Podcast: Unlocking Donor Engagement: Cultivating Joyful Giving

Season 3, Episode 48

In this episode, Amy Eisenstein and special guest Sarah Plimpton, Director of Client Happiness, delve into the critical importance of thoughtful donor cultivation before soliciting gifts for a campaign.

Discover the art of asking meaningful questions that inspire donors and prepare both parties for the big ask. From uncovering donors’ philanthropic passions to exploring their visions for the organization’s future, Amy and Sarah share invaluable insights and strategies to deepen donor relationships.

Learn how to navigate conversations, foster donor generosity, and enhance the joy of giving, ultimately leading to more impactful campaign contributions. Whether you’re embarking on a fundraising campaign or seeking to strengthen donor engagement, this episode offers practical tips and thought-provoking questions to elevate your fundraising efforts.

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Amy Eisenstein:
If you are curious about how to get your donors to open up about their thoughts and dreams, and philanthropic desires before you ask them for a gift, this episode is for you.

Hi, I’m Amy Eisenstein. Andrea has the day off and I have a special guest with me here. That is Sarah Plimpton, who is our Director of Client Happiness. We’re super excited to be talking to you today about thoughtful questions and cultivation that you can be talking with your donors about, or should be, I should say, talking with your donors about before you ask them for a gift.

Why Cultivating Joyful Giving is So Important

Sarah, why don’t you tell us why this is an important topic and why it’s so critical for clients heading into campaigns or getting ready to ask for campaign gifts, to have these conversations with donors?

Sarah Plimpton:
Hi, Amy. It’s a pleasure and a delight to be with you today, and your podcast listeners. Yeah, good questions. Such a rich topic in campaigns. I think that everyone working on a campaign, immersed in a campaign has the looming question out there, of will X-and-such donor consider X-and-such gift at the right moment? That is the ultimately question.

Often times, what I think we’ve found working with clients who are immersed in campaigns is that it can take some time to get ready to ask a donor, or a prospective donor, that big question. Will you give at X level? It often takes prospects time to get ready to hear that question. I find myself often having conversations with non-profit leaders about well, what can we ask in the interim that both prepares donors or prospects to get a closer to being ready to hear that big question, prepares us to affirm a question, “Will you give,” is near-term and whether they’re ready.

Amy Eisenstein:
Yeah. Let’s set the stage a little bit more for listeners. We dove right in, which is something I love to do. But what we’re talking about today is part of the conversation that happens between the feasibility study and asking for a gift, often. This is the interim cultivation that happens once you’ve identified your best lead gift prospects and you need to prepare them, as you said, prepare them to hear the question and prepare yourselves to ask the question. I love thinking about it that way — that there are two sides that need to be prepared. You’re not the only ones that need to be prepared, your donors need to be prepared to hear that big ask.

Hopefully, you’ve included them in the feasibility study interviews and process, and there are likely subsequent conversations that need to be had, and questions that need to be asked before you ask them for a lead gift. Give us an example of a question that inspires donors, or prepares donors, and prepares fundraisers to be asked and to ask?

Sarah Plimpton:
Yeah. Just in full disclosure, I have to give a big shout-out to our advising team; I actually pitched this question to them a couple months ago. I said, “What are your favorite questions to ask donors?” Aside from, “Will you give?” They, in true form, because we have incredible advisors on our team, came back to me with so many amazing questions. I’m just going to pick from some of the questions that they sent our way and talk about what do we like about these questions and how they might advance our relationship with a donor, and lead to readiness.

Focusing on the Joy of the Donor

The first question that I want to share with our listeners is something along the lines of this. “What brings you most joy with respect to our organization?” If you think about what this question is doing, it’s focusing on the joy of the donor, which is such a lovely place to go with a donor, to ask them what is joyous for you about who we are and what we do.

Amy Eisenstein:
Yes.

Sarah Plimpton:
It also gives us clues about what this person is most passionate about, as it pertains to our organization.

Amy Eisenstein:
Yes.

Sarah Plimpton:
Which is so important because that’s really the playbook of where you want to focus your cultivation efforts and energies.

Amy Eisenstein:
Yeah, I think you’re so right. It’s so important to pay attention to why it does this … It gets to the heart of why does this donor care, what makes them feel good about giving to this organization, to supporting it, why is it important to them, or what aspects of your mission is important to the donor.

Not every donor is going to connect or resonate with every aspect of your campaign, or your organization, or your mission. In order to get the biggest gift, to be crude about it, you do want to connect the aspects of the organization, and the campaign, and the mission that spark most joy with each particular individual donor.

Sarah Plimpton:
The other thing that I try to remind myself of a lot, or often, is the fact that people remember what they say far more than what is said to them. To the extent that we can ask good probing questions of our prospects that get them essentially cultivating themselves.

Amy Eisenstein:
I love that.

Sarah Plimpton:
That is really what we want to go for. Not to ask basic questions, or I don’t know, unthoughtful questions, but good questions that get people talking about their own reflections. You don’t have to guess. Let people tell what they joyous about.

Amy Eisenstein:
Yes, right.

Sarah Plimpton:
And the fact that they have an opportunity to talk about it is deepening the joy and is deepening their sense of self, as it connects to that joy.

Engaging Donors with the Future of Your Organization

Amy Eisenstein:
Yes. I love that. What’s another question that fundraisers might ask prospective donors?

Sarah Plimpton:
Another one that came forth when I posed this question to our advisors that I loved was:

“If you had a magic wand, what would you wish most for our organization?”

Or, a variant of that would be something like, “What would you hope that we might look like or be doing 10 years from now?”

Amy Eisenstein:
Right. What’s the impact we might be having, what might we accomplish over the next 10 years?
Sarah Plimpton:
Yeah.

Amy Eisenstein:
If you could wish anything, right?

Sarah Plimpton:
Yeah.

Amy Eisenstein:
If you were the magician.

Sarah Plimpton:
Yeah.

Amy Eisenstein:
Love it.

Sarah Plimpton:
What I think is so magical about that question is it invites people to dream with us for a moment. First of all, who doesn’t like doing that?

Stepping back and thinking big picture about a societal issue that your organization might be tapping into or trying to effect change for. But it also allows you, as a fundraiser, to see:

• What do they hope for us?
• What is the scale of their aspiration for us?
• What impact do they think would be really exciting, if we could reach?

If their aspirations align with what we are in fact doing, or hoping to do, it’s a beautiful segue into a conversation around what you are working on right now and why it’s so impactful.

When the Donor’s Goals are not Aligned with the Organization’s Goals

Amy Eisenstein:
Right. Let me push back for a minute, or play devil’s advocate. I think that one of the reasons that a lot of fundraisers are hesitant to ask a question like this, it could go off in a lot of different directions, is what if there’s not alignment? Or what if they want to do something, or have something happen, that isn’t part of the plan?

Is there any context that’s set up or boundaries that you would put on this question? Or have you talked about the scope of your campaign first, so that there’s guardrails to this conversation? Or are you really letting them sky’s the limit conversation here? What do you think?

Sarah Plimpton:
First of all, that’s such a great question and such an interesting question. I think that trust donors to be partners in the work. The question is really not about what do you want for us 10 years from now, because we’re going to go out and create that reality verbatim. Of course, there are going to be differences. Of course, there are going to be things that aren’t possible, or things that, if the donor isn’t immersed in the program side or in the nuance of the work, maybe can’t happen.

But I think that that’s all more of an opportunity and more of an invitation to explore what is possible and how there are different views, maybe between…

Let’s say you’re the director of development asking this question and a top potential donor answering the question. I think if the top potential donor offers something a little wacky or a little out there, sure that can be a little bit unsettling and destabilizing in the moment. But I would just say, deep breath. Trust that when you ask people for their feedback, and their authentic feedback, what you’re cultivating there is a relationship, which is a back-and-forth, which is a partnership.

Amy Eisenstein:
Yes.

Sarah Plimpton:
Trust that there is a way for you to, I think, us their response to say something like:

“My gosh, that’s so fascinating that that’s where your mind goes. Here’s where my mind goes. Or here’s where we’re heading. What do you make of that?”

Amy Eisenstein:
Yes. Yes.

Sarah Plimpton:
There’s nothing wrong with that, and having a different take on the future.

Amy Eisenstein:
I love it. And also saying:

“I need to really think about that because we never thought about that before. Let me circle back.”

That’s an opportunity for another conversation.

Sarah Plimpton:
Absolutely. Yeah. You’ve just hit something that I think is so important, that can also be so hard. The power of saying:

“I need time to process that.” Or, “I don’t know. Let me get back to you with more information.”

Amy Eisenstein:
Right.

Sarah Plimpton:
That’s perfectly fine to say.

Amy Eisenstein:
Yes. I think people are afraid to say that. They think they have to have all the answers, and that they have to know everything, and having donors in this almost exploratory phase is super helpful. It’s super helpful. All right, excellent.

Let’s move onto another question because there are so many good ones. I think that one of the things that we’re trying to do here, today for listeners, is give you choices and options, and open up your thought process in terms of how to have these conversations with donors. There’s no one-size-fits-all question and there’s no right or wrong question. You might take the questions that we present today and make a hybrid question, and make them your own, and you should. Customize them for each donor and the relationship that you have with that donor. Let’s spit out a few more. What’s another question that listeners might ask of their donors while cultivating?

Sarah Plimpton:
Okay. Before I give you the next question, I just want to emphasize I couldn’t agree more with what you just said, that this is not meant to be prescriptive. In fact, in our Online Toolkit, which clients have full access to as you know, Amy, we have a list, I think it’s four or five pages long, of different types of open-ended questions that you can ask prospects and donors. Now, the intention of this list is not to have anyone take it and ask a donor or a prospect every single question on this list. That would be —

Amy Eisenstein:
Four to five … 100 questions, yes.

Sarah Plimpton:
Your donors would run away. Don’t ever do that.

But the point of it is to say the sky is the limit on good, thoughtful, probing, relational questions that you can ask donors. Use this as a brainstorming tool. That list and our toolkit is there for our clients, and this discussion is meant to prompt thinking in this regard.

Amy Eisenstein:
All right, so thank you for bringing that up.

I just want to let listeners know, who are thinking, “Oh my gosh, we’re not clients. How do we get access to that list?” I encourage you to visit capitalcampaignpro.com. We have a do-it-yourself support system, which includes our Online Toolkit, which is all the resources. If you want access to that list today, we have tons of free resources on the website. That particular list that Sarah just referenced is for clients only, it’s behind a paywall, but you can get access through our do-it-yourself support system, which is meant to be our most affordable option for organizations running campaigns. Go check it out.

All right, next question, Sarah.

Getting to the Heart of Donor Generosity

Sarah Plimpton:
Next question. All right. Amy, how did you learn to be generous?

Amy Eisenstein:
That is a great question. Can I tell you that I have great memories of going to a soup kitchen with my mother as a child. She taught me the importance of giving back to others, both volunteering and through donations. Us personally, we celebrate Hanukah instead of Christmas, and some of the nights we didn’t get presents, we gave to charity instead. As a family, we picked the charities we were going to give to. That’s such a great question, Sarah, because it brings up so many possible answers and opens up the conversation in so many ways. Every donor’s going to have a different answer.

Sarah Plimpton:
Yeah.

Amy Eisenstein:
And have a good, warm fuzzy feeling, hopefully, about that.

Sarah Plimpton:
Yeah.

Amy Eisenstein:
I guess, some people’s answers could be, “I had a hard childhood, so I wanted to give back.” But that’s important to know and hear, too.

Sarah Plimpton:
That’s important to know, too. Yeah, for sure. It also leads to, and I think it depends on the age of your donor or your prospect, but it also leads to a really interesting conversation about how are you teaching generosity in your family? If you’re talking maybe to the matriarch or patriarch of a family who has kids, and grandkids.

Amy Eisenstein:
Yes.

Sarah Plimpton:
How is that being passed down? Both how was it modeled for you, and how are you modeling it?

Amy Eisenstein:
Yeah.

Sarah Plimpton:
It’s such a rich question. It also, I think, it assumes generosity.
It assumes that people are generous and are coming to the conversation with a generous spirit, which I love.

Amy Eisenstein:
Excellent. I love that. Okay, let’s do one more question and then I’m going to throw you a curveball that we didn’t discuss in advance, and that is to talk about one time that you asked a donor any one of these questions. First, let’s give listeners one more question to think about and I’ll give you a minute to ponder that as well.

Sarah Plimpton:
Sure. This is a feasibility study question, but as our clients know, I’m a firm believer that you could use the methodology of a feasibility study all the time. You should always be asking donors great questions.

Asking Donors Where You Fit Among Their Giving Priorities

Here we are, having this conversation about good questions. But one of the questions that I think is important to ask donors, regardless of whether you’re in a feasibility study or not, is where do we fit among your giving priorities? I’m curious, Amy, where does XYZ organization fit among all the places that you sit down and decide we’re going to give every year to these places? Where do we fit?

Amy Eisenstein:
Yeah. It’s such an important to ask donors heading into a campaign, because if you don’t know that you’re in the top two, or the top three, or the bottom 10.

Sarah Plimpton:
Right.

Amy Eisenstein:
Or not on their list at all.

Sarah Plimpton:
Right.

Amy Eisenstein:
That’s a really important context for you as a fundraiser to have, and for them as a donor to think about. Frequently, we’ll ask donors and board members to say:

“For the next three years, would you consider us your number one charity, while we do this campaign?”

Even if we’re number three or number five, could we be bumped up for a couple of years? While we do this amazing project. Such, such an important question.

Sarah Plimpton:
And it changes. Philanthropic priorities shift.

Amy Eisenstein:
Yes.

Sarah Plimpton:
They shift.

Amy Eisenstein:
Yes, for sure. Yes. As somebody in your family gets cancer, or something happens as you age, different ages and stages in life, of course your priorities shift. For sure.

Things You Have Control Over in the Donor’s Life

Sarah Plimpton:
Also, I think that philanthropic priorities can shift from two push factors, push-pull factors. There’s what’s happening in the donor’s life, which you just alluded to. Somebody gets cancer, they’re getting older, priorities change. We don’t have as much control over that as fundraisers, but we do have control over:

• Do we call donors?
• Do we reach out to them?
• Do we engage them?
• Do we invite them to do things?
• Do we include them?
• Do we ask advice of them?
• Do we notice their patterns as donors and signal to them that we see their patterns?

That’s all within our control.

Let me tell you. If you are a fundraiser who is paying attention to those things, who is looking proactively for opportunities to engage your donors and bring them closer to you, you can shift your organization in an upward trajectory as a priority. Similarly, you can lose people. Your people who were once saying, “Yes, this organization is my highest priority, or one of my highest priorities,” that relationship can atrophy.

Amy Eisenstein:
Yes.

Sarah Plimpton:
If you don’t tend to it.

Amy Eisenstein:
For sure, for sure. All right, let me circle back.

How Donors Might Answer These Questions

Can you think of a time or share a story of a time that you asked a donor one of these questions? And were either surprised by their answer, or moved by their answer, or learned something. How did one of these answers help you move the relationship to really ask for a much more thoughtful and generous gift for a campaign you’ve worked on?

Sarah Plimpton:
Yeah. I can give you two scenarios. One of them answers your question, and then the other scenario is a little different, so it’s a curveball back at you, Amy. Okay.

Amy Eisenstein:
Great, let’s do it.

Sarah Plimpton:
The first scenario, in my frontline days fundraising, I remember working with an elderly woman who was a donor to an organization, had been for years, and years, and years. Always steady, giving $2000, $2500 a year to the annual fund. We’re in this campaign and our research indicated that this woman had mega, seven-figure capacity. Maybe lifetime giving was between $30 and $40,000, so she hadn’t scratched the surface on what the research was indicating her capacity might yield.

She was pretty feeble, so it was hard to get her in to meetings and for tours, and all that kind of stuff. It was a lot of quiet cultivation, if that makes sense. I would call her, or I would write her notes, or I would go bring her cookies and have tea with her. I did ask her:

“How did you learn to be generous?”

She opened up to me about her parents, who had been … This was early 1900s, her parents were doing their thing, in the height of their lives. They had really carefully cultivated generosity, much the way that your mother did with Hanukah, and soup kitchen, and all that kind of stuff.

But it was fascinating, because she talked about how, in response to that, her brother had completely shunned giving, and had taken his inheritance and sat on it, and become very miserly. That force had actually empowered her to be even more generous. She shared with me:

“I want to give away all of my inheritance and I am actually working with my kids to make that happen. They know they’re not getting any inheritance.”

It opened up a conversation that I had been thinking, “Maybe we’ll get to a seven-figure place with this woman because the research indicates that.” We ended up securing a multi-seven figure commitment from her, that included estate, giving, capital and endowment. Maybe we would have gotten there anyway, but it was fast tracked because I had this wonderful insight into her motivation around giving.

Amy Eisenstein:
I love that. It’s a great example. Yeah, good.

Sarah Plimpton:
Here’s my other little curveball. This is a question that one of my favorite Capital Campaign Pro clients … Actually, I’m going to be honest. All of our clients are favorites. Really, I have this problem, I fall in love with our clients. But one of my favorite Capital Campaign Pro clients recently got a gift from a donor and it was less than they had been hoping for.

Amy Eisenstein:
Yeah.

Sarah Plimpton:
She was a little disappointed.

Amy Eisenstein:
Yeah.

Sarah Plimpton:
Front lines getting this verbal commitment from a donor, and she’s disappointed. She had a question back to the donor that I thought was brilliant and I’m going to put it out here for all of our listeners. She said, “That’s so interesting. Tell me how you arrived at that number?”

Amy Eisenstein:
Yes, yes. And did the gift change?

Sarah Plimpton:
The gift, to my knowledge, has not yet changed, but it might.

Amy Eisenstein:
Okay.

Sarah Plimpton:
But it might.

Amy Eisenstein:
But there’s insight on the table.

Sarah Plimpton:
There’s insight. There’s insight on the table, yeah. It’s a way to create a breathing moment of you don’t have to say, “Oh my gosh, that’s terrible. I wanted so much more.” You should never say that.

Amy Eisenstein:
Yes.

Sarah Plimpton:
But it just gives you insight into what was going on in their thinking process leading up to this decision.

Amy Eisenstein:
Right.

Sarah Plimpton:
What was that?

Amy Eisenstein:
Excellent. I love that. I love that.

Okay, two things. One is you alluded to this idea that fundraisers would be asking feasibility study questions, and that is not always the case in traditional feasibility studies. I just want to let listeners know, who were really paying attention, that is our model of feasibility study at Capital Campaign Pro, is to teach, and guide, and train you, the non-profit leaders, to ask those feasibility study questions and be in the room with your donors. If you’re curious and you want to learn more, head over to the Capital Campaign Pro website and you’ll see a click down for feasibility studies. You can watch a little four-minute video on what we’re talking about.

Increasing Your Donors’ Joy of Giving

Okay, there’s one more question and it’s about joyful giving.

Sarah Plimpton:
Yeah.

Amy Eisenstein:
Let’s talk about this question, about focusing on t donor’s joy through giving, through giving. Because we started with the question about joy, in terms of what the organization can accomplish, but I think this one has a slightly different and important spin.

Sarah Plimpton:
You’re exactly right. The question is this. “How could our organization be better at increasing the joy of your giving?”

Amy Eisenstein:
Yes. Let’s just pause for a minute and take that in. Let that sink in, wash over us. Say it again, say it one more time.

Sarah Plimpton:
“How could our organization be better at increasing the joy of your giving?”

Amy Eisenstein:
Brilliant.

Sarah Plimpton:
Brilliant.

Amy Eisenstein:
Yes.

Sarah Plimpton:
We’re not asking you to increase the gift. We are asking about how can we increase your joy in giving.

Amy Eisenstein:
Yes. All right.

Sarah Plimpton:
Yeah.

Amy Eisenstein:
Let’s leave it there.

Thank you so much for joining me, Sarah. It’s always a pleasure talking to you about these brilliant campaign topics and really being so thoughtful and strategic, in terms of our fundraising and communicating with donors. Thank you so much for being a guest.

And thanks, listeners, for tuning in today and we’ll see you next time.