I was sitting in a Zoom waiting room, and the donor we were about to ask for an 8-figure gift was late. My colleague and I messaged each other: Should we email him? Reschedule? Keep waiting?

By the time he joined, we only had 20 minutes left to share a bold vision and make a very big ask. He said yes to everything we asked for. Those 20 minutes were enough because of what had happened over the ten years before them.

Many organizations I talk with have donors capable of giving 10 times what they give today, but their largest gifts stay at 6 figures. What’s missing is someone tending those relationships year after year, with a plan that outlasts the fundraiser who started them.

The 12-month problem

“Our gift ceiling is 6 figures. How do we break through to bigger gifts?”

Nonprofit leaders ask me this all the time, especially in regions with pockets of extreme wealth. Here in the Bay Area, you can drive past companies that minted billionaires and still feel like the relationships behind gifts that size are out of reach.

Relationships that lead to 7- and 8-figure gifts can take five to ten years or longer to build. But most nonprofits center everything around an annual budget cycle, with fundraising metrics that reset every 12 months. Our biggest gifts need a 5-year horizon, but we structure and measure our teams’ work around a 12-month one.

If one gift can close this year and a larger one may come 3-5 years from now, guess which gets immediate attention? With payroll and the next board report on the line, that choice makes sense. But a gift three years out doesn’t show up in the team’s metrics, so the hours spent on it don’t count anywhere.

That’s often where the 6-figure ceiling comes from. The gift that could close in 2030 keeps losing to the one that closes in December, sometimes with the very same donor.

Design for the 5-year gift

Here’s how to set up your team and your messaging for gifts that take years to close.

Describe your work in decades

Most fundraising messaging, even for major gifts, describes what a gift does this year. “$50 pays for a week of groceries.” “100,000 funds our youth program for a year.” Those messages raise essential money from donors who want to help now.

A donor considering $1 million or $10 million is often asking a different question: what will be different ten years from now because of this investment? That’s hard to answer when goals reset every year, because we start describing our work by what happened this year.

Leaders first have to look ten years out themselves, at where the people we serve will be. For a job training program, that might be the parent whose new career changes what’s possible for their kids. A land trust can report the acres it restored this season, but ten years out, the story is a creek that still runs cold enough for salmon to spawn.

Most gifts pay for what happens today. The biggest gifts pay for what’s still there tomorrow.

Build relationships that outlast the fundraiser

Many fundraisers move on within two years, long before a transformational gift closes. Big relationships tend to stall at the handoff, because the person who left was the only one who knew the long game: what the donor hopes to change and what was supposed to come next.

So we plan for the departure early. The long-term plan lives in the CRM, not in one person’s head. The CEO and a board member know the donor and the plan well enough to keep meeting with the donor while the job is open. When the next fundraiser arrives, the donor is already in the middle of a conversation with people they trust.

This is often where I begin with a team: finding the relationships that rest on one person and building a plan so the next fundraiser doesn’t start from scratch.

Give the 5-year gift its own goal

Most development teams track their pipeline, but few give anyone a goal tied to it. If a gift officer’s annual review counts only dollars closed, December will keep winning. The donor who renews at $100,000 this December may be the one who could make a $5 million gift in 2030, and the team needs credit for working toward both.

Set a separate goal for the few donors who could make your largest gifts, based on whether each relationship moved forward this year, like a first meeting with the CEO or a first conversation about a gift 10 times larger than their last. Then protect the time it takes.

The decade behind the 20 minutes

So, back to that Zoom call. We had walked in nervous but confident, because the donor had spent a decade deciding what he thought of the organization.

Fundraisers before me had opened the relationship years earlier, and when I stepped in, their notes were waiting in the CRM. Colleagues who had watched it grow were still there, and board members from the early years had stayed involved. He knew so many of us that there was never a formal handoff.

The meeting took 20 minutes. The relationship behind it took a decade.

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One email a month on major and mega gifts, board fundraising, and capital campaigns, drawn from 20 years of doing the work.