Reboot book club questions

1. 1.

   Colonna's central question is 'how are you complicit in creating the conditions you say you don't want?' Apply it honestly to your most difficult current work situation.

2. 2.

   What's the most significant thing from your personal history that you carry into your leadership without consciously intending to? How does it show up?

3. 3.

   Have you experienced the loneliness Colonna describes as specific to leadership? What did you do with it?

4. 4.

   What's a leadership pattern you repeat that you've been unable to explain or change through skill-building? What might radical self-inquiry reveal about it?

5. 5.

   Colonna shares his own history of depression and failure openly. How does a leader's public vulnerability affect the culture around them? What are the risks as well as the benefits?

6. 6.

   What stories about yourself — as a leader, as a professional, as a person — are you most invested in protecting? How might those stories be limiting you?

7. 7.

   The book argues that leadership development is personal development. Do you agree? Or is there a meaningful distinction between the two that the book collapses?

8. 8.

   What would it take for you to do the kind of inner work Colonna describes? What's the obstacle — time, willingness, or something else?

9. 9.

   Colonna writes about working with founders and CEOs who are technically accomplished but internally struggling. What does 'internally struggling' look like from the outside, and what does it cost organizations?

10. 10.

    What's the difference between self-awareness and self-absorption in a leader? Where does the inner work become indulgent rather than productive?

11. 11.

    If you could ask yourself Colonna's central question about one specific situation in your professional life right now, what would you ask — and what would the honest answer be?

How to run the discussion

• Pick six to eight, not all of them. An hour of real discussion covers fewer questions than anyone expects, and racing the list is what makes a book club feel like homework.
• Open with what people noticed, not what they concluded. Asking for a verdict first hardens opinions before anyone has heard each other.
• Let the disagreement run. The questions below that split a room are the ones worth the time; the ones everyone answers the same way can be skipped.
• Ask the quiet person a specific question. A direct, narrow question is far easier to answer than an open invitation to contribute.