Everyone is involved in high-stakes asks, from the executive director to the volunteer fundraiser, but asking the right questions at the right time and listening effectively to the prospective donor can be difficult. Kent Stroman recently joined us for a webinar in which he discussed ways fundraisers can become more comfortable, confident and effective when asking for donations. In case you missed it, you can watch a full replay here:

Full Transcript:

Steven: Thanks for joining us for today’s Bloomerang Webinar, “Seven
Keys to Success in High-Stakes Asking.” My name is Steven Shattuck, and I’m
the VP of Marketing here at Bloomerang, and I’ll be moderating today’s
discussion, and today I’m just really, really excited to be joined by our
very special guest today, and he’s our good friend Kent Stroman. Hey there,

Kent StromanKent: Hi, Steven.

Steven: Thanks for being here. Thanks for taking an hour out of your
day. For those of you who don’t know Kent, Kent is just a really great
speaker. He’s a published author, and he’s been in the nonprofit sector,
working since 1976. He’s been involved in teaching organizational
leadership. He’s impacted a lot of organizations with his passion for
fundraising and all the tips that he’s going to share with us today.

Since then, he’s actually launched his own consulting practice, which
is called “Stroman and Associates.” They work in fundraising, board
governance, strategic planning and leadership development. They’re just a
great organization. They’re a Bloomerang partner and they’re great friends
of ours. So, it’s really a treat to have Kent here with us. I’m really

If you don’t believe I am excited to have Kent, just ask anyone
in his office. I have been absolutely hounding them, driving them crazy,
I’m sure, trying to get Kent to join us, because his presentation is really
superb. He’s a thought leader in the industry, and everyone listening now
is really going to benefit from his teachings.

So, Kent, thanks again for joining us. It’s going to be a lot of fun.

Kent: Oh, you’re welcome Steven. I appreciate the opportunity.

Steven: So, what’s going to happen here today is Kent’s going to kick
things off. He’s got some slides to share with us. He’s going to run
through his presentation, and then, when he’s done, we’re going to jump
right into an interactive question-and-answer session, as we always do on
our webinars. So, if you hear anything that, maybe, you’d like explained
further, elaborated on, or any general questions for Kent, please feel free
to send those over through the chat window, right there on your webinar
screen. I’ll see those and I’ll be fielding those to can’t during the Q&A

So, you’ve got a leading expert here in fundraising, for the next
hour. Please take advantage of it. Ask away, and we’ll try to get to as
many questions as we can, before the 2:00 hour. So, I’m not going to take
any more time away. Kent, I’m going to hand it off to you to get us

Kent: Well, thanks Steve, and, again, I appreciate the opportunity to
connect with your audience, and thank you for that nice introduction.

As we get started today, again, our topic is “Seven Keys to Success
in High-Stakes Asking,” and our focus, really, is on fundraising and what
we would call “major gifts fundraising,” but, as we go along, I would just
encourage everyone to think beyond that. All of us are involved in high-
stakes asking, and take just a moment.

When you think about high-stakes decision, what comes to mind? Maybe
just pause and jot some notes down. I will tell you that when I think of
high-stakes decisions, certainly, the giving of gifts is big. I will tell
you that yesterday I received a request, which, for me, was kind of a high-
stakes ask. I was invited to chair the governance committee for a board
that I serve on. It may not seem like high-stakes, but, if I’m going to do
it, it’s going to be something that I’ll take seriously.

Other things that come to my mind would include asking for a job,
perhaps asking for a promotion, a raise, a new career opportunity, maybe an
opportunity of any kind. Here’s another one. How about asking for someone’s
hand in marriage.

But as you think about a decision that has big consequences – it
could be any number of things, and, so, like I said earlier, we’ll get,
primarily, focusing around the idea of fundraising, but, when were involved
in high-stakes asks, my suggestion is that, first of all, we begin by
answering the question “why?”

[Inaudible 06:03] decision, one that has high-stakes behind it, and
think about the “why” behind your organization. What is your purpose? Why
does your charitable organization exist? As you think about that, I was
encouraged that we put a name and a face on the mission. If you can convey
to your audience the heart of your mission or the core, who it is we serve,
how their life is different as a result of our work, our mission, our
ministry, what have you, that’s the “why.”

When I think about my own situation . . . I’m going to just share
something that’s a little bit of a personal nature, but I’m going to share
with you my “why.” So, you probably saw on the earlier slide that my
purpose in life is to equip, inspire and encourage peer that’s a big part
of the “why” of my life. That’s my purpose.

Then you see my passion, and I do have passion for high-impact
fundraising, not just getting by, and, so many times, the organizations
that we encounter, their definition of success is kind of doing what we did
last year, maybe a little bit better, one, two, three, maybe five percent
increase, my passion is really for high impact fundraising, and the
definition that I would put behind that is one where – after a gift is
made, that there’s a celebration on the part of the one who’s giving and of
those who are receiving. So, that’s my passion.

My vision is to equip the next two generations of fundraisers for
true success, and, by fundraisers, I mean both professionals and
volunteers. I’d be interested to know if those who are online today – right
now, I see there’s 114 attendees – would be interested to know how many are
professionals, do this for a living, how many are fundraisers – excuse me,
how many are volunteers. I guess all volunteers, maybe, are fundraisers.
Put that together. But that is just a glimpse into my “why.”

But by understanding my own “why,” or, in your situation,
understanding your “why,” puts us in a position, really, to communicate
effectively when the stakes are high and when it’s time for a major

So, let’s move on then to tip number two or key number two, and that
is, when we are doing high-stakes asking, adopt a process that works, and
there are a lot of different processes that can be used, but, for whatever
the decision is, I find it helpful for us to define a path between the
beginning and the end.

So, we think about the alphabet. How do we get from A to Z? Well,
fortunately, at school, each of us learned the alphabet, the little song
that goes with it. I’m going to be merciful and not sing that song to you,
but, when you think about that sequence, is there a process that you have
that helps serve your interests and the interests of those that you’re
approaching in fundraising, a process that really works?

I’m just going to share an example of something that’s been very
effective in our work. We call it “The 10-Step Staircase,” and, if you’ll
notice at the top, there’s a door at the top of the stairs. It’s marked
“Yes,” and, in fundraising, of course, we want to see that “Yes” door open.

On step number 10, you’ll see it’s identified “Asking,” and yet there
are nine steps that perceive that. So, picture yourself with me, if you
would, at the foot of those stairs, in the stairway, wanting to get through
the “Yes” door. Now, if we were in person, you would make an immediate
recognition that my legs are longer than a normal person. I can take steps
to, maybe three at a time. If I really take a run at it, I might get four
steps at a time, but, no matter how big a step is, I can’t get through that
with only one step, and that’s the way that I find that it works, also, in
major gifts fundraising. It takes more than one step for us, with our
perspective donor, to get from nowhere to somewhere.

So, we’ve broken these 10 steps down, as you can see, “Getting
Acquainted.” I’m introducing the project on step two. On step three it
says, “Were asking about giving.” Step four: “Asking about Purpose.” Five
is “Asking about Form,” and then six, that’s a big one: “Asking about
Amount,” and, by the way, we believe that the answer to all these questions
belongs to the donor, not to the fundraiser.

So, in our approach, with our philosophy, we never show up and say,
“Hi, we’ve decided that you should give a gift of X.” Rather, I want to
engage the donor in that process and ask them, “What’s your definition of
success for this? Where can you see yourself being involved?”

Then, we move on up to step number seven, where were asking about
timing, and then on eight, naming, if that’s appropriate, and on step
number nine, deciding, how do you go about deciding on something like this?
Then, at stop number 10, were actually asking for the gift.

Now, the point in all this is that we have a process, and, when
there’s a process in place, number one, it helps me know what I should
expect, expect of myself, and, secondly, it helps us to be able to assist
donors as they make their decisions, by giving them an idea of what they
should expect, and, actually, that kind of ties into what I’m going to
point out as step number three, and that is to learn how to ask.

Once you identify a process, even if it’s the one I just pointed out,
it’s one thing to see somebody else’s process, but, whatever you choose,
make it your own. Let it kind of belong to you, be comfortable for you. So,
that’s really a lot of what key number three is about, when we talk about
“Learn how to ask.”

We’re asking for a decision. So, if you’re going to be effective in
learning how, in my experience, it’s essential that you would equip
yourself by someone outside yourself. Now, I don’t know about you. Some
people are identified as “fast learners.” Some are slow learners, and then
there’s some others that, maybe, just aren’t learners at all. Those people,
I don’t think, are on the phone today, but, whether fast or slow, the
assistance of somebody else in the training and equipping process is

I want to commend all – let’s see – 128 now, all 128 people who are
on today’s webinar. I want to commend each of you for taking the time and
making the investment to enhance your asking abilities.

Let me just give an example, again, of a way to equip yourself to
learn how to ask, and you see on the screen there, the Institute for
Conversational Fundraising, and you can see what our mission is: Equipping
leaders to dramatically transform there fundraising results.

[There are] varieties of ways through which we do that, but, I will
tell you, the most impactful is shown on the right-hand side there. It’s
the Asking Academy, and this is a very in-depth program. It spans five
months, but right at the core is a very in-depth, on-site, person-to-
person, what we call “The Summit,” where we’re not only learning about what
to do, but we’re actually doing it. We’re practicing. We’re getting
evaluation from others.

So, when you think about learning how to ask, this is just another
example of some of the kinds of tools that are out there, where people who
have accomplished and created success in their own life are able to share
and learn from each other.

So, let’s move on, now, to key number four, and find that we can be
more effective with asking if we will practice not asking, not asking for
the decision. Now, there’s a time to ask and there’s a time to not ask. One
of the problems that many fundraisers encounter, who talk to me, is all
they know how to do is ask for gifts, and, if all we do is ask for gifts,
we are, unfortunately, not equipping those who we would serve, with the
opportunity to have input into the process.

And I’m going to just share this saying. I’m sure many of you and
fundraising have heard this before – “The longer I live, the more on-target
I believe this is,” and the [saying] goes, “If you want advice, ask for
money, but, if you want money, ask for advice.”

Now, perhaps you’ve had the experience that I have. I walked up to
somebody and I say, “Hi. My name is Kent. I work for XYZ Charity. We don’t
have any money. You do. Can we have it?” So, all of a sudden, I’ve asked
for money, and, immediately, the response I get is, “Well, I’ll tell you
what young man . . . ” Well, guess nobody says “young man” anymore. ” . . .
but I’ll tell you what,” and they go on to give me some advice. It may be
advice that I was looking for, maybe advice that I would never have asked

So, we ask for money and we get advice, and, yet, on the other side
of that equation is, if you want money, ask for advice. So, what kind of
advice do we ask for? These are examples of not asking for a gift. So, I
will ask for advice along these lines: “We’ve envisioned a major capital
fundraising project. You’ve supported us in the past. You’ve been very
engaged, not only financially, but also by sharing your thoughts and your
input. This is another one of those times when I would love to hear your
thoughts with regards to our plans, so that, as we refine them going
forward, we’ll have the benefit of the thinking of someone who’s outside
our organization, outside the boardroom, what have you.” Great example of
asking for advice.

And the neat thing that happens when we do that is the advice giver,
in essence, gets up off of their side of the table, walks around to our
side of the table and, essentially, they join our team. So, as is the case
with each of those nine steps, “before asking,” on the staircase, we’re
practicing not asking for a gift or not asking for a decision.

Another example of not asking for a decision is what we use with
every major ask in fundraising, a very simple gift proposal. So, one of the
ways that we don’t ask for gifts is, early on, during those cultivation
visits, the “get acquainted” or advice visits – one of the things I want to
ask early on is, “May I have your permission to prepare a gift proposal
that would be exactly right for you?” Then I’ll follow that up by saying,
“What I’d love to do is to engage you in dialogue about the project to the
point that, when I do have a gift proposal, it’s one that would be shaped
by you as a result of your input. So, I want to understand what your
priorities and preferences are, where this fits in your overall scheme of
things.” So, again, this is an example of not asking for gift.

So, we have, in that sense, reserved the right to ask later, which
allows us to simply discuss, converse, before hand, so that when it is time
to do the [inaudible 19:54] asking, we [inaudible 19:56] on a very
intentional and well-informed basis.

So, key number four is to practice not asking for the decisions. Now,
with that, I’m going to go on to . . . This is familiar. Right? We just
looked at the 10 Step Staircase earlier, but, again, I just want to
underscore that there are nine steps on here that are steps for not asking
for the decision. They’re asking about input that would go into that

The key, in order for this to be effective, is we have to be sincere,
and one of the things that I would just – I would request, and that is, if
you can’t be sincere in asking for advice and asking for feedback and
eventually be sincere in asking for a gift, there really is no room, in our
profession, for insincerity. So, if you can’t do that, please find a job in
some other sector. I’m sure there will be a place for you there.

So, with that, let’s move on to number five, and on this – we call it
“Put Time on Your Side.” So, the question is, when it comes to high-stakes
asking, how much time do we have in order to get to a “yes” decision?

Let me share a story from my adolescence. I was in a hurry. I wanted
to borrow my dad’s car, because I had a date on Friday evening, and I was
just thinking how impressive it would be if I showed up in the family car
instead of my 1951 Chevy sedan. So, actually, I had never borrowed my dad’s
car before, and I don’t know if I’d even had a date before. So, it was kind
of a big deal for me.

So, it was Monday night. My dad was watching Monday Night Football,
which he loved to do, and I was sitting there in the living room on another
chair watching him watch football and trying to summon the courage, within
me, to ask him, “Could I borrow the family car?” So, I sat and I watched
him watch the football game, and, back in those days, there wasn’t the kind
of remote control that we have today. Actually, I was the remote control.
He would say, “Kent, change the channel.” So, I go up and twist, changing
from one channel to the next. Fortunately, there were only three options,
so that didn’t take long.

If the sound was too soft or too loud, I was the remote. I’d get up
and twist the dial for the sound control. If necessary, [I] might even need
to adjust the rabbit ears on top or move the aluminum foil around to catch
the signal a little bit better.

So, I waited, and finally a commercial came along, an advertisement,
and, so, I jumped in with both feet and I asked my dad, “Could I borrow the
car Friday night?” Well, I think the question probably took him as much by
surprise as I would have expected, but it switched back to the football
game and he didn’t respond. So, I waited and I waited and I waited. Pretty
soon, another commercial came on. So, I said, “How about it? Can I borrow
the car?”

My dad turned and he said to me, Kent, how soon do you need a
decision? If you have to know right now, I could give you a quick
decision.” Well, there was something about the way he asked the question
that gave me a clue that if I had to press too hard, too fast, that I could
quickly get a “no.” So, I thought about it little bit longer, and on the
next commercial I said, “You know, I’ve got as much time as you need in
order to get to ‘yes.'”

So, I want to suggest that, when it comes to fundraising, if we’re in
a big hurry, that we should anticipate either no answers to our gift
proposals or to hear “yes” at minimal levels. So, in order for us to be
effective and put time on our side, there are two risks that we want to
avoid, and I call these, number one, “the risk of early rejection” and,
number two, “the risk of early acceptance.”

So, what is early rejection? Early rejection is where, again,
prematurely, you’re introduced to someone. We ask for a gift, and it’s easy
for them simply to say “no.” We’ve asked. They responded, and we’re done
and they’re done. We hear “no” because they haven’t come to a place where
they’re prepared to just say “yes.” So, one of the risks that we want to
avoid is the risk of early rejection.

Risk number two is the risk of early acceptance, and that’s one where
we make the ask too early and they say “yes” to early. “Sure. Here’s a
check. Here’s $1000,” and we think, “My goodness. They could easily have
given $100,000, perhaps $1 million, but they wrote us a check for $1000.”
Well, tell me this, if a prospect with that capacity has given at that – in
response to our request, how soon could we go back and ask for the rest of
the zeros? I’m going to say not soon at all and not easily. That would
require a great deal of delicacy in order to do that anytime.

So, the antidote, if you would, for these two risks, early rejection
and early acceptance, is to find out the end of this question: when is the
right time for you to make a gift of major importance? It’s a high-stakes
ask, a high-stakes decision. Let’s let the decider advise us when the right
time is, and, by doing that, we avoid the peril of either one of these two

So, the companion that I would put with that is, never ask [inaudible
26:47] of your prospective funder for which are not prepared to receive
either response. If we had time, and perhaps we can do this on some other
occasion, talk through the kinds of questions that we would be asked on
each of the steps going up the staircase, but, when we understand the
timing for the donor or the timing for the decider, it will help us know
when the right time is that we should be asking.

So, key number five, put time on your side. Is the decision urgent?
Is it important? Is the timeline in line for the person for whom were

So, let’s move on now, if we could, and that is to go to key number
six, and we think about Seven Keys to Success in High-Stakes Asking we want
[inaudible 27:47] the barriers. What are the barriers to high-stakes
asking? Well, over the last – let’s see – not last year, but the two years
before that, I had the opportunity in a variety of – all across the
country, to ask fundraising leaders this question, the question you see on
your screen, “What is your biggest obstacle to success in one-on-one
fundraising?” [It’s] kind of open-ended, but I was very interested to hear
the variety of responses that might come from that.

What is your biggest obstacle to successful one-on-one fundraising?
So, over a period of two years, I got responses to that question from 456
fundraisers, some volunteers, some professional staff, and, as you can see,
they couldn’t all give me only one answer to the question. Those 456 people
provided 582 responses, and we boiled those responses down into the 33
categories, actually 34, if you include the favorite, which is called
“miscellaneous,” but I will tell you that those categories surprised me,
and let me just share those with you briefly.

As you look at the screen, you will see how that breaks out, and, in
fact, if you want to see a more in-depth discussion of these obstacles, and
not just the obstacle, but the solutions that pair with them, a big part of
this is included in the second edition of my book, which just came out last
month, and the title of the book is “Asking about Asking: Mastering the Art
of Conversational Fundraising.” In the book, you’ll see, again, the
categories that are on your screen right now.

I’ll tell you what I expected. From earlier response, expected that
the No. 1 category was going to be “fear,” and it ranks quite high, but
you’ll notice that there are three obstacles that were rated even than
fear. One has to do with time. Another one has to do with prospect
identification, but the No. 1 obstacle to fundraising, as you can see at
the very top, is what’s called “Difficulty Getting in,” answering the
question, “How can I connect with people that I’m not either already
connected with or that are busy enough that it’s easy for them to say ‘no,’
when I reach out to them for a cultivation visit or a solicitation visit?”

So, here’s what I want to say first of all, whatever your obstacle
is, you could rest in confidence that you are not alone. You’re a great
company, and you can see any number of obstacles that your peers, your
colleagues, face, and, so, don’t let your circumstance feel like you’re the
only one, but the fact that you’re not alone, they’re still an obstacle.
So, the question is, how are we going to deal with those obstacles?

A couple of the ones that I just want to mention, in particular . . .
I’m just going to hand pick five of them from the top end of the scale. One
is – and this is a big one – it’s called “relationship deficit,” and we
have a relationship any time – excuse me – we have a relationship deficit
when there’s not enough relational capital built up to carry a
conversation, a contact or an appointment.

What’s an example of that? Let’s say there’s someone who is a
philanthropic individual. They’re known throughout the community as being
generous and passionate about various charitable causes. So, we come up
with the idea, perhaps they could, should, might, support our charitable
initiative. Somebody says, “Well, why don’t you go call on them?” All of a
sudden I think, “You know, I don’t know them and they don’t know me.” Well,
that’s an example of a relationship deficit, and whether I’m in a
professional capacity or a volunteer role, I have nowhere to go.

In fact, just yesterday I was working with a very – what do I want to
say – a group of fundraisers who are very dedicated to expanding their
skills, and we [started talking] about some ways that we can create
relationships, even before they’re needed. In fact, it reminds me of a
quote that I heard recently, attribute it to a man, and he said – he
described someone as a person who dug a well before they needed water.
Well, if we wait until we need water and start digging a well, we’re going
to get thirsty and say that way for a long, long time. And I’m going to say
the same thing happens in our relationships. If we wait too create a
relationship until we need to ask someone to assist us with something,
we’re going to be far behind the time.

That’s one of the obstacles I wanted to mention, relationship
deficit, and let me encourage each of us, as fundraisers, as volunteers and
as individuals involved in various walks of life, be intentional about your
relationships. Look for ways to meet people that you don’t already know.
Allow others the opportunity to get to know you. Put that “know, like and
trust” factor on your side. People want to do business with people they
know and they like and they trust.

So, if you aren’t known, you can’t be liked and you won’t be trusted.
So, intentionally building up your relationships.

The second one I want to mention is conflicting priorities, and
that’s a big area of obstacle. One of the things that surprised me when
that popped up was that, often times, the conflicting priorities that are
inhibitors to major gifts fundraising exist inside the organization. So,
we’ve got one person raising money for scholarships, someone else raising
money for the new athletic stadium, somebody else raising money for the
classroom building, and those conflicts of priorities get magnified when we
push them out into the philanthropic marketplace – a huge obstacle.

Here’s obstacle number three, and it’s mindset. I wish we had time to
fully exhaust this one, but mindset, as an obstacle to fundraising, in
essence, boils down to this: it’s a predetermined conviction that someone
couldn’t, wouldn’t, shouldn’t support our project. So, I go out to my
friend Elizabeth and I’m going to ask her for a contribution, and I
approach it from the standpoint, “Elizabeth, you wouldn’t want to support
our project with a gift, would you?” and, immediately, her head is shaking
“no.” She’s simply agreeing with me.

Well, usually, we don’t come right out and say it that way, but
either we don’t have a conviction or passion in favor of the project or we
constrain ourselves. We don’t reveal that passion. So, our mindset, in and
of itself, becomes a detriment.

One of the [things] we can do in this area is what we mentioned
before, and that’s to put a name and a face on the mission, and, as we do,
then it gives us an opportunity to share that with someone else, talk about
the circumstances – the unfortunate circumstances that exist before we come
to the party, how we serve people in the and how their life is different as
a result. When we do that, we’re able to share a positive mindset, and it
will be easy for others to kind of get on board with whatever the project

The fourth one I’ll mention is fear, and I touched on that before,
but, essentially, we’re either fearing failure, fearing rejection, fearing
that were going to hear the word “no,” and one of the best ways that we
have to deal with fear is to, A, get out of the business of asking
questions that generate fear. So, rather than just showing up and jumping
to step 10, asking for a generous contribution, instead, we want to ask
people if they have an interest in what we’re interested in. If they don’t,
let’s bless them and send them on their way, perhaps even help them find
projects, priorities, that do fit their preferences. My experience has
been, if we pursue a relationship, rather than pursuing a transaction, it
will almost automatically remove the fear, in and of itself.

Then, number five, which I mentioned earlier, that’s difficulty
getting in, and, probably, the No.1 tip that we could give, as it relates
to overcoming an obstacle, is to engage others in the process. We recommend
always using a call team that consists of the CEO of the organization and
then someone who is in a peer role with the prospective giver.

So, as a fundraiser, if I’m asking somebody to come to a Cultivation
Lunch, that invitation is going to come across very differently than if
this is a business and more peer relationship, where the invitations
coming, and the CEO is going to join us. The whole topic of difficulty
getting in is almost inexhaustible, but, hopefully, you get the idea of
some of the examples that go with that.

So, again, just to recap, we’ve said that we want to bulldoze the
barriers. Identify the barriers that stand between you and success in high-
stakes asking. Once you identify it, come up with a strategy for removing
that obstacle, and, if you ever feel like you’re stuck, I’ll just share
this quote with you, and that is “Wherever you are, your location becomes
your destination only if you stop moving.” So, don’t stop moving. Again, I
commend you for being involved with that – professional development
opportunities like you are today.

And here is key number seven, and that is to celebrate your success.
Too often, I encounter people – they work hard, they achieve success, and
then they ignore it and go on to working hard. When there is a successful
conclusion, celebrate it. Give yourself permission to feel good about
“yes.” You’ve worked hard. Your donor has placed themselves in the process.
They’ve invested energy and time, as well as money. Let’s find an
appropriate way to celebrate the results.

Let me just tell you that, yesterday afternoon, a client [inaudible
40:22] and I wasn’t able to take the call. So, they left a message, which I
was thrilled to receive, and that is that they had made a solicitation call
earlier this week, and the result was they received a gift commitment,
which will span several years, but it’s $1.6 million. Now, I haven’t seen
or heard the party yet that goes with that, but I think it’s time for
celebration. Wouldn’t you agree?

So, celebrate your success. Give yourself permission to feel good
about “yes,” and here’s another reminder. You’ve all heard the story of the
turtle on a fence post, and there’s a quote that says, “Anytime you see a
turtle on top of a fence post, you know he had some help getting there,”
and whenever we see success in our fundraising efforts, it’s never a single-
handed thing.

I don’t know if Steven mentioned this, but I have a background in
higher education, and I was in a university setting for 25 years. When we
received those large gifts, and when there was time for celebration, I
always look for an opportunity to incorporate the faculty and other staff
members, the administration, into that, because the only way that someone
would make a contribution to an institution of higher learning is if they
have confidence that what’s taking place in the classroom is effective,
that it’s worthy, and that can only happen by the dedication of the

So, again, have that celebration. Realize you may be sitting on top
of the fence post, but you didn’t put yourself there. It took a lot of
other resources to get you to that particular point. So, celebrate. Don’t
do it alone.

As we wrap up the . . . What should I call this? The monologue part
of today’s webinar? I want to share my top tip, and that is “Just ask.” I
think a lot of times it’s easy for us to become paralyzed. We’re going to
wait until everything is perfectly in place and then we’ll make our
request. Well, let me give you a simple mathematical formula here. First of
all, start off with a healthy degree of curiosity, and, then, add to that
some good old-fashioned courage, and the result will be a bold ask, a bold

So, whatever that high-stakes decision is, let me just give you this
encouragement, if you would, a thumb in the back, “Just ask.”

As we wrap up, I just want to share this thought, and that is that,
in essence, all of us are leading from some role – we’re raising funds in
some type of leadership role, and I want to just circle back around to what
I mentioned earlier, and that is that the second edition, recently
released, “Asking About Asking,” if you don’t already have the book, get
one. They’re available at Amazon, at Barnes & Noble or from the publisher
at Charity Channel, and consider maybe equipping those around you, other
staff members, board members, other volunteers, providing them with their
own copy.

So, as we wrap up, I want to encourage you to identify one thing,
just one at least one thing, that we touched on today that you would say,
“This is something I could put to work in my own life, in my own fund-
raising activity. This is something I could do even today,” and take that
one thing, put it to work and allow it to work for you.

As a wrap up to my comments, I just want to share this as a matter of
perspective, and that is that people are more important than ideas. Be
attentive to your people. Ideas are more important than things. Don’t let
things take the wrong place in your priorities. Things are more important,
I think, that nothing, and nothing is more important than love.

So, as you go out in your work, in your life, let love guide you in
your activities, and, with that, I want to say a big “thank you,” and then
Steven, I think, you’re going to field some questions for us.

Steven: Yes. Thank you, Kent. You shared – I mean, you just shared
incredible knowledge with everyone listening. That was a great
presentation. Thanks so much.

Kent: You’re welcome.

Steven: Yes. We’ve got about 10 minutes left for Q&A. I know there were
some questions that came through while Kent was presenting, but if you
were, maybe, waiting on a question or trying to think of something, please
don’t be shy about sending those through the chat box, there. We’ll answer
as many as we can, over the next 10 or 12 minutes.

Like I said before, we’ve got Kent on the line. He is a renowned
expert. Don’t let this opportunity go by. Ask him anything, and we’ll share
some of his knowledge with you, but, Kent, I’m just going to roll through
some questions that have already been asked, . . .

Kent: Okay.

Steven: . . . to get started, and I think that tips number three and
four really got people’s juices flowing. Kelly here was asking, “At what
point in the process do you not ask?” So, when you ask for the advice? Do
you set a first meeting with a potential donor, to ask for that advice, nor
does that come in later meetings? What’s kind of the chronology look like,
you know, when you attempt to do that?

Kent: Yes. So, good question, and that was Kelly, right?

Steven: Yes. Kelly.

Kent: So, here’s what I would say about that, Kelly. First of all, the
learning how to not ask is how to not ask for the decision and, in this
case, not ask for the gift. So, essentially, step 10 is asking for the
gift. Everything leading up to that is not asking for the gift, but it is
asking – it’s asking for advice, for input, for insight. So, all along the
way, you’re going to be asking. You’re just not going to be asking, “Can I
have a check?”

I will tell you that in that process, one of my favorite questions
actually occurs on . . . This is so small I can’t read it. I think it’s on
step number four, but it’s asking about purpose, and one of the questions I
love to ask is, “What would you like your gift to accomplish?” So, I’m not
asking for a gift, but I’m asking about a gift, and when I ask a question
like that, the answer that I hear almost always reveals the soul of the
giver, and once I can get a glimpse into the soul of the giver, it makes
all the difference in the world in how and when that we ask for the gift.

Steven: I absolutely love those guiding questions that you’ve been
suggesting, “What would you like to give to do?” and “When would be a good
time to give?” Those are awesome guiding questions that hopefully people
will start using [inaudible 47:49] been listening.

But we’ve got another question. It came from Angela, and, literally,
as soon as she typed it out, I was thinking the exact same question. She
asked, “What clues do you look for when you’re trying to decide when the
right time to ask?” So, you are a higher ed fundraiser for 25 years. I’m
sure you took a lot of meetings. Was there ever an instance where you were
in a meeting and you were talking to the potential donor and you can kind
of tell that, maybe, this was not the right time or this was the right time
to ask? What were those sort of clues from the other [inaudible 48:28] . .

Kent: Yes.

Steven: . . . if any?

Kent: Okay. So, Angela, that’s a really good question, and, in responding
to it, I have to tell you this – I’ve come to be very suspicious of my
detection of clues, and, Steven, the way you laughed, I think you must have
some similar experience.

Steven: Oh, yes. Absolutely.

Kent: Almost any time I respond to a clue, I’m more likely to misinterpret
then to correctly interpret. So, yes, we want to be actively listening,
but, rather than acting on clues, what I’m going to do is ask about clues.
So, for example – I’ll give you a real life response to that – I was
working with a gentleman who, for a variety of reasons, it was crucial that
he make his gift commitment to a major campaign that we were involved in.
So, [inaudible 49:30] some urgency behind this.

He says, “Well . . . ” This was a conversation taking place in
January. He said, “I can’t make my pledge until after I get with my tax
guy. It was his words “my tax guy.” Now, keep in mind, I’m a CPA. I kind of
have a little bit of understanding of this tax scenario. This was in
January. So, I was immediately inclined to take that clue and interpret it
and come up with an answer for him. The question is “when?”

Now, if you were to hear a comment like that, what would that mean to
you? Naturally, I would think, “Well, he’s talking about tax guy, April
15th, but I just asked. His name was John. So, I said, “John, I’ve got to
ask, when you say ‘get with your tax guy,’ are you one of those early
filers, one of those overachievers that, at the end of February – or excuse
me – end of January, 1st of February, you’re going to be getting with your
tax guy, or are you going to do it on schedule, sometime around the middle
of April, or are you going to file an extension and get with your tax guy
about 10 months from now?”

Of course, we chuckled a little bit about that, made it a playful
inquiry, but he went on to say, “You know, will be getting together
sometime late March, early April.” So, I want to listen for clues, but then
ask for confirmation, and probably the most blatant ask, if you would, is
at the – on that step – I think it’s step number seven, where were asking
about timing, and the way that I like ask that question is, “John, Louise,
but we’re talking about here sounds like a major decision for a gift of
this magnitude. When would be the right time for you to make that kind of
decision?” and then let them answer it and respond to their timetable,
rather than superimposing our timetable on them.

Steven: Maybe not rush to interpret those signals, but maybe just ask
the question. That’s pretty good advice.

Kent: Thank you.

Steven: We got about five minutes more for questions. I got a couple
here. Phil was wondering, “Is there a rule of thumb on how to determine the
size of a gift?” and I know you talked about not asking too early and
possibly shortchanging yourself, but how do you decide how many zeros to
add onto the end of that amount, you know, to use your words?

Kent: Phil, I love your question, and, to me, the question about amount and
what amount to ask for, I think, is a prime example of a mistake that we
make, and that is the believe that we should answer that question. I know
that there’s a prevailing philosophy in the fundraising profession that
says we should show up and decide in advance, “Are we asking him for
$100,000, $1 million, $10 million?” I believe that’s a big mistake. I think
it’s the wrong person answering the questions.

So, in response to your question, we always work with a gift chart,
and, regardless of the size of the project, you know, whether you’re
raising $1000 for support your mission trip, personally, or whether you’re
raising $100 million for the major capital campaign, I believe it’s
essential for us to have a gift chart for a couple of reasons. The first
one is so that we know what we’re looking for. Is the top gift that’s
necessary to make our project successful – is it $1000, $10,000, $100,000,
$1 million? What is it?

So, number-one, it’s valuable to us so that it helps us to know what
were looking for. Number-two, it’s valuable for the prospects, for the
donors, so that they know what we’re looking for. So, once we have that
gift chart, I share that with every high-stakes decider that I’m visiting

I’m just going to use the example of $10 million. If were seeking to
raise $10 million, I’ll put that gift chart in front of them and say
something like this: “We realize that if we’re going to succeed in a
project of this magnitude, it’s going to result from a very small number of
very large gifts and a large number of gifts that are smaller.” At the top
of that chart, we’re going to have a gift that’s someplace in the 1.5-$2
million range, and by sharing the gift chart it helps define, for the
giver, what we’re looking for. So, I’ll follow that up with a question:
“What range of gifts should we be talking about at the appropriate time?”
Then, that’s going to allow them to identify a range, and, within that
range, then I’m going to ask this question, “How will you decide?”

So, again, back your question, Phil, rule of thumb how to determine
the size, and that is determine the size of gifts that the project requires
to succeed, and then put that solution in front of our donors and let them
tell us what they want to be asked for.

Steven: Great. Great. We got about five minutes left. I think we’ll
take maybe one or two more questions. I know we’re not going to get to all
of them. We’re going to share some Kent’s contact info. He’s pretty active
on social media, and I’m sure he wouldn’t mind answering any questions that
we didn’t get to.

We got a question here from Aaron, and Aaron is wondering, “How can
you pose a time-sensitive ask to someone who seems perpetually busy?” So,
maybe you get that meeting and you know you’re not going to get another
shot at this person ever again, how would you deal with that issue, Kent?
Somebody that’s maybe crunch for time and you got one chance to ask and
that’s it, what would you in that kind of situation?

Kent: Okay. Excellent. So, Aaron, I appreciate your question, and the thing
that I’m going to do first is gravitate back towards the most highly
effective approach, which is a written gift proposal. So, if I think I have
only one meeting, the question that I’m going to ask early on is that same
question we said earlier, “May I have your permission to prepare a gift
proposal that’s exactly right for you?” and, if they say, “Well, that’s why
wanted to meet with you today,” then I better have done some preparation
with that in mind, and, frankly, we work with a very compact outline of
gift proposals that, if necessary, you’re going to fill in about six blanks
and you’re going to have that proposal.

So, you may have to do that on the fly, but I’m still going to ask,
“May I get you a proposal?” In my experience, almost always, they’re
willing to say, “Yes, but I need it right away.” So, I’ll just ask, “What
is ‘right away’? Were you talking later today, by the end of the week? What
do you mean by ‘later’?

But, if they insist, you know, you’ve got an audience with him right
now, I don’t have time for another meeting, I’m not going to open your next
email, then I’m going to have, in my pocket, and outline that has enough of
the basics that I can take a pen and, as we visit, fill in the amount, fill
in the timeline and so forth, and put that in front of them.

The reason the written gift proposal is so important is it tells
everybody what it is that we’re agreeing or disagreeing around, and so many
times that’s missing.

Another thing I would just share is – and, Steven, you’ve done a
great job of maximizing of time. We obviously have a time limit, but I
would invite your attendees to visit KentStroman.com or
ConversationalFundraising.com, and there’s a platform there were we can
dialogue further. If you have questions, feel free to contact me and I’ll
be happy to respond to them.

Steven: Yes. Great, and I’ll return that complement to you, Kent. You
actually answered a question, two questions, with that one answer. So, good
job by you there. That was nicely done.

Yes. That was great. I know we’re approaching the 2:00 hour, and I
want to be respectful of Kent’s time and all the listeners. I know we could
probably spend for five hours talking about this stuff. I know I could. I’m
sure Kent could as well, but we do want to wrap things up.

Just so everyone knows, Kent’s contact info is there on the screen.
Reach out to him. Check out his website. There’s a lot of good resources
there. Check out his book. I know that’s a great read. That comes highly
recommended by a lot of our friends and partners, as well.

And, Kent, I’ll give you the final word here, if you want to tell
folks any additional information about how they can find out about you. I
know you mentioned the Institute in the Asking Academy in your website, but
any additional tips for reaching out to you?

Kent: The only thing I would say, and I’m kind of embarrassed now as I look
at slide that you have on the screen, which I gave you – is that doesn’t
include the most recent addition in contact, which is KentStroman.com. So,
feel free to use any of those other avenues or go straight to my personal
website and blog, and I would love to connect through any of those avenues.

Steven: Great. Well, thanks Kent. That was great. We’ve got a lot of
positive feedback in the chat room. Hopefully, all you folks enjoyed this
as much as I did. I certainly learned a lot.

As you exit the webinar today, you’re going to be sent to a little
survey. Please share your thoughts with me. I’ll get those results. I’m
always looking to improve the Bloomerang Webinar here. So, don’t be shy.
You won’t hurt my feelings with any comments. Let me know what you thought,
what you liked, who you didn’t like, and that will help me out a lot, as
well. So, I’ll say thanks in advance for those of you who choose to fill
that out.

We do these webinars once a week. He got an excellent slate here in
March. One I wanted to highlight really briefly is a presentation that’s a
little unique for us. It’s geared toward nonprofit consultants. It’s not
necessarily geared towards fundraisers at nonprofits but, maybe, folks who
have businesses or independent consultancies. You’re going to hear some
advice from Linda Lysakowski and Susan Schafer. They’re going to share some
of their tips from “The Nonprofit Consulting Playbook,” which actually Kent
was a contributor to. That’s also an excellent book. You can check that
out. He shared his knowledge in that book, as well.

So, if that interests you, check out that webinar. You can see all of
our other webinars – are right there on our page for March. We’re going to
be joined by Donor Search. We’re going to be joined by a CPA firm who’s
going to share some financial tips for nonprofits. So, check that out. You
might find something you’re interested in there.

Just some final housekeeping. I will be sending out Kent’s slides, as
well as a video recording of the whole presentation. So, if you wanted to,
maybe, watch it again or check out some of his slides at your leisure, you
can do that. So, look for an email from me later this afternoon, possibly
tomorrow morning, depending on how much YouTube cooperates with me. It’s
usually pretty kind to me. So, I should be able to get that out today.

So, since its 2:00, I’ll say a final thanks to Kent. Kent, this was
great. Thanks a lot for sharing an hour of your time, sharing your
knowledge. It was a lot of fun.

Kent: You’re welcome. You made it easy, Steven. Thank you.

Steven: All right, and thanks to all of you who joined us, who took an
hour out of your day, and we’ll talk you soon. So, thanks again. Have a
great afternoon and a great week.

Major gift fundraising

Kristen Hay

Kristen Hay

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