Bossypants book club questions

1. 1.

   Fey argues that improv rules are rules for good collaboration. Which of those rules — say yes, make your partner look good, don't block — would improve a team dynamic you're currently in?

2. 2.

   She writes about being told women aren't funny, an assertion she eventually stopped trying to disprove and started simply ignoring. What received wisdom have you stopped arguing with and started ignoring?

3. 3.

   The chapters on SNL's read-through process describe a brutal weekly evaluation. How do you handle that kind of recurring public judgment in your own work?

4. 4.

   Fey describes her confidence as performed before it was felt. Has that ever worked for you? What was the cost when it didn't?

5. 5.

   What does it mean to you that she was the first female head writer at SNL in 2000, not 1975? Does the timing change how you read the story?

6. 6.

   The book is funny about the specific absurdity of beauty demands on women in television. How visible are those demands in fields you know well?

7. 7.

   Fey is ambivalent about the Sarah Palin impression — it made her famous for something that wasn't quite her best work. Have you ever had a success that felt like the wrong kind?

8. 8.

   She's candid about the difficulty of parenting while running a show and skeptical of the 'having it all' framing. What would an honest version of that conversation look like, without the platitudes?

9. 9.

   The question 'Is she difficult?' rarely gets asked of men in authority. When and where have you seen that double standard operate?

10. 10.

    Fey says she learned more from bad bosses than good ones. What did your worst professional experience actually teach you?

11. 11.

    The book is about building a career that required being underestimated and then proving the estimators wrong. Is there a more efficient path? Would you have taken it?

12. 12.

    What's the difference between confidence that's earned through results and confidence that's performed until results follow? Is one more reliable than the other?

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.