Deep Questions

A list of questions to get to know someone deeply

January 1, 2022

  • What do you care about? Why?
  • What have you been thinking about lately?
  • How do you update your beliefs and ensure they don’t get stale?
  • What are three experiences have shaped you the most over the past X years?
  • What’s something you wish people talked to you about more?
  • What do you look for in friendship?
  • What's the most interesting thing you learned last week?
  • During what period of your life did you achieve the highest learning rate?
  • What's the kindest thing you've done for someone?
  • How's your level of happiness changed over time? Are you happy now?
  • What's the biggest risk you've taken?
  • What's the central thread to all the things you do in life?