[VIDEO] Nonprofit Boards Members and Their Asking Styles – a Roadmap to Success

In this webinar, Brian Saber will explain how to use his iconic Asking Styles to improve your board’s governance and ability to fundraise. Learn the personality of your board and how it is impacting board meetings (especially today’s virtual ones), leadership, strategic planning and fundraising. Understanding your board members’ Styles will make your board stronger in every way.

Full Transcript:

Steve: Okay, Brian, I’ve got 3:00 Eastern. Is it okay if I go ahead and get this party started?

Brian: Yeah, go for it.

Steven: All right. Awesome. Well, good afternoon, everyone. If you’re watching the recording, I hope you’re having a good day no matter where and when you are. We are here to talk about boards and their asking styles. We’re going to give you a good roadmap to success for your board members and their different personalities and styles when it comes to asking for money.

Thanks for being here. I’m Steven. I’m over here at Bloomerang, and I’ll be moderating today’s discussion as always.

Just a couple of quick housekeeping items really fast. I just want to let you all know that we are recording this session, so if you have to leave early, or maybe you get interrupted, something comes up, or a toddler barges in, no problem. We will get you that recording later on today as well as the slides. Just look for an email from me later on today. I promise you won’t miss it.

But most importantly, a lot of you already have done this, but please feel free to chat in throughout the hour. We’re going to try to save some time for Q&A. We’ve got some interactive elements throughout the presentation. We’d love to hear from you. Introduce yourself now if you haven’t. Tell us who you are, what your role is. If you’re a board member, we’d like to know that too. That’s there for you, and we want to hear from you.

There’s also a Q&A box. There’s a chat box. You can use all of them. We’ll keep an eye on it. Don’t worry. You can send us a tweet. I’ll keep an eye on those as well. But bottom line, we want to hear from you, so don’t be shy at all.

If this is your first Bloomerang webinar, just a quick special welcome to you folks. We do these webinars every single Thursday throughout the year. We love doing it. Great topics. Great speakers. Today is no exception by any means.

But if you’ve never heard of us beyond these webinars, Bloomerang, what we’re most known for is our donor management software. That’s what Bloomerang is. If you’re interested in that, if you’re curious, if you need new software, check us out. We’ve got a great website with all kinds of videos, and you can get a look at us. Even if you don’t want to talk to somebody just yet, that’s okay, too.

But don’t do that now. Wait at least an hour because my good friend, and just always a treat to have him on the Bloomerang webinar series, Brian Saber. How’s it going? Are you doing okay? What’s going on?

Brian: What’s going on? Well, all things equal, I’m doing pretty darn well, I have to say. I count my blessings every day. I feel very lucky in the midst of heartbreak and chaos.

Steven: Yes, and I feel the same way. I feel lucky to have you. It’s always a treat to have you on the series. Normally, we run into each other at conferences and giving each other hugs, but the Zoom will have to do.

If you guys don’t know Brian, check him out over at Asking Matters. He’s my go-to for kind of the style and melding the personalities with how you should approach asking for money. He’s done great webinars for us specifically on his styles. He’s got a really, really cool framework that I think you’re going to want to check out, even after this presentation.

But one of my favorite things I look for: over 30 years of experience. He’s been in your shoes, he knows what it’s like, and he’s also just an awesome person that I think you’re going to have a lot of fun spending an hour with.

So I’m going to pipe down. Nobody wants to hear from me. I’m going to stop sharing my screen and, Brian, we’ll see if you can get your slides working. Let’s see. It’s always a fun transition.

Brian: There we are.

Steven: Nice. Take it away, my friend.

Brian: It worked. Though I don’t see my chat anymore, and I may not be able to. So I’m going to count on you to . . .

Steven: I’ll keep an eye on it.

Brian: Yeah, that would be great.

Well, it is a delight being here. I love the folks over at Bloomerang. Yes, Steve and I used to bump into each other in person. We will one day again. We don’t know when that is. Maybe next spring. And in the meantime, we’re all bumping into each other virtually.

I have been in this business forever at this point, 36 years. And for 25 of them, I was either a deputy executive director, a director of development, or executive director once at a very small organization, once a midsize organization. In every one of those roles, I was the fundraiser.

And most of the time, I train and I write. Actually, I’ve written my second book, which this webinar is about today, and I’m going to give you a special offer on it on the end, so stay tuned. Mostly, I train today. I write. I still ask once in a while.

People look at me and they say, “Oh, that’s Brian. He’s been doing this for 35 years. He’s this. He’s that.” This is really important in particular for board members to hear because this slide is as much me as the one you just saw and the one on the back of the book.

I’m no more the stereotype of a fundraiser than anyone is. We’re going to talk about the asking styles and such. Some of you know them already. I know I recognize some names in the chat. So we’re going to talk about the different types of fundraisers.

I am shy. I’m introverted. I don’t like meeting new people. I’m fine once I meet them, but the thought of meeting them? Not good. I hate special events. I hate any large gathering. I rarely go to a party. I can’t stand the phone. So all of those are me, and yet I’ve been a successful fundraiser. It actually took the asking styles, which we’ll talk about in a minute, to help me feel comfortable.

So that’s who I am. I love working with boards. As Steve said, many thanks to all of you board members who are on today who are taking time out, some time during your day, or if you’re over in England, as I know at least one of you is, in the evening there perhaps. But to take time out to figure out how to be a better board member, how to have a more cohesive board. I’m delighted to be here to help you with it.

I do hope you’ll ask questions throughout. Steve is watching the chat. We will have some time at the end for sure. I love questions.

I think you know you’re going to get a PDF of the slides and such, so you don’t have to write down everything you see here.

The asking styles. So the asking styles came about a decade ago because my then founding partner at Asking Matters and I really were looking at boards. It’s interesting how I’ve come full circle, because a lot of the work I’ve done the last decades has been staff at conferences and such, but it really was about boards. We looked at board members, and we said, “Every organization has a board. Every board member we ask to fundraise. And virtually, no one knows how to do it. No one thinks they can.”

As a matter of fact, so many board members when I’ve onboarded them or I’ve interviewed them have said, “I’ll do anything but fundraise. I hate fundraising. I can’t fundraise. I won’t do it.” And yet we need you all, right? We need you all, and yet there’s this friction for many reasons.

As a matter of fact, if you could, type in what the number one thing is that stops you from being more involved in fundraising for your organization, whatever your role today. And I’m going to try to open the chat again here. Let me see if I can. Oh, I can.

So, if you could, type in what’s the number one thing stopping you from fundraising today. Not sure how or who to approach, time, fear of rejection, losing friends, time, connections, rejection, fear, awkward, awkward, time. And I’m sure time is coming from staff as much as anyone. The right contacts, my board, rejection. This is not easy work. This is the hardest work, whether you’re staff or board.

I do not fundraise. I have not fundraised my whole career because I love fundraising. I have fundraised as a staff member for the same reason board members fundraise: because we care and we want to make a difference. And we figured out this is the way to make that difference, right?

My first jobs were in the performing arts. I wasn’t a dancer, a singer, an actor, or whatever. I loved the performing arts, and I wanted to help them. Then I went on to my university. I loved my alma mater. I didn’t know how to teach. Then I went into social service, and I spent two decades with community-based organizations. I didn’t know how to help teams. I didn’t know how to run a mental health clinic or a food pantry, but I could raise the money so others could do it.

It’s important to realize that, because we’re all sort of in the same boat, and we all have to figure out a way to do it that works for us. So, again, enter the asking styles.

There is no one way to do this work. Yes, when we talk direct mail, when we talk crowdfunding and such, even to some extent special events, there’s a lot of science and a little bit of art. There’s a way to do it. There’s a way to write the direct mail letter and so forth.

When we’re talking about the individuals and developing relationships over time that lead to more significant gifts, we’re talking about art much more than science because it’s who we are as human beings and how we interact with each other that makes the difference. It’s why everyone can be a fundraiser.

You may not be the person who asks for the gift, who says, “Joe, would you consider a gift of $25,000 to Children’s Hospital this year?” But you can be the person who takes Joe to coffee, who sends Joe an update, who does all these other things, which are all an important part of asking and all involve a lot of art. So you need to know who you are in that process.

We thought, “Well, what are the two things that most affect someone’s asking style?” And we say asking style, but we’re really talking cultivation and asking.

The first is how do you interact? Are you extroverted or introverted? Now, people have this stereotype, right? They think extroverts are like if you’re older, as I am, John Candy from “Planes, Trains, and Automobiles.” I don’t know if anyone still watches that film. Or Michael Scott from “The Office.” And if you’re an introvert, you’re like Shrek. You’re hermetically sealed. You never go out.

Julie’s saying, “I love that movie.” I have to go back and watch that movie again. I just remember cringing from it.

Well, these are stereotypes and neither is true. Introverts can be social. It has to do with where we . . . that’s funny. Miriam saying, “I am a Shrek.” I like that. It has to do with where we derive our energy, and that has to do with whether we talk to think or think to talk.

So imagine all the special events we used to go to. Imagine all the Zoom rooms we’re in. If you’re an extrovert, you think on your feet and you talk quickly as you’re thinking. And so, if you’re in a conversation with people and the conversation is ricocheting back and forth, you’re in it.

As an introvert, introverts like to think and then talk. So we might stop to think about the question. If we have to answer immediately, we often don’t answer as fully as we’d like, and then we go back and say it again or something. Well, if we stop to think and then talk in one of these situations, what happens? Someone else talks. So, without knowing it, subconsciously, introverts speed up their thought and talk process to stay in the rhythm of a conversation, and that uses a lot of energy.

So no matter how much I love seeing my friends one-on-one, when I’m done, I need a lot of quiet time. I’m looking right over my shoulder at a big jigsaw puzzle. On the other table, I have my word games. I can spend hours with those.

Now, this impacts how we interact with people, who we’re comfortable meeting, how the session might unfold as we’re having a conversation.

The second is how do you take in information? Are you analytical or intuitive? Do you start with the data and figure out the idea, or do you start with an idea, you have a gut, and then you see if the data supports it? This is going to impact why you love your organization in the first place.

If I ask you, “Why do you love your organization?” you’d give an answer, and I bet you could see if it’s a more intuitive, touchy-feely answer, or if it’s a very factual analytic answer. So this impacts why you love your organization, and therefore how you’re going to talk about it, which is the number one most important piece in fundraising. What are you going to say that represents your passion, your vision, the vision of the organization, the impact it’s making, and so forth?

When we put the two together, we get the asking styles: rainmaker, go-getter, kindred spirit, and mission controller. I’m going to walk through them, I’m going to describe all four, and then I’m going to ask you which one you think you might be, and then I’m going to give you a more scientific way to figure it out. Then I’m going to apply them and show you how this can help you strengthen your board, understand your board, and so forth.

So we start with the rainmaker. When people think fundraiser, they think rainmaker, the analytic extrovert, competitive, “I’m going to close the biggest gift,” goal-oriented, “I’m going to close three gifts. I’m not going to get deterred. It’s all objective for me. I’m not going to take it personally. I can keep going, and I’m going to be very strategic. I’m driving ahead.” Great skills for fundraising since it’s not easy and we need to keep our eye on the price.

Go-getter. The intuitive extrovert, big picture thinker, makes friends easily, creative, high energy, life of the party. Great skills when we’re trying to get people to be enthusiastic or we’re trying to find new people and open up relationships and excite them. Great skills.

Now, by the way, this is not to say you can’t have a little bit of all. We each have some amount of each of these.

Kindred spirit. I’m a classic kindred spirit, an intuitive introvert, feelings-oriented. We wear our hearts on our sleeves. Everything is personal, for me anyway. As hard as I try not to make it personal, it’s always personal. And because I’m so sensitive, some would say oversensitive, I tend to be that way to others. I tend to be attentive and caring. “Well, what would you like to eat? What would make you feel good? As a donor, do you feel heard? Thank you so much for your gift. I really appreciate it. Let me show my appreciation.” Again, great skills for a fundraiser. Very different core skills from the rainmaker. Not to say the rainmaker can’t be caring, and the kindred spirit can’t be strategic.

And then we have our mission controller, the Eagle Scout who always gets the job done, the analytic introvert, systematic, methodical, detailed, responsible, and observant. The most likely to sit back, not talk too much, and watch what’s happening is the mission controller. Great skills for a fundraiser.

Now, I also look at the asking styles through the question each of us asks when we’re trying to figure out, “Well, what’s important to us?”

The rainmaker says, “What’s the goal? That’s going to drive me forward.” It’s quantitative, and it’s in the future.

The go-getter is also looking in the future, but generally, what’s the opportunity? What can we make happen down the road?

The kindred spirit is saying, “What moves my heart? What am I feeling is the right direction to go in here?”

And the mission controller is saying, “What’s the plan, guys? Great to have a goal and opportunities, I’m glad you’re feeling that way, but without a plan, we’re not going to reach the goal. We’re not going to be able to take advantage of the opportunity, and it certainly doesn’t matter what you feel if we can’t make it happen.”

So type in for me, what do you think your primary asking style is? If you had to pick one of these, type in the chat box which one you would choose. Go-getters, mission controllers, kindred spirits, go-getters, go-getters. Lots of go-getters. Intuitives, mission controllers, go-getters, a rainmaker. We found a rainmaker. One more rainmaker. They’re going by quickly. I see some of you putting a slash in here, go-getter with kindred spirit, kindred spirit with go-getter, go-getter/kindred spirit. Very good. Excellent.

So let me share. Some of you were talking about primary, secondary. I’m a kindred spirit/mission controller. I’m definitely an introvert, but I do have that analytic organized side.

I was saying to someone this morning that I have no desire to run anything, but I feel a responsibility for things to get done. So, if no one else will do it, I do it. That’s how I describe kindred spirit/mission controller.

There is, as I mentioned, a more scientific way to find this out. I encourage you to have your entire board take the Asking Style Assessment at Asking Matters. It takes truly two or three minutes. It’s 30 true/false questions. You can take it on any electronic device, and it’s going to give you a primary and secondary result right on the screen and then send some more information to your email. It’s free, available to anyone. Just go to, and you’ll see that button “Find Your Asking Style.”

Julie’s saying, “Yes, that’s me.” I’m assuming you’re meaning kindred spirit/mission controller.

Go-getter/rainmaker. Just so you know, the two have to be adjacent.

Now, you might think you’re a little of all four or very much all four. Just think of it this way. If you’re really feeling, “Gee, I’m really all four,” you could be right at the origin of those two axes. Some of us are uber this or uber that. Imagine us in one of the corners. Some of us are more towards the middle.

Anyway, great tool for everyone to take advantage of because there are so many discussions to have and ways to analyze the board, and we’re going to talk about some of that now.

The key and the reason for the asking styles, the reason we’re here today, is because it’s imperative that board members understand there are many ways to do this, many ways to be effective. No one has it all. I don’t have it all. No one. I’ve never met anyone with it all because we all have different strengths. And because this is about relationship building, we all can be fundraisers and bring those strengths to the table.

So, next, let’s talk about your board’s asking style. By the way, it’s been so fascinating trying to find images, having some images of electronic, some in person, knowing our current world and the world we will get back to at some point. It’s really profound having to figure out how to represent all of that today along with everything else.

So let’s talk about your board. This is a very effective, easy tool. Once everyone has taken the assessment, you can map your board, right? Where does everyone fall? So you see we have three rainmaker/go-getters. We have two go-getter/rainmakers. We have two go-getter/kindred spirits. So you can see we have . . . what is it? Here, we have three, five, seven board members who are extroverted, and we have eight who are introverted. We have six . . . and I might be going in the wrong direction. It might be flipped. But we have six on the analytic side, which means we have nine on the other side. So we can get a sense of the balance.

And let’s say two of your board members are different, right? You can see where if Alice and George aren’t up there in the go-getter category, but are actually down in the mission controller category, you can see just through that how much more introverted and analytic your board is.

So you can get a sense . . . once you see this, you can actually figure out if there are holes. You can figure out why a meeting is unfolding a certain way, right? Do you have a lot of detail people? Do you have a lot of big vision people and such?

How would you describe your board? If you could type that in, we’ll try and read a few of those out, but at least everyone can see them, I believe. Do you think your board is evenly balanced? Do you think you’ve got a lot of something and not a lot of something? What would you say your board is like?

Marcy is saying, “Excellent for visual learners.” I think I’m a visual learner, which is probably why I built them, Marcy. No one has ever said that before.

Amanda is saying, “A lot of mission controllers.” Becky, “An analytic hands-on.” Anastasia, “A lot of mission controllers.” Rainmakers. So what’s happening? If you have a lot of mission controllers, there’s a chance that they may be getting into the weeds, right? You may have to provide a lot of details.

If you’ve got lots of, let’s say . . . and literally, there could be 600 or 700 of you now. Liza is saying, “Mostly mission controller/kindred spirits.” You have mostly introverts. How does that affect the dynamic of your meetings?

I see Chris saying, “Introverted.” Henry says, “Mission controllers.” A lot of you seem to have a lot of mission controllers. Nancy says she’s got a good mix. One of you said a lot of rainmakers. The best is, of course, to have good mixes in anything because you get a lot of different viewpoints.

So think that through. And as I said, a great exercise for your next board meeting is having everyone take the assessment and then mapping this out because you immediately have an aha moment, and you can also begin to respect people for what they’re bringing to the table.

Often, in team dynamics, group dynamics, we tend to get annoyed by someone. “Oh, this person is asking so many questions. I wish they wouldn’t.” Well, it might be really helpful that you have that person who’s asking questions. Once you realize that a lot of you are go-getters maybe, you want that mission controller or you want that rainmaker really digging deep and saying, “Give us a factual answer. This isn’t concrete enough,” and so forth.

We can also now see the difference between boards that are meeting in-person and boards that don’t. Now, there were always boards that didn’t meet in-person. It was usually a conference call. Now we have Zoom. We have the video conferences, and that’s creating another dynamic.

Conference calls were always awful. Board meetings by conference call? Terrible. Very hard for anyone to participate. You can’t read anyone else. Really difficult for the chair. And mostly, we’d get together as boards in-person. We will again, and we will be really excited to do so when that happens. But today, we’re doing much more of it . . . we’re doing almost all of it wherever you are electronically.

So think about, “How are the asking styles of your board impacting you now that you’ve switched to video conferencing?” You know for the next six months, at least, if not more, we’re going to continue to do this. And I think we’ll end up when we’re done having more Zoom calls and not bringing groups together as often because it’s expedient, and we’ve learned how to do it.

Sandra says, “Our board is all overseas, and it’s so hard.” Now at least you’ve got video conferencing. Really hard, Sandra, when it was all phone, right?

So how has the dynamic shifted on your board based on styles now that you’re doing electronics? Has it? What might you be aware of this spring to make sure that the dynamic works?

I’ll share one thing that I’ve noticed. I think it’s gotten even harder for introverts to participate because it’s harder to read the Zoom room than it is when you’re all sitting around a table. When you’re around a table, it’s easy to see someone wants to speak. It’s easy for the chair to see, “Oh, Sue wants to say something,” and call on Sue. In the Zoom room, it’s very hard. You often can’t see all the screens at once. Your chair is not necessarily really adept at Zoom. I find, and I’ve been asking my clients and such, that introverted board members are having a harder time participating. And I’m seeing lots of “agreed.”

So what can you do this spring now knowing this, especially once you all put it up on the board and talk about it? What can you do to encourage the introverts?

Beth has a really good point. Some introverted board members don’t want to be on camera, right?

Of course, Jennifer, we have the difference in skill level, which is a problem, and that’s a separate related problem. But harder to read body language online. What if everyone doesn’t show their camera? So a couple of points there.

Your chair may need to make a point of asking the introverts’ perspective in advance or calling on them because they’re less likely to offer up any suggestions otherwise.

I mean, I’m that way. I never comment in a meeting with other people. I simply don’t. Now, when I train, because I’m aware of that, I find a way for everyone to participate. When I see people who aren’t, I go up to them, and I ask them. I find a way to include them. Now, they may be a little bit on the spot, but usually, once we’ve started to engage, they’re fine. It’s just that the introverts aren’t going to jump in.

So think of how that dynamic has changed, how maybe your uber extroverts could be dominating the Zoom meetings more than they would an in-person meeting, and what you can do about that.

Second one, leadership. Each of your board chairs is going to have a different leadership style.

Rainmaker. The rainmaker board chair’s strength is going to be keeping everyone’s eye on the prize. We move ahead. “This is our goal. We’re all going to move ahead.” When we get off track, “No, let’s get back on track.” We want to move ahead.

Go-getter keeps the big picture alive, right? “Let’s not get too bogged down in the details, everyone. Let’s remember why we’re here generally. This is our vision.” A go-getter, more vision. Rainmaker, more impact. But both of them looking in the future.

Kindred spirit, “Let’s remember who’s being impacted here. Let’s remember why we’re here. Let’s not forget the people.” We can be very scientific and so forth, but at the end of the day, we’re talking about people and impacting their lives. So a kindred spirit chair might be very focused on that.

And a mission controller is going to make sure everything is doable.

Now, those are great skills, but there are also challenges. So you see where each one . . . and you’ve seen all sorts of rubrics like this in the past, I’m sure. DiSC and this and that. The rainmaker is going to offer strategy. The go-getter, vision. The kindred spirit, heart. The mission controller, plan. But each has a challenge.

So rainmakers are not big on process, might not be great at letting everyone talk. “We really know where this is going, so let’s just finish it up.” You can’t do that when you have a team, right?

Go-getter can be . . . I just covered my slide. What did I say? Unfocused. That’s right. Can be unfocused and a little all over the place, let the meeting be a little bit too organic.

The kindred spirit can be . . . I apologize. The chat is in front of my slides. Can be overly empathetic. I’ve done this a million times, but still each deck is a little different. So the kindred spirit is going to want to hear everyone’s opinion and might let things go long for that reason.

And the mission controller might be inflexible. “Okay. We’re on to the second agenda item. It’s 2:22, and we’ve only allotted eight minutes, and we have to move on.”

So every leader is going to have strengths. Every leader is going to be challenged in a certain way with the rhythm of the conversation and the meeting. And some of that will be relative to the board members and their styles.

Beth is saying, “It sounds like it’s better to increase interaction overall during every meeting.” Completely. If all you have is reporting, you’d need to as quickly as possible, Beth, move to what we call a consent agenda where reports are sent in advance and board members approve or not and only say something if there is a comment that needs to be discussed so that there is more time for discussion during a board meeting.

Let’s see. I see some people already taking the assessment while we’re on here, which is great.

Next, strategic planning. So we come back to that whole idea of strategy, vision, plan, and heart. What do you think your board is best at? Type that in. Which of the four of these do you think your board is best at? Strategy, vision, heart, or plan? Which one do you think they’re best at? I’m seeing vision, heart, a lot of vision and heart, some strategy, vision, heart, plan. So, not surprisingly, less strategy, which makes sense because we’ve also heard that few of your board chairs are rainmakers.

Some of this will be based on your executive director, CEO, president, and some on your board chair. Where is leadership at, and how is that impacting each of these pieces? How is it impacting strategic planning?

Again, Judy is saying, “Well-balanced,” which is wonderful.

James is saying, “What’s the difference between strategy and plan?” Good question, James. Strategy is higher-level, big-picture thinking. Plan is the tactical stuff that supports it.

You need each of these. You need a go-getter with the vision to start. “If we go in this direction, we can eradicate poverty.”

And the kindred spirit is saying, “This is the population we need to work on. This is important work. This is what we’re going to do.”

The rainmaker is saying, “Okay, what’s the strategy we’re going to use? Are we going to try and get food? Are we going to teach nutritional classes? What’s the population? Where are we going to do this work?”

And the mission controller is saying, “Well, if we’re going to do food distribution, this is how we’d have to do it, and this is how we’d need to be set up.”

So very important especially for strategic planning, but really any sort of discussion, to have a range of voices at the table, which is why it’s good to have a range of asking styles on your board.

Now, we can’t always pick and choose, though in my book I talk a little bit about recruiting. Generally, our nonprofits do not have the luxury of choosing among 100 potential board members, but to the extent you can choose or at least try to figure out your potential board members, you can get a sense of who might fill one of these holes in terms of the perspective they bring to the organization.

We often think about skills. Well, you want a lawyer and an accountant and a marketing person and a communications person, maybe a real estate person, and this and that. But if every one of those people was a kindred spirit, or a go-getter, or one asking style, that would make your board lopsided, and it might not matter that they have all those different skills because you might have other bigger challenges.

Miriam, I love your question. “What if you and your ED fall in the same quadrants? From a leadership standpoint, is it good to have similar styles?” So it’s great to complement each other, though it can be challenging.

I find rainmakers very challenging. They make me nervous. I appreciate them from afar, but when I work with them, it sometimes gives me some agita. So I have to get over my agita because I really need the rainmaker. Same thing, go-getters, mission controllers.

My founding partner, Andrea Kihlstedt, is a go-getter. Her husband is a mission controller. And founding the asking styles helped her finally figure out her marriage.

I know many of you know Andrea because she’s been on Bloomerang. I think she may be on . . . she might have been on just recently, or she’s coming up. I saw her there.

We won’t get into all the personal ways this can help, though you can imagine how it will. So opposites really complement each other, but can have challenges working together, right?

You could say two rainmakers together might butt heads. Two kindred spirits together might be afraid to push back at each other. So once you realize this, you can acknowledge it with each other in a safe space. It sounds like therapy, and maybe in a way it is. But you also can figure out how to complement yourselves.

As you say, Miriam, the ED and board chair are both in the same quadrant. You might want to make sure that second in command, vice-chairs, or treasurers and such of your board have some of the other styles to balance you out. It’s a thought.

Again, we don’t always have the option of choosing, but we at least have the option of analyzing through a lens and taking what we’ve learned to improve our performance.

Fundraising. Okay. Wouldn’t this be nice if we were all sitting in an office in a conference room without masks having a great time? One day, we will.

So how does this impact fundraising, which is so important for board members? Well, remember back when we were talking about analytic, intuitive, and stuff, we talked about the different stories? You have your own story as a board member. I’m talking specifically to board members now, all of you who are on.

There’s no elevator pitch. There’s nothing you have to say, except what’s passionate and authentic to your experience. If you speak from that point of view, whatever you say to someone else is going to be compelling.

There’s no elevator pitch, as I said. If everyone on the board is given a script and says the same thing to everyone they meet, that is bad. Unless you’re an amazing actor on the board of a theater or something, and even then, it’s going to sound canned because they’re not your words, and it’s going to be hard for you to be passionate about something someone else said.

So we’re all going to use different vocabularies to tell a story about the same organization. We’re going to tell different stories. It’s the number one most important thing for you as a board member in order to be a good ambassador, advocate, cultivator, recognizer, thanker, all the roles that you can play.

You can also see now how board members can partner. There are lots of ways to partner: two staff, program and fundraising, two fundraising, two volunteers. Let’s say you have someone you partner with already. You’re a board member, and you go out with the executive director. What are your styles, and what does that mean?

Now, of course, if you can pick and choose, you pick your opposite.

I know there are a bunch of you from Chicago. I have worked with Northwestern Settlement House for 30 years, specifically with Ron Manderschied. If you know him, type that in the box. He is one of my idols and dearest friends, now working on yet another campaign now that he’s retiring. He’s a go-getter. We’ve been in a thousand meetings together since 1990, and we bring the intuitive.

Now, I’m thrilled that he brings the extrovert and is more comfortable at the beginning of a meeting, but we’re always coming from the intuitive side with our story. I love Ron. If you were a rainmaker, it might be even better, though maybe he’d intimidate me. Who knows? But we’ve been a good team focusing on the intuitive, and I think you’re seeing it on this side of your screen.

So you can think about this in the fundraising lens as either finding a partner or, again, analyzing through a partnership.

I’m a big believer in partnering. I love to partner, to cultivate, and to solicit. And I think it can be very effective building multiple relationships with an organization, and it makes it more comfortable and allows you to be more effective.

I promised you two exercises, which right now we can do from home. So here’s the first one. Choose someone you would partner with to solicit. Take a guess at their style or share them. It’s something you can do on your own, or you and another board member can do together at your next board meeting. If you’re in a Zoom room, you could break into breakout rooms, and in pairs of two or more, do this and talk about these basic things. “How do we complement each other? What might our challenge be? Who would take our various roles?”

This will help you or your board members feel more empowered to do this work, to see a pathway through, and not just be told, “Please go out and solicit so and so for a sponsorship gift,” out of nowhere.

The second exercise is breaking into groups of three where everyone makes a one-minute case of support. They tell their story, and then you have a discussion on how your asking style impacted your case, and then you repeat that.

So Rita is asking, “What’s the link for the analysis for the asking styles assessment?” You go to, and you’ll see “Find Your Asking Style.”

So before we take questions, I’ve set up a page at where you’ll find a PDF of the slides . . . I think Steve may also send those out . . . and a whole bunch of bonus materials. There are only three listed here, but there are some forms up there I noticed. There are like eight or nine different things. You can just pick them and download them.

I mentioned my books. So I am doing a book special, and for the next month, I will personally inscribe and ship for free my book, and I will include one of my nifty door hangers. I have these great hangers. I hope you can see. That says, “I am making fundraising calls. Please do not disturb.” So I will inscribe and ship for free and enclose one of those door hangers if you want to buy the book, and there’s a link from the main page.

And here we are, question time. Jennifer loves the door hanger.

Steven: That was awesome, Brian. I just want to say thanks really quick before we get to the questions. That was awesome. Every time I hear you talk about the styles . . . I always saw the board members, so it was nice to have the board member deep dive. Thank you.

Brian: Thank you. I’m going to type the link to the assessment in the chat box right now while we’re looking for questions.

Steven: Cool. Yeah, it should maybe be clickable for people that way.

Brian: Yep.

Steven: I love it. Yeah, we’re getting a lot of adulation here in the chat. So good job. We’ve got time for questions, probably 15 minutes or so, so don’t be shy. There’s a Q&A tab and a chat tab. If you put in the Q&A tab, it might be a little easier for us to see you. We don’t want to miss you.

But a couple people asked about the style of the person being asked. Does their personality maybe make you do things differently, might be outside of your preferred quadrants, or any changes in the strategy there? What about the . . .

Brian: Great question. Who asked that question?

Steven: Amy. Our buddy Amy

Brian: Amy, thank you. It’s a great question. So, in a longer or different webinar, I would have covered that as well. It’s brilliant. Yes, you want to take into account your donor’s asking style.

First, I get the question, “Well, how do you know your donor’s asking style?” Wouldn’t it be great if before meeting you could say, “Can you please go online and take this two-minute assessment and tell me your asking style?” We can’t do that. But if we know people pretty well, we have a sense. We can tell from the questions they ask in advance of meeting them.

If someone asks for a lot of information, rainmaker/mission controller. If they want strategy or outcomes, rainmaker. If they want to look at your long-term plan or details, maybe mission controller. If they like communicating by email rather than phone, probably mission controller or kindred spirit. If they say, “Oh, don’t send me anything in advance. Just come talk to me,” go-getters. If they say, “Well, I’m only going to give you 20 minutes,” rainmakers.

The way we set up meetings, the way we communicate by phone or email or other will give you a sense of who they are.

Let me say you should always be yourself. When people ask me what I attribute my success to, I think people think that I have some secret sauce and when I go into a meeting, I can get Steve to give a gift way beyond anything he ever thought of.

Steven: You’re magical.

Brian: Right. I am not, and I do not do that. I don’t think anyone has ever given me a gift they can’t afford or . . . I mean, people give me more than they might have thought they’d give, but not because I’m doing some magic in there.

I just lost my train of thought, but what I was . . . let’s see. What was I going to say about that? I’ve been successful, one, because I went out and did the work. Even though I didn’t particularly like it, it was important and I did it.

Two, I always was myself. I couldn’t not be myself. I’m a little ironic. I joke. I get nervous. And I think being real was so helpful.

So I’m encouraging you all to be real, and that means being real with your donors. Yes, if you have a donor who’s an introvert and is quiet and you know that, like in any relationship, you need to leave room for that donor, for that person to talk. You need to wait longer after you ask a question for the person to answer.

If you know you’ve got a real strategic rainmaker donor, and you’re a kindred spirit, you know maybe to bring some materials, or you know you’re going to get a question or two about that. Well, you can prepare to do that and still be yourself. You still tell your case.

If your story is a heartwarming story, and you’ve got a rainmaker donor, the rainmaker will ask you follow-up questions, “Oh, that sounds great, and what are the outcomes?”

Steven: I love it.

Brian: So, yes, really important, Amy. Great question. And there’s so much you can analyze and figure out in advance and in the moment with that. Thank you.

Steven: We could probably do a whole hour or more on that. That’s a good one. Maybe we will next time. Why not?

My buddy Amanda here . . . I love this question. “How can we as staff support the different asking styles amongst the team?” She says, “Say we have a kindred spirit preparing to make an ask to a friend. How can we prepare them, support them, build them up as leaders in the organization?” What do you think?

Brian: So one of the bonus materials on that page at Asking Matters is how to support each asking style. It shows in four different columns in different ways how you can do that. That’s great for staff with board members or other staff.

There are a whole bunch of free materials at Asking Matters. I honestly can’t even remember what we have up there anymore, but if you go there, you’ll find more on this subject.

I think if we’re talking staff, if everyone on the staff takes the assessment, you’ll have a better understanding of how to support your staff basically. You’ll say, “Oh, okay. That’s why. This is a rainmaker. I’m going to keep the meeting shorter and I’m going to make sure to . . . we’re going to talk outcomes,” whereas that’s going to be harder for a kindred spirit. So I’m not going to impose the same exact review model or the same exact expectation for those two because the lens they use is so different.

Steven: That makes sense.

Brian: Each one of these questions could be a whole session because they’re . . . The beauty of the asking styles for me . . . and obviously, I live and breathe them. I love them. It’s that they’re easy to get. Once you know what you are, you don’t have to say, “Oh, what am I? I can’t remember what . . .” It’s so easy to see what you are relative to others, and it’s so helpful in getting people to relate to each other better generally.

So, to the point of staff, just knowing each other’s asking style will help. Then you can laugh.

Andrea and I, we got along really well until we almost killed each other. Now we’re even closer than ever. But she can go on forever in processing stuff as a go-getter, and I can’t absorb that much and I can’t keep responding to her. So I would stop talking, and she would take it personally when I just couldn’t . . . I needed time to think. And so we finally decided that our meetings couldn’t be any more than, like, 30 or 40 minutes.

We got to know each other because of the styles and respect each other. So I think that will happen.

Steven: Knowing Andrea a little bit, that’s funny to hear that story because I can kind of see it playing out in my head. I love it.

Brian: She has endless amazing ideas, and I need time to absorb them.

Steven: Yes. Me too. I’ve been on the receiving end of that.

A couple people asking about Zoom. We’ve been living on Zoom. We can’t get in person with people for in-person meetings. Any differences in any of this when we’re in a virtual setting or maybe even over the phone?

Brian: Yes. Great question. I’ve been interviewing people who are frontline development officers and are out there making these asks. I think I’m going to write a blog post about this shortly.

So what’s happening? Well, they’re shorter. You’re not having hour-and-a-half or two-hour lunches. They’re shorter meetings, which means there’s less time for chat.

One development officer I was talking to just yesterday, who is a kindred spirit/mission controller like me, is finding she’s got to use more of her mission controller. She needs to be better planned in advance to make sure to use that time well. That’s particularly important for a go-getter because the go-getter’s meetings tend to be longest. So you need to be a little more structured.

I’ve been asking about technology issues, and today most people are finding that most donors are getting the whole video thing, and you can have a conversation. They actually have said, as we probably know from our work, that the conversation is actually more focused, and people stay more focused because it’s harder to wander when you’re so up close.

If you know any therapist, they’re challenged with this today because it’s just too intense for a therapist and a client. There’s no way for the client to look away or look down. You’re looking at each other. That serves us well in fundraising where we’re both really on the same side. We should be on the same side. And so the conversation is more collegial. It keeps us connected to each other. So that’s been a positive.

Of course, there’s no travel, so you can get more work done.

And lot of electronic work always took place, whether it was by email or by phone. So a lot of the phone conversations are now becoming Zoom conversations, and that’s a benefit because it’s always helpful to see the face and be able to see the reaction in real-time as you’re discussing gifts by phone.

I’m not hearing of a lot of reticence to doing it by Zoom. People realize this is the future, and this is what the organizations they care about need.

When we are talking about face-to-face, one-on-one, we tend to be talking about the individuals who have a richer relationship already with the organization, so they’re more inclined to take the extra step of having a Zoom meeting.

There have been more spouses involved because, in many cases, everyone has been working from home. So it’s actually been easier, and it’s important with significant gifts often to make sure you have all the decision-makers in the room. How often have we been negotiating a gift with someone not realizing there is a partner, spouse, significant other who needs to play a role? Easier to get everyone together.

So there have been a number of pluses. Nothing replaces in-person. We can’t wait to be in-person with everyone.

I love being with donors over food. So I miss breaking bread with people. I think we’re in a good mood when we eat. It feels good to eat. There’s a certain leisure to the meeting, which I prefer. It gives us more time to go around and for it to be natural. So I’m missing that, and I think that’s a challenge.

So lots of differences, but people are ready for it. People have been incredibly generous since this started. The giving numbers have remained strong. There was a dip immediately because everyone was in a, “What are we doing?” But then they came back really strong in GivingTuesday and the second . . . the signs have been great. So I say go out and make it happen this spring. There haven’t been a lot of downsides to that.

Steven: Yeah. This is great.

Brian: I mean, is that what you’re hearing, Steve? You’re out in the field.

Steven: Absolutely. Yeah. We had people with their best years ever in 2020, and I think it’s largely because they’re proactive. So, yeah, get out there and do it.

Brian: Yes. People might decline, but always offers. And a lot of people have made a lot of money this year. Unfortunately, the divide has got even worse, which is horrific, but a lot of people are in very good shape and are feeling very lucky.

Yeah, the video has . . . at the beginning, it was very hard, and then you had to be really sensitive to where people were at, but I wrote some scripts. Actually, if you come to this site, there’s a page “Asking in the time of a pandemic” or something. And I have a couple of scripts I wrote. I probably need to update them, but I think they’re still relevant. I introduce where we’re at and say, “I know this is a crazy time, but would you consider?”

I don’t ever want to assume for my donors that something is not doable. I always want to leave the decision in their hands.

So, if you go to the site, you’ll find them. There are a bunch of letters there, and you just grab them and make them your own.

Steven: Cool. Yeah, if you decide for the donor, then there’s no chance, but if you ask, at least there’s some chance. That makes total sense.

Here’s one from Mandy. I like this question a lot. During the board recruitment phase, is that too early to start trying to ascertain their style? Should you maybe wait for that later, maybe do it while you’re kind of listening behind the scenes? What do you think?

Brian: Again, wouldn’t it be nice to say, “Can you fill this out?” I was talking to someone from an organization, a different organization, yesterday who uses the asking styles a lot and does a really strong board recruitment job. They don’t use them literally to recruit, but they have every new board member take the assessment immediately as one of their onboarding tasks.

Most people find it fun. It is just two minutes, and they learn something about themselves and it helps you have a conversation with them.

Of course, from the questions you ask . . . I’ve also done work on this. Actually, there’s something in the book on it. So there’s a chapter on recruitment in the book, not to hawk it too much.

Steven: Go ahead.

Brian: But Chapter 11, the last chapter, is on it. I talk about in there questions you can ask potential board members that will help you understand who they are. So the questions they ask, but also the questions you can ask them, which will give you a grasp of their style, including “How do you interact in groups?” and “How would you address this issue?” Like, “We have an issue here. If you were a board member, how would you address that issue?” And you can learn a lot. Just in general, they’re great questions, but they’re asking styles related.

Steven: Nice. What about someone who feels like they can move to any of the styles at will? A couple people have asked, “I have someone on the team that is kind of a chameleon or myself.” Is that good? Do you think that maybe they should zero in on one strength, or what do you think?

Brian: Well, I think we are who we are. So I am shy and introverted. As a matter of fact, my next book is going to be on that. I’m really excited to write that book. I won’t be excited to promote it and get on screen to talk about it, but I really want to write it.

But I have learned, “Here I am. I present in front of all these gazillions of people all over. I go to all these conferences.” I’ve learned how to use different pieces and make things work, but I am still who I am.

So we all do that in life. To get through life successfully, we have to figure out how to interact in different circumstances. We need to be ourselves, but we act differently in different situations and with different people. We do that. That’s part of our personality. We have different tools, and you develop some over time.

I’ve spoken to so many executive directors who never really . . . they came from the programmatic intuitive side maybe, right? I mean, not that you can’t be analytic on the program side, but then here they were left running this organization.

I just was on a call with someone this morning from an organization that helps children with learning differences who said, “Yeah, I was a program person. I became an executive director. Now, after all these years, I’ve got the strategy and everything.” So you can learn the other piece. You can bring more of it out while still being who you are. You still are who you are.

Steven: I love it. That might be a good way to end it. We’re almost out of time. Brian, this was awesome. I knew it would be, but it exceeded even my high expectations. So thanks for doing this.

Brian: See, if I pay you enough, Steve. No, I’m joking. Anyway, always a delight being here. It was great having this wonderful, huge group today. Thank you all for the input, and thank you for being out there fundraising, especially board members.

I will close by saying it is not generally fun, even though fundraising starts with F-U-N. It is really hard work. I’d be happy if I never did it again, but we make the world a better place. Every one of you on today is helping to make the world a better place, and I am really thankful for that. And thankful for you, Steve, and Bloomerang. You’re great guys there, really great operation. Thank you.

Steven: It’s easy for us. We get to bring on the experts, and they do the hard work. It’s fun for me. I feel like I get a CFRE every week. This is awesome.

Check out Brian. Get the book, There’s a ton of resources there. I mean, we were just thinking of them as we were going along. So go there, get the scripts, get the assessment, send it to your team.

Brian: And stay safe, everyone. Hopefully a better day is coming, but . . .

Steven: Yeah. We’ll see each other soon, I’m sure, Brian. I just want to talk really quick . . .

Brian: I can’t wait.

Steven: Yeah, it won’t be long.

Great webinar next week. Our buddy Madison Gonzalez is going to talk about virtual fundraising. Madison has been blogging for us on a weekly basis for a long time, and she finally got around for a webinar. She’s awesome, and she’s here in Indy. I love the local connection as well.

But same time, same place. Next Thursday 3:00 pm. Eastern. We’re going to record it, so if you can’t make it, if you’re too busy, you’ve got something else going on, register anyway because then you’ll just get the recording as soon as it’s done.

Speaking of the recording, we recorded this one, and I’m going to email it here before dinnertime. So just be on the lookout for that. You can share this with your board and keep the knowledge going.

We’ll call it a day there. Thank you all for hanging out with us for an hour or so. Like Brian said, thanks for all you do, and stay warm, stay healthy, and hopefully we’ll talk to you again next Thursday. Bye.

Brian: Bye-bye.

Kristen Hay
Kristen Hay
Kristen Hay

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