I love asking people questions. The best questions are ones which require novelty to answer and generate discussion. A single great question can reveal more about who a person is, how they think, and how perceive the world than hours of small talk.

Curiosity is the path to understanding.

Here are some of my favorites:

  • If you were to encounter an all-knowing entity and had the opportunity to ask it one questions and receive a true answer, what question would you ask?
  • If you could choose your lifespan, assuming good health throughout, how long would you choose to live?
  • Is there anything you would die for?
  • Your current thing blows up, vanishes, or goes bankrupt, what do you do instead?
  • If you were given a grant of $1B to leave your mark on the world, what sort of things might you do with the money?
  • What is something you’ve changed your mind about?
  • What is something about you that I might find surprising?
  • What was the most difficult thing you’ve ever had to do?
  • Which of your habits conflicts with your values?
  • Which of your beliefs would be the most difficult to change, even in the face of overwhelming evidence?
  • Are you afraid of death?