1. If a company adopted fractional leadership tomorrow, what’s the first visible cultural change they’d notice?

2. How do you personally decide where to keep control and where to decentralize decision-making in your own businesses?

3. What do you believe most leaders still don’t understand about the value of fractional leadership?

4. Which human skill becomes more valuable?

5. Beyond emotions, heart, and soul..are there other human abilities you believe AI will never truly replace? Or do you think, except for humanity itself, AI could eventually replace almost everything?

6. Imagine you are a futurist looking ahead. How do you see the world shaped by AI in 10 years? And then, in 100 years?

7. How do you bring lessons from being a father and grandfather into your approach to leadership?

8. What does “freedom” mean to you in this chapter of life, and how has that definition changed over the years?

9. Which personal rituals outside of work (like cigars, travel, or reflection) most influence your effectiveness as a leader?

10. You’ve said transformational insights often happen when traveling, not at the desk. What’s the most powerful idea that ever came to you while walking in a foreign city?

11. How do you personally recognize the “greenlights” that tell you it’s time to pivot, try something new, or double down on what you’re doing?

12. When you feel a dip in motivation, what rituals or practices help you shift energy back into flow?

13. Who motivates who at yorCMO: you or your team? Is motivation a one-way or two-way street?

14. What's a moment when you feel so motivated and inspired by your team?

15. What does working “together” mean to you? What values matter most when you collaborate with others?

News & Updates

1. What book(s) or article(s) did you read this past month that stayed with you? What takeaways do you have?

2. What event(s), talks or experiences did you attend this past month that stayed with you? What takeaways do you have?

3. What podcast(s) did you listen to this past month that stayed with you?