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On this episode of Bloomerang TV, Dan Shephard, CFRE of The Shephard Group joins us to discuss how to lead your donors to the decisions you want them to make.

Full Transcript:

Steven: Hey there, welcome to this week’s episode of Bloomerang TV, thank you so much for tuning in. My name is Steven, and I’m the VP of Marketing here at Bloomerang. And this is our first episode in our new building. We recently moved into our new global headquarters for Bloomerang. The background is a little different, but it’s the same great content, and I found a really great way to kick off our first episode in the new space. It would be to invite my buddy Dan Shephard over to have a chat with us. He’s the principal over at The Shephard Group. Hey Dan, how’s it going?

Dan: It’s terrific. Thank you.

Steven: It’s awesome for you to be here. I know you’ve done a webinar for us. It’s good to talk to you face-to-face. But before we get into it, I want to let you have the chance to tell folks all about yourself, and what you guys do over at the Shephard Group.

Dan: Thank you, Steven. Put simply, I’m a teacher. What I teach is the skill sets that are useful to frontline fundraisers. That means if you are a major gift officer, a planned gift officer, etc., if you’re one of the people who meet with the few of your organization’s donors who give the lion’s share of the gifts, then you are one of the people I teach and train and coach.

Steven: Now, one thing in terms of frontline fundraising that I’ve heard a lot of fundraisers sort of give as advice is they recommend that you, and it’s sort of counterintuitive, but that you don’t ask for money. You actually asked to have a conversation, have a chat with someone to ask for feedback and ideas rather than just being blunt and sort of asking for money right away. Can you explain the strategy behind that and why you’re a believer in that sort of concept and strategy?

Dan: Yeah, when I think of that I think of one of our famous fundraiser’s sayings. One of those cliches. It’s the one that goes, “If you ask people for money they’ll be happy to give you advice. But if you ask people for advice, they’ll give you money.” And as far as the strategy goes, the saying invites that fundraiser to examine what he asks for and how he asks.

You know the traditional way of pursuing a major gift was to look at the suspected donor’s rated gift capacity, search for some emotional connection between that person and your organization. And then once you cultivate interest in a gift, ask for that rated gift capacity amount, without, sadly, giving much thought to how the prospect might be able to afford it.

Now gift motivation is addressed in detail, but what to ask for is based on a system that I think isn’t much more detailed than blind faith, and that’s hoping that the researchers got it right. This traditional approach has left a lot of money on a lot of tables, because fundraising professionals don’t tend to probe into the next layers of potential. They don’t look for the details beyond confirming gift motivation, and beyond that gift capacity score. They don’t seek to look for what purpose the suspect might consider a gift, or how the gift plan might be structured. Which means examining issues like what and how matter as much as deciding up front who you want to talk with.

Steven: And how do you decide, who are the best prospects to have a conversation with? Because it seems like if you have a large donor database, there might be lots of potential people that maybe you would want to start that process with. But how do you decide who are truly the best prospects for that major gift conversation?

Dan: And the word “who” is key here, because you heard me already talk about for what, and how, but the first issue that you want to ask about is who and it’s a thing that you ask yourself. Who should I identify from our massive contacts list as the best possible major gift prospects? You start by looking at the people who seem to have the most likelihood, based on research, to consider talking with you about a gift. And that’s where prospect research and those gift capacity ratings really do come in handy.

Up front, in determining who you want to contact, and by the way it’s a big reason I like Bloomerang’s donor search integration and that’s a glad, shameless plug. Because an effective contact management system has got to include some way for the fundraiser to decide who are those most promising people to approach, and to spend his time and the organization’s money on. But then . . .

Steven: All right. So how do you actually approach that conversation? Because I feel like people are very aware of when a fundraiser or anyone is going to be asking for money. And so you do your prospect research, and you identify the best prospects, how do you start that conversation out?

I was talking to a fundraiser earlier today and they were concerned that any approach or phone call or email is going to be viewed as a solicitation and that’s going to turn people off immediately. So how do you actually get that conversation started in a way that they think it’s truly about feedback and interaction and things like that?

Dan: Yeah, when I was designing some of my training and coaching programs, I took some time to reflect on my own experience with major gift planning. And I discovered, in hindsight, a consistent pattern. When I was successful, I had invited conversations about decisions on these four issues. Why, for what, how, and only finally, will you? Because I think you start asking for the gift when you ask for that first conversation, when you request that discovery visit.

So how you begin has a huge bearing on how you end. And that of course leads us to that first decision that helps the new possible donor make the decision with you and that’s why. Why am I willing to meet with a fundraiser? Because, as you said a few minutes ago, they do know who you are, and they do know what you want. Why might I want to consider a contribution? And I’ll bet he wants to ask me for a big one.

Steven: So what are some of those probing questions that may lead the prospective donor off that trail of being a true solicitation? What are some questions you can actually ask to get that conversation rolling and make it sort of meaningful on a personal level?

Dan: I call those triggering questions. They’re the things that you can set yourself up for when you ask for that visit instead of the cliched, the old go-to, “Hi, I’m so-and-so with such-and-such and I’ll be in Indianapolis in several weeks and I’d like to drop by and tell you all of the good news from our organization.”

Steven: Right.

Dan: Which just puts you in a corner of your own making. The key is to ask for something specific. And we go back to that old cliche that we started with, and by the way we’ve got a new initiative, and I’d love to sit down and ask your advice about that. People do love to give advice. And then you pursue that thing once you’re in the meeting. You can say after all the introduction and the getting acquainted, “By the way, recall when I asked you to meet that I said that I wanted to thank you for your past support and to ask you for your advice.” So you’ve already opened the door for yourself.

But once you get past that, you want to get to the point of transitioning the conversation with what I called triggering questions. Things like, “Tell me what’s your fondest memory of your time as student,” or how about those favorite summer camp experiences, or there’s always this, “I would love to know why you have supported us so generously and for so long,” because you want to get to the heart of that emotional commitment, and it’s then that you can comfortably pursue the actual gift conversation, which is about for what and how.

Steven: And it occurs to me as I’m thinking about your system, the for what and how, and why and will you, does that all have to happen in the same conversation or can that be split throughout maybe one or two different conversations? I think a lot of people sort of rush to make it all happen in one half hour meeting, and I’m curious what your thought is in terms of, does it all need to happen all at one time, or can you kind of split that up over multiple engagements or interactions.

Dan: Well in 28 years of doing it, it rarely happened all at once. And that was only with experienced philanthropists, who really knew who I was and what I wanted. It’s all about the relationship-building.

But if you know going into the relationship that this is the agenda that you want to pursue, and that when you have the opportunity to say, “Well it’s wonderful to learn that you are so interested in this particular program, or this is where your passion lies. What I’d like to do now is turn our conversation to asking you to think about for what you might consider making a significant contribution? And it might be directly related to this thing you’ve been telling me about, why you care,” or you might transition into something a little bit more specific. But then you get into the details of for what, that possible and most promising gift designation.

And after you’ve finished with that part of the conversation you can say, “When we talk next, and that might be in two weeks or it might be in two months, what I want to do is turn our attention to the next question that I want us to explore together, and that’s how you might make a meaningful gift for this thing that you’ve told me is so important to you. And that means when the gifts might be made, with what assets it might be made, and in conjunction with what considerations and priorities that I hope you’ll share with me. So where would you like to start this part of our conversation?”

And you build on it. And it takes weeks, months, years. But if you know from the beginning where you want to end, you know the map.

Steven: So how do you segue from that how, to the actual will you? Which I guess is just sort of the direct true appeal. How do you actually make that transition? You’re doing all these good things, you’re sort of nurturing them, you’re having a great conversation.

I feel like a lot of fundraisers, maybe, they simply don’t ask. They do all this great work and they have all these great conversations, but then either the ask never happens, or it’s done in a poor and impersonal way. How do you actually make that ask happen?

Dan: Well in fact by asking all these other questions, you are asking for the gift. In fact I tell the people I train, you start asking for the gift when you ask for the first meeting. Because, again, they know who you are. But to the point, if I have gone through this careful and thoughtful intentional process whether it’s over one or ten meetings of reminding you why it is you care about our organization, and inviting you to tell me for what at our organization would you really consider doing something significant, and then working with you to figure out the best way to say how, whether it’s an outright gift, or a deferred gift of some asset, etc. I put that all in front of you.

And when it’s time to sum it all up, to say, we’ve been through this, and you’ve told me this, and we’ve figured out together that this is what is appealing to you, one of the fascinating and really fun parts of the work is that if you do it that way, quite often you don’t have to ask for the gift because it is offered. Because the prospect will be looking and saying, “Well yeah, this is what I want to do, and you’ve helped me figure out the best way to do it, so how do we get started?”

And those are incredibly rewarding experiences because you’ve earned those gifts. But sometimes the prospect will get a little bit of cold feet. And you need to simply ask. And the way I do that is I just reiterate, we’ve been through, this we talked about why, we talked about for what, we talked about how, and I think it’s time to ask you if you’d like to make this commitment. Will you do this?

Steven: What happens if you get an answer that is a no or a maybe or a maybe reflects that kind of cold feet thing? Do you keep pressing? Do you say, okay, thanks for your time and never call again? What do you actually do that with that negative response that maybe the thing you were least hoping to hear from your prospect? How do you overcome that situation?

Dan: I get to give you my favorite answer to many questions, Steven. And that is, it depends. In this case it depends on what kind of a vibe you’re getting, what look in the person’s eye you’re seeing, what their body language is, because at this point, you’ve invested considerable energy, you’ve invested of yourself, you hope by this time you’ve built some trust and you can speak with a little bit of candor. And to simply ask, what’s in the way? What is it we need to address? And then, if you’ve built that level of trust you’re going to get an honest answer.

Steven: I’m looking at your why, and what, and how, and will you system, and it really reminds me of a traditional sales funnel. You’re kind of bringing them down through it to the logical conclusion. And I’m wondering, what’s your opinion of people who sort of flip the funnel, and they go right to the will you? I feel like that’s probably why a lot of people fail because they go right to that direct ask, without going through all these nurturing and very personal steps that you’ve laid out. Do you think that’s what most people do? They go right to the will you, and maybe that’s why the success rates aren’t as high for those folks?

Dan: Far too many do it exactly that way. Especially for younger fundraisers you haven’t learned yet. One of the reasons I started The Shephard Group after doing this work for 28 years was to say that it doesn’t have to take you 28 years to how to learn how to do this. Let me show you what I found out worked, and in conversations with dozens of peers over 28 years what I learned from them what works. You can learn in a few weeks or a few months what it took us decades to learn. And if you do it this way, and not that way, we think you’re going to do better.

Steven: Yeah, maybe that is a good place to end.

Dan: It works.

Steven: Yeah, it definitely works and I like what you brought up about the young fundraisers. Maybe a good way to end would be to ask if you were to talk to a first-time fundraiser, someone who’s going out to start prospecting their first major gift. What’s one piece of advice you would give to those people? Beyond everything you said already, maybe a quick little tidbit for those folks?

Dan: Well, we talked about beginning with the end in mind, and now that we’re at the end, we’re going to go back to the beginning, because the advice is simply this. Don’t ask for a contribution. Ask for a conversation.

Steven: That’s it.

Dan: It really is.

Steven: It seems so easy. Well, Dan, this was awesome. I really love the advice. I love the system. Maybe you can tell folks how to find out more about The Shephard Group and how they can find you online and all that good stuff.

Dan: Well thank you so much. The website is That’s also the email. My telephone number is 843-693-5719 and I appreciate that opportunity Steven.

Steven: Yeah, and I appreciate you coming in and chatting with us again. And if you’re watching this, and now we’re at the end, and you have a free hour or so, check out the webinar that Dan did for us a few months back. You can watch the full recording. Just look on the Resources tab just above this blog post, and you can hear more from Dan. I think you’ll really enjoy the presentation. This was awesome for being here, Dan, thanks a lot, and hopefully we’ll talk to you again soon.

Dan: I look forward to it.

Steven: All right. Thanks to all of you for watching. We’ll catch you next week with another great episode of Bloomerang TV. So we’ll see you then. Bye now.

Major gift fundraising

Kristen Hay

Kristen Hay

Marketing Manager at Bloomerang
Kristen Hay is the Marketing Manager at Bloomerang. From 2018 - 2020, she served as the Director of Communications for the Public Relations Society of America's local Hoosier chapter. Prior to that she served on several different committees and in committee chair roles.