How to Talk About Planned Giving Without Scaring Your Donors
Say the words "planned giving" out loud in a donor meeting and watch what happens. Shoulders tense. Someone glances at the door. The warm conversation you were having about the mission suddenly feels like a meeting with an estate attorney. For a lot of us in development, that flinch is exactly why the whole topic stays buried at the bottom of the to-do list, year after year.
I understand the hesitation. When I was raising money in ministry, the idea of bringing up a gift in someone's will felt like I was asking them to think about dying so my budget could survive. It seemed cold, even a little manipulative. So I did what most fundraisers do. I avoided it, told myself we would get to it "someday," and focused on this year's appeal instead.
What I have learned since then is that the fear is almost entirely about the words we use, not the thing itself. Your most faithful donors already think about legacy. They think about what they want to be remembered for and where they want their resources to land when they are gone. The conversation is not scary to them. It is only scary to us, because we have never been shown a gentle way to start it.
Why the Words Do the Damage
Most planned giving conversations go sideways before they even begin, and it is usually the vocabulary's fault. "Bequest," "estate," "deferred gift," "charitable remainder trust" — this is the language of lawyers and accountants, and it makes a warm relationship feel like paperwork. When a donor hears those words, their brain files the conversation under chores, not generosity.
There is a second reason it feels heavy. Planned giving forces a subject most people spend a lot of energy avoiding, which is their own mortality. If you lead with wills and death, you are asking someone to sit in a feeling they would rather not feel, and then hoping they associate that feeling with your organization. That is a hard thing to pull off.
But here is the part that gets me genuinely excited about this work. The discomfort lives on our side of the table more than theirs. A donor who has supported you for fifteen years has already decided you matter. What they are missing is not willingness. It is an invitation, offered in language that sounds like them instead of their attorney.
The Gap Between Willing and Asked
The numbers here are worth sitting with, because they reframe the whole thing. Bequest giving in the United States totaled an estimated $45.84 billion in 2024, which is roughly 8 percent of all charitable giving in the country. Gifts made through a will or trust are the quiet engine underneath a huge amount of nonprofit funding, and most of it comes from ordinary, loyal donors rather than the ultra-wealthy.
Now the frustrating side. Only about a quarter of Americans even have a will, and a small fraction of those name a charity. Yet the appetite is there. The National Council of Nonprofits points out that many donors are simply waiting to be asked — a large share who say they would consider a gift in their estate have never once been invited to talk about it by an organization they love.
Read those two facts together and the picture is clear. The bottleneck here is us. People are ready for a conversation we keep deciding not to start, mostly because we are afraid of a flinch that, more often than not, never comes.
If the hard part for you is knowing what to actually say, you do not have to write those scripts from a blank page.
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Start With the People Who Already Love You
The instinct is to think planned giving belongs to your wealthiest names, so you build a list of the three or four people who could fund a wing of the building. That is the wrong list. Legacy gifts tend to come from your most loyal donors — the ones who give steadily and modestly for years, not the ones who write the single biggest check.
This is good news for a small shop, because you already know who these people are. They are the monthly givers who never miss. The volunteer who has shown up every Saturday for a decade. The couple who mentions your mission at dinner parties. Their loyalty, measured over time, matters far more here than their capacity in any single year. If you have ever looked at donor lifetime value, these are the names that sit quietly at the top.
Start there. Pull the donors who have given for five or more years, regardless of amount. That is your legacy list. It overlaps more with your most engaged relationships than with your biggest gifts, and the good work you are already doing to steward those people is exactly the groundwork a legacy conversation needs.
How to Bring It Up Without the Flinch
The whole thing turns on one shift: talk about impact and meaning, not mechanics. You are not asking someone to update a legal document. You are inviting them to make sure the thing they have poured into for years keeps going after they are gone. In my experience, framing a gift around the causes a person already cares about lands far better than asking them to "leave a bequest."
Here is language that keeps the temperature warm. Instead of "Have you considered including us in your estate plan," try something like, "A lot of the people who love this work want to make sure it continues even after they are gone. Is that something you have ever thought about?" You are not pushing for a decision — you are opening a door and letting them walk through it at their own pace.
You can also let it ride alongside a natural moment. When a donor mentions they are getting their affairs in order, or a spouse has passed, or a grandchild was just born — those are the moments legacy is already on their mind. Your job is simply to connect the mission they love to the future they are already thinking about, without dragging death to the center of the table. That kind of timing turns an awkward ask into a welcome one, and it fits naturally into the same cultivation rhythm you use for every other relationship.
The Vehicles Are Simpler Than You Think
Part of what makes planned giving feel intimidating is the assumption that every gift requires a trust and a team of advisors. The truth is that the vast majority of planned gifts are simple. More than nine out of ten come through a plain gift in a will or a beneficiary designation, not through complex instruments. A donor can name your organization in their will in a single sentence, or list you as a beneficiary on a retirement account or life insurance policy with a form that takes five minutes.
That simplicity is where you can be genuinely helpful. Most donors do not know how easy it is, and they assume the process involves lawyers and cost they cannot spare. When you can say, "If you ever update your will, we would be honored to be included, and it is usually just one line," you have removed the biggest barrier in the room. You are making generosity feel doable instead of daunting.
Some of your donors will have more capacity and more complex situations, and that is where the right structure can multiply what they are able to give. A whole life insurance policy, for instance, can let a donor keep giving during their lifetime and leave a much larger gift behind — without touching the assets their family depends on. This is exactly the kind of strategy most nonprofits never bring up, simply because no one on the team feels equipped to.
If a donor's situation calls for something beyond a simple bequest, you do not have to be the expert in the room. That is what partners are for.
Interested in learning more about how a whole life insurance policy could benefit your nonprofit? Connect with a team member at Sage & Main.
Where to Start This Week
You do not need a formal legacy society or a glossy brochure to begin. You need one honest conversation. Here is what I would do in the next few days.
Build your legacy list. Pull every donor who has given for five or more years, regardless of gift size. Loyalty over time is your best signal, not wealth.
Add one soft line to what you already send. A single sentence in your newsletter or thank-you letter — "Some supporters choose to remember us in their will" — plants the seed without any pressure.
Have one real conversation. Pick the most loyal person on your list and, at the right moment, ask the gentle version of the question. You are opening a door, not closing a deal.
Make the yes easy. Have the simple bequest language ready so that when someone says "how would I even do that," you have a five-minute answer instead of a homework assignment.
Legacy giving grows the same way trust does, one conversation at a time. Continue the good stewardship you are already doing, add a gentle invitation to it, and give your donors the chance to say yes to something they have quietly wanted to be asked about all along. You would be surprised how ready they are.
C.J. Bergmen is a pastor, licensed counselor, and fundraising strategist who helps organizations and generous individuals approach giving with honesty and long-term vision.