What AI Can’t Do in Fundraising
I recently asked ChatGPT a simple question: What are you good at, and what are you not good at? What surprised me was how clearly it named its own limits. It described itself as a strong thinking partner, writer, and organizer, but also acknowledged that it cannot build trust, read a room, carry moral responsibility, exercise judgment shaped by lived experience, or truly understand what matters to a person unless that person says it out loud.
Reading that response, I was struck by how familiar it sounded — because those limitations map almost perfectly onto the core of fundraising work. The very things AI cannot do are the work we have to do to cultivate major donors.
Trust built over time.
Partnerships forged through shared experience and values.
The ability to intuitively sense emotions, hold silence, and build authentic relationship.
If even the tool at the center of today’s AI conversation can clearly articulate that it cannot do these things, then it’s worth asking a more important question: What happens to major gift fundraising if we start pretending it can?
A Meeting That Didn’t Go As Planned
Years ago, I joined a college president for a meeting with a prospective lead donor. The goal was to begin a conversation about a seven-figure campaign gift.
Instead, the donor pulled out a legal pad and walked us through a long list of frustrations—decisions she disagreed with and disappointments she’d been carrying for years. The president was visibly deflated. This wasn’t the meeting we expected.
We could have redirected the conversation or defended the institution. We didn’t. We read the room. We listened. We acknowledged what we heard and thanked her for being honest. No rebuttals. No counterpoints. Just attention.
Trust Before the Ask
It wasn’t obvious we should even talk about the campaign but exercised our judgement and saw that the donor was more open, not less. So we asked if she’d be willing to hear more about the vision and continue the conversation. She said yes.
We shared the case, named the need for leadership support, and invited her to consider a seven-figure gift—without pressure. Over the months that followed, the president stayed engaged around both her concerns and the college’s future.
The result wasn’t just a lead gift, but a lasting partnership.
That gift didn’t happen because of a flawless ask. It happened because trust was built in a moment when listening mattered more than moving the agenda forward.
Where AI Is Genuinely Helpful
If I return to my original conversation with ChatGPT, what it said it was good at was both accurate and useful. It can organize information, summarize complex material, draft and refine language, surface patterns, and act as a thinking partner as ideas take shape. Used well, AI can save time, reduce friction, and help fundraisers prepare more thoughtfully for their work.
These are meaningful contributions, but they sit at the edges of major gift work, not at the center.
The Work Only Humans Can Do
Building trust. Reading a room. Exercising judgment shaped by experience. Cultivating long-term partnership and shared ownership between a donor and an institution.
These are not inefficiencies to be eliminated. They are the work.
If AI helps us do less of what machines do well so that we can do more of what only humans can do, it will strengthen major gift fundraising. But if we mistake speed for wisdom or automation for relationship, we risk hollowing out the very practices that make transformational philanthropy possible, meaningful, and enduring.
*This story is based on a combination of situations and has been adapted for confidentiality and illustrative purposes.*
