50 Conversation Starters with Major Donors

Major Gifts

By Jeremy Reis

Developing strong relationships with major donors is crucial to the growth and success of any organization. To forge these connections, engaging in meaningful and memorable conversations is key. We understand that initiating dialogue with influential philanthropists can be intimidating, even for the most seasoned professionals. That’s why we’ve compiled a comprehensive list of 50 conversation starters tailored specifically for major donor interactions.

This carefully curated collection of conversation starters is designed to help you build rapport, delve deeper into the passions and motivations of your donor, and explore their connection to your organization’s mission—all without directly asking for financial contributions. These questions and prompts not only facilitate open and genuine communication but also lay the foundation for a lasting partnership between your organization and its most valued supporters.

So, whether you’re a seasoned fundraiser or just starting in the field, keep reading to discover the art of engaging major donors in meaningful conversations and fostering relationships that truly make a difference.

  1. How did you first become involved with our organization?
  2. What aspect of our mission resonates with you the most?
  3. Can you share a personal story or experience that inspired your philanthropic journey?
  4. How do you choose which causes to support?
  5. What are your long-term philanthropic goals?
  6. Have you been able to visit any of our programs or projects in person?
  7. Are there any specific projects within our organization that you’re particularly interested in?
  8. How do you prefer to stay informed about the impact of your giving?
  9. What motivates you to give back to the community?
  10. How do you involve your family or friends in your philanthropic activities?
  11. What has been your most rewarding giving experience so far?
  12. Do you have any ideas for how we can better engage with our supporters?
  13. Are there any challenges or opportunities in the philanthropic landscape that you’ve noticed?
  14. How do you envision the future of our organization?
  15. Are there any collaborations or partnerships you’d like to see us explore?
  16. What do you think our organization’s greatest strengths are?
  17. Is there an area where you think we could improve?
  18. What are some other organizations or causes that you support?
  19. How do you measure the success of your philanthropic investments?
  20. Can you share a story about a time when you witnessed the impact of your giving firsthand?
  21. How do you stay connected to the communities we serve?
  22. Are there any pressing issues or trends you feel our organization should address?
  23. What advice would you give to someone new to philanthropy?
  24. How do you balance your personal and philanthropic interests?
  25. Do you have any philanthropic role models or mentors?
  26. How do you stay informed about the causes and issues you care about?
  27. What inspired your initial interest in philanthropy?
  28. Are there any books, documentaries, or other resources that have influenced your philanthropic journey?
  29. What are some unique ways you’ve seen organizations engage with their supporters?
  30. How do you decide which projects or initiatives to fund?
  31. How do you think the philanthropic landscape will evolve in the next decade?
  32. Are there any key milestones or moments in our organization’s history that stand out to you?
  33. What role do you think philanthropy plays in addressing global challenges?
  34. What types of projects or initiatives do you find most compelling?
  35. How do you ensure your giving aligns with your values?
  36. What do you think sets our organization apart from others?
  37. How do you see technology influencing the future of philanthropy?
  38. Do you have any suggestions for how we can better communicate our impact to donors?
  39. What do you hope to see our organization accomplish in the next five years?
  40. Are there any innovative funding models or strategies that you find particularly interesting?
  41. How do you prefer to be recognized for your support?
  42. What are your thoughts on the role of corporate social responsibility in philanthropy?
  43. Do you have any thoughts on the relationship between philanthropy and public policy?
  44. What kind of legacy do you hope to leave through your philanthropic efforts?
  45. Are there any emerging issues or fields that you think warrant more attention from the philanthropic community?
  46. How do you think our organization can better adapt to and address the needs of our beneficiaries?
  47. What role do you think storytelling plays in effective philanthropy?
  48. As someone who has made a significant impact on our organization through your generous support, could you share what initially inspired you to become involved with our cause and what continues to motivate your philanthropic efforts?
  49. In your experience as a philanthropist, what have been the most memorable moments or accomplishments that you’ve seen come to fruition as a direct result of your support? How do these experiences influence your ongoing involvement with charitable organizations?
  50. Considering the multitude of causes and organizations seeking support, how do you determine which initiatives align best with your values and philanthropic goals, and what advice would you give to others looking to make a meaningful difference in their communities?

These 50 conversation starters provide a valuable resource for engaging with major donors in a way that fosters connection, trust, and mutual understanding. By initiating meaningful dialogue, you not only strengthen your organization’s relationship with these influential supporters but also pave the way for continued collaboration and success.


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