Episode 125
Episode 125 of Tales From the Trenches Tuesdays once again features Sarah Grebow, a major gift consultant who works with nonprofits and charter schools on philanthropy strategy, donor partnerships, and coaching development staff and boards. She has spent more than two decades in the field, with a particular passion for education and youth causes.
The best canvas she was ever on? One that most people would have walked away from before it even started. The donor was a lapsed major gift prospect — someone who had given substantially in the past and stopped. The file was thin. The relationship was cold. Sarah was going to be in his city for other reasons, so she reached out. His response? Hostile. He was angry at a former dean, felt the university had mishandled his engagement, and told her point blank there was no reason to visit — he was never giving again. Most fundraisers would have moved on. Sarah asked if she could still come anyway.
He gave her ten minutes.
At the ten-minute mark, Sarah acknowledged the agreement and gave him the out. He kept talking. Because buried under all that anger was someone who still cared — about the students, about the institution’s future, about being seen as more than a name in a database. She left him in a better place than she found him. He started giving again. She calls it one of her proudest visits, not because of the dollar amount, but because of what she learned and what she left behind.
The Worst Visit
When I asked about the worst visits, her answer surprised me. It wasn’t the one where she later found out the donor had a criminal history that research hadn’t flagged before she walked in the door — though that was understandably unsettling in hindsight. The visits that bother her most are the ones that wrap up too neatly. No loose ends. There were no new questions. No next steps that light her up.
It shouldn’t be neat afterwards. I should have lots of next questions, next actions, next plans of engagement.
For Sarah, a tidy visit is a warning sign. A messy one means something real happened. And that standard — holding herself accountable to curiosity, to motion, to genuine relationship-building — is exactly what separates a transactional fundraiser from a major gifts professional.
Because major gifts is not for everyone. It takes a particular kind of person — someone comfortable with ambiguity, patient with process, genuinely curious about other human beings, and completely unbothered by the transactional. Sarah put it plainly: if you love the organization and you care about people, the strategies are learnable. The heart is not. What she’s describing isn’t a job skill. It’s a disposition. And the visit in Florida — the one nobody wanted, the one that started with anger and ended with a renewed annual fund gift and a donor back in motion — is a perfect illustration of what that disposition looks like in practice. You show up anyway, listen, and leave them better than you found them. And you walk out with more questions than you arrived with.
That’s the work.
Just click on the picture of Sarah below to hear our conversation.
L’chaim,
jack
