5 min read

The pandemic gives us an opportunity to engage with donors on a more personal level. Here are four questions to engage your donors more candidly.

I have come to appreciate what our quarantined world offers as opportunity. Take these three things that I noticed during quarantine:

  • There is not another time in my career that I can remember people being so willing to not only answer the call but spend time talking to “the fundraising guy.”
  • Humans everywhere have a deep desire to connect—and many go beyond that and have a desire to be actively helpful.
  • This short window is the very best time to set yourself and your organization apart from others.

…nowhere in there did I use fundraising words. You know, the weekly-meeting repetitions of cultivation, stewardship, solicitation . . . the list goes on. Fundraising as such isn’t important right now. Perhaps fundraising as such never was important.

Yes—our organizations need to be bold with our visions and our invitations to donors. But what these last few weeks have demonstrated more than anything is that fundraisers need to be so much more bold with our conversations. As a fundraiser, you only need two tools to do this well AND serve well both your donors and your organization. Those two tools? Curiosity and care.

These reinforce one another—and strengthen both your organization and your donor relationships. The only way any of us can properly care for someone is being curious about their thoughts and feelings—and most importantly, by being curious about the world they envision and desire.

When was the last time you walked into a one-on-one meeting with your chief development officer and the evaluation criteria sounded like this: Over the last week, how many times did you have bold conversations with a donor? Over the last week, how many donors told you how they want to transform our community?

My guess is not many of us are evaluated in that way. But isn’t that exactly what our job should be? By using curiosity and care, aren’t we able to partner with donors in life-giving and purposeful ways?


I have had some of the most interesting and fulfilling conversations of my career over the past several weeks. I attribute much of that to people not simply giving daily reports motivated by a “bottom line.” People are actually concerned about others. Not in an end-of-year-tax-deadline sort of way, but in moving, thoughtful, and—dare I say it—loving ways.

These conversations have not happened by mistake. My calls and virtual meetings do not have agendas, but they are carefully crafted to ensure that the other person guides and I am merely the opener for his hopes for the world. How do I make an attempt to do that? I particularly like these four questions to elicit powerful stories from the past and hopes for the future.


This question will give you a sense of hierarchy of thought and hot spots. Does she respond to you with political commentary, social observations, societal concern, or maybe all of the above?

The important aspect of this question is that it allows the donor to answer the question she hears. Usually, that comes from what is most present in her mind. There are plenty of leading conversations and prompts in the world right now—don’t add to that. Be someone who comes not only to listen, but to listen to what is most important to that other person. And that is not something you or I could define for her.


A few weeks ago, I had a call where this is the only real question I asked. The man I called brought up the period during and after World War II. He gave me incredible, personal insight on what it sounded and felt like to ration—the exact opposite of hoarding toilet paper!

How he talked about his parents also gave me a sense of why he is one of the most generous and thoughtful people I have ever met. The beauty of this question is that it opens the floor for your donor to make a connection and tell a story about his life. Usually, you get glimpses into defining moments—and what an honor it is to be invited into that memory!


First, imagine I’m the donor, responding to that question . . . I can tell you that I’ve come to believe that breakfast is the most important meal of the day—regardless of what I eat. I have so enjoyed getting to have breakfast with my three kids each morning. They’re funny, they’re smart, and they have the whole day and world ahead of them. If I only see them after I get home, they’re working through whatever cruelty the world has doled out. You know, like only getting to watch 30 minutes of cartoons instead of 300, like they had hoped.

See what happens here? Now you know what working from home has allowed me to change (having breakfast at home). You found out about my family and kids (make a note to refer back later). And you just got a couple ideas on how to better care for me, as a person. Now imagine the fundraiser’s response. I’d be sending that donor a $3 box of my favorite cereal I ate with my own kids (Lucky Charms), with a quick note that says, “This was my favorite cereal to eat with my kids. For you, it can be a little motivation to stay at home for breakfast . . . even after quarantine. Thanks for sharing your story with me—and for all you do for our community.” That’s just good listening and caring for others. It’s humane and good in the first place—and from that, it will benefit your work and your organization.


This may be the most important ask you can ever make. That gentleman who gave the recount of WWII? His answer was simple: “Call and check in on me once-in-a-while . . . make sure I’m still here.” He might have meant that as a literal sentiment. I hope not! But I think what he was expressing was his desire to talk and connect. Those are easy things to do—and if we’re taking seriously our charge to care for others, they are absolute necessities.


I think a lot about what I am going to take with me back into “normal life,” when our stores and sports and restaurants are once again open without restriction. I hope that these conversations follow—that they are bold, without restriction. Questions that once felt very personal—maybe too personal—I now view as simply human. People everywhere are craving the opportunities to tell stories and share hope. Our job is simply to open that human connection.

Perhaps asking bolder, better questions doesn’t stop with our donors. While we cannot—and should not—give up entirely on hallowed fundraising words like “solicitation” and “cultivation,” maybe we should take as our charge to also ask better questions of our fundraisers, questions that get to the heart of the work we should all be doing.

What questions are you asking—and what kind of answers are you receiving? Have you engaged in any perspective-changing conversations? I am curious to know—please email me and share! And, if there is something that fits, please tell me what I can do for you.

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