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Kent Stroman, CFRE

About Kent

Obstacles to Asking - Part 1

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 1 of a two-part series. You can read Part 2 here.


So why write about obstacles anyway? I have two primary objectives for this chapter.

First, since we all bump up against barriers from time to time, I want you to rest confidently in the fact that you are not alone. Statistically, there is a 96.5 percent chance that the stumbling blocks you encounter in your face-to-face fundraising activity have already been identified in our research. And even if your specific challenge isn’t named here, you’re still in great company. Don’t let your difficulty deceive you into giving up. The path you’re on, if you persist, leads to success in fundraising plus some really important life lessons.

Never give up.

Second, I share these common obstacles for the purpose of revealing how to overcome them. Someone wisely stated, “The difference between those who succeed in life and those who don’t lies not in whether they encounter difficulty. Rather, the difference is how they respond to difficulties.”

With these two purposes in mind, look for yourself in the paragraphs below, take comfort in knowing you are not alone, and focus more on the solution than the problem.

Here’s an all-too-common scenario in the charitable sector:

  • Our organization has a dedicated staff with an intense passion for the mission.
  • The board functions fairly well and is running smoothly.
  • Our paid professionals and volunteers genuinely want to help others.
  • We have identified our desired outcomes and know exactly how to measure them.
  • The only thing lacking is the resources necessary to deliver our services to those who need them.

So our plan of action is simple, right? We just need to raise money. But something is holding us back . . . What is it?

This is the scenario we put in front of hundreds of not-for-profit leaders over a two-year period. But we sharpened the focus even more.

We realize that every serious fundraising effort requires success in two key realms:

  1. A large number of small gifts
  2. A small number of large gifts

Historically, we expect 80 percent of the dollars to come from only 20 percent of the donors.

We have lots of ready-made solutions for the large number of small gifts:

  • Direct mail
  • Online giving
  • Raffles
  • Payroll deduction
  • The ever-present large-scale fundraising event
  • Product sales (popcorn, cookies, candy bars, wrapping paper, ad infinitum . . . ad nauseam!)

But when it comes to the small number of large gifts, our minds seem to slam shut like a steel trap. We’re overcome with mental paralysis. Occasionally someone will offer up the common fantasy, “Let’s just send letters to Bill Gates and Warren Buffet, and they’ll write big checks to fund it all.”

Against this backdrop I have spoken with numerous audiences of philanthropic leaders—professionals and volunteers alike—and asked this question:

“What is your biggest obstacle to successful one-on-one gift solicitation?”

In other words, what holds you back?

And they answered . . . Did they ever! I have to admit the candor and insight they offered was stunning! Some of the responses were predictable. But right in the midst of the most expected replies, a number of veritable “gold nuggets” appeared.

Careful analysis of the 594 responses uncovered thirty-three themes along with another sixteen replies (2.7 percent) that shared no commonality and were placed in a thirty-fourth category cleverly labeled “Miscellaneous.”

None of the obstacles are insignificant. Each represents a true hindrance to success for someone diligently engaged in charitable endeavor.

I would love to address every obstacle on the list. (In fact, I have an idea in mind . . .) However, due to the limitations of space and time, I’m limiting my focus here to a select handful. The remainder will be addressed in a subsequent publication where, as Paul Harvey famously intoned, you’ll learn “the rest of the story.”

Before going any farther, let me ask for your experience. What are your top obstacles to successful one-on-one gift solicitation? (Be specific, and please don’t limit yourself to the categories listed above.)

1. __________________________________________________

2. __________________________________________________

3. __________________________________________________

Now, while you’re in the feedback mode, take a moment to write a vivid description of what would be different for your NPO if you could completely fund your mission:





  • Whose life would it change? ___________________________
  • How? ___________________________
  • What problem would be solved? ___________________________
  • What difference would it make—in you? ___________________________

Take the time to dwell on these thoughts. Develop a clear picture of what success would actually look like in your organization. Does the smiling face of a child you once served come to mind? Perhaps the name of someone who felt alone, abused, or neglected . . . but no longer does.

Sear that image into your memory. Let the story of past success motivate you to identify your obstacles to asking. Then we can methodically dismantle them as you learn what it means to “master the art of conversational fundraising.”

I’d love to hear your story. You can call my personal cell phone at (918) 914-2811 or email [email protected] to join the dialogue.

Up Next: Part 2

In Part 2 I discuss five of the most daunting obstacles to asking for gifts are:

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

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