The Most Important Planned Giving Question Is Often the One We Never Ask

By Mack Graham, CFRE

During my time at CCS Fundraising, one question consistently made me uncomfortable during campaign feasibility studies:

"Have you included this organization in your will?"

Every time I prepared to ask it, I expected hesitation. It felt deeply personal, and I worried donors might see it as intrusive.

Instead, I experienced something completely different.

More often than not, donors welcomed the conversation. Some had already included the organization in their estate plans, and the organization simply didn't know because no one had ever asked.

That experience permanently changed how I think about planned giving.

Planned Giving Is Having a Moment

According to the 2026 Giving USA report, charitable giving reached a record $617 billion in 2025. Among the most notable trends was the remarkable growth in bequest giving, which increased by nearly 20%, making it the fastest-growing source of charitable support.

At the same time, the report reinforces another reality: a relatively small percentage of donors continue to account for a significant share of philanthropic giving.

For nonprofit leaders, these trends present both an opportunity and a challenge.

The Barrier Isn't Complexity

Many organizations assume they need a sophisticated planned giving department before they can begin talking about legacy gifts.

In my experience, that's rarely the biggest obstacle.

The bigger obstacle is confidence.

Organizations often hesitate because they worry they'll offend loyal supporters or because planned giving feels like a conversation reserved for wealth advisors and attorneys.

But legacy giving doesn't begin with legal documents.

It begins with relationships.

Stewardship Comes Before Solicitation

The strongest planned giving programs aren't built on brochures or complicated gift vehicles.

They're built on years of trust.

When someone has supported your mission for decades, volunteered, served on a committee, or consistently invested in your work, a legacy conversation shouldn't feel unexpected.

It should feel like the natural continuation of a relationship.

Sometimes the most meaningful question isn't:

"Would you consider leaving us in your will?"

It's simply:

"Have you ever thought about the legacy you'd like your generosity to leave?"

Every Organization Has Future Legacy Donors

Planned giving is often viewed as something only large universities, hospitals, or national organizations can prioritize.

I don't believe that's true.

Every nonprofit has long-time supporters who care deeply about its mission. Many have already considered how they'd like to be remembered.

The opportunity isn't limited by organizational size.

It's limited by whether we're willing to begin the conversation.

Final Thought

I've come to believe that planned giving isn't really about estate documents.

It's about relationships.

It's about trust.

It's about stewardship over time.

The organizations that embrace that mindset won't just receive future gifts.

They'll strengthen donor relationships today.

Mack Graham, CFRE