Jun
23
2026

Tales From the Trenches Tuesdays: Episode 131

June 23, 2026

EPISODE 131

Episode 131 of Tales From the Trenches Tuesdays is the last of the series featuring Penny Harris, the founder of Renewable Philanthropy that helps nonprofit leaders rethink donor renewal. Her path started not in a development office but in civic life — a decade with the League of Women Voters, producing the first candidate forums in her community and the first statewide U.S. Senate debate with public broadcasting. That experience led her to Maine Public Broadcasting, and eventually to a gubernatorial appointment to the University of Maine System Board of Trustees. By the time she became a professional fundraiser, she had already interviewed a thousand donors and learned, firsthand, what it means to build trust rather than chase transactions.

That experience shaped her answer to a question that’s been haunting the sector: why does the average fundraiser now last just 16 months in a role? Penny points first to the people fundraisers report to. Most CEOs, she says, have never raised a dollar themselves, yet they feel the pressure of the bottom line — so they hover, redirect, and second-guess instead of trusting the plan. She recalls a hospital executive who asked her to organize a retiring doctor’s reception, then refused to let her turn it into a fundraising opportunity. When she pushed back, asking why bring in a fundraiser at all if not to raise money, he had no answer — and quietly handed the job to someone else.

The deeper issue, she argues, is how leadership frames the work itself.

They just see it as asking for money rather than inviting people to join the community of people who are supporting.

From the Trenches

That framing shows up again in a story she tells about a major-gifts officer at Tufts. A board member mentioned a friend who’d just given more than a million dollars to another organization — surely good for some support to Tufts too, even if not on that scale, the board member figured. The fundraiser didn’t stop there. She asked the board member to arrange a lunch, then took it from there herself — getting to know the donor, finding the program she’d actually want to support. By the time the relationship had run its course, the gift to Tufts topped a million dollars — more than anyone, including the board member, had expected.

Renewals, Penny insists, depend on that same kind of ownership. Fundraisers, not executives parachuting in for a handshake, are the ones who keep donors coming back.

Her message to nonprofit leadership is direct: step back and let the people you hired do the job you brought them in for, or watch them walk out the revolving door for good.

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

L’chaim,

jack