High Growth Handbook book club questions

1. 1.

   Gil argues that the CEO's job changes fundamentally at scale. What specific behaviors that help in the early days hurt later, and how do you know when you've crossed that threshold?

2. 2.

   The book has a strong thesis about board management. Have you seen a board that functioned well for a founder, and what made it work?

3. 3.

   The COO question — when to hire one, who it should be, what they should own — is one of the most practically useful in the book. How would you answer it for a company you know?

4. 4.

   Gil says the first executive team rarely scales all the way. How do you manage the transition from executives who built the company to executives who can run it at the next level, without destroying the culture they created?

5. 5.

   The M&A chapter treats acquisitions as talent and capability plays as much as revenue plays. Does that framing match what you've observed in how companies actually use M&A?

6. 6.

   Culture documentation — writing down what's informal — is described as a scaling necessity. When does that documentation help, and when does it become bureaucratic in a way that actually degrades culture?

7. 7.

   The book is explicitly written for post-product-market-fit companies. What's the risk of reading it before you're there?

8. 8.

   Several of the interview subjects are very candid about mistakes. Which mistake described in the book seems most common, and what makes it hard to avoid?

9. 9.

   Late-stage fundraising is described as a narrative exercise. What's the most compelling narrative a company you know has told about its future, and did it match reality?

10. 10.

    Gil is both an operator and an investor. Does that dual perspective make the book more useful, or does it sometimes create a tension between what's good for founders and what's good for investors?

11. 11.

    The handbook format means different sections will be relevant at different points in a company's growth. Which chapter would you read first if you were facing a scaling challenge today?

12. 12.

    What does High Growth Handbook leave out that you'd want from a complete guide to scaling a company?

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.