The Ask—Helping Donors Get Where They Want to Go

Last month, in my coaching class, we did a “wheel of life.”  A circle, divided by spokes.  Each spoke was named:  Physical Environment, Career, Money, Health, Friends and Family, etc.  On the horizontal axis, from the center to the left side of the circle were tiny numbers from 0—at the center—to 10 at the perimeter.  The exercise was to rank our level of satisfaction with each life area and then draw a curved line to create a new perimeter. I’m not generally a big fan of exercises such as these, but this was interesting: Of the twenty plus people in the class, more than 75% had money as their lowest level of satisfaction.  Even more interesting to me were the side conversations I had where most people said it wasn't so much that they were dissatisfied—though you can always have more—as they were worried or concerned.  In other words, their relationship to money was fraught.

I don’t think my classmates are unique.  Most of us are anxious or uptight about money.  More than sex, it dominates our thoughts and often controls our actions.  Conversations about money are often tense and uneasy.  Is it any wonder, therefore, that we get nervous at the thought of asking someone for a charitable gift?

Perhaps because it is so difficult, most trainings on making “the Ask,” which, by the way, is always capitalized as if it some sort of holy grail (or, more accurately, Holy Grail) focus on structure.  You know:

  • The introduction: some chit chat to put everyone at ease
  • The purpose:  why we have gathered here—something that gives me pause. Would we really have gotten this far without the prospect knowing why??
  • Making the case:  Well, okay if this is for some small change, but when the ask is going to be large, the case should have been made way back when.  All you should really be doing at this point is connecting some dots, between the project, the person, the outcomes.
  • The ask.  The big moment.  But typically there is nothing said beyond (and this always in bold) Be quiet!!!  The first person who speaks, loses.  Err…I always thought of fundraising as a situation where we all win.  Being asked is being offered an opportunity. Giving is a good thing. And let’s be honest, getting—it’s a good thing, too.
  • Responding to objections
  • Getting the answer
  • Agreeing on next steps.

All well and good, but I don’t actually think that most asks go quite like that.  Certainly not asks for very large gifts.

For those, by the time you get to the Ask, all those bullet points above have been dealt with. There should be no surprises.  Indeed, when the appointment is made it is generally best to be clear:  I want to meet to finalize your gift for…..

There should also be no surprises about the gift range.  You may not get what you ask for, but the ask should not be a jaw dropper (either because it is too high OR too low).

The important thing here is to say it simply and don’t second-guess how the prospect will respond.  Don’t offer payment options or different gift vehicles—that comes later, when you are negotiating the terms.

Most importantly, don’t choke.  The number may seem high to you, but unless you’ve really gotten it wrong, it won’t seem that high to the prospect.  Which, of course, doesn’t mean you will get it.  Capacity—the ability to give at a certain level—is one thing.  Inclination and desire are entirely different.

A friend recently told me about a very wealthy gentleman—one of the wealthiest in our very wealthy town (Los Angeles).  He was marginally involved in the organization, so they knew they weren’t going to get a mega major gift.  They did, however, hope for a 6 figure one.

At the meeting, the CEO asked this gentleman for a gift of $100,000—which would be for him like a gift of $100 for me.

Without blinking an eye, he pulled out a check.  And as he handed it over, he said, “This is for $10,000.  It’s the most I’ll give.  It’s what this organization’s value is to me.”

They tried; they cajoled.  But in the end they understood that the gift he gave was the largest they would receive from him unless they found a way to connect him more tightly to their organization.  And that, alas, was unlikely.

But let’s circle back the wagons.  I started this by talking about the tensions most of us have with money.  It makes us fearful of asking; of deciding on the size of the ask; and too often it leads us to offer “solutions” via multi-year pledges, planned giving vehicles, and—worse of all—forgetting that fundraising is simply a way to provide an opportunity to the donor get where he or she wants to go.


Janet Levine works with nonprofits and educational organizations helping them to get where they want to go with strong fundraising programs and clear goals for their future.  Learn more at