Discussion guide for

When We're in Charge: The Next Generation's Guide to Leadership 

by Amanda Litman

First, thanks for reading and for wanting to talk about it — that genuinely means a lot. I'm always happy to Zoom into a book club meeting. Just email me at hello@amandalitman.com and if I can make it work, I will.

So much of this book is designed to make you ask questions about who you are, how you show up, and what your team needs from you.

I encourage you to pull from whichever chapters hit closest to home and use those as your jumping-off point.

Below are some additional questions to guide your conversation. Email me if you land on others worth adding — I genuinely want to know.

On identity and generation

1. What feels most true about how your generation leads — and what generational stereotype do you most want to reject?
2. How has generational tension shown up for you at work? Have you ever been on both sides of it?
3. What did you absorb from the bosses who came before you — good, bad, or complicated?
4. Who were your earliest examples of leaders? What did you learn from them, and what are you actively trying to unlearn?
5. The book acknowledges that "responsible authenticity" doesn't carry equal risk for every leader — that the costs aren't distributed equally across race, gender, and identity. How has your identity shaped the persona you feel safe bringing to work?

On showing up

6. How do you think about authenticity in your leadership? What's your version of it — and what are the limits you've set around it?
7. The book draws a distinction between being your real self and your full self at work. What's the difference to you? Where's your line?
8. Was there ever a moment where you brought too much of yourself to work — and what happened?
9. What does "professionalism" mean to you now, versus what you were taught it meant?
10. What part of being a leader surprised you most? What did you feel totally unprepared for?

On the internet and social media

11. The book argues your social media presence is a strategic communication opportunity, not just a personal outlet. Has that reframe changed how you think about what you post?
12. Have you ever posted something — or held back from posting — because of how it might land with your team, your audience, or your organization?

On your team and culture

13. The book makes the case for creating space for politics at work — not avoiding it. Where do you draw that line, and has the current moment shifted where that line sits for you?
14. The book gets into a lot of specific policies: a four-day workweek, vacation and sabbatical policies, family leave, communication norms, AI, and more. Were there any you think you could actually implement where you lead? What would it take?
15. Have you ever experienced the tension that comes with too much transparency? Which of the challenges in that chapter resonated most?
16. What mistakes have you made as a leader — and what did you actually learn from them?

On rest, community, and ambition

17. The book argues that sustainable rest isn't a personal responsibility — it's a leadership one. What have you built (or what do you wish you'd built) into how your team works to make rest real?
18. What tools or practices have you used to build community — at work, or outside of it?
19. How has your relationship to ambition changed over time? What caused those shifts — and would you make the same decisions again?

To close

20. The book asks you to develop your own leadership framework — not copy someone else's. What does yours look like now? What's still in draft?
21. After reading, what's one thing you're actually going to change about how you show up — as a leader or as part of a team?