Winning words for raising money

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Jossey-Bass Short Format Series
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Other Titles by Laura Fredricks
The Ask: How to Ask for Support for Your Nonprofit Cause,
Creative Project, or Business Venture, Updated and Expanded
Edition

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Copyright © 2013 by Laura Fredricks, JD. All rights reserved.
Published by Jossey-Bass
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first edition

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Contents

Introduction

1

The Five-Step Process
1

Step One: Know Exactly What You Want

2

Step Two: Prepare Your Conversation

13

3

Step Three: Deliver With Confidence

19

4

Step Four: Clarify the Response

27

5

Step Five: Plan Your Next Move

35

Conclusion
About the Author

5

41

43

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Introduction

S

electing the right words and delivering them at the right

time puts you on the runway, ready to take off and raise
money. I share this with you because in all my years of traveling nationally and internationally, doing what I love most—
training people and businesses to ask for what they need and
deserve—I have noticed that many people do not actually ask
for money, because they are searching for the perfect words
to use that will convince and persuade someone to give them
money for whatever they need. They tell me their own words
sound shallow, trite, and scripted. In searching for an easy and
quick way to raise money, they ask me to share the perfect asking words, or they ask whether they can borrow the language
that other successful fundraisers use to get money.
I focused on these challenges for quite some time, which
motivated me to write this piece. It is also a logical extension—
“the next chapter,” as Oprah would put it—of my last book,
The ASK: How to Ask for Support for Your Nonprofit Cause,
Creative Project, or Business Venture ( Jossey-Bass, 2010). In The
ASK I covered every aspect of asking, from analyzing your
views on money through dealing with all the responses you
will get to your ask and how to handle each one. I reference
1

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2 | Winning Words for Raising Money

The ASK throughout this piece because it can provide backup
information for certain concepts presented here. In Winning
Words I direct a laser focus on what I have discovered is crucial

to asking success: finding the right words and saying them at
the right time.
When I first started putting together the concepts for
this piece, I wondered, Why does the process of selecting the right
words come easily to me, and why do I have a passion to write about
it? Believe it or not, the answer came to me while doing my
legal credits so that I can maintain my attorney license. Yes, it
is true, and here’s the story. The years I spent writing appellate court decisions, dissecting depositions, cross-examining
witnesses by breaking apart their testimony, and then carefully choosing the most persuasive words I could use in my
designated twelve minutes of oral argument (facing a timer
with a flashing green, then amber, then red light) before the
3rd Circuit Court of Appeals—all of these gave me the training, discipline, patience, and, at times, “insanity” to see how
the right words can really make the difference in getting the
results you want, every time.
My sole intention with this new piece is to help thousands
of people worldwide feel positive, charged up, enthusiastic,
and empowered to find their individual asking words and their
right delivery time. The win here is for you, the reader, to put
in the time and energy in the exercises throughout this piece;
then you will have your own hand-tailored asking playbook
that you can put into action immediately. You’ll find over sixty
winning phrases you can use and ten exercises; in short, everything you need today to raise money.
Finding the right words takes concentration, presence,
and focus, because you have to take into consideration the

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Introduction | 3

words you are comfortable with as well as the words that will
resonate with the person or people you are engaging. That’s just the
first part. Next, when will you present your carefully selected
words? If you do it too soon, you may be giving away the best
part of your conversation, and then how will you keep the
focus and attention of your conversation? If you do it too late,
then you may have completely lost control of the conversation
and it will take much more work to get it back on track. If you
follow my five-step process, in order, you will have everything
you need to let the words and your own personality lead you
to success.
The emphasis throughout this piece is on finding your
words and timing them so that you can raise money. The term
“raising money” or “asking for money” that you will see in this
piece can be applied to any professional or personal need, such
as raising money for nonprofits, getting start-up funds for new
businesses and creative endeavors, and having more time off
from work—which equates to money. The examples you will
see throughout will put money in your hands, if you follow and
apply each of the five steps.
Selecting the right words at the right time to ask for
money is your new path of empowerment. Why is this so important? Among other reasons, the global recession over the past
several years has made it extremely challenging for people and
businesses to get ahead and stay ahead. People at all levels
in nonprofit and for-profit organizations—be they CEOs,
management, sales force, executive directors, development
directors, health care providers, social service workers, environmentalists, animal rights advocates, and artists—struggle
to engage their staff, donors, management, investors, customers, and clients because all too often they are speaking at, not

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4 | Winning Words for Raising Money

with their audiences. Well, that ends right here! My five-step
process will ensure that you select your right words and deliver
them at the right time so that you can raise money. I will show
you how to tailor the five steps to your particular needs so that
you can immediately apply the process to your situation. Rest
assured, I have tested this over and over again on a multitude
of diverse people and businesses internationally, and it works.
In addition to providing the structure you need to find
your own winning words, this piece is also filled with examples
of how you can apply those words through some very familiar
conversations. I am certain you have previously experienced
these situations and simply did not know what to say. I have
done the exact same thing myself.
Lastly, you will find throughout this piece some openended questions that you need to answer to ensure that your
winning words have your voice, your brand, and will reflect
your own personal style. The open-ended questions also help
you to get a better understanding of what the decision maker
is thinking so that not only can you prepare your best asking
words, but also you will know how to close the gift or deal
much sooner. How sweet is that?
So let’s take this important journey together. Watch and
see how you can get on the trajectory to greatness with your

winning words.

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1

Step One: Know Exactly
What You Want

W

henever I experience a challenge I cannot overcome or

see others struggle with a barrier to their success, I do one
thing: I create structure. This harkens back to my law school
days, because every legal issue presented a set of questions
that had to be answered before I was 100 percent convinced
I had the right legal approach. Ever since, having something
concrete, structured, and focused that I can use whenever I am
challenged gives me confidence and helps me find an immediate and rewarding solution to the challenge.
So I have created the five-step process for finding the right
words and delivering them at the right time. Think of this process as a series of boxes that you have to check off, one by one.
If you jump from box one to box three, skipping box two, you
will not have all the elements for success. The complete process is not all that time consuming, but it does take discipline
and focus—and, yes, a bit of soul-searching—to work through
each step. Although I cannot guarantee a perfect outcome each
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6 | Winning Words for Raising Money

time, you will have the satisfaction of knowing that you followed the perfect approach each time.
The first box—the first step—is to know exactly what you
want. I know what you are thinking right now: “Of course I
know what I want!” But do you know all the details of what
you want? Thus my first open-ended question for you is
“What do you want: how much, how many, how often, and why?”
This is all about quantifying the need.
Let’s take these one by one. First, how much do you want?
For fundraising, this would be the exact amount of your gift
ask. This needs to be a number, not a range, and not “more than
you gave last year.” You need to know that you want $5,000,
or $50,000, or $500,000, or $5 million for your organization.
Look at the difference between these two ask scenarios:
“We are hoping that you will continue to be such a wonderful
and generous donor this year.”
or
“We would like you to consider a special and important gift
of $50,000.”
What does being a “wonderful and generous donor” mean?
The person being asked may be thinking that she should give
whatever she gave last year, especially because the asker used
the word “continue.” Why make this a guessing game? Why

not simply state the exact amount—in this case, an “important
gift of $50,000”?
The how much can also apply to an exact number of shipments, cost of the products, level of commissions, percentage
of total revenues, or the dollar amount for a raise. So right

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Step One: Know Exactly What You Want | 7

now, write down exactly what you want for one or more asks
you would like to make.
Second, how many? Again, nothing commands a conversation more than defining the need in quantifiable terms. So
you need to answer the question: how many do you want? To
illustrate, let’s look at the difference between a general ask and
asking for a certain amount:
“I’d love to have more personal days in my job.”
or
“I’d love to have four more personal days in my job each year.”
This is all about giving the decision maker the exact picture in her mind of what it is she needs to address. Now we
know it is four days we need to consider.
Third, how often? The best way to think of this in terms
of the previous example is how often in time units you want
something. Would that be once a year? One day every quarter?
Four in the summer? Here is an example of how how often can
be nebulous—or absolutely clear:
“It would mean the world to me if I could get more vacation
time with my family.”

or
“It would mean the world to me if I could get two weeks more
vacation time with my family this year.”
Vacation time needs to be defined in quantifiable days or
weeks. I have seen the how often dropped off of many conversations because the person assumes that detail will come out

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8 | Winning Words for Raising Money

later or that the person they are speaking with will ask them
how much do they mean? Do not let these important words
fade away—or, worse, hold them back until another point in
this conversation or a later conversation.
Lastly, we have the emotional part of the equation: why?
Why do you need something? Why are you asking for it?
Why is it important to you and/or others? This is where the
soul-searching I referred to in the Introduction comes into
play. Here are two asks that illustrate how you can clarify and
quantify your why:
“Your prospective gift of $50,000 for our trauma unit will be
inspirational and will transform lives.”
or
“Your prospective gift of $50,000 for our trauma unit will be
the largest of its kind and will help meet the immediate
needs of five deserving patients for life-saving care. In
addition, it will inspire our fifteen prospective trauma unit

donors to join in your generosity by making their own
gifts.”
Here is the difference between these two asks. In the first,
we do not know the number of patients who will directly
benefit; the size of this one gift is simply “inspirational.”
In the second, we know that five patients will be served and that
the gift has leverage because there are fifteen other prospective
trauma unit donors who will be inspired to give at or near this
$50,000 level. There is a world of difference in content, message, visual image, and motivational impact between the first
version and the second, because the why is clearly defined.

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Step One: Know Exactly What You Want | 9

Do this exercise and think about why you have an immediate need for something and whether or not you can detail its
importance. If you need more personal time in your job, as in
the earlier example, you might define the why as follows:
“The four additional personal days added to my existing three
personal days a year would give me one full week off so
that I could devote the time to volunteer for my church’s
humanitarian mission in Costa Rica.”
or
“The four additional personal days would give me one day a
quarter that I could use to finish my certification so that I
can apply these skills to my job sooner.”
Now you see how answering each part of the how much,

how many, how often, and why? question will quantify and clarify
exactly what you want so you can express yourself in a new way
so that others can see and fully understand your need.
It is also worth the exercise time to decide what it is you
do not want or are unwilling to compromise. In other words,
what is negotiable and what is not negotiable? Again we go
back to quantifiable terms; let’s see how this plays out in the
preceding examples.
“We would like you to consider a special and important gift
of $50,000.”
What if the donor responds, “I am afraid all I can do for
you this year is $25,000”? This amount is certainly a great gift,
but you had your sights set on a higher “special and important
gift.” In this instance, as the asker is not targeting the gift to a

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10 | Winning Words for Raising Money

certain area or restricting the gift, after some probing about
the $25,000 gift level it would be wise for the organization to
accept this amount, show the donor how the gift is to be used,
and then, in the very near future, ask the donor whether you can
revisit the possibility of her making a gift at the $50,000 level.
In the example of asking for four more personal days, what
if the supervisor says,
“Four is definitely too many, but I can give you one.”

You have some decisions to make. You do not want to lose
the one personal day you’re being offered; at the same time,
one extra day may not be enough to accomplish what you need
four days to do. I suggest that the best tactic is to graciously
thank the supervisor for the one day and ask some open-ended
questions such as these:
“Though I am very pleased to have this additional day, it is
important to me that I have the four full days. Do you
think we could both meet with human resources? They
may have a solution for how we can get to the four days.”
“Is there a particular time of year when personal days are
decided? If so, can I renew my request for the three additional days at that time?”
This way you get at least the one day and you preserve
your right to come back and ask for the other three.
In the “vacation time off with the family” example, what if
the boss says,
“No, I can’t give you two additional weeks off to be with your
family.”

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Step One: Know Exactly What You Want | 11

This seems cut-and-dried, but knowing what you do not
want may mean that you no longer want to work at a job that
offers so little vacation time. It may mean that you accept the
decision and go back to work, but you are not thrilled with

the decision, and you begin pondering an exit. You do not have
to let it get to the point of leaving your job if you use some
carefully worded open-ended questions. In the personal days
example, you can use the following open-ended questions to
see whether you can reach a workable result:
“Is it the ranking in the company or the years of service that
govern vacation time?”
“Can I carry forward unused vacation time from last year and
combine it with this year’s vacation time so that my family
and I can get away for a longer period?”
The point is to keep your options open, because you never
know; there may be a way to get what you asked for at a later
time.
In the trauma unit example, in which the donor is asked
for $50,000 for the immediate needs of five deserving patients,
what if the donor says,
“I would love to be amongst your top donors, so let me do this
gift over a five-year period.”
Pledging out payments is very common in nonprofit fundraising. This is where knowing what you will take and what
you cannot take is crucial. Will the institution accept five-year
pledges for this amount or is that only for gifts of $100,000
and above? If the institution has a gift acceptance policy

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12 | Winning Words for Raising Money

that states that gifts under X amount can be pledged for a
maximum of only three years, what will you tell the donor?
As we will see in the next chapter, it is always beneficial to
be prepared, and that means knowing exactly what you want
as well as what you do not want or cannot accept—and ultimately, what you are willing to compromise. Knowing exactly
what you want is the first part of your success in finding your
winning words.
Know Exactly What You Want

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2

Step Two: Prepare Your
Conversation

N

ow that you have a solid idea of exactly what you want,

we can move on to step two of the five-step process: preparation. This step is very easy to skip, because in your mind you
have played the conversation you want or expect to have, over
and over again. In general that is a wonderful exercise to do;
however, it does not totally prepare you for what may happen
before, during, and after you make the ask.
The preparation I suggest can be broken down into three
parts, all of which involve compiling lists, in writing, so you

can review and refine them. The lists are
1. Any and all anticipated “what ifs” that may arise for your
ask
2. Responses you want to give to address each issue
3. Open-ended questions you will have ready to keep the
conversation alive when you may not be ready to give a
direct response

13

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14 | Winning Words for Raising Money

The “what ifs” on the first list are all the things you anticipate may happen or may be said. Here are some examples:
What if the donor, customer, or investor will only speak with you
on the telephone and you want the conversation in person?
What if the person chronically cancels?
What if, after you ask for money, the person or company cannot give you an answer, but you need some initial funds as
soon as possible?
The point of the “what if ” exercise is to be proactive before
you have the conversation; to think of all the things that can
occur and challenges that can arise. It flows directly into the
second part of the preparation: writing down the responses
you will give to the anticipated questions and issues. Let’s see
what responses you could give to our “what if ” examples:
“As part of our personal outreach at our nonprofit/company,

it is vitally important that we maintain strong connections
with our loyal supporters/customers. In-person meetings
are a priority for us.”
“We are all so busy; I can be as flexible as your schedule permits. Would meeting in person in two months be more
convenient?”
“We totally understand that important decisions take time. As
we have shared with you, for this project to be a success,
it must be up and running within two months. Can we
discuss the possibility of your company’s pledging the total
amount and giving us just an initial pledge payment now?”
The third part of preparation is to create open-ended
questions (those that cannot be answered with a simple yes

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Step Two: Prepare Your Conversation | 15

or no); these act as your safety net when you may not get the
exact response you wanted. I like to use open-ended questions
because they provide the breathing room needed to probe the
possible motives or concerns of the person considering
the request. Sometimes you cannot or do not want to give a
direct response but rather need more information first. Here
are some examples of open-ended questions:
“We appreciate that you cannot decide at this time. Can you
share with us: is it the amount or the timing?”
“Thank you for sharing with me that our request exceeds your

budget. If your company makes multiyear gifts, this may
give us an opportunity to discuss ways we can benefit each
other.”
“Yes, we have been speaking with other people, so your prospective investment will be joined with others. We would
be happy to share with you our pipeline for funding. Have
we assured you that your investment will not be the only
one dedicated to this project?”
As you begin this preparation exercise of writing down the
three lists, reflect back on all any and all communications you
have had in the past with the person or people you want to ask
for money. There are clues imbedded in these communications, in the content and tone of the words, the frequency of
their communication, and the mode of communication. (We
will delve into this topic in much greater depth in Chapter
Five.) For example, let’s say you have been working with a
wealthy donor who has given your organization a good gift,
but now you want to ask her for a larger, significant, meaningful, transformational gift. If it’s been your practice to call, and

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