The executive director, president, or CEO is often the driving force behind a nonprofit, inspiring staff, donors, and beneficiaries alike. Think of Geoffrey Canada, raised by a single mom in the South Bronx, who has gone on to transform Harlem and the future of community development with his organization, the Harlem Children’s Zone. Or Wendy Kopp, the college student who turned her senior sociology thesis into Teach For America, an engine in today’s education reform movement. As you consider whether to invest in a particular nonprofit, this is your opportunity to meet a great leader and be a catalyst to his or her success.

Meeting with the executive director of an organization you’re hoping to support can provide insight into how he or she thinks about challenges, how you could support the organization, and whether there’s potential to build a strong working relationship. Now is the time to dig deeper and form a perspective about whether the executive director has what it takes to meet the challenges of running the organization and whether your views are in sync about some key issues.

By the time you’re ready to interview the nonprofit leader, you will likely have done a fair amount of research. If you haven’t, it may be a good idea to do some initial research before engaging the nonprofit leader—refer to our Donor Decision Tool for guidance on how to get started. As always in the grantmaking process—and in particular when requesting time from busy leaders—you’ll need to balance your desire to learn more with respect for the time of the person you’re talking with.  

If you only have an hour, posing questions around the eight areas below should help you cover the most important ground.

1. How did you become involved with this organization? (Or, if the leader also founded the organization: Why did you start this organization? How has it grown or changed over time?)
2. Can you tell me about the work your organization does and the program or programs you run? [As a follow up, what differentiates you from other organizations?] (Here you are trying to get at how the organization is unique while confirming your impression of what causes or people it serves, what programs it offers, and how it gets results.) What do you think your constituents or beneficiaries would say is the best thing about your organization?
3. What results does your organization achieve? How has your program improved over time?
4. What are your goals for the next three to five years? What priorities will help you achieve them? What barriers are in your way?
5. What proportion of your revenue for next year will come from similar sources to this year’s revenue? Do you have plans to increase this consistency over time? (Here you are trying to get a sense of how stable/unstable their revenue picture is, and how dependent it is on a few decision-makers.)
6. Where is your leadership team strong, and where does it need development?
7. What is the hardest decision the organization has had to make recently, and how did you evaluate the tradeoffs involved?
8. What do you, personally, spend most of your time on?

If you have time to cover more, refer to  Philanthropic Sourcing, Diligence, and Decision-Making: An Equity-Oriented Approach.