Brian Saber recently joined us for a webinar in which he taught how to ask for individual gifts in a way that suits you personally, making you more comfortable and more effective. In case you missed it you can watch the replay here:

Full Transcript:

Steven: All right, Brian, is it okay if I go ahead and kick us off officially?

Brian: Absolutely.

Steven: All right. Cool. Good afternoon, everyone if you are on the East Coast and good morning if you are on the West Coast or somewhere in between. Thanks for joining us for today’s Bloomerang webinar, “Asking Styles: A Revolutionary Concept in the Field.” And my name is Steven Shattuck and I am the Chief Engagement Officer over here at Bloomerang and I’ll be moderating today’s discussion.

And just a couple of news and notes before we begin officially–I just want to let you all know that we are recording this presentation and I will be sending out the recording as well as the slides later on this afternoon. So, if you have to leave early or perhaps if you want to review the content later on, you’ll be able to do that. Have no fear, just look for an email from me later on this afternoon with all those goodies.

Please feel free to make use of that chat screen right there on your webinar interface. We’re going to save some time for Q&A at the end. So, don’t be shy. Send us your questions and comments and we’ll try to get to just as many of those before 2:00 Eastern as we can. You can also follow along on Twitter. You can send us your tweets there. Use the hashtag #bloomerang or send us a message directly @bloomerangtech.

If you are listening today via your computer speakers, if you have any trouble, try dialing in by phone. We find the phones are usually a little bit better quality. If you have a phone nearby and don’t mind doing that, give that a try before you give up completely. Usually the phone is a little bit better than the internet audio. So, just look for that email from ReadyTalk that went out about an hour ago and you’ll find that phone number.

If this is your first webinar with us, I want to say a special welcome to you. We do these webinars just about every Thursday here at Bloomerang. But in addition to that, we offer donor management software. So, if you’re interested in that or perhaps going to be shopping for something soon, check us out. You can even watch a short video demo and get a sense of all the stuff the software can do. You don’t even have to talk to a salesperson if you don’t want to. So, visit our website if you are interested in learning more.

But for now, I am super excited to introduce today’s guest. He is my new friend. He’s joining us from a snowy New Jersey. His travel got bogged down today. So, we were beneficiaries of that. He’s hanging out with us for the next hour or so. Brian Saber–Brian, how’s it going?

Brian: It is going well. Thank you. Thanks for having me today.

Steven: Yeah. Thanks for being here. Absolutely. Boy, I can’t remember getting more registrants for a Bloomerang webinar. We’ve got over 1,100 people registered for that. It is a testament to how awesome Brian is. If you guys don’t know Brian, he is the President over at Asking Matters. I just love that name. It has so many dual meanings. I love it.

He is a fundraiser. He is a two-time executive director. He ran major gifts at Brandeis University up in Massachusetts and he is a frequent workshop presenter, speaker, trainer. He’s helped lots of organizations including Prevent Child Abuse America, the Archdiocese of LA, Social Venture Partners International, NPR, Volunteers of America. Brian, I don’t know how you have time for all this and still do webinars for us. So, this is awesome. Brian is a great guy.

Brian: My pleasure.

Steven: He’s going to help us all learn about face-to-face solicitation. I’m going to pipe down and let Brian take it away. He’s going to do a little screen share and then we’ll get going. So, Brian, it’s all yours, my friend.

Brian: Okay. Great. Well, thank you so much for having me here today. I’m delighted to be with you to talk about the asking styles. I did get that wonderful introduction. I hope I can live up to it. I have been working in the field since I graduated college. I didn’t grow up thinking I’d be a fundraiser. I didn’t go into the nonprofit world thinking I would be a fundraiser. I just wanted to make a difference and I think that’s the story for most of us. One day someone asked me to help with a special event. One day someone asked me to read a grant proposal and next thing I knew, I was a fundraiser.

Even though I spend most of my time now coaching, training and speaking on the topic, I actually still fundraise, as all of you do. I’m finishing up a capital campaign in Chicago. I’m sure there are some of you on the line from there. I’ve been working with Northwestern University Settlement House in West Town, actually for 25 years. And I’m about to start a campaign closer to home. I’m in South Orange, New Jersey. The campaign is in Millburn for the Education Foundation there. In both those cases, I am helping with lead asks. I made most of the lead asks in Chicago.

I put that out there because I am in the field. I still find asking both fascinating and it’s important to understand daunting because people say, “Brian, he’s the expert. He’s been doing it. He’s the slick guy. Of course he can do it and can do it well, but I’m not him. I think it’s important for everyone to understand that I am not more a classic fundraiser–we’re going to talk about what that is or isn’t anyway–than any of you.

This is not necessarily what I was born to do, but it turned out to be what I was good at and could bring to the field. But it still challenges me in some way even after being on more than 3,000 solicitation meetings in my career. So, I like to frame my presentation in that context because I am there alongside with you.

So, today, we’re here to talk about the asking styles. The asking styles came about when Andrea Kihlstedt, who I know has been a presenter here as well, she and I build Asking Matters. Our thought was, “What can we bring to the field? Where is a key challenge?” We realized that people do struggle to fundraise, to understand how to do it well. They think that there is just one way to do it and they don’t know that way.

What we realized from our own careers was that there are really many different ways to be effective, many different ways to ask. They’re different and they’re dependent on who we are. Asking is as much about a relationship as it is any best practices. That relationship is dependent not only on knowing who your donor is, but knowing who you are and understanding your strengths and your challenges and working with them.

So, we decided we were going to focus on someone’s asking style. So, of course the question was what would the key characteristics of an asking style be? Not surprisingly, the first one is how do you interact with people? Are you extroverted or introverted? Where do you derive your energy? Now this doesn’t mean introverts don’t like to be with people, right? This doesn’t mean that introverts are loners. But there’s an energy equation here. Some of this comes from whether you talk to think or think to talk.

So, picture yourself in a special event, in some large group. Well, in that group, the conversation tends to ricochet around. It goes fast. You go from our grouping to another. Well, for extroverts, since you are good at thinking and talking at the same time, that plays into the rhythm of that type of conversation. It doesn’t take your energy. In a way you thrive on it because things are moving fast and you’re keeping up with it.

For an introvert who thinks first and then talks, you can see where the rhythm in one of those conversations at a special event can be a little challenging. It also can be when you’re meeting someone new or when you’re in any situation that might cause a little awkwardness or anxiety, such as you’re sitting down to ask someone for a gift, where you want to think first and then talk, whereas the extrovert is very comfortable just talking as he or she thinks. Very important characteristic.

And the second characteristic is how do you take in information? Are you analytic or intuitive? Do you start with the data and then figure out what the idea is, what the conclusion is? Or do you start with an idea? You have a gut and then you see if the data supports it. This is important. It number one affects why you care about an organization, why you’re even working at an organization and how you’re going to communicate about that organization to others.

When we put the two characteristics together, we get the four asking styles at Asking Matters: rainmaker, go-getter, kindred spirit and mission controller. So, I’m now going to describe the four of them to you and when I’m done, I’m actually going to put up a poll or Steve is going to put up a poll for us that will ask you which style you think is your primary asking style. We say primary because no one fits cleanly in one box or quadrant in life. Depending on the situation, we might feel more or less analytic. We might us more of our intuitive side. But generally, one of these four sounds more like us than the other.

So, let’s walk through them. So, we start with the rainmaker, the analytic extrovert. This is the classic fundraiser, meaning, when people think fundraiser, when they hear someone’s a fundraiser, this is who they think the fundraiser is, someone who’s really goal-oriented and competitive and driven, always has his or her eye on the prize, wants to close that gift, wants to get the big gift, wants to come out on top, very strategic about how he or she goes about it to ensure that result, very objective, everything is fact-based.

Now, some of the reason people think this is that stereotypical or ultimate fundraiser is because these are very sales qualities, right? This idea of being goal-oriented and competitive and driven to close the gift, to close the gift, these are great qualities for fundraising. They’re just not the only ones. This is not to say the rainmaker only has these qualities, but the rainmaker has these qualities in spades.

Contrast that with the go-getter, our intuitive extrovert, just much the opposite. Lots of energy, creative, quick on one’s feet, engaging, life of the party, the go-getters like parties and gatherings more than anyone. They’re so comfortable walking in when the party is roaring and being in the mix. They’re big picture thinkers. I actually am very drawn to go-getters in life. Very interesting. I think it’s because of the passion and because of that energy and that big picture thinking about the future–go-getters.

Kindred spirits–I am a kindred spirit, some think I cover that very well through all my presentations and I come off as so confident and able to do things. I think that’s because I’m a bit of an actor, like a presenter in my coaching and my training and such. But actually, when you dive in deep, an introverted intuitive.

First of all, we’re feelings-oriented. That’s good in terms of relationship, though sometimes that can make us conflict-averse, which is a challenge, which ends up being very thoughtful and caring and attentive, great skills for fundraising, where we’re supposed to help a donor feel good and get connected to the organization, feel heard, feel seen. Great skills, as you can see, vastly different core skills from the rainmaker.

And then we have the mission controller, the analytic introvert, the Eagle Scout, the person who always gets the job done–systematic, thorough, methodical, responsible, the best listener of the four. We all know listening is a really key trait in fundraising. Mission controller is very happy to sit back, observe and listen, very detailed. Again, great skills, different from the others.

Now, one other way I like to look at these asking styles is through the question each of us asks when we’re trying to figure something out, why something is important to us, how we’re going to move through something. So, the rainmaker asks what’s the goal. That goal is usually quantitative. It’s easy to measure. What’s the goal? That’s what’s going to drive the rainmaker, trying to reach that goal.

Now, the go-getter is also looking at in the future, but it’s more general because the go-getter is an intuitive. So, it’s more what’s the opportunity? What’s the opportunity? The kindred spirit, for the kindred spirit, it’s very personal. So, what moves my heart? What am I feeling? The mission controller asks, “What’s the plan? How are we going to get from point A to point B to point C?”

So, take one more look at these and then I’m going to quickly give the screen back to Steve so he can launch our poll. So, here you see it. What do you think your primary asking style is–rainmaker, go-getter, kindred spirit or mission controller? We’ll give you maybe 10, 15 more seconds at most.

Don’t overthink this. Of course, based on our style, the analytics are going to probably think it through more, the intuitives are just going to have a gut. So, the kindred spirit and go-getter responses are probably going to come in first. So, we’ve got a couple of hundred of you. So, Steve, let’s close the poll and share the results and see what we’ve got.

So, hopefully you can all see those on the screen now. This is not surprising. Rainmaker, only 10%. Now, part of this is that we tend to think we’re a little less analytic and a little less extroverted than we might be. But in truth, well, first of all, as we can see, we’re all represented here, right? Now, 59% of you say you’re either a go-getter or a kindred spirit, meaning you self-identify as intuitive.

And a full 64% of you say you’re kindred spirit or mission controller. You’re introverted. Now, whatever scientifically you might or might not be, how we see ourselves is how we lead our lives. So, very few of us lead our lives as that rainmaker type. So, either very few of us can be a good fundraiser, or more to the point, we all can be good fundraisers. We all have a different skillset. The goal is to apply those skills so that we can fundraise more effectively and more comfortably.

So, let me take back the screen and let’s continue with the presentation.

So, I often get asked, “Is there a more scientific way to know my asking style?” and there is. So, not now, but after, you can go to our website either on your computer or your tablet, your phone, and there’s a 30-question true/false assessment there. It takes only a couple of minutes to answer the questions and it will give you a primary and a secondary asking style. So, it might say you’re primarily go-getter, secondarily kindred-spirit, which means that intuitive side predominates or you’re primarily rainmaker secondarily go-getter, which means your extroverted side does.

So, that shows where your strength is but also sometimes where your challenge might be. You can imagine if you’re very intuitive or analytic or extroverted or introverted, then you might have to actually compensate for that in some way. This tool is free. I recommend everyone on your team take the asking style assessment because then you can discuss with each other what your strengths are. You can figure out how to work with each other based on your personalities, maybe even how to partner based on that. We’ll talk about that briefly in a minute.

But the key to take away here is that none of these styles is necessarily any more or less effective than the other. They are just different. They’re different.

So, now that we have an idea of our asking style, we’re going to apply it. So, at Asking Matters, we teach according to a framework we developed called the five steps of the ask. Those five steps are selecting prospects, preparing the ask, setting up the meeting, asking for the gift, and following through. I’m going to go through the steps and at each step give you an example of how to use your asking style to your best advantage.

So, let’s start. We start with selecting prospects. So, remember our asking style. Just because someone is a great prospect for the organization doesn’t mean this person is the best prospect for you. Now, if you’re a very experienced fundraiser, you’re going to have a big toolkit to work with, right? You have a lot of skills you’ve developed. You may be able to fundraise equally well with anyone. Though I find even today I fundraise better with certain types of people even after all those asks.

But for most of us who are less experienced, this can really make a difference. Let’s think of our board members. Almost all of you, I’m sure, are working in organizations and you’re trying to get your boards to fundraise. They have very little experience. How do you match them up so that they’re going to have a better chance of success? Here are some guidelines for how your asking style might impact who’s best for you.

Rainmaker–we’ve got 10% of you on the line today–rainmakers, absolutely give rainmakers top-dollar prospects because rainmakers are the most motivated to maximize the gift. It’s that goal-orientation. It’s the drive. It’s the competitiveness. We all don’t actually have that same amount of that. So, the rainmaker is most likely to maximize that gift. Rainmakers are great with their business contacts because they use those contacts professionally and personally and rainmakers are great with new prospects because they like the challenge. Can I turn this person into a donor?

Now, go-getters tend to like new prospects as well, but it’s because they like meeting and befriending new people. They find it interesting getting to know people and actually are the most likely then to continue those relationships often on a social level. Go-getters are fine with their friends and acquaintances because for go-getters, life tends to blur together, the professional and the personal.

Boundaries aren’t as strong with go-getters. So, they’re often the most willing to solicit their own friends and acquaintances, not so kindred spirits. It took me 25 years of my feelings-oriented, touchy-feely personality to realize that my soliciting friends and family was really loaded. Some didn’t give or they didn’t give to the extent they could. I always took it personally and I finally realized where I volunteer that friends and family were not going to be the people I solicit.

So, who do kindred spirits solicit well? If you’re starting out or you’ve got a board member and you want that board member to get some early wins, go to those likely to say yes, where the issue isn’t whether someone will give, but how much, board members who are required to give, regular ongoing donors, close volunteers, the organization’s friends, not the kindred spirit’s friends, but the organization’s friends. What’s important for a kindred spirit is to develop a track record and become more comfortable because that fear of rejection, which everyone has to some extent or most of us have, is really compounded for the kindred spirit.

Then we’ve got mission controllers. We’re mostly talking about individuals today because almost all charitable dollars come from individuals. And 7.5% of all those dollars come from small family foundations or individual foundations where the money is parked somewhere for tax reasons, for the future, there’s a family dynamic. It’s really an individual, a couple of family making the decision.

So, why mission controllers? Because foundations tend to be a little bit more structured, a little more formal, a little more procedural than an individual just getting his or her own money out of a checkbook. That works well for a mission controller who likes structure and planning and framework. So, if there are guidelines, if there’s a proposal and so forth, that is in the mission controller’s comfort zone. Also, the mission controller is going to be good at following that plan.

Mission controllers are fine with their friends. That’s their objective side and methodical side of getting it done. Here’s an interesting one, should-be-seens. I talk about the mission controller being the Eagle Scout, the good dooby who gets everything done. We all have good intentions. Okay, I’m going to contact these four people and ask for a gift. Then things interfere and time lapses or we start to feel a little shy about going out and asking. But if you give a prospect or an assignment to a mission controller, the mission controller is going to get that done.

So, if you have someone who really should be seen because you’re not sure you’ll get a gift otherwise, maybe someone thinks there’s mission creep or they had a bad seat at the benefit or they didn’t like the thank you note they got, there are so many reasons why a donor might have his or her feathers ruffled, you want to make sure that person is seen and heard. So, you might assign that person to a mission controller.

Here’s another way to look at the asking styles in terms of prospects. That is whether you’re analytic or intuitive, we’re going to talk about case for support in a minute. The spoiler alert is that the case has to be your own. It’s not about saying what you think the donor wants to hear. But to the extent that you and your donor are both analytics or intuitives, you tend to talk the same language to begin with.

Now, I have my buddy in Chicago, Ron Manderschied, the President of Northwestern Settlement. He’s been there the whole 25 years I’ve been working there. We’ve been on at least I say 500 but it could be 750 meetings together. He’s a go-getter. So, what’s interesting is we’re both intuitives, which means neither of us comes with the analytic side. Now, it doesn’t mean we can’t answer a question an analytic donor has, but we don’t tend to talk in an analytic way because it’s just not us.

So, we’re aware of that. We try to compensate for that. But when we’re with an intuitive, the conversation has a different rhythm. So, we could spend an hour on selecting prospects, but we’re on to preparing the ask. We are going to talk here about–I think we’ve got two items, but the main one is making your case.

So, a case. This is my definition of a case. A compelling set of ideas crafted into a story that moves the teller and the listener. The keyword here, as I mentioned just before, is teller. This is your story. This isn’t an elevator pitch. Everyone is not saying the same exact thing in the same words because you’re trying to build a relationship and that’s based on authenticity. No one wants to be in a relationship with someone they see as inauthentic. So, you’re trying to establish that authentic relationship with your donor.

If you’re authentic to who you are, your case for support, your story will be compelling to the listener. It’s much more important to be that than to try to tell your donor what you think your donor wants to hear. In most cases, we don’t actually know what the donor wants to hear. There’s an ideal in fundraising and then there’s what’s real. The ideal is you know your donor really well before you ask. The reality is most of the time we don’t.

Now, Jerry Panas, I’m sure you’ve all heard his name, he’s been on my fundraising program and I asked him point blank, “Jerry, how often have you had to ask someone for a gift the first time you met the person?” He said, “Fully half the time.” Fully half the time. Donors don’t necessarily want to give us the same amount of time we’ll give them. We know they won’t, right? We’d sit with them often if they’d give us the time to build the relationship.

So, the reality is we don’t always know what they want to hear except us being authentic and passionate. So, our asking style is really important because remember, we’re going to come at it, each of us, from our unique perspective. We’re going to make our case from that point. So, the rainmaker is going to use facts and figures, outcomes, goals and strategies to make the case.

Now, in every case, best practice is you need to talk about impact and vision. We don’t get into detail on that here today, but impact and vision. But how you talk about the impact and vision you’re making is going to depend on your style. So, the rainmaker is going to use this toolkit to do that. The go-getter is going to talk in much more general, bigger picture terms about vision and the possibilities out there.

The kindred spirit is going to talk more personally in very much so individual stories. Participants or clients of the program and his or her own story, meaning not why they love the organization, but maybe how the organization impacts them, how their life perspective has been impacted by the organization and so forth.

And the mission controller is going to use methods, systems and plans. How are we having an impact and fulfilling our vision? What are the steps and the systems we’re using to get there to have that success? We’re all telling stories, but they’re different stories based on our asking style.

Really important point because I think people struggle with this as much as anything and this keeps them back. People think they need to know everything about an organization. This is particularly true for board members and that they don’t. You don’t have to know everything. What you know, you have feel passionately about and be able to communicate passionately.

So, I mentioned, I alluded to this idea of partners. I’m a big fan of partnering on asks. It might be because I’m a kindred spirit and it gives me a little bit more confidence to do it. But I think there’s a lot to be gained in almost every case Once in a while, I must meet with someone one on one. There’s some relationship or confidentiality issue or whatever. But usually, I can partner. There are lots of permeations for partners depending on relationships, depending on hierarchy, depending on who’s available and such and many of them can work.

I find when I partner, it makes the ask richer because we can play off each other. Each of us has strengths. We get to an awkward point, someone else can pick up on that. Someone can hear where I’m leaving something out and add that in and so forth. It helps in terms of planning, going together, debriefing afterwards, so big fan of partnering.

The asking styles can be a roadmap. The ideal is to partner with someone diagonally across the grid because if you do, then you’ve covered all the bases, meaning you have your extrovert, your introvert, your analytic and your intuitive or at least a bit of each. Then wherever your donor is on the spectrum here, you probably can relate. It’s helpful to have an extrovert and an introvert together on the ask because one is going to talk more and one is going to listen more.

So, when I’m in my meetings with Ron, it’s actually perfect because he’s the visionary, the head of the organization. So, it works well that he’s the extrovert who does most of the talking. I sit back and do the listening. You can’t do both at the same time, really hard to do. So, when I’m sitting back and listening, I’m watching it unfold. I can watch the reaction of the donor. I’m listening to what Ron has said. So, I then can help steer the meeting.

Also, my go-getter friend Ron tends to talk a lot. We joke that he can go on and on. Now, over the years, we’ve developed some systems to work through this. One of them is I try to sit next to him so I can kick him under the table. If I can, I make some odd look with my eyes and he sort of now can tell by the way I’m looking at him that it’s time for him to be quiet. If not, sometimes I have to just say, “Okay, Ron, we’ve got to move on. We love hearing from you, but we’ve got to move on here.” So, he will go long. I’m the one who’s listening and moving us along. Partnering is great and the asking styles can help.

So, then setting up the meeting. So, at Asking Matters, this is a complete separate step because in many ways, this is the meeting, I think this is that first fearful step where you don’t want to make a mistake and you’re trying to figure out best practices, how do I do it to try to ensure I get a meeting.

Over the years, I’ve fielded many, many questions on this. Some people say, “You have to pick up the phone and call.” I say, “Absolutely not. Email has been my best friend for 15 years. I am really thrilled when I don’t have to pick up the phone. I’ve never liked the phone. I find it difficult even in my personal life often. I love email communication.”

And the bottom line is that of course you need to communicate in a way that’s going to reach the donor. If a donor doesn’t have email, you’re going to call. Or if a donor only works by text these days, some do, you might have to text. You have to take into account how you’re going to get in touch, but you have to take into account who you are, what’s going to be comfortable because that’s going to help get you out the door and what’s going to be effective.

So, we’re going to by nature do it differently. The rainmaker is going to be very strategic and decide is this phone or email. By the way, sometimes it’s a letter first and then a phone call, but rarer these days since email is so common. The go-getter is very spur of the moment and is the most likely to just phone because the comfort level is there.

As a matter of fact, it’s fascinating because when I think of my go-getter friends and peers and such, they’re the more likely to call me out of the blue. If my phone is ever just going to ring, it’s often a go-getter. Fascinating, right? So, go-getters, you’re comfortable, you can make the most on the phone.

Kindred spirits? Not as easy. We’re much more likely to send a letter saying we’re going to follow up or email because we find it a little more awkward calling someone out of the blue. Then what happens if that person is short on time, then we can’t make our whole pitch and such–not as easy for us to wing it at that point and move the conversation ahead.

For mission controllers, since you are so formal and detailed, you’re more likely to write first because it is true that in writing, you can make more of a case to start. You can lay things out and then follow up with them with a call. So, our asking style is going to impact how we reach out to setup that meeting.

Asking for the gift. So, at asking matters, we use a concept developed by my cofounder, Andrea, called the arc of the ask to help us move through this conversation in a very systematic intentional way. We have to plan for it. We need to conduct this meeting and there are steps. We don’t get to walk through all the steps here in detail, but the kicker here is that moment when we’re going to ask for a gift. Would you consider a gift of a certain amount for something? We do always ask for an exact amount. This is best practice. It’s harder for some of us than others, but we really must do that.

Even getting to this point, think of the difference in styles. I don’t have it laid out on a slide for you, but you can imagine where the rainmaker, who’s not big on process is going to tend to want to get to this question earlier, “Okay, let’s just get to the meat of it. Let’s ask this question.”

The go-getter is in his or her own moment as Ron is and might ask too late or might even resist asking because why ruin the party? We’re having a good time. Why interfere? The kindred spirit will have a tendency to put off the ask a bit because that’s where that feelings-oriented conflict averse side comes out, “Gee, how long can I put it off?”

The mission controller is going to go back to the arc of the ask I just showed you and say, “Ah, it looks like the ask is in the middle. I’m 30 minutes into an hour long meeting. It’s time to ask. So, the mission controller probably needs to be a little bit more flexible in when to ask.

So, the first difficult step in fundraising, I think, is trying to setup the meeting. The second one is asking for the gift. Then the third is being quiet after you’ve asked. We’ve all had that experience. We’ve asked. Then what happens with the silence afterwards? Our donor is now taking in this new information. We’ve asked for something, hopefully something personally significant. We need to give the donor a few seconds to respond.

As a matter of fact, I always recommend have something to drink. I’m going to take a sip right now and you’ll see, “Would you consider a gift of $5,000 for our library expansion?” I just took five seconds. It’s actually a pretty long amount of time for someone to think and respond. As a matter of fact, always accept a donor’s offer a drink. One, it’s polite and two, it’s great to have that water, I forgot the word I wanted to use, but to have that water by you to grab that sip.

So, who’s going to have an easy time, who’s going to have a difficult time being quiet? Well, it’s going to be a little challenging for the rainmaker who’s driven to close the deal. The silence might be filled with more facts. So, you’ve got to make sure not to do that. You’ve made your case. You asked. It’s time to be silent.

Hardest for the go-getter, right tendency to keep talking, doesn’t like the silence, feels like it ruined the moment. Easier for the kindred spirit, “I’m glad I got that over.” Sometimes out of nerves, you might go on. Mission controller will shine here. “The plan says I should be quiet. Easy for me. I like sitting back and observing anyway. I’m happy to hear what the donor has to say.”

So, the key here, as you can tell, is each step of the way, we need to understand who we are, what are strengths are what our challenges are try and work with those. The more we understand them and embrace them, the more successful our asks are going to be.

So, now we have one more step in the process. We have follow through. If you do have questions, by the way, I can’t see them at the moment, please start typing them in because I’ll be finished in two or three minutes and we’ve left time for questions. I’m sure there are some and Steve will share them with me.

So, follow through–rainmaker, we all have our strengths. We all have our challenges here. The rainmaker, really good at tying down details and reporting progress and thinking through some further strategy.

But the bottom line for the rainmaker is he or she would just as soon move on to the next “sale” because for the rainmaker, it’s very quantitative, which means going and getting the next gift and the more gifts I get, the better it is, as opposed to, “Now this donor’s made a gift. Now I have to cultivate this person. Pay attention to this person for the next year until I ask again,” not really high up on the rainmaker’s list, something to think about. Let’s go back to that partnering, right?

So, maybe there’s a tag team. If you as a rainmaker no you’re not particularly good at this ongoing cultivation, is this something someone else can do? Who would be better at it?

Go-getter is really good in terms of making people feel appreciated in that moment because of that enthusiasm, that energy that they bring. They’re likely to stay engaged. But I sometimes find a little more on the personal side than the business side. I’ve seen some fundraisers become friends. The asking style most likely to befriend a donor over time is the go-getter.

So, you’ve got to watch out for that and keep it professional. But also the go-getter tends to just do things quickly, very intuitively. And some of this does need a bit more thought. I’d ask the go-getter, slow down a little bit, think it through a bit more, and strategize about this relationship with this donor over time.

Kindred spirits, good at making donors feel appreciated. If anyone today is going to write a handwritten note, it’s the kindred spirit, but we can have a problem moving on. I faced this early in my career where I spent too much time with either low level donors who weren’t going to move up or people who just wanted to be entertained.

I actually did very well over the years with, I must say, with widows. When I worked with Brandeis University, I dealt with a lot of widows and I actually realized some of them really just enjoyed my company. I had to move on and say, “You know what? My job is to raise a certain amount of money and I can’t give equal attention to everyone.”

And the mission controller, great on all that systematic thorough stuff. If anyone is going to write a good contact report saying what happened in the meeting, it’s the mission controller. You can imagine easy for a mission controller, very difficult for a go-getter to sit down and write that all out.

The mission controller has to make sure not be too methodical. We’re talking about asking in person. That means we’re talking about everything being customized and individualized, in your own voice, so nothing sounds cookie cutter. So, that’s something for you to watch out for as you go along.

So, those are the five steps. Those are the asking styles. Now Steve, I’m happy to entertain questions.

Steven: Awesome. We’ve got a lot of questions here already.

Brian: Good.

Steven: If you were sitting on your hands, now is the time. We’ve got an extra probably 12 or 13 minutes we can devote to questions here. So, if you haven’t asked one but something is on your mind, let us know because obviously Brian is super smart and super knowledgeable. Brian, thanks, this was really awesome. I was sitting here taking notes, especially when you were talking about kindred spirit.

Brian: What’s your style?

Steven: I think kindred spirit, which it was nice to know that you are as well. I’m usually a little introverted, although I’m not shy, but I am introverted. That’s kind of where I landed.

Brian: Got it. Questions?

Steven: Here are some questions. Livia was wondering, “Why do you need to ask for an exact amount? What’s the importance of putting on that actual right to the dollar amount?”

Brian: Yes. Okay. There are two reasons. The first is that your donor is expecting it. You’ve asked your donor to come to a meeting. Would you consider meeting with me, I’d like to ask you to meet with me, however you phrase it, to talk about a gift to ABC Community House? Your donor assumes you have something in mind. There’s some credible reason and something specific. If you don’t have an exact amount, it feels like fishing, right?

When you say, “Would you consider a gift of $5,000?” you are telegraphing to the donor a lot. It means you’ve thought this out, you’ve thought about the relationship. They assume it means you’ve thought this through and for some set of reasons, this is the right amount to request. You and I know we obsess on this. This is the number one thing we obsess on because we’re trying to get it “right.”

So, we go back and forth, “We should ask for $10,000 because they had a really good year,” oh yeah, but they just finished remodeling their kitchen and blah, blah, blah. “Oh yes, but they made this size gift somewhere else.” So, we actually do spend a lot of time thinking about it. If our donor were to say, “Gee, how did you come up with that amount?” You could credibly say how you came up with it.

Now, your premises might not have been right, but it shows you’ve thought it through. That all gets telegraphed when you ask for an exact amount. People sometimes will say, “Can I ask for a range?” Never. If you ask for $5,000 to $10,000, what’s the difference? Why give $10,000. You’re saying anything from $5,000 to $10,000 would be good.

Well, I’m not likely to give more. I’m trying to come through for you. I’m the donor. I want to come through. I want to be seen as good. We’re empathizing with each other. We’re in-person. Now you’re telling me I can come through. I can be seen as good if I give $5,000 or $10,000. I’ll give $5,000.

Steven: Right.

Brian: So, a range doesn’t work. And we’re guiding someone. We’re negotiating. So, we’d have to have a starting point so that people understand the range in which we’re trying to work with them.

Steven: And it seems like people would gravitate towards the lower amount and arrange anyway, right?

Brian: Absolutely. I know people are afraid of asking for too much. Once in a while, I’ve had a donor react in some bad ways. As a kindred spirit, I felt awful about it. But then I came to realize you know what? Why did that donor take it out on me? First of all, we’re supposed to be on the same side here. Second of all, doesn’t this donor want me to raise as much money as possible?

So, is this donor saying I shouldn’t shoot for the stars with him or her? I should do that with everyone else, but I should ask for a lower amount here? My job is to raise as much money as possible. I’m the good dooby doing that either as the staff member or volunteer, just tell me I’m out of the ballpark, be an adult about it.

Steven: Right.

Brian: And if I always feared asking for too much, I’d always ask for too little and that’s not my job. Then some people say, “What if I could ask for too little?” then the donor says yes right away. Well, you know for next year to ask for more because this should be a long-term relationship with multiple gifts and you’re getting a better sense each time you meet and talk about a gift of what the donor’s capacity is.

So, I think if you actually can’t ask for an exact amount, it is a red flag that it might not be the time to ask. The relationship might not be strong enough to ask. There should be enough relationship there to withstand let’s say an ask that turns out to be way out of line.

Ron and I, we were in a meeting for this. We asked somebody for a quarter-million dollars and we got $25,000. We wanted $250,000 over five years. This person gave us $25,000 in one. But there was a history. There was a relationship. She didn’t hold it against us. It turned out in another day and time, it might have been right, but there were extenuating circumstances. Her husband was just retiring, so their life was changing incredibly. She didn’t hold it against us. Anyone who does, that’s their problem and we need to try not to take that personally. So yes, next question. That’s a good one.

Steven: I love it. Here’s one from my buddy, James. James is wondering, “Can people have a split personality when it comes to asking?” Is this only binary? Can you only be one of the four? Can you be a hybrid?

Brian: I don’t know. Yeah. That’s why the asking style assessment gives you a response. Some people are going to end up smack in the middle, right in the middle of that intersection because they’re not ultra-analytic or intuitive or something. What it’s hard to be is a really strong rainmaker and a really strong kindred spirit or go-getter and mission controller because those are really diagonally opposite from each other.

But yes, you’re going to have each of those characteristics. The question is what are you playing to most? Through the asking styles, we’re trying to create a framework to help you figure out who you are and how that impacts how you go about fundraising. So, that’s really what you should take from here, that you have a distinct personality and you’ve got strengths and challenges. It’s not that binary, like anything else.

Steven: Brian, we’ve had a lot of people ask about the arc of the ask. It’s a term you mentioned earlier. Would you mind diving a little deeper into that in just a couple minutes?

Brian: Sure. What can I say in a few minutes that would be relevant? You cannot have a very successful ask if it’s not intentional and thought out in advance. You can’t wing it. So, here I am, speaking a little bit more to go-getters who are so comfortable in the moment, they’re the most likely to wing it because they can wing most of it.

But asks are systematic. Like anything else, so in the arc, you start, you have to settle. We’ve all come from someplace else, you’re visiting someone in an office. You’re getting together at a restaurant, whatever it is, we’re finally shutting our phones down five seconds in advance of talking, whatever. We’re now in the same place physically.

We’ve got to get in the same place emotionally. So, we settle and we ask personal questions and we learn about someone. Then we have to start exploring and we need to learn. Then in the middle, we ask and then we explore some more because we have to explore the answer we got before we can firm and close. This is the arc.

And each step of the way, we’re trying to learn. It’s all about asking questions and getting the donor to speak, which should be a relief to most of us. It’s not about going in and sharing everything but the kitchen sink with the donor. There’s this adage that we remember the least of what we hear. We remember more of what we say and the most of what we do. There isn’t a lot of do in a meeting. But to the extent the donor is talking, the donor is going to remember what he or she said.

And if we throw in everything but the kitchen sink, the donor will remember very little of it anyway. So, the whole meeting is based on us asking powerful questions to learn about the donor and to get the donor to share what’s important, what’s important to you. What impacts your philanthropy? How do you decide how to make your philanthropic gifts? What first interested you in us? What would you like to know about us?

So, the arc helps us figure out each step of the way what are the questions to ask. So, first they’re general questions about personal life, “How are you? How’s the family?” then we get into the relationship with the organization and the relationship to philanthropy. We ask for our gift. It’s a brief couple of minutes, that case. Then we’re spending more time trying to figure out their answer.

If we’ve asked for a personally significant gift, chances are they’re going to say maybe. I need to think about that. We need to understand what it is they need to think about and what other information they can use and what might help convince them to make the gift. Is it an issue of timing? Is it knowing more about the program? Is it that they need someone else’s input–a spouse, a lawyer, children, whatever?

So, it’s a very intentional conversation. You keep moving it along. You can’t get in there and chat for half the time personally. You can’t get in there and ask right away because you have to learn first. You can’t ask at the end because then you don’t have to explore. So, it’s being intentional about that conversation every step of the way.

Steven: That makes sense. Brian, we’ve got a lot of kindred spirits listening today, I think I saw that in the poll. Maybe you’re not surprised.

Brian: Yes.

Steven: A lot of people struggle with that face-to-face interaction. What advice do have for people that struggle with becoming friends with their donors, getting the conversation going? It seems like a lot of these KSs are maybe shy by nature. How can they psych themselves up for that in person meeting?

Brian: Yeah. It’s not easy. It’s easier with people we know. Once we’ve gotten to know people . . . I develop relationships well with people I know. I know there are a few people I know who are on today and this will surprise them. Never in my life do I go up and introduce myself to someone. I cannot do it. I don’t do it at a party. No one knows because I cover well, but I do not because I am shy.

The few people on will not believe that, but I never do. I have to figure out how to make it work. If I go to a party–and I rarely do–I always am the first one to arrive. Why? Because for me, if I arrive first, as people arrive, one, the next person has to talk to me, there’s no one there. So, I automatically have someone to talk to. And it’s easier for me to meet people in a gradual way than to move in.

Now, it’s funny because I have a friend who’s a kindred spirit. She does just the opposite because she has issues. But she’s afraid of walking into an empty room because then she thinks she has too much responsibility. She feels if she walks into a full room, she can find someone she knows to gravitate to because that’s her comfort level. I fear that I’ll walk into that room and I won’t know anyone. The people I knew won’t be there, whatever, so I have to get there early.

So, I guess I’m saying we need to think about how to make it work for us. We want to ease our way in. The beginning of the meeting is going to be more difficult to us as kindred spirits. I always make a list now of the questions I want to ask at the beginning because just by having written them down, it makes it more likely I can recall them. It’s that muscle memory.

If I write them down, then they’re in my head. That makes the beginning of the meeting easier for me. I partner on a lot of asks partially to get through that because it makes it easier if I’ve got a partner. It’s less daunting. As I mentioned, the first meeting is hard, but once I know someone, it is easier. Then I enjoy getting to know them better, that one on one. I like the one on one, but it does take energy. It takes more of our energy.

So, being in the right mindset–that includes, by the way, reminding ourselves it’s not about us. There are a whole bunch of things you have to remind yourself up before you go out to be focused and strong. One of them whatever happens, if I did my homework, if I’m being respectful, if I’m asking questions, whatever, I’m doing my job. Whatever happens is not a reflection on me. I know I’m a good person. I know I’m a thoughtful person. As I said, I’m doing my job.

So, one more point, donors are often anxious. So, the other thing to consider–and this is a good icebreaker–is to say, “Thank you so much for meeting with me. I know it can sometimes be awkward. It just shows how much you care that you’re willing to meet with us to talk about a gift to the institution.” We admit it’s awkward. But we do it for the betterment of society, to help this organization we both care about thrive.

So, there are a number of things we have to do as kindred spirits that maybe a go-getter doesn’t have to do because there’s a more natural comfort level there. But it isn’t easy. It’s not easy. It’s easier, I find, with people I don’t have a very close personal relationship with.

As I get to know donors really well, it can get a little awkward for me again trying to keep it from being personal. “Okay, you know me so well. We’ve worked together for all these years and now you’re not going to give me the gift I asked for?” It can get a little difficult. There’s that sweet spot between not knowing anyone at all and knowing someone too well, for an introvert.

Steven: Right.

Brian:Yeah. I don’t know if that’s helpful, but these are the things that go through my mind all the time.

Steven: Well, Brian, we’ve probably got time for one more question and there’s way more than one question remaining. Would you be willing to take questions via email or Twitter later on?

Brian: Yeah, not Twitter. I’m not on Twitter.

Steven: No Twitter?

Brian: Absolutely. My email is Feel free to email me a question and I’ll give you an answer because obviously we can’t get to them today. I’m happy to do that, truly. Yeah. So, is there one more to ask before we close?

Steven: One more last one, I thought it would be a good one to end on. A couple people entered this webinar about maybe a preconceived notion of what type they were and were maybe illuminated today. What advice would you have for people who maybe thought they were one kind but found out today they were another? Not to have an existential crisis or anything, but what advice would you have?

Brian: Actually, run to the therapist. No.

Steven: Right.

Brian: One is this is just a guide. It’s 30 questions. Well, actually, I don’t know how people . . . people must have taken the assessment because if you self-selected today, then you self-selected who you think you are.

I’m going to assume some of those people might have taken the assessment while the webinar was going on and were surprised that they thought they were A and it came out as B. I would ask you to ask–you might ask people who know you well, number one, what do you think they are. But keep in mind that honestly, one question–there are 30 questions–one question answered differently could tilt you just to the other side of the line.

Now, if you thought you were a rainmaker and you came out kindred spirit or go-getter or mission controller, that’s a little harder to reconcile. But if you thought you were in adjacent quadrant primarily, that could be that you’re right on the line. If our assessment had 60 questions instead of 30, you might have ended up on the other side of the line.

So, I wouldn’t worry because at the end of the day, you do have a sense of who you are and you’re going to act based on who you think you are to a great extent.

Steven: Right.

Brian: So, that would be my advice.

Steven: Cool.

Brian: I’m assuming most of these are tangential, that it’s adjacent asking style and that it’s just a matter of the assessment being limited.

Steven: Yeah. Well, take the assessment folks, don’t run out to the therapists just yet. Please do email Brian if I didn’t get to your question, I apologize for that, but we’re about out of time. So, Brian, this was awesome. This was really great. Thanks so much for hanging out with us for an hour or so.

Brian:It was my delight. I want to wish you all the best. It is not easy fundraising. It is not “fun” for most of us, but it makes this huge difference in the world and so I’m really delighted you guys are out there with me doing it. Thank so much for having me today.

Steven: Check out Brian’s website. Go to Email him. Obviously a wealth of information. But thanks to all of you for hanging out with us for an hour or so today. Hopefully you’re all staying warm and dry out there this winter.

We are taking next Thursday off. I hope you won’t mind if I take a week off. But we are back two weeks from today with a really, really cool presentation from my buddy Judy Smith out in Arizona. She’s going to talk about how to approach women donors, female donors specifically. She’s got some really cool new research and data to show that may give us some insights in how to approach female donors specifically.

So, don’t miss that one. Obviously if you’re anything like my household, my wife runs our charitable giving as so many households do. Check that one out. It’s going to be really cool, really interesting. If that one doesn’t quite tickle your fancy, there are other webinars that you can register for right on our webinar page. We’d love to see you on another Thursday hopefully two weeks from now.

So, thanks again for hanging out with us. Look for the recording. I’ll email that out a little bit later on. Hopefully we’ll see you again soon. Have a good rest of your Thursday and a good weekend and we will talk to you again soon. Bye now.

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.