How Planned Giving Relationships Drive Long-Term Generosity

Planned giving is sometimes treated as a technical specialty, something reserved for large organizations with attorneys on call and files of financial instruments. In truth, it’s far simpler — and more powerful. The same foundations that sustain every mission-driven organization — clear purpose, genuine relationships, and steady communication — are what make planned giving thrive.

Occasionally, a gift structure may be complex, but most legacy commitments arise from something much more human: belief. Donors make planned gifts because they believe in a mission that matters and trust the people who will carry it forward.

Where Planned Giving Really Begins

Every legacy gift starts with a relationship.

“Legacy giving is primarily the result of long-term relationships,” Joe Chickey, senior vice president and senior consultant at the Sharpe Group, said. “Donors who include you in their wills have truly included you as a member of their family.”

That spirit of belonging grows from everyday stewardship, not technical expertise. When organizations treat donors like family — by listening carefully and asking open-ended questions about their passions, life changes, and hopes for the future — those relationships naturally deepen into legacy commitments.

For any nonprofit leader, the first step isn’t forming a department or hiring a specialist. It’s clarifying the story about why the organization exists, how it changes lives, and how that change can last well beyond one fiscal year.

Mission Before Mechanism

There are countless giving vehicles available today, but the tools aren’t the point. If organizations ground planned giving in mission rather than mechanism, donors will see it as the next chapter of their support rather than a new or complicated request.

Lisa Chmiola, CFRE, assistant vice president of development at Loyola University New Orleans and founder and chief fablanthropist at Fablanthropy, often tells fundraising professionals that asking about legacy is simply an invitation to learn more. Most planned gifts, she said, are made through simple bequests or beneficiary designations, which are easy for donors to arrange without a legal team. And once a donor commits, the key is consistent attention.

“Perhaps one of the easiest and most impactful ways to steward a legacy donor is reaching out at least once a year for a conversation,” Chmiola said. “You’ll learn what’s changed in their life and ensure they feel connected.”

Even smaller organizations can begin where they are: Mentioning legacy giving in thank-you calls, adding a brief line about bequests in annual reports, or sharing stories of other donors who gave through their wills. These small steps normalize the idea that legacy giving belongs to everyone.

The Donor Experience Matters

Wayne Olson, president and CEO of the Winter Haven Hospital Foundation, has long urged nonprofits to stop viewing supporters merely as donors. He points to Walt Disney’s practice of treating customers as guests — and staff as cast members — to illustrate how belonging builds loyalty.

“The mission belongs to those who fund it,” Olson said. “We are here just to make it happen for them.”

When fundraisers see their work through that lens, gratitude replaces solicitation. Each interaction becomes about the donor’s experience, not the organization’s needs. That shift builds trust — the kind that leads to enduring generosity.

“People will trust you when they know you are genuinely interested in them and their best interests,” Olson said.

Integrating, Not Isolating

Planned giving should be in the bloodstream of an organization, not in a silo. Boards, CEOs, development officers, and volunteers all shape a culture where legacy giving feels natural. 

Many of the largest bequests come from donors who have given small gifts over many years, Chickey said. Their loyalty, not their income level, predicts their generosity.

Olson echoes that integration mindset, warning against treating planned giving as a separate department.

“The donor wants to give in the way that’s best for them,” he said. “They don’t think about annual fund, then major gifts — they just think about giving.”

When everyone on the team understands that continuity, legacy giving stops being a transaction and becomes part of the organization’s DNA.

Hope for the Future

At its core, legacy giving is an act of optimism. It’s a donor’s way of saying, “I believe this mission will still matter tomorrow.” As Olson shared, real generosity grows when people feel cared for — and when leaders are willing to pave new pathways rather than fence off the possibilities.

Planned giving isn’t complicated. Strong planned giving relationships are built on clarity of mission, genuine connection, and consistent communication. When those foundations are strong, planned gifts follow naturally and sustain the organization — and the hope it inspires — for generations to come.

The preceding content was provided by a contributor unaffiliated with NonProfit PRO. The views expressed within may not directly reflect the thoughts or opinions of the staff of NonProfit PRO.