By Laurence A. Pagnoni, MPA
Author, The Nonprofit Fundraising Solution | Former Faculty, NYU Heyman Center for Philanthropy, School of Professional Studies
They give every year, year after year.
They are a dying breed. In an era of declining donor retention where the 2024 Fundraising Effectiveness Project found that fewer than half of all donors gave again the following year, these donors are an anomaly: They show up, they renew, and they do not need to be re-acquired.
They are like living endowments. The cumulative value of a donor who gives $500 a year for twenty years is $10,000, and that is before you account for the estate gift that may follow.
And be assured they are the most probable source of estate gifts, significant late-in-life gifts, and blends of the two.
Cerulli Associates projects $123.7 trillion will transfer between generations by 2048. Charitable bequests totaled $45.84 billion in 2024 alone — roughly 8 percent of all U.S. charitable giving, a share that has held steady for four decades. Your most loyal donors are at the center of that transfer.
“They will surprise you with the size of their estate gifts as the Great Wealth Transfer unfolds — unless you take them for granted.” Laurence A. Pagnoni, MPA
The research is unambiguous: mid-level donors who have given consistently for ten or more years are among the strongest planned gift prospects you have. Wealth screening often misses them. A donor giving $250 a year for fifteen years signals a depth of commitment that a net-worth figure doesn’t capture. The average planned gift exceeds $78,000, according to Giving USA. The average donor makes their first planned gift at age 52.8. More than half do so when they write their first will.
These donors are already inclined toward you; but they need to feel seen and understood by you. You need a real relationship with them.
Why Loyal Donors Stop Giving — And How to Keep Them
Here is the paradox: loyal donors are often the least cultivated. Because they give reliably, they receive the same appeal letters and event invitations as everyone else, but nothing more. Their loyalty is treated as a given rather than tended with care. That is a strategic error. These donors are not giving out of inertia. They are giving because they believe in what you do. But belief, unattended, erodes. And when it does, the loss is not just this year's gift. It is everything that gift might have become.
The remedy is not complicated. It is a conversation. Not a solicitation — a conversation. One that says: we know you are here; we are grateful you are here, and we want to understand what keeps you coming back.
What to Ask Loyal Donors to Strengthen the Relationship
What follows is not a list of discovery questions. A skilled fundraiser already knows the answers to the basics — the donor's history, their interests, their connection to the mission. These questions are designed for a deeper level of conversation: one that presumes years of trust and invites the donor to reflect in ways they rarely get the chance to.
They are not interview questions. They are the kind of questions a trusted advisor asks a longtime client. Use them in a donor meeting, a phone call, or over lunch.
The goal is not data collection — it is to make the donor feel what they are: essential, valued, and worth a real conversation. Here we go, I offer seven, but feel free to add, subtract or modify for your own style. In some donor meetings when I’ve used these questions, just one has been sufficient!
1. "If we are to continue to earn your trust, what about us do you hope will never change? Why?"
This question invites the donor to name what your nonprofit’s identity means to them. The answer tells you what not to change, and it surfaces what a loyal donor holds most dear about your work.
2. "What about us, in your estimation, needs to change? Why?"
Loyal donors have experienced you long enough to have a perspective. This question signals that you are not fragile, that you welcome honest feedback from them. Most will be gentler than you expect. Some will hand you the clearest strategic insight you have ever received from outside the building.
3. "When have you been most satisfied with your relationship with us? When were you the least satisfied?"
The first half surfaces what you are doing well. The second half is where the real learning is. Donors who answer the second part honestly are donors who trust you enough to tell you the truth. Treat that trust accordingly. If their answer does not include the second part, find a way to ask the question again. It’s that important.
4. "What could we do more of to demonstrate your value to us?"
Note the framing: not "how can we thank you better," but "how can we show you that you matter here." The distinction is significant. This question positions the donor as a partner whose presence shapes the organization — because it does. Sometimes this question is awkward because the donor may genuinely not know. If that happens be prepared to suggest a few things that may appeal to them: would they like to meet our CEO? Would they like to tour our program?
5. "If this organization were to close its doors the year after you're gone, what would be lost that couldn't be replaced?"
This is one of the most powerful questions in planned giving cultivation — and it never mentions planned giving. It invites the donor to articulate irreplaceable value and to imagine a future without the organization's presence. That imaginative act, quietly, opens the door to a conversation about ensuring that future.
6. "What do you think we don't fully understand about the people we serve?"
This question presumes the donor has thought deeply about your mission. Most loyal donors have. It respects their experience and invites a perspective that staff and leadership rarely hear. The answers are often the most surprising and among the most useful.
7. "Has the way you think about philanthropy changed over the years — and how has that affected how you think about us?"
This is an invitation to reflect on their own arc as a donor. The answer often reveals where they are in their estate planning thinking without you having to raise the subject directly. It is also simply a generous question, one that treats the donor as a person with a whole life of giving behind them, not merely as a prospect.
How to Turn a Donor Conversation Into a Planned Gift
In your donor conversation, truly listen without being defensive, and, if it’s by phone, take notes, ideally right into your donor database. If it’s in person, take notes soon afterward while the conversation is still fresh. What a donor says in an unguarded moment is more valuable than anything a wealth screening report will ever tell you.
Follow up in writing within a week. Obviously don’t send a solicitation, but send a message that acknowledges what you heard and what it meant to your nonprofit. Name something specific they said. That specificity is what separates a genuine follow-up from a form letter, and loyal donors know the difference instantly.
If the conversation touches on legacy, continuity, or what your organization’s future should look like, do not let it pass unremarked. These are not accidental subjects. When a donor begins to talk about the long arc of your mission — what it would mean for it to endure, what would be lost if it did not — they are telling you about where their heart is. Ask gently whether they have ever thought about including your nonprofit in their estate plans. More than half of donors who eventually make a planned gift do so when writing their first will, and many simply need to be asked whether it is something they have considered. The ask does not need to be elaborate, but it does need to be sincere.
Be sure to flag the conversation in your CRM with enough detail to fully recall it, not just “good meeting” but the specific themes that emerged, the moments of candor, the questions that were asked, and whatever follow-up was promised. A note you can return to in six months is worth ten times a note you wrote for the moment. Return to it before your next touchpoint with the donor, and let the donor see that you remembered.
The loyal donors who will shape your organization’s future through estate gifts are not waiting for a brochure. They are waiting to feel that the relationship is real, that the people on your side are paying attention, that their years of giving have been noticed, and that someone cares enough to ask a hard question and stay for the answer.
“The relationship you tend today funds the mission for decades. The deeper conversation is the cultivation.” Laurence A. Pagnoni, MPA
The Great Wealth Transfer is already underway. The donors most likely to direct a portion of it toward your organization are the ones who have already demonstrated that they will. All you have to do is check in with them and ask questions that show you care — and mean it.
Related reading at the Blog: What Is a Transformational Donor? How to Identify and Cultivate Them
What question has opened the most meaningful donor conversation you have ever had? Share your experience in the comments section of the website.
Laurence A. Pagnoni, MPA, is one of the nonprofit sector’s most trusted voices on fundraising strategy and philanthropic leadership. He is the author of The Nonprofit Fundraising Solution and has led more than twenty successful fundraising campaigns across the United States. He served on the faculty of the NYU Heyman Center for Philanthropy and Fundraising, School of Professional Studies. His newsletter, The Nonprofit Fundraising Solution, reaches more than 2,500 subscribers weekly on LinkedIn. He writes at laurencepagnoni.com and answers your questions there.
