2025

My new metric for a great conversation is how often the other person says, "Good question."

It's pretty straightforward: aim for questions that reveal a deeper story or—best-case scenario—questions they've never answered before.

That's tough to master, but there's a useful hack: ask something you have no clue how they'll respond to, or something that makes them a little uncomfortable. If it's too easy to answer, it won't spark depth.

Example Good Questions:

• What is something your best friend would say you're the best (and worst) at?
• If I become the most important person in your life in 10 years, what did I do?
• How would your best friend describe your life in 5 years? (Don't be humble.)
• What's something you do only because society expects you to?