How to Talk About Bequests Without Being Morbid? A Legacy Challenge

The challenge fundraisers face when seeking legacy gifts is to secure commitments without striking a morbid tone.

One increasingly popular way to ease into such conversations is a “legacy challenge,” which offers matching funds that go immediately to a nonprofit. Typically, a donor or an institution offers a match that is either a fixed amount or a percentage of the current value of the bequest, usually with a cap that might go up to $25,000. The match is offered for a limited time period, such as a year.

The timeline gives a sense of urgency that pushes frontline fundraisers to discuss legacy gifts and encourages donors to make or reveal bequests. “One of the reasons the legacy challenge is so powerful is because it gives a non-death related deadline to do it now,” says Russell James, professor of charitable financial planning at Texas Tech University.

Legacy challenges have become a common topic at professional conferences, say fundraisers and consultants. “I think they’re great tools,” says Nathan Stelter, president of the Stelter Company, and former chair of the board of the National Association of Charitable Gift Planners. “We’ve definitely seen them grow in interest in the last five to 10 years.”

Stelter says multiple studies indicate that only one in three donors share in their lifetimes what their giving intentions are upon their deaths. That leaves the other two-thirds of donors with hidden intentions. “With some donors, there is a hesitancy to share the details of their gift,” says Kara Barnes, senior gift planning officer at the Smithsonian Institution. “This is a way to help motivate donors to do so.”

Being transparent has benefits to the donor. “We want to encourage people to document their gifts because we want to make sure that we are using the gift in the way that they envisioned it being used,” says Louisa Sizemore, senior director of gift and estate planning at the University of Texas at Austin.

James says fundraisers need to understand donor psychology to comprehend legacy challenges. “The motivation is not to sign the gift because you might die,” he says. “The motivation is to sign the gift because you can inspire other people to make this gift.”

“We’re very comfortable with the fact that other people die,” he adds, “but not comfortable with the idea of planning for our own end of life.”

Legacy challenges tend to be more common at larger nonprofits with the staff to execute them, such as universities and hospitals, Stelter says. But he has also seen them used in health care, international aid, and arts and humanities nonprofits.

In a legacy challenge that ran from late 2023 to early 2025, the Washington National Cathedral began with $1 million for a matching fund which came from two individual donors, says John W. Jensen, the planned giving director for the cathedral. Fundraisers then asked donors to estimate the current value of legacy gifts and offered a 10 percent match for gifts of up to $250,000. Shy donors who didn’t want to name an amount could get a $1,000 flat match. Past donors who had already made a legacy pledge but not named an amount could get the percentage match simply for revealing the amount. The legacy challenge ultimately raised $35.8 million, Jensen says.

The $25,000 cap on percentage matches didn’t stop some donors from making gifts well over $250,000, says Jensen, adding that “it was an incredibly effective tool.”

“We got a lot of information from donors who we had no idea had put us in their estate plans and people that we thought might give us five or $10,000 who ended up committing a couple of hundred thousand dollars.”

As the cathedral discovered, learning about bequests from donors can reveal broader insights. “It helps you really understand what your pipeline is,” says Tracy Malloy-Curtis, vice president for legacy giving at Mal Warwick Donordigital, a fundraising consulting firm with offices in Washington and San Francisco. “It identifies people who are potential major donors, who might not have been on your radar. If someone is leaving a multi-million-dollar gift to you, and they’ve never been on your radar as a major donor, quite often, the planned gift can lead to a major-gift discussion.”

Legacy bequests, she says, “are not a terminal gift. They’re a gift in the gift ecosystem.”

Malloy-Curtis says the initial request to seek funds for the match is “a great ask,” especially if taken to a donor with a strong interest in securing an organization’s future. The minimum return on investment for the funds put up for a match should be ten to one, she says, with ten future dollars generated for each dollar of matching funds. “But I have not worked on a single challenge,” she says, “that has been less than 20 to one or more.”

‘Flat Match’ vs. a Percentage

Typically, fundraisers ask donors seeking a legacy match to provide a written good-faith estimate of what their bequest would be worth at the time they submit a gift bequest form, since gifts tied to investments can fluctuate. Some organizations ask for copies of beneficiary sections of documents, such as life insurance policies, trusts, or investments, to prove a bequest. Malloy-Curtis thinks donors are less squeamish about discussing the size of gifts than many fundraisers are. If asked what a gift would be worth if they “died today,” she says donors are apt to grab a piece of paper and figure it out. “I’ve talked to thousands of donors over the years, and none of them gets annoyed at this stuff,” she says.

The goal of a legacy challenge, Malloy-Curtis believes, should be dollars raised, not the number of donors. “The reality is we have rampant wealth inequality, and most of the revenue is going to come from a small number of donors.”

Some fundraisers prefer a “flat match” — say $1,000 for any size gift — since they believe a flat match is easier to explain and simpler to execute. Barnes at the Smithsonian has become a flat-match fan because “the less language you need to describe the legacy challenge, the better.”

Others say that the percentage approach — perhaps 10 percent up to $10,000 — is more apt to get fundraisers what they want, which is to learn the potential sizes of gifts. The flat match “doesn’t inspire people in the same way,” says Malloy-Curtis.

There is also debate among fundraisers about whether to allow donors to steer match money to a specific program within a nonprofit, or if all matches should go to unrestricted funds.

At the Smithsonian, Barnes says, matches have gone to unrestricted funds unless they are six figures or more, in which case the amount triggers a discussion with the donor about if they want to endow a curator or a directorship or create another specific endowment.

When Challenges Work

Who wins with legacy challenges? Organizations that provide a sense of permanence, consultants say. Barnes says that at the Smithsonian, conversations with legacy donors focus on “preserving and protecting this institution for years to come.”

A ten-year-old local food bank that doesn’t yet have a planned-giving program probably shouldn’t launch a legacy challenge, says John B. Kendrick, a fundraising consultant based in Washington. But James at Texas Tech says young local nonprofits could partner with a longstanding community foundation that could manage the funds. The new nonprofit “could borrow that sense of permanence,” James says.

Smaller charities should consider whether they have enough donors, typically older ones, in their database to use a legacy match. Generally, to maximize gifts, James says nonprofits need to approach potential donors in their late 80s or early 90s, when research suggests many are signing the relevant documents. “Wealthy people die older,” he says, “and wealthy charitable people die even older.”

Larger organizations sometimes layer multiple legacy challenges. Sizemore started out as the first planned giving officer at Friends of the Earth, the environmental group, where she used a $500 match for each legacy bequest. Now that she is at the University of Texas at Austin, she is helping to run multiple legacy challenges simultaneously. One is for members of the boards and advisory councils of the universities’ colleges, schools, and centers. Another challenge is for new bequests, and another is for those upgrading their bequests by at least $100,000.

“What I love so much about legacy challenges,” she says, “is you can scale them to whatever your group is, and to whatever budget you’re working with.”

Messaging Matters

Consultants and fundraisers are unanimous in their belief that nonprofits should sharpen their case for support before launching a legacy challenge. The most successful legacy challenges are based on an urgent, tangible argument, Malloy-Curtis says. The match alone is not enough.

Vague messaging like “leaving a legacy of hope for future generations” won’t cut it, she says “You have to say, ‘This is why we need this gift. This is what will happen if we don’t get it. This is what we could potentially achieve.’”

The firm Malloy-Curtis works for specializes in progressive causes, and she says that while most legacy propositions are uplifting, the opposite approach might work in the current political environment. Donors may be thinking, “I’m terrified about what’s going to happen in the future, and I’d like to preserve some of these values at a time where that seems really challenging.”

“That’s an unusual case for support that is resonating in a real way right now,” she says.

Barnes at the Smithsonian says conversations with donors should avoid becoming transactional — ‘we are trading this match for your bequest.’ Instead, she describes matches as a way of honoring and celebrating bequests.

That messaging tone, she says, should be part of marketing throughout the challenge, from initial outreach to thank-you letters.

Creating Cohesion

Often, fundraisers say, legacy challenges can build cohesion, particularly in large development departments, where frontline fundraisers may all have individual goals, such as raising annual or major gifts.

That cohesion is built by the nature of legacy challenges, says Malloy-Curtis. “It’s easier to share a match opportunity, as opposed to saying ‘Tell me about your estate plan.’” Using that approach, she says, “you’re able to pull in lots of folks across an organization as ambassadors for legacy giving.”

The goal, Malloy-Curtis says, “is to have fundraisers talk to donors more holistically about the impact they want to make now and later.”

Fundraisers with legacy-challenge experience emphasize that careful execution matters. Gift officers need to be briefed. Matching funds must be tracked. Marketing and communications departments need high-quality materials. Donors must be told where their match wound up.

“It’s one thing to have a great marketing program,” Kendrick says, “but if you fall down in executing, people will be upset at you.”