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Listen to the weekly podcast “Around with Randall” as he discusses, in just a few minutes, a topic surrounding non-profit philanthropy. Included each week are tactical suggestions listeners can use to immediately make their non-profit, and their job activities, more effective.

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Episode 244: Cultivating Generosity Over Time: The Best Gifts Don't Just Show Up

Transformational philanthropy doesn’t happen overnight—it’s the result of patience, humility, and deep trust built over years. Too often, organizations focus on immediate needs and campaign timelines instead of donors’ passions and timeframes. This story highlights how a client took the long view, nurturing a relationship with one of the rare 0.1% capable of extraordinary giving. By personalizing stewardship, showing appreciation, and listening with humility, they created space for generosity to grow naturally into something truly transformative.

Welcome to another edition of Around with Randall, your weekly podcast for making your nonprofit more effective for your community. And here is your host, the CEO and founder of Hallett Philanthropy, Randall Hallett.

I'm so honored that you take a few minutes of your time to join me, Randall, on this edition of around with Randall. Something happened this week with a client. Not quite to the conclusion, but the fact that it occurred. And the way it's been handled really elevated its story to today's episode. And it's about the importance of the long term vantage point view of philanthropy.

When we do this in the right way, we've talked about this a million different bean machinations, directions, episodes about transformational giving. What we're really talking about is elevating the donors passion, their needs, their desires to make a difference to its highest levels with less impact. Thought, emphasis placed upon what we do. Would be more coming out later this year about that more formalized way for me.

We are at this juxtaposition where if we view the value of really what we do, placing our donors their needs, how they want to give as the center point of everything that we do. Then there's this cross current that's occurring against us. So a couple of examples. Sometimes we have campaigns where we have a very specific need that the organization has clearly identified.

There's all the components they've done. You've done all the right things, but the donors, the ones at the top, and we know 95% of the dollars coming, 5% of the people. So that 5% is pretty important. Don't want to give it to that project. But yet that's the priority of the organization. Our metrics work against this. I need a gift.

This year, we too often look at metrics in annualized time frames rather than longitudinal over several years. So we're trying to force donors into this. The idea of needing cash. We've talked about this with CFOs. I tend to talk about it a lot. Did so just this week where CFOs are we need the cash. You need the cash.

But the best gift opportunity may not be a cash gift may not be cash this year. Maybe it's planned. Giving all these pressures that we have push us away from what we really want to do, which is maximize the gift, not for our benefit, although we do benefit, but for the donors benefit, what it is they're trying to accomplish.

Which brings us to this story. I work with this client, have for a number of years. There's a particular prospect family donors. They give that they have been trying to position in the right way in the conversations, not position them to give to what they don't want to give to. But figure out what it is they will give to.

And there are these external pressures that are occurring on a constant basis that are in a campaign, but the story's not real. Sure, this is where they want to give and that there's metrics and they're more pressure on that than ever, and that there's an immense amount of conversation around needing cash for any type of projects. And yet, in the middle of all of this is a family, a couple who are trying to figure out what their philanthropy should be, what it is they want to do.

And they are not just the 5% giving 95%. I would argue they're not the 1% that are giving 70% of the dollars. They're the point 1% that can give it all. And the pressures that we mentioned, the needs haven't led to the types of gifts that this family is at the highest levels possible to give. The joy of the story is, is the way in which the client and maybe I've supported this endeavor.

They deserve the credit, have taken patience to do it in the right way. And it's a story. And then the tactical outcomes, which we talk about all the time on this podcast, make sure you have that. We got to remember, how do you do this? So let's talk about this journey for just a second. Kind of the philosophical.

This has been interesting to me because I as I talk about all the time in in Omaha, kid in there's more millionaires and billionaires per capita in Omaha, Nebraska than anywhere else in the United States. I have come through my own to steal from Prince and file the seven pieces of philanthropy. I've heard me talk about it. The academic study of how the kind of the seven categories of donors are.

I come from a dinosaur family now, small D not big D meaning philanthropy. Something I grew up with. Not in terms of like, oh my gosh, you know, there's the Hallett Foundation that's at work. Mom and dad's, mom and dad were always talking about how we helped our world, and they could do things financially, as particularly as they got older, more significant things.

But it was never about the money. It was about our responsibility. And when I look at a dinosaur, you have a responsibility to make your community a better place. I always think about philanthropy is a natural part of what I grew up with now. We didn't use that word. I didn't have the education nor the experience I do today.

But as I look back, it was a natural part of many things that we did. This story tells us something that I think we need to always keep in mind. The first part philanthropy sometimes isn't natural to many people, and that's the case in this story. The prospect donor family had came from nothing. And when I say nothing, that may be actually more than that, but through an incredible amount of hard work over the course of time, in addition to immense amounts of great fortune and being in the right place at the right time, they've made millions is probably an understatement.

But the way in which they grew up now, as they close into their 90s, doesn't lend itself naturally to philanthropy. And you might have this experience. You're working with someone, you think they should get it. You work with other people that kind of look like them. They get it. But this individual, this family, this couple doesn't. You're like, why don't they get it?

Well, because they've spent their life acquiring. They're not used to giving. It's not that they don't want to be generous. It's not that they don't want their community to be a better place. It's not as if they don't even understand that. Like, I got to do something here because I can't take it with me. And there's too much of it.

It just isn't natural. And it's almost as if we have to find a way to teach them how to do this. And we'll talk more about that here in a few minutes. The second thing is, is that we tend to too often think about what we need rather than what they want, which actually positions you back into number one.

Because if you truly do this in the right way, it may take a longer period of time to teach them what philanthropy could be or give. At least give them the options to make them feel the value of philanthropy. It may not come easily. The third thing is, is that giving, even if they have a better understanding as they grow into philanthropy, that giving is on their time, not ours.

And yet our metrics and our calendar years, our annual years, our campaign lot timelines all are pushing against this natural thought that, frankly, we should be more aware of what they're trying to do in their time frame. We all know there are always exceptions, but we all know that the idea of giving grows in the right relationship because it's based on trust.

If we do this in the right way, and that's going to start leading us into the tactical here in a few moments that it's a marathon, not a sprint to get to transformational that the first time. Gifts aren't going to be normally those transformational gifts. There's a courting process on top of all of this. Philosophically, maybe it's statistically a better way to put it is our donor retention is horrible.

It's at the lowest levels we've seen in many years, decades, probably ever. And that keeping repeat donors engaged is really hard, even when they have lots of money. So when you put all of this together, the idea of culture cultivating generosity over time, we have things that are competing against those transformational gifts in terms of campaigns and metrics and timelines, that giving doesn't come naturally to some people as it does to others, that it's in their time frame, not ours.

It's got to be based on what they need, their passion versus what we need, which is a project or a purchase or something. And that donor retention is going down. Brings us to when it's done well, you realize this is what we should be doing all the time. And so let's talk about the tactical totally stolen from my client.

Certainly somebody I'm interacting with regularly with them on this and many other relationships, they get the credit. How do you do this without getting frustrated, angry, disappointed and realizing there's something bigger if we do it the right way? So the strategy I'll put into kind of a three year process, because that's what this was. But you could extend it out to 4 to 5, ten.

The first thing is, is that what we think of is giving may or may not be connected to what they think of as giving, because we think of rich people just making these large gifts. The first thing is to realize that no matter the size of those first gifts and remember, perfect example, maybe in your world is the most likely planned estate giving prospect.

Is a regular donor $100, $250, $500. Maybe they're giving $50 a month. Maybe they're giving $10 a week. They're giving is kind of embodied in the regularity of their choice to be philanthropic. For you. The key here is to do a couple things. Number one is to personalize as much as you can. This process, the client for which I'm referring, approached them about being a lead donor on a fairly large campaign issue several years ago, three plus years ago, and basically the understanding of the industry for which the client is involved with how philanthropy fits into it, how philanthropy actually really works, was so distant from what the nonprofit thought, what the client thought,

versus what the donor ended up thinking about. Now they got a very low six figure gift, because in some ways, that was almost a kiss off gift. That's how much money there is. But what I was fascinated by was that they took that initial gift, which was disappointing even at six figures take off a couple zero moves, $1,000 in this particular case, and they personalized communication around the connect that they had with this donor couple family that they, number two, showed impact.

Let us tell you what this means. And they expressed a deep amount of appreciation, even though there was disappointment. The other thing that they did was is they worked around this couple with people that could talk, who were free to talk, wasn't a lawyer or anything of that confidential nature around feedback. What did they hear from the donors about all of this?

They actually asked, what did you think about all of this? It was a very vulnerable moment when that was done. So when you think about someone's relationship and the growth for this story or any of yours, start with these four promises in that first gift or amongst the first gifts or your first communication. Maybe they've been giving for years and you're integrating into the relationship is that you want to personalize impact.

So they see value. That's how you elevate and you express, no matter how disappointed you are, the immense appreciation if they I'll put it this way, the lower six figure gift, the appreciation that they provided them on a personalized basis was the same. Appreciation they would give a 5 or $10 million donor. And we talked about that, about how if you want to elevate them to 5 or 10 million, treat them like 5 or 10 million, because maybe they'll be pulled in that direction.

And then lastly, they asked about feedback with the people around them. Kids, hey, Mom and Dad, think about this. Did we handle it well? Were they comfortable? Advisors that are can talk legally? Was this comfortable for them? Personalized impact appreciation feedback in those first communications, those first gifts. That's what you focus on. That's what's most important. Which brings us to subsequent gifts.

Moving into year 2 or 3, whatever it is, those next several conversations, this personalization continues because somebody has to own this relationship. One person for the client was assigned to this particular situation and the family to make sure there was a lot of communication and not just philanthropy driven, dollar driven, solicitation driven, in fact, almost none from stopping by the house when actually true story when somebody wasn't feeling well to drop off some soup to a bunch of one on one, just, hey, I just wanted to chat, have a cup of coffee, see how you're doing too, inviting them into conversations and then not asking them for more money.

It became a single person's responsibility to build out that relationship based on that first gift. Remember treating this like the gift they wanted, not the gift they received.

The other thing is, is that there was a written, developed, creative stewardship plan personalized from bringing videos, possibly to behind the scenes access to recognition. All of this led to further communication contact. Most importantly, trust. But the most important piece of deepening this kind of stage to is the transparency that's necessary for trust. There were conversations that sometimes did not go as well as the my client wanted with campaign chairs, with board chairs, with the principal gift officer who was assigned to this, where they talked about, we would love to have you more involved.

We're so appreciative of everything you've done demonstrated that, but we'd love to have you more involved. We know that you like the organization. We know you love this community were a big part of that. Can we continue to talk? That level of transparency, I think, more than anything else, provided them the next series of conversations. Which brings us to kind of stage three, how to elevate, how to increase.

So the first thing that I really took away in all of these discussions was the humility that it required when they were hoping in the second stage, it would jump from, let's say the gift was about 100,000, the first gift to the 5 million they wanted, and it wasn't going to get there. Were against what we talked about at the top.

So forces, calendars, metrics, dollars needed. It wasn't going to happen that there was a sense of humility, not to force around peg into a square hole, that if we really believe in what we do, the relationship, it's best for them when we do what's best for them and not what's best for us. That didn't help bring in dollars for this particular campaign, that this sense of humility, that it's trust based philanthropy, that they will trust us more than anything else and then increase the ways in which they engaged.

If we think about playing giving, which I love talking about as the deepest, most legacy driven, most personal type of gift, one might make. That's along the lines of your five, ten, 15, $25 million gifts as well. You have to spend time in this because that's how you're going to get to the trust levels to figure out when is the right time to ask, how should it be delivered, who should be involved, how to handle the rejection, the not now responses with a sense of grace.

The idea of formalizing a process where you have humility and you are pushing. But gently guiding. Like as I always talk about it, being a Sherpa in their journey, finding where the holes are filling those holes will get you to where you want to go, which to my client was all of a sudden the project that they weren't interested in.

Two and a half, three, four, three years ago, after recognizing that, respecting that, receiving an incredible wasn't a kiss off gift because they were still engaged, but it wasn't what they wanted for the thing they wanted, and holding that and using it and then showing the impact and personalizing stewardship and building trust and showing up without asking and including them and things and asking their opinion, finding out their passion, making all these connections, staying involved, bringing other people in led to a conversation where somebody finally said, maybe we should consider this at a much higher level.

What we originally talked about, it was always kind of brought up in the background. I don't have the announcement that the gift has been made or received, but the process to me is more important. So you got kind of three stages of tactical takeaways. How do you get into the deeper, more meaningful conversations? Here's the mindset that you have to have.

So six things to keep in mind. The second part of the tactical you have to have patience. You have to be willing to avoid frustration or at least showing it, and realize that smaller gifts today may lead into bigger and should lead into bigger gifts of tomorrow. Number two, you have to have humility that you have to listen to what the donor tells you.

Timing, connection. What is it that they want? Which brings us to kind of to a, which is one of the six passion. It's not about what you need. It's about what they want to do. Sometimes they work perfectly together, but all too often we're trying to force them to give you what we need. I keep saying no, no, no, no, what is it they want?

And that was part of this conversation with the client constantly. They're going to do something. Can we figure out what it is? We kept trying to find different ways of asking, bringing other people to kind of have the conversation. Which brings us to number three. How do you develop trust part of the strategy in this long term conversation we've had with this particular donor, what the client did all the great work was who else do we need to bring in?

It turned out the kids were not. Maybe it's helpful, but there's a financial advisor that absolutely is quintessential. We began a process of engaging him and that helped open some doors. Thoughts? If it's not just your trust, how do you build out the trust that you actually care about the relationship? Doing things with them that when it's not about asking for money, it's also about can you bring in other people that they do trust?

Number four, I mentioned this earlier, but I think it's essential openness. It's the meeting of recognizing what they want and being honest and telling them what you're trying to do as well. We'd like you to be more involved. We just like to keep talking about it. Openness gets you trust. And how to do that. Number five is just something very general is understanding.

Understanding of where they are. Understanding of what they believe, understanding of what they comprehend and what we do, and also understanding that not every donor is the same process. It's also an understanding that it's going to take time to develop. At most of the instances, we have to take time to develop these relationships. Passion and humility, humility, having or patience and humility with passion being a part of humility, trust, openness and understanding.

If you kind of look at it in those ways from a kind of a humanistic perspective, the relationship building process within the three kind of major areas, how you treat the gifts even though you may be disappointed, the first gifts, or maybe jumping into the relationship after they've made many gifts, that you start building, that trust and how you do that, and then leading in toward what might be possible down the road.

What you end up with is better opportunities, which is what makes this profession great. Today, I'm hoping, is a small example in a very short way of a roadmap how to get to transformational with some practical examples. And it's been fun to watch the client realize we're getting closer, we're getting closer, we're getting closer. And maybe someday I'll be able to come back on and say, let me tell you how you close that kind of make a gift after multiple years of cultivation, that would be great for everybody.

And I think it actually going to happen because my client has done an amazing job of not making it about the gift, but making it about the people, the relationship that they're building. That's when great philanthropy occurs. Don't forget to check out the blogs at Hallettphilanthropy.com. Two per week. Interesting. I got a three part series that I just I'm putting up about the failure of The Giving Pledge and what it might mean looking forward.

Also, if you'd like to reach out to me podcast it’s hallettphilanthropy.com. Don't forget that philanthropy fills an interesting gap. Social the world in which socially we look at philanthropy, what I think of as filling a gap free enterprise on one side, government on the other. Free enterprise doesn't want to do things because it doesn't make money.

Government is not always the most efficient or doesn't do it at all. And in between the two is philanthropy, nonprofits. The work that we believe in. When we do this right, we're filling that gap. We're providing things for our community services, physical structure support, communication and outreach. However you want to look at it for what you do for people, for places in our community, as I say, the back end who are wondering what happened.

And we're people who make things happen. We find other people who want to make things happen for the things, the people, as we discuss that are wondering what happened, if we can do this every day, fulfilling that Gaelic phrase that I use all too often, we'll make things happen, so we'll watch things happen. Then there are those who wondered what happened.

We don't tend to talk about people in the middle. They watch what happens. They're not going to be the people we help and they don't want to help. That's okay. Maybe some day they move. This is what you do. It's valuable. It's necessary, it's needed. And as we have a little bit ups and downs and topsy turvy world, philanthropy smooths out a lot of things because people need help.

I can't imagine spending my career doing anything else. What value do you have? Hopefully you look at the mirror and think like I do. Doggone it, I'm happy, satisfied, joyful. I get to do what I do. Even though there are frustrations like gifts not reaching the level we think. As we've talked about today, stick with it and be someone who makes things happen.

You'll make it happen for yourself. And by the way, for a lot of other people along the way, I'll look forward to seeing in the next time, right back here on the next edition of around with Randall. Don't forget. Make it a great day.