Ask a development director how their endowment is doing, and they'll usually tell you about performance: the latest return, how the market's been treating the fund, what the investment committee said last quarter.
It's rarer for them to mention the donors they are stewarding and prospecting to support this long-term initiative.
Once an endowment is established, many nonprofits shift into maintenance mode. The fund exists, it's invested, and growth becomes something the market handles rather than something the fundraising team actively pursues. But an endowment doesn't have to grow through investment returns alone. It can grow because donors keep choosing to grow it. One of the keys, however, is knowing who to ask and how to have that conversation.
When many nonprofits think about endowment prospects, they think about their biggest current donors: the names at the top of the giving report. But endowment giving doesn't have to be about current gift size. It's often about trust, loyalty, and a donor's sense of what they want their giving to mean over time.
Some of the most meaningful endowment gifts come from people who've never written a large check in their life, such as a donor who's given $100 a year for two decades, or a longtime volunteer who believes in your mission more than almost anyone in the room.
Fundraisers have a helpful way of thinking about this. Strong prospects usually sit at the intersection of three things:
For many gifts, fundraisers lead with capacity. For endowment and legacy gifts, connection and inclination tend to matter more. A donor doesn't leave a lasting gift because they can. They do it because they care, and because they've decided your mission is worth being part of after they're gone.
It also helps to remember that some endowment-ready donors may not see themselves that way yet. They rarely raise their hand and say, "I'd like to leave a legacy gift." More often, they're simply loyal, engaged supporters who've never been invited into the conversation. Part of your job isn't to find people who are already planning a legacy gift. It's to recognize the people who would consider one if someone gave them the opportunity.
A few donor "types" worth keeping in mind as you look:
Often, this list of donors won't show up at the top of a standard giving report. That's exactly why they're so often missed, and why knowing what to look for matters as much as knowing where to look.
You likely already have donors like this in your database. Here's what to watch for:
You probably don't need a new system. You need to pull the right reports from the one you already have, and most CRMs can do all of this without any extra tools.
Instead of sorting by total giving or largest single gift, sort your donor list by years of consecutive giving. Look for donors who've given every year (or nearly every year) for 10+ years, regardless of gift size. This single report often surfaces your strongest legacy prospects: people who show up on the annual fund list, not the major gift list.
Filter for donors giving $100–$500 annually who've done so for at least 5-10 consecutive years. These donors are frequently overlooked because their gift size doesn't trigger major-donor attention, but their consistency says something a single large gift can't.
If you have any wealth or capacity data layered into your CRM (from a screening tool, or even just what you know informally, such as homeownership, career, family business), compare it against actual giving. A donor with clear capacity but modest, steady giving is often intentionally holding back for something bigger, and that's worth a real conversation.
Many CRMs let you search free-text notes. Try searching for terms like "will," "estate," "bequest," "in memory," "trust," or "legacy" across donor notes and call logs. You may find that someone already mentioned something to a staff member. A comment that got logged and never followed up on.
These relationships often live in a different part of your CRM (or a spreadsheet) than your giving records. Cross-reference the two. A board member who's also a 15-year consistent donor is a strong combined signal.
Donors who consistently show up to events, tours, or volunteer days but give modestly are showing you engagement that isn't yet reflected in dollars.
Legacy readiness isn't static. A donor's life stage, notes, and giving pattern shift over time. Running this once a year (tied to your annual data review or planning cycle) keeps your list current instead of stale.
Once you've pulled these lists, the goal isn't to rank donors by a score. It's to build a working list of names your team keeps an eye on and begins developing even deeper relationships with.
This is the part that tends to make people nervous, and understandably so. Nobody wants to sound like they're rushing a donor toward end-of-life planning.
The good news: it's rarely a "pitch" at all. It's usually just a genuine conversation about impact and legacy, led by the donor's own interests, not your fundraising calendar.
The best legacy conversations often begin long before you ever mention the endowment. Ask a loyal donor why they've stayed with your organization all these years, or what first drew them to your mission. Their answer tells you what they care about most, and that's the foundation everything else is built on.
Donors give to a legacy because it reflects something about who they are, so the more you understand that, the more natural the conversation becomes.
You don't need a script, and you definitely don't need a solicitation. A simple, sincere question can open the door:
"You've supported us for so long, and it's meant so much to our work. Have you ever thought about what kind of impact you'd want to leave behind?" Then give the donor room to tell you what they're already thinking about, or what matters most to them.
Some donors will light up and want to talk right away. Others will need time to sit with the idea. Both responses are fine. A legacy conversation isn't a single meeting with a yes or no at the end. It's usually a series of smaller conversations over months, sometimes years. Your job is to plant the seed and keep the relationship warm, not to close.
Early on, resist the urge to explain bequest language, beneficiary designations, or tax specifics. That comes later, and often with the donor's own advisor in the room. What moves a donor at this stage is picturing the difference their gift could make: the students who'll still be served, the programs that will still exist, the mission that will carry on. Keep the conversation on the "why" and save the "how" for when they're ready.
Give the donor a graceful way to decline or defer without feeling awkward. Something like "There's no pressure at all, and no timeline. I just wanted you to know this door is open whenever you're ready." keeps the relationship comfortable and leaves room for the conversation to continue down the road. A donor who feels respected today is far more likely to come back to the idea tomorrow.
If a donor expresses any interest, note it in your CRM right away, along with what they said mattered to them. These moments are easy to lose track of, and the details matter later. A quick, thoughtful follow-up ("I've been thinking about what you shared, and I'd love to keep the conversation going whenever you are ready") shows the donor you were genuinely listening, not just prospecting.
The through-line in all of this: legacy conversations aren't transactions, and donors can tell the difference. When you approach them with real curiosity and no agenda beyond understanding what the donor wants, the "pitch" feeling disappears entirely, because there's no pitch. There's just a relationship, and an invitation.
Identifying these donors isn't a single afternoon's work. It's a habit, a way of listening a little more closely to people you already know. Start with one conversation. You might be surprised who says yes.