Deep Questions

A list of questions to get to know someone deeply


• 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 that 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 central thread to all the things you do in life?