Series Overview
After almost five decades in nonprofit resource development, I’ve encountered a persistent puzzle: why do donors who freely communicate about their outright gifts suddenly grow secretive when it comes to planned giving? Join me through this series as I share what I’ve learned about solving this mystery—one donor relationship at a time.
Lesson 1: The Paradox of Planned Gift Disclosure
When I arrived at the University of Louisville in the mid-1970s as a 23-year-old with the grand title of “director of estate and gift planning,” I quickly encountered a perplexing situation. Donors would gladly tell me the University was in their estate plans, yet despite my encouragement, they would not disclose information regarding their intended gifts. Each person offered a different reason for their secrecy.
This experience repeated itself throughout my career across multiple institutions. Donors who would share intimate details about their lives and passions when making outright gifts would suddenly erect walls when the conversation turned to bequests. I found this shift in behavior both fascinating and frustrating.
What I’ve come to understand is that planned giving represents the ultimate personal act between a donor and nonprofit. It involves mortality, family dynamics, financial security, and legacy—topics that naturally trigger greater caution and privacy.
As development professionals, we must recognize this shift not as rejection but as a signal that we’ve entered territory requiring a different approach to relationship building and trust.
Key Lesson
Planned giving conversations activate different psychological triggers than annual or major giving discussions. Understanding this fundamental difference is your first step toward successful bequest cultivation.
Lesson 2: The Stakes Have Never Been Higher
In my decades of fundraising experience, I’ve never seen a wealth transfer opportunity as massive as the one we’re currently facing. According to recent data, an estimated $84.4 trillion worth of assets will transfer through estates in the coming decades. For perspective, in 2023 alone, giving by bequest in the United States totaled $42.68 billion.
Yet despite this tremendous opportunity, research indicates that fewer than 25 percent of donors who include nonprofit organizations in their estate plans notify the organization of this fact. This information gap creates significant challenges for institutional planning and stewardship.
The generational variations in estate planning readiness reveal interesting patterns:
- Baby Boomers: 57.5% have estate plans
- Silent Generation: 54%
- Gen X: 53%
- Millennials: 43%
- Gen Z: 39%
Meanwhile, only 32 percent of Americans currently have a will in place. The reasons I hear consistently from prospects include “I haven’t gotten around to it,” “I don’t have enough assets,” “It’s too expensive,” or simply “I don’t know how.”
For development professionals, this combination of massive transfer potential and low planning participation creates both challenge and opportunity. Our role must include not just securing gifts but helping donors understand the importance of having an estate plan that benefits them and their families first—with charitable giving as a natural extension of their values.
Key Lesson
The wealth transfer opportunity is unprecedented, but capturing it requires us to engage in broader financial literacy and estate planning conversations with our constituencies.
Lesson 3: Why Donors Keep Their Planned Gifts Secret
Through countless conversations with donors over five decades, I’ve identified recurring themes in their reluctance to disclose bequest intentions. Understanding these concerns has helped me develop more effective approaches to planned giving conversations.
From my experience and supported by research from experts like Jeremy Reis and Malcolm Burrows, here are the primary reasons donors hesitate to share their planned giving details:
- Fear of Mortality. I’ve found that many donors avoid estate discussions simply because they’re uncomfortable confronting the reality that these gifts take effect after their death.
- Financial Insecurity. One wealthy couple I worked with for years pulled a significant endowment gift “off the table” as they aged, growing increasingly concerned about having sufficient funds for their health needs.
- Complexity and Misunderstanding. The technical language of planned giving can intimidate even sophisticated donors. I’ve seen brilliant business owners grow uncomfortable when confronted with unfamiliar terms like “charitable remainder trust” or “life income gift.”
- Trust Issues with Nonprofits. Donors often express concern about how their gifts will be managed and whether their intentions will be honored decades into the future.
- Privacy and Family Dynamics. Many donors worry about family reactions to their charitable intentions, particularly when children may view charitable bequests as diminishing their inheritance.
- Fear of Fundraising Pressure. I’ve had donors explicitly state they don’t want to be “hassled” by receiving increased solicitation if their bequest intentions become known.
- Desire for Flexibility. Donors often prefer keeping options open, knowing they can change their plans without having to explain themselves to an organization.
Key Lesson
Each donor’s reluctance stems from a unique combination of these factors. Listening carefully to identify their specific concerns is essential to addressing them effectively.
Lesson 4: Tales from the Planned Giving Trenches
Throughout my career, I’ve experienced both heartbreaking failures and remarkable successes in securing bequest commitments. Let me share two contrasting stories that illustrate crucial lessons.
When Everything Went Wrong
I worked with one couple for many years who gladly gave thousands of dollars annually to our organization. Our relationship was warm, and they seemed to genuinely enjoy our regular visits discussing the impact of their gifts.
When we began exploring a significant endowment fund through a planned gift, something changed dramatically. Though they agreed in principle, they never signed the documentation. As financial representatives and family members entered the conversation, their demeanor shifted. They became increasingly concerned about having sufficient funds for their health and well-being as they aged.
Not only did they decide against the planned gift because of what they perceived as a “complex new concept,” but they also discontinued their annual giving entirely. I still remember the joy that had once lit up their faces when I described how their gifts made a difference in someone’s life—joy that disappeared when the stakes and complexity increased.
When the Stars Aligned
In a happier scenario, I secured a multi-million-dollar bequest from a male widower under nearly perfect circumstances. Three factors came together beautifully:
First, his secretary of 40 years served as a volunteer with our nonprofit and deeply loved our organization. Second, his financial advisor sat on our board. Third, the gift honored his late wife and directly connected to his life’s work.
During our meetings, he expressed concern about having funds for his health care needs. I suggested he begin making significant current gifts against the balance of his future bequest, with the remainder to be paid upon his passing. Ironically, he made just one current gift before he died. The arrangement worked perfectly for everyone involved—he had no children and wanted to leave a meaningful legacy, while his support network helped him feel confident about his decision.
Key Lesson
The path to successful planned gift disclosure often depends on creating a comfortable support network around the donor that includes their trusted advisors and addresses their practical concerns.
Lesson 5: Breaking Through the Disclosure Barrier
Based on my decades of experience working with planned giving donors, here are the approaches I’ve found most effective in encouraging bequest disclosure:
Simplify the Process
I’ve learned to explain planned giving options in straightforward language, avoiding technical jargon that creates unnecessary complexity. When meeting with donors, I focus on the impact their gift will have rather than dwelling on the mechanics of the giving vehicle.
Build a Community of Legacy Donors
One of my most successful strategies has been connecting potential planned giving donors with others who have already completed their plans. Host annual events specifically honoring legacy donors, providing recognition that makes them feel valued while showing prospective donors they’ll join an esteemed group.
Emphasize Strict Confidentiality
I always stress to donors that our conversations and any information they provide are strictly confidential. This explicit assurance helps address their privacy concerns and builds trust in the process.
Focus on Long-Term Impact
I’ve found that emphasizing how their gift will create lasting change helps donors see beyond the short-term financial considerations. Stories about what previous legacy gifts have accomplished provide tangible examples of potential impact.
Engage Holistically
Some of my most committed planned giving donors started as board members or volunteers. Continually ask your donors to be involved with your organization—to serve on boards, become ambassadors, volunteer, and attend events. When they feel wanted and appreciated beyond their financial capacity, they become more willing to disclose their planned gift intentions.
Include Organizational Leadership
Whenever possible, I arrange for the CEO of my nonprofit to join an early visit with planned gift prospects. This special attention makes donors feel like valued partners in the institution’s future rather than just sources of funding.
Remember: Family Comes First
I always begin by promoting the concept of having an estate plan that benefits donors and their families first. Only after acknowledging this priority do I ask if they would consider including our charity.
One wealthy major donor I worked with had three children. Over time, she developed such a connection with our nonprofit that she referred to it as her “fourth child.” This meant our organization would eventually receive one-fourth of her estate—a testament to the relationship we had built with her family over many years. She later became a board member and chaired a capital campaign in an area dear to her heart.
Key Lesson
Creating an environment of trust, recognition, and ongoing engagement transforms the disclosure conversation from intimidating to inspiring. Success comes through constant communication, positive relationship building, and creation of a trusting environment—one prospect and donor at a time.
