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Kent Stroman, CFRE

About Kent

Obstacles to Asking - Part 2

Asking about Asking: Mastering the Art of Conversational Fundraising, Second Edition

This article is an excerpt from Chapter Two of Kent Stroman's groundbreaking book, Asking about Asking: Mastering the Art of Conversational Fundraising, Second Edition (CharityChannel Press).

Editor's note: This is Part 2 of a two-part series. You can read read Part 1 here.

Here we go . . . five of the most daunting obstacles to asking for gifts are:

  • Relationship deficit
  • Conflicting priorities
  • Mindset
  • Fear
  • Difficulty “getting in”

And we begin with . . .

Relationship Deficit

Have you ever had this experience?

You’re at the ballpark for a springtime baseball game with three other families. You’re ready to sink your teeth into a piping hot “brat”—with all the trimmings—when an unfamiliar teenager interrupts the party to ask for money. How do you feel?




Mildly irritated?

Extremely annoyed?

It could be any of the above . . . except generous. But what if the solicitor, instead of being unfamiliar, is the daughter of your best friend from college days? How would that change your reaction? Any of us would most likely be eager, willing supporters.

Why the difference?

It’s the relationship. And we’ve repeatedly emphasized the importance of relationships in fundraising. And, frankly, it’s no different in any other dimension of our lives. Relationships matter. A lot.

Oftentimes, however, we find ourselves in fundraising situations with an insufficient basis for the request. I call this a Relationship Deficit, and it interferes mightily with fundraising success.

Here’s how our colleagues described the obstacle:

  • I don’t really know my constituents.
  • I question whether I have done enough cultivation.
  • How can I learn the donor’s capabilities (money and time)?
  • I can’t ask for big gifts because I’m new to the community.
  • I haven’t built relationships to the point where I can make the ask.
  • I don’t know sufficient information about the person who is being solicited.
  • I find people unresponsive to my attempts to engage them in support of our organization.
  • I don’t know how to introduce myself to someone who doesn’t already know me or my organization.
  • I don’t know who is best to ask for what and who I should involve in asking about the potential gift.

Regardless of how it is expressed, the idea of soliciting a donation from an unknown or underknown entity certainly does present a major roadblock. Have you ever been approached that way? It’s uninspiring at best. And can be downright annoying at worst. If not offensive.

Lee G., general manager of a symphony orchestra, described her obstacle as “not understanding the true reasons/values a donor would consider supporting our organization.”

How to Overcome the Relationship Deficit Obstacle

All of life consists of relationships. Successful fundraisers find ways to form new relationships, cultivate relationships, sustain relationships, and enhance relationships. If nothing else, we are all in the relationship business.

My advice? Make a game of it. I’m not suggesting you become too casual about those who would support your cause. Rather, look for ways to press yourself beyond your present comfort level.

Consider this scenario:

You are seeking a contribution for the annual fund from Acme International. You feel comfortable with approaching Charlie, the vice president of corporate affairs. Instead, raise your sights and engage Arthur, the CEO. Don’t know how? Try this approach: “Charlie, I’ve been in our community for three years and have yet to meet Arthur in person. Could you introduce us?” Upon meeting Arthur, begin to climb the 10 Step Staircase as described in Part Five.

You can rapidly create a strong relationship with a high-stakes request. People can easily ignore one another when there is nothing—or very little—at stake. But when it comes to a major contribution, it has to become personal.

Conflicting Priorities

Everyone faces time pressure at work, at home and, in general, in life. We all want to get more done than can possibly fit into the twenty-four hours we are each given every day. But that’s a different topic than Conflicting Priorities.

What do you do when you have two high-value objectives, each of which takes you in an opposite direction from the other? It presents the classic definition of a dilemma, which fundraisers encounter on an almost daily basis.

Take a look at how the respondents described their situations:

  • Getting out of the office and seeing prospects
  • Prioritizing one-on-one solicitations in my schedule
  • Making the time to identify prospects and make appointments
  • Being tied down with day-to-day stuff in my small development shop
  • Doing too many things since I’m essentially in a one-person office
  • Dealing with our gift-prevention office (i.e., getting clearance to meet with our donors)
  • Having too many competing institutional demands on my time (i.e., paperwork)
  • Constantly being asked to do other things instead of cultivating and soliciting gifts
  • Making/prioritizing time to solicit the funds that I know are available

Kourtney C., development associate for a humane society, is hindered from “staying on task to make donor calls and set up appointments. It is so easy to be distracted by other duties, even when they are less important.”

How to Overcome the Obstacle of Conflicting Priorities

We all find ways to do the things we view as important. Which is more important: soliciting contributions, preparing reports, or stomping out the daily fires at the office?

One of our biggest mistakes is to believe we can get it all done. We decide we can’t start raising funds until we finish our administrative work. The reality is administration will never be finished! So if we’re ever going to raise money, we must limit our time on administration to do so.

If you’re going to be criticized for something, let it be for underserving your administrative duties while overachieving your fundraising goals. Not vice versa.

Here is something that helps me. Years ago Norm Edwards, my mentor and friend, shared this saying with me, “What matters gets measured. And what gets measured gets done.” I have discovered numerous applications for that axiom. But I needed something even more practical and have modified the saying as follows, “What matters gets scheduled. And what gets scheduled gets done.”

Try implementing this principle as follows to help resolve your conflicting priorities:

Step one: Set your priorities. Decide on a balance for your life for right now. Don’t overthink the issue. Realize you can always make adjustments later if needed.

Step two: Schedule a regular time to call on major donor prospects. For example, block your schedule between 7:30 a.m. and 1:00 p.m. every Tuesday, reserving the time solely for major donor cultivation and solicitation.

Step three: Contact the decision makers for your top three prospective donors and schedule twenty-five-minute meetings with each of them next Tuesday morning.

Step four: Walk away. On Tuesday morning, turn your back on everything except meeting with prospects. If you end up with more time than appointments, adapt the old industrial practice of “management by walking around.” Try “donor development by walking around.” Simply drop in on some of your supporters, without an appointment, with a message like this, “Hi Beth. I don’t have an appointment but was nearby and just wanted to stop and let you know how much we appreciate your past support. Your annual contributions to our scholarship fund have impacted the lives of students you may never meet. On their behalf, I want to say ‘thank you.’”

And with that, be prepared to go on your way. Or, more likely, be available to chat for a few minutes with Beth regarding topics of interest to her. Bring a progress report to share if she is interested. Tell a recent success story regarding your programs. Take as much time as she wants, leaving Beth on a positive note and feeling confident about the high rate of return her investment is earning through your mission. This is some of the best donor development work you can perform. You will fully enjoy it. Beth will love it! And you can count on being invited back.

You’re building relationships with donors through fundraising rather than building a relationship with paper through administrative duties. Which sounds more fun?


Henry Ford, founder of Ford Motor Company, aptly described the Mindset obstacle by saying, “Whether you think you can, or you think you can’t—you’re right.” The mental predisposition we take into the fundraising marketplace may create the greatest competition we will ever face. It’s tough to compete with ourselves!

To get a glimpse of the many forms this obstacle takes, take a look at this sampling of responses:

  • I’m intimidated by money.
  • Distance. I’m not one of them (an alum).
  • Our organization does not need the money.
  • I don’t feel comfortable asking for money.
  • I don’t want to “guilt” people into donating.
  • I don’t want the donor to feel obligated to give.
  • I feel like asking gets in the way of the relationship.
  • I don’t want to take advantage of personal relationships.
  • I want to be able to fundraise without sounding like I’m begging.
  • I need a creative way to be a potential donor’s number-one choice.
  • People are tapped out. The same donors are giving over and over.
  • The donor I’m asking already is giving to other organizations.
  • It’s hard to ask for a gift that doesn’t offer an immediate return for the donor.
  • When approaching donors, I discover they usually don’t know about our organization and simply reject us.
  • The constituents we serve represent a topic that is taboo in society (violence against women and children).
  • I feel intimidated by powerful, wealthy prospects when making personal visits and don’t feel worthy or equal enough to make the ask.
  • I’m young and it’s tough to be taken seriously by major donors. They prefer to talk to my boss or others more seasoned within the agency.

The Mindset obstacle is illustrated by Melanie P., development director of a women’s shelter, who says, “My challenge is having a valid argument in asking for funds. I need to make people feel like they really want to donate.”

How to Overcome the Mindset Obstacle

This may be the most significant obstacle we can face as fundraisers. On one hand, a change of mind is the easiest of changes we can make since our own mind is one of the few things in life we really have any control over. Yet changing one’s mind is perhaps the most difficult task we ever face. It’s a bit of a paradox.

And, although a change of mind is difficult to achieve, I readily accept the challenge for this reason: No truly worthy accomplishment takes place without first a change of mind. I think Jim Stovall said it best when he declared, “You change your life when you change your mind.” He should know.

Jim’s life was a mess. As a young man, he lost his eyesight. And if that wasn’t enough, he came to a place where the other circumstances in his life were adverse and overwhelming. His home was a nine-by-twelve-foot self-imposed prison. With almost no will to live, Jim realized that unless something changed dramatically—and very soon—his life would end.

The life-changing difference for Jim was imperceptible to the human eye—at first. He didn’t hit the proverbial jackpot in the casino next door. He wasn’t the recipient of random charity. He didn’t discover a brass lamp with a genie inside waiting to do Jim’s bidding. No. Jim changed his mind. He began to see himself as the master of his own fate. Somehow he got a glimpse of the reality that “your attitude almost always determines your altitude in life” (source unknown).

You can learn more about Jim in his book The Way I See the World (available through or your favorite book retailer).

The obstacles detailed here are representative of the countless ways we impose self-limitations on our effectiveness. If we believe we cannot accomplish a certain thing, we are invariably right. Everything within our being strains to validate our own beliefs.

The good news is, however, that if we believe we can accomplish a certain thing, we are also right. Why? Because everything within our being strains to validate that belief as well.

Take Melanie’s mindset for example. She sees it as her job to “make people feel like they really want to donate.” What are her chances for success with that task. How about zero? Have you ever made another person really want to do anything? It’s doubtful. So let me offer a small adjustment to Melanie’s approach.

Ask your prospects what they really want to donate toward. Ask what they want their philanthropy to accomplish. And once you understand their answers, invite them to partner with your organization to achieve their goals by doing what they desire. Empower others to reach their goals rather than handing them your problem and asking them to solve it.

Be aware of your own attitudes and predispositions and intentionally reject any unhealthy messages you may be giving yourself.

Here are a few examples:

Do you feel:

  • intimidated by money;
  • you’re not “one of them”; or
  • too young to be taken seriously?

Your limiting factor is adopting a mindset that the issue is about you. But it’s not about you.

Fundraising—successful, one-on-one, major fundraising—is not about you. It’s about the donors. Their view of money. Their sense of belonging. Their age or position in life.

Consequently, make fundraising about them. How do they want to use their money? Do they feel connected to the mission and constituents you serve? Are they uncomfortable visiting with someone younger?

Ask yourself how you know what you think you know in answer to these questions. Then challenge your answers. Most of us, including me, have an innate tendency to make things up regarding others. Most of the things we make up are erroneous and generally detrimental in one way or another.


How can one small word, consisting of just four letters, capture so many different meanings? The topic of Fear as a barrier to success in gift solicitation is addressed in Chapter One, “Stage Fright,” of Asking about Asking: Mastering the Art of Conversational Fundraising, Second Edition, but our research shows it’s a much broader issue than previously imagined.

To gain insight into some of the myriad forms fear takes in the minds of fundraisers, check out these descriptions from our peers:

  • The fear of failure paralyzes me.
  • I need courage to ask for a gift.
  • My lack of confidence makes me fearful.
  • I fear the rejection of my request for support.
  • My fear is that it becomes some kind of confrontation.
  • I feel very apprehensive with the very idea of making an ask.
  • I fear being told “no” after spending so much time seeking the gift.
  • I’m afraid my request for a gift will come across as not making any sense.
  • I’m afraid my request will be for an amount that is too large or too small.
  • I am just afraid to ask because I don’t think people would want to give.
  • I don’t like to be turned down when an honest and positive presentation has been made.

When describing her obstacle, Dena A., gifts manager of a zoo, said she is “afraid of making our donors feel like they aren’t already giving enough [when asking for larger gifts than they have previously given].”

How to Overcome the Obstacle of Fear

Fear is the emotion we feel when we encounter the unfamiliar. It is a sense of anxiety that accompanies a new experience. The antidote to fear, therefore, is a plan. One of the biggest challenges in life is deciding what to do when you don’t know what to do.

For example, I have never asked Bill Gates for a gift of $100 million. For this country boy from Garden City, Kansas, that’s a huge number. I can’t even comprehend it. And to make such a request of Bill Gates would scare me spitless. Can you see how these fears are examples of redefining the issue so it is suddenly all about me? Who cares where I was raised? It’s not about me. Who cares how big the number seems to me? It’s not my money. It’s not about me.

Rather, successful major donor fundraising is about the donor. Garden City has no relevance to Bill Gates when being asked to fund hunger alleviation in West Virginia. The amount of $100 million is not a new or unfamiliar number for him. We must shift our basis of comparison from ourselves to the donors, the organizations, the missions, and the constituents we serve.

I take great comfort from the example of one of our nation’s most notable leaders, President Theodore “Teddy” Roosevelt. His exploits give me the impression of a man of boundless courage. His story, however, begins with a different picture entirely.

Timothy Egan, author of The Big Burn, writes, “As a boy, he [Roosevelt] was afraid of horses, afraid of wild animals, afraid of what lurked behind a tree in the dark. But he taught himself to pretend that he was brave, and in this way became fearless. ‘By acting as if I was not afraid I gradually ceased to be afraid,’ he said.”

Are you as shocked as you read these words as I was when I first did? Teddy Roosevelt . . . afraid of the dark? You’ve got to be kidding! This man was the youngest-ever president of the United States. He is often described as masculine, outdoorsman, boxer, cowboy, leader, explorer, hunter, soldier, and rancher. You wouldn’t think he ever had a timid bone in his body. Roosevelt’s oft-repeated slogan was, “Speak softly and carry a big stick.” It doesn’t sound remotely possible that he and I have anything in common. But we do. It’s fear.

The way Teddy Roosevelt handled fear as a sickly child is a great lesson for budding fundraising stars: Pretend to be brave. Act as if not afraid. Make a plan.

The only way I know to overcome my fears in fundraising is to implement a three-step solution I call “Get on PAR .”

PAR stands for:


P repare

In order to fully prepare for your next fundraising call, get ready for the task by having a brief chat with yourself. Ask yourself these few questions. Then tell yourself how to deal with your own answers.

Ask Yourself

  1. What, specifically, do I fear? (I’m afraid the prospect is going to say, “I have absolutely no interest in donating any of my hard-earned money to feed hungry children!”)
  2. Why am I seeking donations? (I have a personal passion to ensure that no child in our community goes to bed hungry.)
  3. Who will gain if I receive the gift I seek? (The 2,837 needy children in Charles County will.)
  4. Who will lose if I don’t receive the gift I seek? (The 2,837 needy children in Charles County will.)

Tell Yourself

  1. Step up, Kent. It’s time to set aside your personal discomfort and act decisively on behalf of someone else’s needs. (Remember, hunger is a true need—not just a want.)
  2. It’s not about you.
  3. You can do this.
  4. Those 2,837 hungry children are depending on you.
  5. Generous donors are depending on you.
  6. Donors want to give more than you want to ask.

With the preparation phase behind you, it’s time to act. Build your confidence by what you choose to ask and tell the person you’re meeting with. Begin by telling.

Tell the Prospect

  1. I’m new at fundraising for disadvantaged children and feel a little uncomfortable.
  2. I don’t know exactly how to ask this, but . . . (proceed to your question).

Ask the Prospect

  1. Would it be out of place for me to ask you about helping feed hungry children in our community?
  2. [Or] Has anyone ever talked with you about the problem of childhood hunger in our community?

Here’s a big tip to place between telling and asking the prospect: Ask for money only after asking at least three purposeful questions about something besides money.


Having defined your fears and acknowledging the same to your prospective donor, take time now to evaluate the experience with a brief review of the process.

  1. What happened regarding the specific thing I was afraid of?
  2. What could I do differently next time?
  3. What could I do the same next time?
  4. What other lessons did I learn?

Difficulty Getting In

You can’t solicit a gift if you can’t cultivate the donor. And you can’t cultivate if you can’t meet with the donor. And you can’t have a meeting if you can’t get it scheduled. Put it all together, and you have an everyday recipe for nothing:

  • No appointment
  • No meeting
  • No cultivation
  • No ask
  • No gift

Difficulty Getting In can be a challenge for anyone—from the most seasoned fundraising professional to someone just getting started. This obstacle reared its ugly head more often than any other in our research. Combine all the obstacles in the eighteen categories at the bottom of the list, and this one is even greater still.

Rather than try to speak for those who identified this as their top obstacle, I’ll have you take a peek at how they saw the problem:

  • Initiating the first meeting with someone I do not know
  • Getting beyond the gatekeeper to begin the conversation
  • Networking to get the contacts for face-to-face meetings
  • Getting the individual to commit to a one-on-one meeting
  • Gaining access to the decision makers (they often don’t know me)
  • Board members who are unwilling to open doors to prospects
  • Actually getting in the door for face-to-face time with donors
  • Getting people to answer phone calls/emails or return messages
  • Not having someone to do an introduction so I can get my foot in the door
  • Getting in touch with the manager who handles the budget for contributions
  • Getting an appointment with prospects who have relationships with our agency
  • Booking appointments (people are reluctant to meet because they are afraid I will ask them for donations)

Lisa P., grants manager of a medical center foundation, faces the barrier of not being able to “get in the door to meet with the right person.”

How to Overcome the Difficulty Getting In Obstacle

Responsibility for getting the appointment belongs to the fundraising professional (CEO, development director, etc.). Nobody cares more about the meeting than the person whose job it is to fund the mission. Someone has to DRIVE the process. If you wait until the task becomes a priority for the peer or prospect, you will find yourself in crisis mode—and it will be too late.

Tip one: Take ownership for the results.

You must enlist the support of others, but don’t wait for them to initiate action. You must do the work through others.

In Part Four, “The People Involved in Asking,” you will find the rationale for engaging others in the fundraising process. Because of their independent positions, volunteers can do things that staff members are disqualified for because of their positions.

Tip two: Chart your course.

  • Decide who you need to meet with. (Why this particular person?)
  • Do your research.
  • Identify the best link. In other words, who can the prospect not say “no” to?
  • Prepare the peer to set up the meeting.
  • Prepare the script for your request. (What will the ask sound like?)
  • Craft a fallback position.
  • Explain how to preempt a decline (or handoff).

Tip three: Frame your purpose for meeting.

Is it to get the prospect to give up something unwillingly? Or is it to gain unique insight into a problem that matters deeply to the prospect?

Are you meeting to get a gift? Or to give a gift? There can be a huge difference. Chapter Eighteen of Asking about Asking: Mastering the Art of Conversational Fundraising, Second Edition elaborates on the importance sincerity, character, and integrity play in the fundraising endeavor. If you are not pursuing funding with genuine sincerity, solid character, and complete integrity, please find another profession and leave this work for someone who is.

Discipline yourself to be religious in giving the gift of the three "A"s:




When we set aside a specific time to meet with another person, we are giving the gift of audience. We realize that other people’s time is important. They realize our time is valuable as well. So the simple act of setting aside time for the other person is a gift. Cherish the gift you give as much as the gifts you receive.

When you are with someone, be with them. Give the gift of attention. Regardless of the distractions and drifting you experience when meeting with your prospect, discipline yourself to set them aside. Your prospect merits your full attention. Don’t leave your prospect wondering if you are present in body but absent in mind.

Don’t hold so rigidly to your preconceived agenda that you prevent yourself from noticing what is important to the other party. Give the gift of awareness. Someone once advised that if you want to understand other people, notice what they notice. You will undoubtedly identify areas where your interests overlap. Build on this common ground.

Having given the gift of the three As, you can move forward with the three "B"es:

Be inviting (winsome) rather than demanding.

Be inspiring rather than insistent.

Be eager rather than desperate.

The confidence you possess as you seek to “Get In” with prospective donors will almost automatically predispose others to accepting your request for meetings. (For more depth on this topic and ways to overcome all the other obstacles, watch for our upcoming title.)

Plan of Action

As you acknowledge the obstacles you face in seeking major gifts, realize you are not alone. Every successful fundraiser started right where you are today.

Identify what it is—specifically—that holds you back.

  • Complete the exercise on page 14, naming your top obstacles to successful gift solicitation.
  • Create a clear, compelling picture of the benefits of successful fundraising in your organization.
  • Answer the questions on pages 14 and 15.
  • Apply the principles used in this chapter to dismantle the obstacles you encounter in your unique circumstance.

Copyright © 1992-2019 CharityChannel LLC.



  1. Claire Axelrad on March 22, 2018 at 5:28 pm

    I love the way Kent has framed these all-too-common obstacles. I know there's a lot more to this book, but a development professional could do a lot worse than simply reading this chapter (thoughtfully, with a pen in hand) and (1) seeing what's holding them back; (2) making a plan to overcome their own obstacles. Thanks so much for sharing!

  2. Kent Stroman on March 23, 2018 at 8:07 am

    How nice - thanks so much Claire!

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