Dare to Lead book club questions

1. 1.

   Brown distinguishes between professing values and living them. What are your two core values, and what's a recent decision you made that tested them? Did they guide you?

2. 2.

   What does armoring up look like for you specifically? Cynicism? Perfectionism? Intellectualizing? When in your work day does the armor come on?

3. 3.

   Think about the last time you gave feedback that was 'unclear' because you were protecting someone's feelings. What were you actually protecting?

4. 4.

   Apply the BRAVING inventory to a key relationship at work — a manager, a direct report, or a peer. Where is the trust strong? Where is there a gap?

5. 5.

   Brown says daring leadership requires showing up without all the answers. What signals in your organization still punish not-knowing? What's the cost of those signals?

6. 6.

   Who is in your 'square squad' — the people whose feedback you actually weight? Are they in the arena themselves? Do they actually know you and your work?

7. 7.

   What's the last failure you experienced at work? How did you handle the aftermath — with armor, or with genuine reflection and learning?

8. 8.

   Brown argues that belonging requires people to show up as themselves. What does your organization do — intentionally or inadvertently — that requires people to cover or perform?

9. 9.

   Where in your leadership are you avoiding a difficult conversation by telling yourself it's not the right time or the other person isn't ready?

10. 10.

    The book connects vulnerability to creativity and innovation — the argument that you can't have one without the other. Do you see evidence of this in your own organization?

11. 11.

    What would have to change in your team's meeting culture for genuine uncertainty to be expressed safely rather than managed out?

12. 12.

    Brown says clear is kind. What's something you could say more clearly to your team or your manager that you've been softening because it feels unkind?

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.