Mar
17
2026

Tales From the Trenches Tuesdays: Episode 117

March 17, 2026

Episode 117

Episode 117 of Tales From the Trenches Tuesdays once again features Sarah Grebow, a consultant to nonprofit organizations and charter schools specializing in major gift philanthropy and corporate and foundation giving. With over 20 years of experience, she coaches nonprofit executive directors and development staff on individualized donor strategies. Sarah also leads board trainings on engaging high-level prospects.

One of Sarah’s core arguments is that major gifts require an organizational commitment to patience. Boards and leadership need to understand upfront that rushing a large ask — without proper engagement — doesn’t just risk the gift, it damages the relationship and the institution’s reputation. Instead, she advocates for layering a donor’s connection to an organization over time, through annual giving, event involvement, board participation, and genuine conversation. Every touchpoint is an opportunity to learn more about the donor and refine both the ask amount and the timeline accordingly.

Sarah is candid about the internal dynamics that get in the way of great fundraising. Having seen colleagues and supervisors alike guard prospects rather than collaborate, she firmly believes that a scarcity mindset hurts everyone. The fundraiser, the institution, and the donor. In her own experience, building a reputation for collaboration opened doors and created stronger donor relationships than protectionism ever could. She speaks from experience, having rebuilt a damaged donor relationship that grew into a multimillion dollar gift, only to watch institutional politics complicate what should have been a shared win.

Perhaps most refreshing is Sarah’s reflection on her own growth as a fundraiser. Earlier in her career, she felt pressure to have every visit go perfectly. Now she approaches donor meetings from a place of curiosity rather than anxiety, welcoming the unexpected.

This is about an upward trajectory of the relationship, that is more about me learning than it is about me presenting or me getting something that I want.

That shift in mindset, she says, is what ultimately makes her a better fundraiser and builds the kind of trust that leads to transformational giving.

Just click on the picture of Sarah below to hear our conversation.

L’chaim,

jack