Let’s be honest—most people don’t like asking for money. In fact most of us don’t like asking for anything. So, why do we not only solicit individuals for charitable gifts, but do it in person?

You’re about to step up and speak to your supporters at your organization’s annual fundraising gala. You’re about to issue a “call for cash”—asking attendees to give anywhere from $1,000 to $25,000 more. 

Last year, the gala’s donations fell shy of the targets, so the pressure is on. How do you ask for a major philanthropic gift in a way that makes your supporters eager to play a huge part in your organization’s success? 

In my book, How to Raise $500 to $5000 from Almost Anyone, I offer a multitude of fundraising how-tos, from identifying prospects to setting a goal to offering meaningful thank-yous. But perhaps the most difficult aspect of soliciting a donor is what I want to focus on here.

By now, we all know the importance of asking a donor for a specific amount—“I’m hoping you’ll be able to join us with a gift of $500.” That’s challenging enough for most of us, but here’s something even harder: asking for a contribution and then remaining silent.

The list of things that can keep us from getting out to ask is really long. Not enough time. Fear of rejection. Not thinking our donors are ready. Not wanting to step on relationships. Are any of these on your top 10 list?

At the end of the day, what gets us out there is mostly a combination of enthusiasm for the cause and a sense of responsibility.

I’ve been asking for gifts for more than 40 years. Some as modest as $50, others for $100 million. You could say I’m acquainted with the do’s and don’ts of motivating donors.

In my book Asking you’ll find a detailed approach to soliciting major gifts. In this article, I’ll simply highlight eight suggestions to keep in mind as you prepare yourself and your board for the big push.

If you’re a fundraiser, it’s often helpful to think like a donor.

When leading workshops, I encourage people to flip this mental switch. “How many of you have ever given away money to anybody for any reason at all?” Of course, all the hands go up.

Then I ask people to pair off and talk about why they give. These small groups generate a long list of reasons; here’s one of the most popular. Giving feels good.

I test this with the participants. “How many of you have ever made a charitable gift and felt good about it?” Again, everyone raises their hands.

This leads to another challenging question: Why are we so uncomfortable asking people to do something that makes them feel good when they do it?

Here’s a natural, friendly and much more successful approach to major gift fundraising.

I’m showing you how to develop a warm, easy relationships with your major gift prospects. Relationships where they feel heard and understood. A relationship that builds trust and credibility.

When you take a donor-centered approach to a major gift, you let the donor lead the way. She feels entirely in control. She never feels “presented” to or pushed.

And she’s much more likely to end up with a generous major gift coming from her heart—and she’s with you for the long term.

All nonprofits want to excel at major gifts fundraising. Or don’t they?

In my 30 years in major gifts fundraising, I have seen familiar roadblocks get thrown up to keep money from flowing into the organization.

Tax benefits are icing on the philanthropy cake. What to do when the icing is melting?

First, the good news.

The sky is not falling.

Let me be honest. It’s no secret—asking for a major gift is ... scary. It’s one of the biggest challenges fundraisers face.

It’s a personal question which enters what is considered a taboo area of conversation—someone else’s money. Even after years of experience, every donor conversation is personal and therefore different. There’s always the unknown.