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Authentic Questions to Deepen Your Donor Relationships

“You have two ears and one mouth for a reason.”—Epictetus

My greatest lesson so far as a newly-minted teacher is this: the right question is more important than the right answer. Questions challenge, engage, and stimulate. They are invitations to a deeper understanding of something.

I’m wrapping up my first quarter as an adjunct faculty member in Seattle University’s Master of Nonprofit Leadership program. Lucky for me, I am team-teaching with Peter Drury, fundraising expert and Vice President for Mission Advancement at Make-A-Wish Alaska and Washington.

One of the thrills of teaching fundraising 101 is rewinding my 25-year career back to the essentials. Peter and I recently role played a donor conversation for Planned Parenthood in front of our class. Our students were particularly interested in what everyone thinks is the key question: will you make a gift? It struck me that this is the least powerful of all the questions for donors. Once you are “making the ask,” you hopefully know everything you need about someone’s values, beliefs, and experiences to make the right ask.

The more important questions, the Authentic Questions, are those that lead up to and follow the ask. They promote dialogue and deeper understanding of each other and the organization. So what are these authentic questions?  Here are my favorites, arranged by phase of the donor relationship:

Identify: What’s most important to you in your life?

At this point, you are starting a conversation with someone you know little-to-nothing about. Maybe they’re at one of your events for the first time or maybe you’re having coffee to introduce them to the organization. This is a good time to cast a wide net to understand who they are and whether their life philosophy could overlap with your organization’s mission.

Your goal with this question is to listen for their values, beliefs, and important life experiences and whether they care about your mission.

Qualify: How do you spend your most precious resources (time, talent, and treasure)?

Once you have a sketch of a potential donor’s life philosophy, then you can explore how they live out those values and beliefs. You can better understand where they work, participate in hobbies, vacation, volunteer, and donate—and why they do these things. How someone spends their money, working hours, and spare time tells you a lot about what matters most to them.  

Your goal with this question is to listen for interest in learning more about what your organization does and how they can get involved.

Cultivate: What’s your greatest hope for our organization? 

Once you progress to this question, you have determined a potential donor cares about your mission and wants to become more involved. This is a good opportunity to treat them as a partner in your mission. You can demonstrate this by inviting them to dream along with you about a better future for the community. Maybe they want you to grow faster or improve your facilities. Their ideas could reveal how they want to support your mission and the best program, person, timing, and amount for The Ask.

Your goal with this question is to listen for ways to align their hopes, talents, and interests with your organization’s funding, volunteer, or leadership opportunities.

Steward: How can we share the impact of your gift with you?

Listening doesn’t stop after they make a gift. This is the time to pay close attention to how they want to be thanked, recognized, and stewarded. As Penelope Burk has found, you must thank the donor, confirm how their gift was used, and share the impact of the last gift before you ask for the next gift. Many organizations do the first two well, but the third piece is often forgotten.

Your goal with this question is to listen for how they want to hear about the difference their gift is making in the organization’s work in the community.  Specifically, listen for how often and in what way they want to hear from you.

You can start by asking yourself this: over the course of a relationship with a donor, do you listen more than you speak? Whatever your answer, you can hone your conversational and listening skills by selecting one of the “Authentic Questions” to jump start an upcoming donor conversation. I have found donors appreciate these real questions, and they lead to great conversations. Try it. You never know what you will hear!


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