54 Essential Questions About Fund Development

Fund development is not a separate and independent activity that can be pulled out whenever there is need, focused on by only a few, and ignored the rest of the time. Instead, fund development is an ongoing, rewarding (but invasive) process that engages all staff and every board member in some way.

Here are my 54 essential questions to ask yourself about fund development. Use these questions to stimulate thinking and conversation among your staff and board.

Questions for you personally and professionally:

1. What are your own assumptions and how do you challenge them?

2. How do you raise questions and put issues on the table?

• How do you stimulate dialogue with your organizations (both volunteer and professional)?
• How do you stimulate dialogue with your colleagues and with your professional associations?

3. What’s the value of – and risk of – cage-rattling (challenging and provocative) questions?

4. What are the cage-rattling questions that your organizations need to explore?

5. What are the cage-rattling questions that you need to explore personally / professionally?

6. How do you define risk? What level of risk can you / are you willing to take?

Process questions:

7. How do we develop the essential questions and with whom?

8. What’s the process for asking and beginning to answer the essential questions?

9. Where should which questions be asked?

10. Whom do we engage in which conversations?

11. How do conversations move from place to place, people to people?

12. How do we bring it all together when decisions must be made?

Questions about your donors and about relationship building:

13. What role does customer service play in nurturing donor relationships and retaining loyalty?

14. Do you and your organization focus enough on the lifetime value of your donors – and the implications of that?

15. How would you complete the following sentences? How might your donors complete the following sentences in relationship to your organization?

• “I used to give to XXX but now I don’t because XXX”
• “I am a donor to XXX because XXX.”
• “I am loyal to XXX because XXX.”
• “I used to not give to XXX but now I do because XXX.”

Questions to ask your donors:

16. “Why did you first give?” (from Richard Radcliffe)

17. Why do you give to our organization? What does our mission mean to you? How would you describe our mission?

18. What are you hearing in the community about our organization? How do you describe us to others? What are you saying about us?

19. What are your interests and disinterests?

20. Share with me your life’s journey.

21. Share with me the people you see as leaders and mentors in your life’s journey.

22. Why do you keep giving to our organization? How do we maintain your interest and keep in touch with you?

Questions about building a culture of philanthropy:

23. How does a culture of philanthropy apply to soliciting low-income clients and who makes these decisions?

24. Is building a culture of philanthropy any different than building a culture of excellence?

25. How do we engage linear thinkers in culture building because they don’t always value process?

26. Do we understand ourselves and our own motivations for giving well enough?

27. Do we have the courage to treat everyone the same? Do we treat our donors better than our clients? Do we treat all donors the same?

28. How do employment practices impact a culture of philanthropy?

29. How can we ease people’s fears about money?

Questions about engaging volunteers:

30. Does it really matter if we engage volunteers in fund development? Why or why not?

31. To what degree does volunteer engagement add value – and how?

32. If you had a choice – to hire more staff to help do prospect / donor cultivation and solicitation OR to engage volunteers more fully – which would you choose? Why?

33. What do you mean by engaging volunteers?

34. What is the difference between engaging in tasks and process?

35. What would you define as an effective use of volunteers in the most effective philanthropy / fund development program?

36. Which volunteers do you engage now in what? Why? What changes might you choose to make, why, and how would you make such changes?

37. What are the barriers to volunteer engagement – from your perspective and from the volunteers’ perspective?

38. What drives your best volunteers crazy and what makes them very happy? How can you fix the crazy stuff and capitalize on the happy stuff?

39. Your agency’s best volunteer just called and said s/he is leaving your organization and giving his/her time to another. (Who is this in your agency? Pick a real person.) What do you think are his/her reasons for leaving? How could you have prevented this? What questions does this situation raise for your organization?

40. What does it mean to empower volunteers? How does this add value – or not? Why?

Final questions:

41. How do you define philanthropy and your role as a leader? Is part of leadership acting as a change agent? What would that mean?

42. Is a nonprofit about more than service? What might that mean?

43. How do we encourage a philosophical framework as well as strategies and techniques?

• Have you articulated your own values and philosophical framework for your work?
• How do your definitions affect your career choices?

44. How do we prepare ourselves and our organizations to learn and change?

• How do we empower ourselves to ask the questions?
• How do we empower others to do so?
• Where should various questions be asked and what is the asking and conversation process and who decides what?

45. What is organizational culture? How do leaders help define, change and nurture culture?

• What does a culture of greed look and feel like and how does it affect an organization, its people, and the community?
• What does a culture of philanthropy look and feel like and how does it affect an organization, its people, and the community?

46. Are philanthropy and fund development about maintaining the status quo – or are they about change?

• Have we truly explored what the status quo means – and how we reinforce or challenge it?
• Is part of our job to help our organizations have this conversation?

47. I think it’s a privilege to have clients, donors, and volunteers. But is that the way we behave, as leaders and as organizations? How do we nurture genuine relationships between donors and the organization’s mission?

48. What do we mean by a civil society and civic capacity?

• What is the role of the third sector in creating a civil society and civic capacity?
• How do politics affect civil society and civic capacity?

49. Should philanthropy be a democratizing act? What would this mean?

50. What is the nature of politics in philanthropy? How do politics affect our organizations, philanthropy, and our profession?

51. What does privilege have to do with philanthropy?

• Have you examined your own privilege?
• Do your board and staff ever discuss privilege?

52. What is power?

• What is the nature of power in philanthropy, governance, and fund development?
• What is the nature of power when we discuss diversity and inclusion?

53. How are privilege, power, and politics linked? How are they linked to philanthropy and fund development?

• What are the implications for civil society and civic capacity?
• What are the implications for your organizations, your career, and your vocation?

54. How familiar are you with traditional philanthropy and social change / progressive philanthropy?

• Is traditional philanthropy enough to create a civil society and civic capacity?
• How does the history of philanthropy and the body of knowledge reflect traditional philanthropy and exclude social change / progressive philanthropy?
• Why is social change / progressive philanthropy the poor and often forgotten stepchild in our communities and in our nations?
• What role do professional associations currently play in reinforcing the status quo or facilitating dialogue about social change? So what?

What would you add to this list? Let me know in the comments below!

For more questions (both cage-rattling and not!) see my book Strategic Fund Development: Building Profitable Relationships That Last.