1. What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?
2. What purchase of £100 or less has most positively impacted your life in the last six months (or in recent memory)? (Brand and model, where you found it?)
3. How has a failure, or apparent failure, set you up for later success? Do you have a “favourite failure” of yours?
4. If you could have a gigantic billboard anywhere with anything on it —metaphorically speaking, getting a message out to millions or billions — what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)
5. What is one of the best or most worthwhile investments you’ve ever made? (Could be an investment of money, time, energy, etc.)
6. What is an unusual habit or an absurd thing that you love?
7. In the last five years, what new belief, behaviour, or habit has most improved your life?
8. What one thing could you do that you aren’t doing now, that if you did on a regular basis, would make a tremendous positive difference in your personal life? What one thing in your business or professional life would bring similar results?
9. Have you ever engaged with self-help, mentoring or coaching? If so, how?
10. What advice would you give to a smart, driven student about to enter the “real world”? What advice should they ignore?”
11. What are bad recommendations you hear in your profession or area of expertise?
12. What frustrates you the most about your industry and the way companies are run in it?
13. In the last five years, what have you become better at saying no to (distractions, invitations, etc.)? What new realisations and/or approaches helped? Any other tips?
14. What does a balanced life look like to you? Has work or a project you have been focused on caused you to neglect other areas of your life?
15. When you feel overwhelmed or unfocused, or have lost your focus temporarily, what do you do? (If helpful: What questions do you ask yourself?)
16. What does leadership mean to you?
17. Which people have most inspired you in your life and why?
18. What do the words principles and values mean to you?
19. If you had a forum to speak to 50 leaders, what question would you pose to them, to get them thinking about and being better leaders?