The Sizable Impact of High Stakes Asking

How do you ask your donors for contributions to your cause?

In this interview, Amy Eisenstein sits down with Kent Stroman, President of the Institute for Conversational Fundraising, to discuss the concept of “high stakes asking” and the sizable impact it can have on your fundraising efforts.

We’re proud to sponsor Amy Eisenstein’s video series! Be sure to check back on our blog for more conversations with some of the top experts in the nonprofit sector. To see other free resources that we’ve collaborated with Amy on – like research studies and webinars – please visit https://bloomerang.co/resources/.

Full Transcript:

Jay: Hello. I’m Jay Love with Bloomerang and we’re delighted to bring you the following video. One of the things I wanted to point you to is our website where there are additional education materials that would provide on an on-going basis. Whether it’s a weekly webinar, eBook downloads, various blogs, etc. from experts from across the world that will help you be better with your fundraising. Enjoy the video.

Amy: Hi. I’m Amy Eisenstein. Today I’m thrilled to have my good friend, colleague, and mentor, Kent Stroman here, he is the founder of the Institute for Conversational Fundraising and the Asking Academy, and we are going to talk about asking today. Hi, Kent.

Kent: Hi, good afternoon, Amy. Great to see you.

Amy: Thanks so much for joining me. Today we are going to talk about the keys to success in high stakes asking.

Kent: So high stakes asking, thank you for asking by the way. So when I think about high stakes asking, here’s what I’m not thinking about. We ask lots of questions, the answer to which doesn’t have any consequence: “What did you think about last night’s ballgame?” Or “what do you think about tomorrow’s weather forecast?” Either way, the answer doesn’t much matter. When I think about high stakes asking, its where there some consequence that goes with it.

Amy: Yeah.

Kent: For me, an example of high stakes asking, I one time asked a man for his daughter’s hand in marriage.

Amy: Yeah, it’s very high stakes.

Kent: High stakes.

Amy: Yeah.

Kent: Neither one of us had any idea the stakes on that one. But that’s high stakes. Asking for a job, asking for a promotion, asking somebody to fund a business proposition, or in our line of work, asking for a really large contribution. A contribution is very large in the context of the giver.

Amy: Yeah. And of course, as you know, we’re not really asking for the contribution. We’re asking for somebody to help cure a disease, or solve homelessness, or clean the environment, or provide arts.

Kent: Absolutely.

Amy: So, I mean that’s high stakes.

Kent: Right. The consequences are great.

Amy: Yeah.

Kent: And so, when we’re making that high stakes ask, I think we approach it differently than we do asking about the weather or yesterday’s ballgame.

Amy: Yeah. And hopefully, we do a little preparation. How else do we approach it differently?

Kent: Oh, man. So many ways. I think we got to start with our definition of what is success? And old school says success is “I get what I want.” And our approach is very different. We say success is helping the other party make a well-informed decision. So again, whether they’re asking for the job, the marriage, the gift. I don’t want to just to extract money from another person and call that fundraising. In fact many times I think when that happens that’s not success at all. It’s the first step down the road to failure.
But on the other hand, if I can work with a prospective funder, whether it’s an individual, a business, a foundation, or whatever, work with them to understand, what are their objectives? What do they want to accomplish philanthropically? Does that coincide with what we’re involved with? And if so, what might that look like? What would be the involvement that would bring the most delight to the donor?

Amy: I absolutely love that because so often we do think about if we get the gift, that’s success. But if the donor isn’t happy and we haven’t fulfilled their mission, their philanthropic mission, and it doesn’t match our mission, then there is a serious disconnect and we’re going to lose that donor. So how are you building lifetime relationships, looking at the third, fourth, and fifth gift down the road? And really approaching our mission, right?

Kent: Exactly. And I like to think about what’s going to happen with the prospect after our meeting. So if I get that reluctant gift, that unwilling gift, that coerced, gift or what we call go away money. What’s the conversation going to be like with them at their next cocktail party?

Amy: That’s right.

Kent: And you won’t believe what happened. I gave those people money just to get them out of my office.

Amy: Yeah.

Kent: I mean, how much value is that gift? And I want to say that’s worth less than no gift.

Amy: Yeah.

Kent: On the other hand, what you do and what I do and that is at that next meeting that person says, you can’t believe the conversation that I had with Amy Eisenstein. The organization that she’s representing. You know what? We were so thrilled to make a contribution and to know the difference that that’s going to make on the people they serve, just really warms my heart.

Amy: That’s right. I always tell people that if the donor is not thanking you after giving a gift, then something might be wrong, right? I mean, because it’s confusing to think about as the fundraiser that the donor would give us money and thank us. But really when it is a meaningful gift, that is what happens because the donor should feel great about that gift and that’s exactly what you’re talking about with high stakes asking.

Kent: That is, when you said those words it reminded me of some experiences that I’ve had exactly like that. In fact, one that comes to mind is with an older couple. And we sat in my office, they signed some very official documents, this was a charitable gift annuity. Okay, pretty technical. But they signed these documents. And after we’d finished with the paper work, we just sat there and visited. And before they left all three of us had a moment in tears.
And it wasn’t regret, but tears of joy. And here is what they said to me, “We never dreamed that we would be able to make a gift like this to an organization that has meant so much to us.” Now to me, that’s the definition of success. What do you think?

Amy: Absolutely, oh my gosh. Powerful stuff, right?

Kent: Oh, sure is.

Amy: So I understand you’ve done some research on the obstacles to high stakes asking. So tell us about that.

Kent: Okay, yeah. So, actually, we focused in specifically on asking for larger gifts. So the question was, what’s your biggest obstacle to, what we say, face to face gift solicitation?

Amy: Right.

Kent: And I had the opportunity to hear from fundraisers literally across the country, volunteers, paid professionals, hundreds, hundreds of responses. We were able to consolidate those down into 33 different categories.

Amy: Okay.

Kent: In a minute I’ll tell you the top five. But first I have to tell you the most memorable responses that I got. I was speaking at a conference, this was in St. Louis, and I remember I asked a few people in the room to share their response to the question. There was one guy about two-thirds of the way back. He raised his hand and he said, “My biggest obstacle is our gift prevention office.”

Now, I hadn’t heard that term before. I had to ask him to repeat it, and he said, “Our gift prevention office.” Well as soon as he said it, I knew exactly what he was referring to. And too many times we have those elements in our organization. It’s as if their job is to keep gifts from happening.

Amy: Right.

Kent: Evidently they had a very effective gift prevention office.

Amy: My gosh.

Kent: But that went in a special category all of its own.

Amy: Yeah.

Kent: The five top categories that came out of that, one is relationship deficit. There’s not enough relationship for us really to have a serious in-depth conversation.

Amy: Okay.

Kent: We’ve got to get better acquainted with each other, either personally or at the kind of the organizational mission level.

Amy: Right.

Kent: The second is what I call conflicting priorities. They don’t care about what we care about. What is our mission? If our mission is all about youth sports and theirs is all about arts for the elderly, there is no intersection there.

Amy: Yeah.

Kent: And so, when the priorities aren’t the same, we think it’s not our job to get them to change their priorities.

Amy: Right.

Kent: There priorities are theirs, by definition, right?

Amy: That’s right. Then it’s not a good donor for your organization.

Kent: Absolutely, yeah. So that’s an obstacle. And here is another one, mindset. Oftentimes as fundraisers we go into meetings with the wrong mindset. Here’s an example, “She would never give.”

Amy: Yes.

Kent: Or, “She will most certainly give.”

Amy: Right.

Kent: Okay.

Amy: Yes.

Kent: So the mindset is one of expectation and maybe even entitlement, perhaps even disenfranchisement. But the wrong mindset.

Amy: I think that’s such a good point. I worked with a woman once who, she had the right mindset. And she knew she was going to get a gift and she would just say, “I don’t know what the details are yet. But I’m off to find out. And I’m going to talk to the donor about and see what they want to do. But that expectation is that I’m coming back with something because this mission is too important not to.”

Kent: Good point.

Amy: And it was fun to work with her. So what’s number five?

Kent: Well, let me go to number four first.

Amy: Oh, did I skip four? Sorry.

Kent: Well, I threw an extra one in to begin with.

Amy: All right, go ahead.

Kent: But remember I’m the accountant who can’t count. Number four is fear.

Amy: Okay.

Kent: And most often as I peel back the layers a little bit, somebody said “I’m fearful.” I asked them, “Fearful of what?” “We’re afraid that the other person is going to say no.” And one of the things that we do is help them get out of that because if they say no that’s their answer.

Amy: Right.

Kent: And we want to know their answer. Not give them ours. And so, one of the things that we do is, is get out of the yes/no question business. Yes/no is kind of a fact, it’s a closed question. What’s more important is these open questions, which aren’t head questions but they’re heart questions.

Amy: Right.

Kent: And one way we get out of fear is I want to understand your heart so when I ask, what are your philanthropic priorities over the next 12, 18 months? There’s no yes, there’s no, no, in that. We begin to hear what their priorities are.

One of my favorite questions is what would you like your gift to accomplish?

Amy: That’s a great question. What would you like your gift to accomplish? Love it.

Kent: It’s amazing to hear the unique responses that come out of that. Again, there’s not a yes, and there’s not a no. But as I listen to that, if what they want to accomplish has nothing to do with our mission, I want to salute them for their clarity and wish them well on their way, maybe introduce them to somebody who is working in the space that’s going to bring most delight to their heart.

Amy: That’s right.

Kent: So anyhow, we get out of fear by really engaging in conversation and focus on the donor. Number five . . . and by the way, thank you for asking.

Amy: What’s number five, Kent?

Kent: It’s difficult to getting in, sometimes people say, well I know who I need to talk to, I know where they are. But how do I get there from here?

Amy: Good.

Kent: And so oftentimes it’s not a direct path from here to there. Sometimes it’s kind of the zig zag and that’s where one of the key things that we include in the whole Asking Academy experience is the involvement, the crucial and strategic involvement of appear in that process.

Amy: Right.

Kent: And if I can bring a board member into the room, a fundraising volunteer, somebody else who knows me, who knows our organization and who also knows the other party, they can bring about an introduction. It’s like borrowing somebody else’s relationship because it just elevates the introduction to a whole different level.

Amy: That’s right and it brings trust, and gravitas, and all of the rest of it to that situation. So that is fabulous. What a great list. So, any parting thoughts? What are your final words of wisdom and what do you want to fundraisers to do? What are their next steps to really ask in this way?

Kent: Well, I’m going to give you maybe a little bit different kind of response than what you might expect. But I want to say that to really be bold in the area of fundraising, brings about the intersection of courage and curiosity. Courage and curiosity. So curiosity, we want to have a genuine interest and curiosity about the people that we’re talking with.

Amy: Right.

Kent: Again, what do they care about? We can talk all day about what we care about. That’s not really that relevant. I mean, sure we need to know what the mission is, they need to know what the mission is.

But if I’ve got curiosity, but then if I pair that with courage, courage to do what? Courage to really take big steps, ask that question.

I love to ask people if you were fully informed and adequately motivated with regard to this project, what might be the largest range of gift that you might even consider? I mean it takes some courage to ask that.

Amy: It does.

Kent: But if I don’t know the answer, and I don’t, if I go into it with the mindset that I don’t know the answers to my questions, you do. And it’s something I want to know, I want to ask a strategic question so I can listen strategically, understand what you want to accomplish, and then help you make your dreams come true. And at the same time, it’s going to make the dreams come true of the constituents that our mission serves day in and day out.

Amy: Beautiful. Beautiful. Kent, thanks so much for being here. I’ve loved chatting with you and I look forward to talking with you again soon.

Kent: It’s always a pleasure.

Amy: Thanks.