# 50 Go-To Questions for Deeper Connections ## The Founder 1. What's the most significant constraint or bottleneck you currently face, and what's one unconventional way you could solve it? 2. If you had to start a new company tomorrow, what would it be and why? 3. What's a belief you hold about your industry that very few people agree with? 4. How do you balance the need for a long-term vision with the urgency of short-term execution? 5. What's a failure you've experienced that taught you a valuable lesson? 6. What's one venture or challenge you'd undertake if the fear of failure was not a factor? 7. What are the most important values you want to embed in your company culture? 8. How do you identify and attract the right talent? 9. What's your process for making difficult decisions under pressure? 10. If you were to receive information that your current plan will ultimately fail, what reasons would you anticipate for this failure? 11. What legacy do you want to leave with your work? 12. How do you recharge and avoid burnout? 13. What's the best piece of advice you've ever received as a founder? 14. How do you foster innovation and creativity within your team? 15. What's a book that has significantly influenced your approach to business? ## The Philosopher 16. If your life was a book and you were its protagonist, what chapter are you currently in? What's the next chapter? 17. Are you evolving into the person you once aspired to be? 18. What is a concept or idea you've changed your mind about recently? 19. What does a meaningful life look like to you? 20. How do you practice intellectual honesty in your daily life? 21. What are the core principles that guide your life? 22. In what ways do you challenge your own assumptions? 23. What question are you currently wrestling with? 24. What's a complex topic you've been trying to understand better? 25. How do you distinguish between what is true and what you want to be true? 26. What does it mean to live a good life? 27. How do you approach learning and acquiring new knowledge? 28. What's a piece of art (book, movie, painting) that has deeply moved you, and why? 29. If you could have a conversation with any philosopher, living or dead, who would it be and what would you ask? 30. What are you willing to struggle for? ## The Seeker 31. What gave you energy this week? 32. What pulled away energy? 33. What did you create this week? 34. What were the special moments of ambedo (a kind of melancholic trance in which you become completely absorbed in vivid sensory details)? 35. What spiritual lessons have you learned recently? 36. In what ways has the universe shown you that you can trust it? 37. What do you want to manifest in your life right now? 38. Which of your habits feels like a placeholder for something deeper you crave? 39. What's an experience that has profoundly shaped who you are today? 40. What are you genuinely curious about right now? 41. What's a part of yourself that you are just getting to know? 42. When do you feel most like your true self? 43. What are you grateful for in this moment? 44. What's a dream you've had that you still think about? 45. What does your intuition tell you about your current path? 46. What's a fear you are working to overcome? 47. How do you connect with your inner child? 48. What does it feel like when you are in a state of flow? 49. What's a conversation you've been avoiding? 50. If you could give your younger self one piece of advice, what would it be? --- **The question that best represents your core identity is:** **What is a belief you hold about your industry that very few people agree with?** This question combines the Founder's drive to innovate and challenge the status quo, the Philosopher's commitment to independent thought and truth-seeking, and the Seeker's courage to explore uncharted territory. It speaks to your desire to not just build, but to build something meaningful and different, based on your own unique perspective.