159. Today’s Gifts, Tomorrow’s Legacy
How Do You Weave Legacy Giving Into Major Donor Conversations?
The best way to integrate planned giving into major gift work is to treat today's gift and tomorrow's legacy as one conversation about impact. Watch for readiness signals like long-term loyalty and life transitions, ask one hopeful, future-focused question, and bring in the right partners when the donor leans in. That's the heart of this week's episode of The Intentional Fundraiser, "Today's Gifts, Tomorrow's Legacy."
Who this is for: Major gift officers, development directors, executive directors, and board members at small and mid-sized nonprofits. You'll walk away knowing which donors to talk with about legacy, what to say, and who to bring to the table.
Let’s get into it
Many of your major donors are thinking about legacy right now.
They're updating estate plans. They're talking with advisors about this year's tax changes. They're wondering what their generosity will mean twenty years from now.
And many major gift officers still aren't bringing it up. They worry a legacy question will muddy the current ask.
In this episode, I share the story of a donor and the one question that changed his relationship with the organization he loved
Why should major gifts and planned giving be in the same conversation?
The donor had given to a literacy nonprofit for eleven straight years. His development director was about to ask him to renew a three-year pledge, and she didn't want to complicate things by raising planned giving.
But the donor kept asking whether the reading program would still be here someday. He was already having the legacy conversation.
So after he renewed and increased his gift, the development director asked, "What would you want this program to look like twenty years from now?" Two months later, the donor named the organization as a beneficiary of his retirement account.
I like to think of it this way. The current gift is the fruit. The legacy gift is the roots. You'd never ask a gardener to choose between them. In my experience, donor-centered legacy conversations rarely shrink the current gift. They tend to deepen engagement.
What signals show a donor is ready to talk about legacy?
In the episode, I walk through five green lights:
Loyalty. Long, consistent giving is often a stronger signal than gift size.
Life transitions. Retirement, a new grandchild, selling a business, or the loss of a spouse. Please be gentle with grief.
Future language. Phrases like "I want this to keep going" or "What happens to this program down the road?"
Deep involvement. Board members, longtime volunteers, former staff, and families your mission has served.
The donor brings it up. "I just updated my will" is an invitation, not small talk.
How do you start a legacy conversation without it feeling morbid?
Lead with hope. Legacy conversations aren't about death. They're about the future a donor wants to help create.
I recommend a "both/and" approach. Talk through the current gift first and honor the donor's decision. Then open a door with one gentle question, like "What do you hope is true about this work twenty years from now?"
Then listen. You're not making a second ask. You're inviting the donor to think out loud with you.
Who should be involved: planned giving specialists or donors' advisors?
Both, at the right time. You stay the relationship lead. A planned giving officer, consultant, or community foundation partner joins once the donor shows interest, usually in the second or third conversation.
Treat donors' financial advisors and estate attorneys as partners, not gatekeepers. And after a commitment, keep stewarding. Many legacy gifts can be changed, so annual updates, invitations to see the work, and thoughtful recognition all matter.
What can you do this week?
Here are three steps you can finish in under an hour:
Add one legacy question to three to five upcoming major donor meetings.
Scan contact reports for your top twenty donors and look for the five signals. An AI assistant can help you spot future-oriented language, as long as you keep sensitive donor details out of public tools.
Gather your legacy basics: your legal name, tax ID, and sample bequest language, ready to send the same day a donor's advisor asks.
For the full conversation, including how to set up roles with your planned giving partners, give the episode a listen.
I'd love to hear from you
Connect with me on LinkedIn and tell me: what's one legacy question you plan to add to your next donor meeting?
Your donors want their generosity to matter for a long time. Make room for that conversation, and you'll both be glad you did.
Frequently Asked Questions
Q1. Who is this approach best suited for?
This approach is designed for major gift officers, development directors, and executive directors at small and mid-sized nonprofits who want to grow current major gifts and legacy commitments together without handing donors off. It works especially well if you already have a group of loyal, long-term donors and access to planned giving expertise, whether on staff, on contract, or through a community foundation.
Q2. How much time should I expect this to take each week?
Most fundraisers can get started with about one to two hours per week focused on preparing legacy questions, reviewing donor signals, and following up with interested donors. The more important piece is consistency. Protect this time on your calendar so it doesn't get swallowed by internal noise.
Q3. What if my organization is small and I wear multiple hats?
The principles still apply, but you may need to scale the tactics. Start with a lighter version of this process that you can realistically sustain, perhaps three to five donor meetings with one legacy question each month, and expand as you see results. You don't need to be a technical expert. You need to know your donor and know who to call.
Q4. How do I know if it's working?
Look for early signals like more donors answering future-focused questions openly, legacy interest noted in your CRM, and advisors reaching out for your bequest language. Over time, you should see this reflected in more documented legacy commitments, stronger long-term retention, and more donors making both current and planned gifts.
Q5. Where does AI fit into this, if at all?
AI is there to reduce friction, not replace your relationships. Use it for spotting future-oriented language in your contact reports, drafting a tailored legacy question for a specific donor, or turning your notes into a warm annual stewardship update, while keeping the human work of listening, discernment, and relationship-building firmly in your hands.
“Legacy conversations aren't about death. They're about the future a donor wants to help create.”
Tammy Zonker, Major Gift Expert, Keynote Speaker, Author
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