1. How did you get into that?
  2. What are the biggest challenges you face?
  3. What do you think the next big innovation is in your industry?
  4. Is this what you always wanted to do?
  5. Do you have any rituals or habits that you think make you successful?
  6. What advice would you give me on this?
  7. How is the best way to start that?
  8. What the best book I can read on your industry or role?
  9. Do you have any apps you use?
  10. What are you goals for this year?
  11. How did you start doing that? What was the catalyst?
  12. Do you know anybody who is doing this well?
  13. What do you think your key skills are?
  14. How do you stay motivated when it gets tough?
  15. What did you do at 30 to set yourself up for what your doing now?
  16. How do you balance it all?
  17. What other areas of your life influence your work or vice versa?
  18. Would you suggest doing an MBA or using that 50k to invest time and money into those areas specifically
  19. How would you disrupt this plan and how would you defeat this plan?