How to Take the Fear Out of Asking

April 6, 2015 Marc A. Pitman

I’ve heard that on the list of things people fear most, “asking for money” usually ranks higher than “untimely death”! Does it for you? The good news is, it doesn’t have to! I firmly believe fundraising is one of the best jobs on the planet. This plan will help you start believing that too!

Start with a plan

When I teach schools how to ask for money, I use the phrase “Get R.E.A.L.” The letters in REAL stand for:

  • R – Research
  • E – Engage
  • A – Ask
  • L – Love

Let’s look briefly at how each step takes the fear out of asking.


The first step is to research. But before you research who you’ll ask, make sure to research the project or reason you’ll be inviting them to invest in. This is the step that the traditional “Cultivate-Solicit-Steward” model of major gift fundraising leaves out.

You’d think you’d know your project and how much it’ll cost, right? I once asked a leader of two nonprofits who was opening a third one overseas how much he was trying to raise. It took him 20 minutes to figure it out for himself! As a coach, I’m fine with waiting. But donors won’t. They’ll expect you to know.

As you figure out what you’re accomplishing and what it’ll cost, run it through something like my or Blackbaud’s version. This will give you the answer to the question, how much do we ask for?

On the calculators, you’ll see the number of gifts required at each level. Using that guide, start building a names list of people who could conceivably be asked to give that much. Only then do you start researching those names. You can use free tools like Google, ask your board members to rate them, or invest in analytic services like Blackbaud’s Target Analytics or DonorSearch.

This research helps you lay the foundation of your school’s fundraising plan, but don’t get stuck here. You haven’t raised any money yet!


In Ask Without Fear!, I liken the “engage” step to dating. This is the time you get to know the people you’ll be asking. And the time they’ll get to know you. This is where you show them that you see them as people, not ATMs.

The trick about engaging is to know when to move to the ask. Your school can’t afford you getting stuck just “cultivating” donors and parents. As a fundraiser, your job is to raise funds. So while some major gifts take a lot of cultivation, most can be started sooner rather than later.

If you are in your first meeting and you discover they’re passionate about what you’re planning on asking them for, you could easily say:

”Wow! I had no idea you were that passionate about this. I didn’t come here to ask you to invest in it, this time…but could I? Or would it be better to follow up with you in a couple weeks?”

Donors won’t get offended by that kind of polite ask. And you’ll win either way. Either you’ll ask them now, or you’ll have an excuse to call them up in a couple weeks.


Which brings us to the ask. Can you see if you’re researched your goals, researched your prospects, gotten to know them a bit, how much easier the ask is? You’ll have a much better idea what aspect of your fund will resonate with the donor. But this is still the scariest step because you’re putting that parent or alum on the spot, asking them to make a commitment.

Here are a few pointers:

    1. Step up the appointment clearly – In the “engage” step, you could just call a person up for a cup of coffee. But here, it’s better to say you’d like to meet with them about “a project” or “about their support.” I like the soft approach, something that indicates an ask without getting into the ask on the phone. My friend Andrea Kihlstedt prefers a much more direct approach to scheduling solicitation. She wants to figure out the objections before she even gets in the room. You can choose either style. Both work. Andrea and I have raised millions of dollars for schools and other nonprofits.
    2. Ask for a clear dollar amount – Asking for a vague “support” confuses the donor and disappoints you. They have no idea what you mean. They may think $250 is generous when you were thinking $25,000. So do them the courtesy of being direct. I find it helps to practice the ask beforehand. I tend to talk to my steering wheel, trying out different asks, letting myself get comfortable with the words and the dollar amount.
    3. Shut up – There’s really no nice way to say this. The most uncomfortable part of the entire process comes right after you make a clear ask. The silence is good. Sales trainers say “He who speaks first loses.” I don’t know about that. Nonprofit fundraising isn’t a “win/lose” thing. For me, it’s showing respect to the person you just asked. They need to process your request. They need to think about whether they want to give, who they’d need to convince, and how they’d make the gift. This takes time. Some people are fast processors; others are slow. Do you know how you’ll know when they’re done processing? Yep. They’ll speak.

The ask sort of puts you at odds with the donor. You’ve put them on the spot, asking them to take action. Everything after this is to show them that you’re on the same team. You may suggest breaking the gift into annual payments, or monthly. And they may tell you reasons they feel this isn’t a good time for them. It’s best to see that as a request for your help. It’s like they’re saying, “I want to give but I see this obstacle.” Your job is to now help remove those obstacles.


The last step is “love.” It’s easy to do with a person who says “yes” to your ask. You probably already have systems at your school to determine when a gift or pledge acknowledgement is sent, who writes a personal thank you note, and what size gift merits a phone call. But this is also the step that, in the first 90 days after the gift, you need to show the donor the impact their gift has made. This proves to them that you are interested, and grateful, for them as a person, not merely for their wallet.

But this step is crucial even if the donor says “no” or “not now.” Especially for schools. We will always be able to claim a relationship with parents and alum. If we handle their “no” well here, they’ll typically be more open to an ask at a later date. We once had an alum ask for a $40,000 gift back from our school (about 10% of our annual fund). We returned the gift. But we also aimed to strengthen the relationship the alum had with the school.

It worked. 18 months after asking for the $40,000 gift back, the alum made a $500,000 commitment to our capital campaign!

Final thoughts on fear

One of the best pieces of wisdom I’ve heard is that courage isn’t the absence of fear. Courage is facing fear and moving through anyway. There’s no doubt that fundraising takes courage. But after you’ve done it a while, you’ll start seeing some donors’ eyes light up with joy at the gift they’re able to make. That will get you excited to ask more. You never know who’s day you’ll be making!

That’s why I call fundraising one of the best jobs on the planet!

For a more detailed, but still concise form of a plan, go read the Do It Yourself Fundraising article at

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