How to Build Relationships With Trustees and Inspire Them to Give

Early in almost every client engagement, the trustees want to know who I know. Which philanthropists are in my Rolodex. Which major donors I can bring to the table.

After 35-years as a fundraiser — across causes, cities, and organizational sizes — the question still comes, and it comes early.

I am not opposed to discussing donor profiles. Knowing the attributes of a likely major donor is legitimate work. I do my prospect research before those conversations, including research on the trustees themselves, so I understand their giving history before we sit down.

But here is what trustees almost always leave out of that conversation: themselves.

They talk about other people's money as though their own gifts were secondary — a footnote to the real fundraising work. I think that gets it exactly backward. 

Why Trustee Giving Has to Come First

I do not expect every board member to be a major donor. What I do expect is that each trustee gives a gift that is significant for them — whatever that means given their circumstances.

This is what it means to have skin in the game. A trustee's gift does real work: it covers annual fundraising expenses and signals to every other prospective donor that the people closest to the organization believe in it enough to give their own money. That signal is worth more than most trustees realize.

The best fundraising conversations I have with trustees are not pep talks about duty or obligation. Those rarely move anyone. What works is building a real relationship — sitting with someone long enough to understand what they care about, what they have to give, and why this particular mission matters to them. 

The $32.15 Gift That Has Stayed With Me

Years ago I served on the board of a nonprofit that worked with people experiencing homelessness. A colleague on that board — who was himself a former client of the agency, formerly homeless — gave $32.15.

That was a significant gift for him. He gave from his want, not his surplus.

I count it among the best gifts I have ever cultivated and solicited. Not because of the amount. Because of what it demonstrated.

For those familiar with the Gospel of Mark, the parallel is clear. Jesus watches a widow drop two small coins into the temple treasury — worth almost nothing by the standards of the day — while wealthy donors give from their abundance. He tells his disciples that she has given more than all of them. She gave everything she had.

My colleague on that board was that widow. He was not thinking about other people's money. He was thinking about his own right action, his own responsibility to the community that had helped him. And in doing so, he showed the rest of us the way.

That is what fundraising leadership looks like at its core.

What "Higher-Profit" Work Actually Means

Peter Drucker called nonprofits "human-change agents." Their product, he wrote, is not a pair of shoes or a government regulation. It is a changed human being — a cured patient, a child who learns, a young adult who finds their footing.

Building on Drucker, I think of this as the higher-profit sector — higher-profit because the returns are measured not in dollars but in changed lives. The profit is human.

If that framing is right, then the fundraiser's job is not merely transactional. It is to help trustees understand that their gift — whatever its size — is a stake in that transformation. That it makes them part of something that outlasts any single donation.

How to Have the Conversation

Have it in private. Not in a board meeting, not in a group setting. One on one, with enough time to go beyond the agenda.

Ask questions and listen. Find out what the trustee cares about most, what they have given elsewhere, and what connection they feel to this particular mission. The goal is not to deliver a pitch. It is to understand the person well enough to make the ask meaningful when you do make it.

The gift that follows from that kind of relationship is a different thing entirely from the gift that follows a duty lecture. One comes from conviction. The other comes from compliance. Conviction holds. Compliance fades.

Build the relationship first. The giving follows.

What has your experience been in talking with trustees about their own giving? Share your thoughts in the comments section.