Questions for meaningful conversations

18 Questions to Spark Meaningful Conversations

LONG HORIZONS
• What's something you believed 10 years ago that you don't believe now?
• If you could give your 22-year-old self one piece of advice, what would it be?
• What do you hope people say about you when you're not in the room?

HIDDEN INSIGHTS
• What's the most important thing you've learned that you can't teach?
• What question do you wish people would ask you more often?
• What's something you're convinced of that most people disagree with?

VALUES & MOTIVATIONS
• What's worth doing badly?
• When do you feel most like yourself?
• What would you do if you knew you couldn't fail?

RELATIONSHIPS & GROWTH
• Who has had the most influence on who you are today?
• What's the best compliment you've ever received?
• What's something you've changed your mind about recently?

REFLECTION & MEANING
• What are you optimizing your life for right now?
• What's something you do that you wish more people did?
• What's a small thing that brings you disproportionate joy?

CURIOSITY STARTERS
• What's the most interesting thing you've learned recently?
• What is your tombstone tweet (one tweet for eternity)?
• What's a question you've been thinking about lately?