May 25, 2026 · 37 min · 12 segments
This episode honestly changed the way I think about planned giving. I sat down with Tess Conrad and walked away realizing that planned giving isn’t just for giant institutions with fancy development…
Okay, let's kinda do, 'cause I literally had a conversation just this morning with someone about the power of planned giving, and she was saying that she ran an organization where planned giving made up for a significant percentage of their operating budget, but from folks who, prior to the planned gift, had given like $50, so they weren't really big givers, and yet were leaving million-dollar gifts.
So talk a little bit about that, because you've talked about how planned giving can often come from the most unlikely of sources.
Like, one of my favorite anecdotes is Deborah Antoine told me that when she was raising money for Channel 13, her biggest givers were retired school teachers who left a planned gift.
People who'd given like very small amounts through their whole life, then dropped a significant gift.
So talk to me, how do you actually identify planned giving prospects when you're looking at your whole portfolio?
Yeah.
You're touching on a few things there, and really, if you're fundraising from individuals, this is the path to long-term growth.
And you probably have way more potential estate gifts in your database than you realize, because the main thing is loyalty, not how much they give in lifetime.
Because there are so many people like those retired school teachers, or maybe someone who just worked in the trades, or ran a little like mom-and-pop construction company.
They don't have a lot of cash to give in their lifetime, but they bought a house in a city back in the '90s, and it's appreciated in value a lot, and they saved for retirement, and they had a pension.
So they end up with all of this wealth that they realize that they want to share because it's more than, sometimes even these people are like, "I came from pretty modest backgrounds, and I don't want my kids to be handed this much." So they want to still provide for their kids, but share the wealth with charities and causes that they care about.
And so if I were to look at their portfolio, who might I identify as potential folks that I might reach out to for a planned giving conversation?
You really want to look for that loyalty factor.
So I would look for someone who has at least five years of giving.
More, the more the better, and consistently giving over those five years.
And on top of that, if they are giving and they're a volunteer, that's also a really good indication.
Or they're coming to a lot of events, or very engaged, in the email list.
Also, people who give in honor and in memory can be good legacy giving donors, because people will also give through their will in honor and in memory.
So potentially like my monthly givers might be folks that I might talk about a planned giving gift to.
Yeah.
If someone's been a monthly donor for five or more years, that's great for legacy giving.
Okay, let me ask another question that I get a lot, which is, Tess, is there any way that I can ask about the amount that is being left? Because I think a lot of people are out here, we know that you can't ask about timing, obviously, but is there a way that we can ask about amount without seeming grubby?
Th- this is a loaded topic because yes, there are ways that you can ask, but it has to be done so carefully, and also the real question I want you to be able to answer is why do you want to know? Because a lot of the time it's not for fundraising, it's not for your relationships, it's to appease your finance team.
The challenging thing is a lot of donors give percentage of their estates.
Mm-hmm.
Okay, let's kinda do, 'cause I literally had a conversation just this morning with someone about the power of planned giving, and she was saying that she ran an organization where planned giving made up for a significant percentage of their operating budget, but from folks who, prior to the planned gift, had given like $50, so they weren't really big givers, and yet were leaving million-dollar gifts.
So talk a little bit about that, because you've talked about how planned giving can often come from the most unlikely of sources.
Like, one of my favorite anecdotes is Deborah Antoine told me that when she was raising money for Channel 13, her biggest givers were retired school teachers who left a planned gift.
People who'd given like very small amounts through their whole life, then dropped a significant gift.
So talk to me, how do you actually identify planned giving prospects when you're looking at your whole portfolio?
Yeah.
You're touching on a few things there, and really, if you're fundraising from individuals, this is the path to long-term growth.
And you probably have way more potential estate gifts in your database than you realize, because the main thing is loyalty, not how much they give in lifetime.
Because there are so many people like those retired school teachers, or maybe someone who just worked in the trades, or ran a little like mom-and-pop construction company.
They don't have a lot of cash to give in their lifetime, but they bought a house in a city back in the '90s, and it's appreciated in value a lot, and they saved for retirement, and they had a pension.
So they end up with all of this wealth that they realize that they want to share because it's more than, sometimes even these people are like, "I came from pretty modest backgrounds, and I don't want my kids to be handed this much." So they want to still provide for their kids, but share the wealth with charities and causes that they care about.
And so if I were to look at their portfolio, who might I identify as potential folks that I might reach out to for a planned giving conversation?
You really want to look for that loyalty factor.
So I would look for someone who has at least five years of giving.
More, the more the better, and consistently giving over those five years.
And on top of that, if they are giving and they're a volunteer, that's also a really good indication.
Or they're coming to a lot of events, or very engaged, in the email list.
Also, people who give in honor and in memory can be good legacy giving donors, because people will also give through their will in honor and in memory.
So potentially like my monthly givers might be folks that I might talk about a planned giving gift to.
Yeah.
If someone's been a monthly donor for five or more years, that's great for legacy giving.
Okay, let me ask another question that I get a lot, which is, Tess, is there any way that I can ask about the amount that is being left? Because I think a lot of people are out here, we know that you can't ask about timing, obviously, but is there a way that we can ask about amount without seeming grubby?
Th- this is a loaded topic because yes, there are ways that you can ask, but it has to be done so carefully, and also the real question I want you to be able to answer is why do you want to know? Because a lot of the time it's not for fundraising, it's not for your relationships, it's to appease your finance team.
The challenging thing is a lot of donors give percentage of their estates.
Mm-hmm.
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