Additional Resources
On this page, you’ll find additional resources (coming soon) as well as the diagrams and illustrations from The Deep End book.
There is also a ‘discussion and reflection guide,’ which includes questions for:
- Individual reflection
- Board discussion,
- Leadership team discussion
- Looking ahead
Coming soon…
To help you continue that journey, we’ve created additional resources to support learning and implementation, including:
- Expanded discussion guides for individuals, boards, leadership teams, and classrooms
- Downloadable versions of tools in this book
- Facilitator guides for book clubs, board retreats, and leadership teams
- Additional articles, videos, and practical resources
- Updates and companion materials for future books in the Finance and Fundraising Capacity Series
You’ll also be able to join our mailing list to receive new resources, practical insights, and announcements as future books in the series are released.
We hope you’ll continue the journey with us—and, even more importantly, continue building organizations that are financially healthy, strategically led, and equipped to create lasting
Discussion and Reflection Guide
Whether you’re reading The Deep End on your own, with your board, as part of a leadership team, in a book club, or in a university classroom, these questions are designed to move the conversation from ideas to action.
Rather than trying to answer every question, choose the ones that feel most relevant to your current situation. The value of this book isn’t measured by how quickly it’s read but by the conversations it inspires and the decisions it changes.
Individual Reflection
1. Which part of Alex’s journey felt most familiar to you, and why?
2. What financial conversation have you been avoiding?
3. Which belief about money, fundraising, or leadership challenged you most while reading this book?
4. Where do you recognize a scarcity mindset in your own leadership?
5. If you created your own “What I need to learn so I don’t sink” list today, what would be on it?
6. What is one leadership habit you want to begin and one you want to leave behind?
Board Discussion
7. Does our board clearly understand the true cost of delivering our mission?
8. Are we governing from financial clarity or reacting to financial surprises?
9. Which financial information helps us make strategic decisions, and which simply reports history?
10. If Alex became Executive Director of our organization tomorrow, what financial realities would surprise her most?
11. What conversations are we avoiding because they feel uncomfortable?
12. What would financial stability look like for our organization three years from now?
Leadership Team Discussion
13. Where are we relying on heroics instead of well-designed systems?
14. Which recurring problems are really symptoms of deeper organizational issues?
15. If we adopted a “Reality First” approach, what difficult truths would we need to acknowledge?
16. Which of our programs are fully funded at their true cost?
17. What signals would we include on our own organizational dashboard?
18. Where could greater financial clarity reduce stress for our staff?
Fundraising Discussion
19. Are we asking donors to fund activities or to invest in lasting impact?
20. How well do we explain the full cost of our mission?
21. Are we apologizing for infrastructure instead of explaining why it matters?
22. Which supporters are ready for a deeper conversation about the future of our organization?
23. How could we strengthen our stewardship after someone makes a gift?
24. What would change if we consistently approached fundraising as an invitation rather than a request?
Looking Ahead
25. If your organization were to write the next chapter after this book, what would its title be?
26. What is one action you will take in the next thirty days because of what you’ve learned?
27. What conversation needs to happen first?
28. How will you know that your organization is becoming financially healthier and not just financially busier?
29. What would your community experience differently if your organization achieved long-term financial strength?
30. What does “moving from financial chaos to clarity” mean for your organization today?
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The Deep End Book is perfect for conferences, retreats, board meetings and gifts. If you’re interested in placing a bulk orders of 10 or more copies, please reach out for special pricing.