You know the donors. They've been giving $100, $500, maybe $1,000 annually for years. Faithful. Committed. Reliable. But when you think about asking them to include your nonprofit in their will, something stops you.
Maybe it feels too forward. Too morbid. Too much like you're asking for something they can't afford.
Here's what most fundraisers miss: your mid-level annual donors are often your best planned giving prospects. They've already proven their loyalty and commitment. They just don't know yet that they can make the kind of transformational gift that typically goes to organizations with bigger budgets and fancier galas.
According to research from FreeWill, bequests accounted for $45.84 billion in charitable giving last year. The average bequest? $46,594. That means your consistent $500 donor could potentially leave a gift that's the equivalent of nearly 100 years of their annual support.
The question isn't whether you should talk about planned giving. It's how to make these conversations feel as natural as any other donor stewardship touchpoint.
Why do fundraisers avoid planned giving conversations?
Research shows that donors who are directly asked to make a bequest are 17 times more likely to do so than those who aren't asked. Seventeen times.
Yet most small nonprofits don't have active planned giving programs. Why?
The mortality elephant in the room. Talking about someone's will means acknowledging their eventual death. For many fundraisers, especially those newer to the field, this feels uncomfortable or even inappropriate.
Assuming planned giving is only for the wealthy. When you hear "estate planning," you might picture donors with vacation homes and stock portfolios. But the reality is that anyone with assets (a home, retirement savings, life insurance) can make a legacy gift.
Lacking a clear starting point. Without formal planned giving training, many fundraisers simply don't know how to begin the conversation. What do you say? When do you say it? How do you transition from talking about their annual gift to discussing their will?
Fear of seeming transactional. You've worked hard to build authentic relationships with donors. Bringing up their estate plan might feel like you're reducing the relationship to what you can get from them.
These concerns are valid. And they're also surmountable once you understand that planned giving isn't a separate category of fundraising, it's a natural extension of the donor relationships you're already building.
Who should you actually be talking to about planned giving?
Before diving into how to have these conversations, you need to know who to have them with. More than 50% of planned giving donors had been supporting their chosen organizations for longer than 20 years. The average age when donors make their first planned gift is 52.8 years old.
This tells you something important: planned giving isn't about wealth screening or age targeting alone. It's about relationship depth and demonstrated commitment.
Look for donors who have given consistently. Someone who's made a gift for five consecutive years, regardless of amount, has shown loyalty that predicts future major support. They've voted with their wallets, repeatedly, that your mission matters.
Pay attention to donors who increase their gifts over time. A donor who started at $100 and now gives $500 is signaling growing commitment and likely growing capacity.
Watch for personal connections to your mission. Donors who volunteer, attend events, or share your content on social media are emotionally invested beyond their checkbooks. Research from DonorSearch shows that donors who are positively affected by your mission or have conviction in your work are prime planned giving candidates.
Don't overlook mid-level donors. These supporters often fly under the radar because they're not major gift prospects yet. But people who can't make large gifts during their lifetime often use legacy gifts to make the kind of impact they've always wanted to make. Your $1,000 annual donor might have $500,000 in retirement savings and a paid-off house.
Consider donors approaching life transitions. Retirement, empty nesting, milestone birthdays, the loss of a spouse...these moments naturally prompt people to think about their legacy and get their affairs in order.
The key insight? Many of your current loyal supporters are ready for this conversation. You just need to know how to track and identify these patterns in your donor data.
How do you make planned giving campaigns feel less awkward?
The secret to natural planned giving conversations is grounding them in something concrete. Here are practical approaches that work:
Start with a mailing or email series. Before picking up the phone, educate your donor base about legacy giving through your regular communications. Include a section on your website about ways to give. Send a newsletter highlighting a donor who's made a bequest (with their permission). Create a legacy society and invite people to join.
This does two things: it normalizes the topic, and it gives you something to reference when you do reach out personally. "I wanted to follow up on the information we sent about legacy giving" is far less awkward than launching into estate planning out of nowhere.
Connect planned giving to specific opportunities. If you're running a capital campaign or have a major initiative, frame legacy gifts as a way to participate beyond current cash flow. A donor who gives $1,000 annually might not be able to pledge $25,000 over five years. But they could make a commitment of $12,500 now and $12,500 through their estate, achieving something they never thought possible.
Once a donor names your nonprofit in their will or as a beneficiary, their annual giving typically increases as well. You're not cannibalizing current support, you're deepening engagement across the board.
Lead with your title or program focus. If your role includes planned giving responsibilities, say so when you call: "As part of my work with our legacy giving program, I wanted to reach out..." This signals the purpose without being presumptuous. Or frame it around a program they care about: "You've been such a consistent supporter of our literacy program, and I'd love to talk with you about ways to ensure that work continues long-term."
Ask about their existing planning first. Rather than leading with your ask, open with curiosity about where they are. "Have you had a chance to work on your estate planning?" or "Do you have a will in place?" These questions show you care about them, not just their potential gift. Many people haven't done this work yet, which opens the door to provide resources and help.
Build the relationship before the ask. For major planned gift prospects, schedule an initial conversation with no agenda other than getting to know them better. Let them share their story, their connection to your mission, their hopes for the future. Active listening and genuine curiosity create the foundation of trust that makes bigger conversations possible.
The most important principle across all these approaches? You're not manipulating or pressuring anyone. You're offering donors a way to express values they already hold and make an impact that aligns with commitments they've already demonstrated.
What do you actually say when you bring up planned giving?
Let's get tactical. You've identified a long-time donor, you've decided to reach out, and now you need actual words. Here are conversation starters that work:
For donors who've been giving for years: "You've been such a faithful supporter of our work for [X] years. As we think about the future of this organization, I'm hoping you might consider including us in your estate plans. Many of our long-time donors have found that making a bequest allows them to make a much larger impact than they could through annual gifts alone."
For donors with specific program interests: "I know the [specific program] has really resonated with you. Some of our donors who are passionate about this work have chosen to create an endowed fund or include us in their wills specifically to ensure this program continues. Would you be interested in learning more about those options?"
For donors approaching retirement: "Congratulations on your upcoming retirement. This is often a time when people review their estate plans. If you're doing that work, I'd love to share information about how some of our supporters have included [your organization] as they've thought about their legacy."
For conversations that start elsewhere: Sometimes planned giving comes up organically. A donor mentions they're updating their will, or they ask about your organization's long-term stability. When that happens, simply say: "I'm so glad you brought that up. We have several donors who have let us know they've included us in their estate plans, and it means so much to know that our work will continue because of their generosity."
According to planned giving experts, the key is asking open-ended questions that invite donors to reflect on their values and aspirations. Questions like "What do you hope your legacy will be?" or "What values are most important for you to pass on?" naturally lead to discussions about charitable giving.
Skip the jargon. Don't say "charitable remainder trust" or "charitable gift annuity" in your initial conversation unless the donor brings up complex giving vehicles. Instead, use plain language: "Some donors include us in their will," or "You could name us as a beneficiary of your retirement account."
Make it easy. Have sample bequest language ready to share. Connect donors with free will-creation tools. Remove every possible barrier between their interest and taking action.
Always follow up in writing. After the conversation, send a thank-you note and any promised information. Document the conversation in your CRM so the relationship continues smoothly even if staff transition. Building a strong stewardship system ensures these important relationships don't fall through the cracks.
How do you steward planned giving commitments?
Getting the commitment is just the beginning. What happens next determines whether that bequest intention stays in the will or gets quietly removed during the next update.
Create a legacy society. Even if it's simple, just a name and annual thank-you event, recognizing planned giving donors publicly (with their permission) reinforces their decision and inspires others.
Thank them immediately and sincerely. A planned gift commitment deserves more than a form letter. Write a personal note or make a phone call expressing genuine gratitude for their vision and trust.
Stay in touch without constant asks. Send impact updates, invite them to special events, and maintain the relationship you've built. The goal is keeping them engaged with your mission so they remember why they made this commitment in the first place. Effective donor stewardship keeps planned giving donors connected to your work long before their gift is realized.
Celebrate milestones. On the anniversary of their commitment, send a note. On their birthday, call to say thank you. These small touches reinforce that they're valued partners, not just future revenue. Use tools like DonorDock to surface these milestones automatically so you don't have to pull reports or remember to call.
Keep talking about planned giving broadly. Don't treat legacy gifts as a one-time conversation with a select few donors. Make it part of your regular donor communications. Include legacy society members in your newsletter. Share stories (with permission) about why people choose to leave bequests. This ongoing visibility keeps planned giving top-of-mind and reduces the awkwardness for everyone.
What tools and systems support planned giving for small teams?
What you do need is organization, consistency, and the right support systems to make this doable.
Use your CRM to track everything. Every conversation about planned giving should be logged. Every commitment should be flagged. Every follow-up should be scheduled. This isn't busy work, it's institutional memory that protects relationships during staff transitions and ensures no donor falls through the cracks. Modern donor management systems help you segment and track planned giving prospects alongside your other donor journeys.
Identify loyal donors systematically. Rather than relying on gut instinct about who to approach, use your data to find giving patterns that indicate readiness. Look for consecutive years of giving, increasing gift amounts, and engagement across multiple channels. Tools that help you track donor data effectively make it easier to spot these patterns.
Build simple donor journeys. Start with basics: long-time donors get educational materials about planned giving. Donors who respond with interest get a personal call. Donors who make commitments enter a legacy society stewardship track. Document these steps so anyone on your team can continue the work. Check out our Smart Steward Method if you need a framework to follow.
Leverage automation for consistency. Set annual reminders to reach out to planned giving donors on their commitment anniversaries. Schedule quarterly nurture emails to your legacy society. Use technology to ensure consistent touchpoints without requiring manual memory. When you balance automation with personal touches, you create sustainable stewardship that feels both efficient and authentic.
Document your bequest language and make it public. Put sample will language on your website. Include it in your donor newsletter. Make it so easy to include you in their estate plans that the only barrier is their own decision-making, not logistical confusion.
Partner with experts when needed. For simple bequests, you don't need specialized counsel. But for donors interested in charitable gift annuities, charitable remainder trusts, or other complex vehicles, connect them with qualified financial and legal advisors. Your job is facilitating the gift, not providing financial advice.
According to recent data, nearly $9 trillion will be inherited over the next decade. If just 5% of that goes to nonprofits, we're looking at half a trillion dollars for charitable missions. The organizations that will capture those gifts are the ones building relationships and having conversations now, not the ones waiting until they have "capacity" for planned giving.
How do you scale planned giving without scaling your team?
Small nonprofits often assume they can't pursue planned giving because they lack dedicated staff. But research from the National Council of Nonprofits shows that organizations of all sizes successfully implement planned giving programs by starting small and focusing on simple vehicles like bequests.
Focus on bequests first. Don't try to offer every possible planned giving vehicle. Bequests are the simplest to understand, easiest to create, and most accessible for average donors. Master this before expanding to more complex options.
Integrate planned giving into existing touchpoints. You're already stewarding major donors, thanking recurring supporters, and engaging mid-level givers. Add a planned giving component to these existing relationships rather than treating it as separate work.
Make it a team effort. Your executive director, board members, and program staff all interact with donors. Train them to recognize opportunities to mention planned giving and equip them with simple language to use. You don't need one person doing everything, you need everyone contributing to the culture of legacy giving.
Set modest but specific goals. Start with "We'll have three new planned giving commitments this year" rather than "We'll generate $X million in planned gifts." You won't realize most of these gifts for years or decades, so early success metrics should focus on commitments, not dollars.
Tell stories that inspire others. When donors see their peers making planned gifts, it normalizes the behavior and creates social proof. With permission, share why someone chose to include you in their will. These stories do more marketing than any brochure ever could.
The truth is, you don't need a bigger team to start a planned giving program. You need to start having conversations you're probably not having now. Every week, pick one or two long-time donors and reach out just to say thank you and learn their story. In those conversations, listen for openings to mention legacy giving. Plant seeds. Follow up. Document everything. Repeat.
The long game: why planned giving matters beyond the dollars
Yes, planned gifts will eventually become transformational revenue for your nonprofit. But there's something more immediate and more human happening in these conversations.
When you talk to donors about including your organization in their will, you're asking them to think about their legacy. What do they want to be remembered for? What values matter most? What change do they want to continue making in the world even after they're gone?
These are profound questions. And when donors choose to answer them by naming your nonprofit, they're saying that your mission is part of their identity. That's a level of commitment that changes how they engage with you today.
Ready to strengthen your donor relationships and build a sustainable future? See how DonorDock can help you track donor patterns, automate stewardship touchpoints, and make planned giving conversations feel natural with tools designed for fundraising teams who want to think bigger.
