Why Most Planned Giving Conversations Fail Before They Begin

A woman in her 50s considers her planned giving options in a quiet moment of reflection

In Brief

Donors are ready. Most organizations aren't. Mark Dobosz of Mozaic Senior Life draws on four decades of research to show why most planned giving conversations fail before they start — and what actually works. The barrier isn't money, mortality, or donor hesitation. It's the language we use when we finally decide to ask.
Reading Time: 6 minutes

Twenty-seven years of observation across more than 10,000 nonprofit professionals points to one conclusion: donors are ready. Most organizations aren't.

Image: Adobe Stock / File #223696672

Charitable bequests totaled $45.84 billion in 2024. The average bequest is approximately 40 times larger than the same donor’s typical annual gift — and roughly 200 times the donor’s largest annual gift to the organization.¹¹ Only 1 percent of nonprofits have an active planned giving program.1

Those three sentences tell us the money is there, the impact is substantial, and most of the sector has not figured out how to have the conversation.

The question is not whether planned giving matters. The data settled that decades ago. The question is: how do donors actually feel about it? And what do those feelings tell us about how we should be doing our work?

The Term Itself Creates Distance

Start with the language, because the language is getting in the way.

Dr. Russell James, inducted into the National Association of Charitable Gift Planners Hall of Fame in 2021, has done the most important research on planned giving communication available to practitioners. When donors were presented with three phrases — “make a gift to charity in my last will and testament,” “leave a legacy gift to charity in my last will and testament,” and “make a bequest gift to charity in my last will and testament” — positive responses fell sharply with the second and third options. The word “legacy” confused donors. The word “bequest” confused them further. In a separate study, donors were twice as likely to want to learn more when the topic was framed as “gifts in wills” compared to all other tested language.2

The sector has built an entire vocabulary for a conversation most donors do not understand. We talk about bequests, charitable remainder trusts, and deferred gifts. Donors think about what they want to leave behind and whether their family will be taken care of. When we lead with our language instead of theirs, we lose them before we start.

The fix is straightforward. Donor-facing materials should say “a gift in your will,” “a future gift,” or “a way to continue your support after your lifetime.” The technical terms can follow once the emotional connection is made.

What Gets in the Way of Planned Giving Conversations

The primary barrier to planned giving is not financial. It is emotional.

The Giving USA Special Report, Leaving a Legacy: A New Look at Planned Giving Donors, found that only 7 percent of participants said the estate planning process was easy. The average age at which donors made their first planned gift was 52.8, and 53 percent established that first gift when they wrote their first will.3 These donors were not responding to a solicitation. They were acting on values they had already decided to express.

From the Publisher

Paul Schervish and John Havens identified a phenomenon called “psychic poverty,” in which even objectively well-resourced individuals feel financially insecure.4 That insecurity is a direct barrier. Donors worry about longevity and healthcare costs. Until they feel financially secure, a gift from their estate feels like a risk. There is also the matter of mortality. Any conversation about wills requires donors to acknowledge that they will die. Many development officers avoid it. So do donors. The result is that the most impactful gift a person may ever make goes undiscussed.

The solution is not to push harder. It is to earn the right to have the conversation. Jen Shang and Adrian Sargeant’s research shows that donors who have integrated generosity into their identity — who see themselves as people who give — are significantly more likely to make planned gifts and sustain them.5 That identity develops through repeated positive interactions with an organization, not through a single ask.

What Motivates Donors to Say Yes

When donors do commit, reciprocity is among the most powerful drivers. Research from the Centre for Sustainable Philanthropy finds that many legacy supporters want to give back because their lives were touched by the organization’s work.6 In senior living, healthcare, and education settings, this is not abstract. The gratitude is real. The planned gift is an expression of it.

The GIVE Study, conducted by GOSUMEC Foundation USA, found that donors who moved through four relational stages — Gratitude, Impact, Voice, and Engagement — gave more, gave at deeper levels, and brought others with them.7 By the time a legacy conversation happens, the emotional decision has often already been made. The development officer’s role is not to persuade. It is to facilitate.

That changes the nature of the work. We are not closing. We are accompanying. But accompaniment requires that we first clear away the assumptions that keep most programs from starting at all.

The Myths That Stall Programs

“Planned giving is for major donors.”
Research shows average bequests above $55,000 for older donor cohorts, with many of those gifts coming from consistent annual givers at modest levels.8 Loyalty predicts planned gift potential far better than annual gift size.

“Asking is intrusive.”
Legacy donors are typically among the most engaged supporters an organization has. A well-timed conversation rooted in genuine relationship is not an intrusion. It is an invitation.

“Our donors are too young.”
The average age at which donors wrote their first will was 44.3 Donors in their 40s and 50s are making these decisions right now. Most have not yet decided where their charitable commitments will land.

“We tried it and it didn’t work.”
Programs without consistent marketing and dedicated stewardship rarely produce results. The failure is usually structural.11 Donors cannot give to a program they have never heard about.

The Opportunity Is Too Large to Ignore

Adults 60 and older comprised 23.4 percent of the U.S. population in 2023 — more than 77 million people — and their collective wealth has grown by 30 percent since 2019.9 Bequest giving has represented between 8 and 10 percent of total American philanthropy for four consecutive decades.10 That is not a trend. It is a structural feature of the philanthropic landscape. As the largest wealth transfer in American history continues to move between generations, organizations with active planned giving programs will be positioned to receive gifts that change their financial trajectory for decades.

The organizations not building these programs now will spend years trying to catch up.

Four Things to Do Differently Starting This Week

Audit your language.
Remove “bequest,” “legacy gift,” and “planned giving” from every donor-facing piece. Replace them with plain language: “a gift in your will,” “a future gift,” “a gift from your estate.”

Start with your most loyal donors.
Identify the ten donors with the longest consecutive giving history regardless of gift size. Longevity and consistency are your best predictors of planned gift potential.

Ask.
Most donors who would make a planned gift never do because no one asked. A genuine, unhurried conversation about a donor’s long-term values is the ask.

Build a legacy society.
Give it a name that reflects values, not mechanics. A society creates belonging and social proof. When donors know others like them have made this commitment, the decision becomes easier.

The Core Truth

Donors do not feel ambivalent about planned giving because they lack generosity. They feel uncertain because the conversation has too often been led by technical language, premature asks, and institutional impatience.

When we lead with curiosity, build with patience, and honor the personal gravity of this decision, donors respond. The research confirms it. Forty years of giving data confirm it.

The gifts are there. The donors are ready. The question is whether our organizations are.

From the Publisher
Endnotes
  1. Giving USA 2025: The Annual Report on Philanthropy for the Year 2024. Giving USA Foundation. Published 2025.
  2. James, Russell N. III. “Planned Giving Language Research: Words to Use and Avoid.” Summarized by iMarketSmart, March 2023.
  3. Giving USA Foundation and Elizabeth J. Dale, PhD. Leaving a Legacy: A New Look at Planned Giving Donors. Giving USA Special Report. Chicago: Giving USA Foundation, 2019.
  4. Schervish, Paul G. and John J. Havens. “Wealth and the Commonwealth: New Findings on Wherewithal and Philanthropy.” Nonprofit and Voluntary Sector Quarterly 30, no. 1 (2001): 5–25.
  5. Shang, Jen and Adrian Sargeant. “Identity-Based Fundraising: How Donor Identity Drives Major Giving.” Centre for Sustainable Philanthropy, Plymouth University, various years.
  6. Sargeant, Adrian and Shang, Jen. “Bequest Giving: Motivations, Barriers, and Best Practice.” Centre for Sustainable Philanthropy / University of Plymouth, 2010.
  7. Bindra, Sanjay. “The GIVE Arc: Why Relationships — Not Campaigns — Create Donors.” GOSUMEC Foundation USA / philanthropy.org, 2026.
  8. Indiana University Lilly Family School of Philanthropy. The Philanthropy Outlook and related bequest research, 2024; Giving USA 2025 analysis of bequest segments; and PlannedGiving.com field observation (1998–present, just over 10,000 nonprofit professionals).
  9. DonorSearch. “4 Key Takeaways for Nonprofits from Giving USA 2024,” August 2024.
  10. Giving USA Foundation. Giving USA 2024: The Annual Report on Philanthropy for the Year 2023. Chicago: Giving USA Foundation, 2024.
  11. PlannedGiving.com field observation across 27 years, working with just over 10,000 nonprofit professionals through client engagements, training programs, webinars, and subscribers. 1998–present.
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