I’ve been in this industry 26 years. Worked with over 5,000 nonprofits. And the same mistake keeps showing up.
Fundraisers think if they just understand the tax law better, their planned giving program will take off.
It won’t.
Planned giving is a human decision that requires legal execution. Get that backwards and you’ll spend years wondering why your bequest pipeline is empty.
The Technical Trap
Look, you need to know the basics. Gift annuities, CRTs, beneficiary designations, donor-advised funds, how capital gains work with appreciated stock. I’m not saying ignore that stuff.
But I watch fundraisers treat planned giving like it’s a continuing education course. They memorize payout rates. They can quote IRS code sections. They build spreadsheets comparing charitable remainder unitrusts to annuity trusts.
Then they sit across from a 74-year-old donor and lead with “let me explain the tax implications.”
And they wonder why the meeting went nowhere.
Why Donors Actually Give
First, there’s the dopamine effect — the neurological reward system that reinforces generosity and meaning. Dr. Sanjay Bindra has written about this extensively on Philanthropy.org. But that’s a deeper conversation for another time.
Here’s what’s really happening when someone decides to leave your organization in their will:
They’re thinking about their mother who died in your hospice. Or the scholarship that changed everything for them in 1978. Or twenty years of Sunday mornings in your pews.
That’s the gift. The emotion is the gift. The tax deduction is how they explain it to their spouse or their accountant. It’s rationalization, not motivation.
Most planned giving marketing has this completely inverted. Go look at the average nonprofit’s legacy giving page. It reads like a textbook. Raw legal language. Diagrams. Payout-rate charts nobody asked for.
Who is that for? Not donors. Maybe it makes the development director feel thorough. But it’s not raising money.
What Actually Works
The fundraisers who build real planned giving programs do something different. They shut up and listen. They ask about the donor’s life, not their assets. They figure out what this person cares about and why your organization is part of that story.
Then—only then—they mention that there’s a way to make that vision permanent.
The giving vehicle is the last conversation, not the first.
And here’s the other thing: you don’t need to be the expert on every technical detail. That’s what the donor’s attorney and CPA are for. Your job is to plant the idea, nurture the relationship, and make the introduction when it’s time. Trying to be the legal expert almost always backfires. Donors sense when you’re out of your depth.
The Point
Planned giving programs don’t fail because fundraisers lack technical knowledge. They fail because the fundraiser never built enough trust for the donor to have the conversation in the first place.
You can memorize every section of the tax code. Won’t matter if donors don’t feel like you understand them.
This is a people business. Always has been.
