The Magic Formula for Making a Confident Fundraising AskLet’s talk about a moment that strikes fear into the hearts of even the most seasoned fundraisers: the ask itself. Not the stewardship. Not the cultivation. Not the coffee chat or the tour. The moment when it’s time to name a number and ask a question. I’ve trained hundreds of folks, from student callers to major gift officers and presidents, and this is where so many otherwise capable fundraisers freeze. They hedge. They mumble. They talk around the gift instead of actually asking for it. That hesitation is what sinks so many proposals—because if you don’t ask clearly, the donor doesn’t know how to answer. Or worse, they walk away unclear on what you needed from them at all. The good news? Asking well isn’t about being fearless or charismatic. It’s about structure. It’s about using a reliable, repeatable framework that gives you confidence and helps the donor have clarity. Here’s what I call my Magic Formula for Making the Ask—and it works whether you’re asking for $100 or $1,000,000. 💬 The Magic Formula: Questioning Opener + Mission Moment + Dollar Amount + Silence Let’s break each part down so you can feel grounded the next time you find yourself sitting across from a donor (or dialing the phone or typing an email, for that matter). ✅ 1. Questioning Opener This is one of the biggest giveaways that a fundraiser isn’t comfortable asking: they frame their “ask” as a statement instead of a question. ❌ “We’d love it if you’d help out with a gift this year.” ❌ “It would be wonderful if you supported us again.” ❌ “We’re hoping you’ll get involved this year.” None of these are technically wrong, but they leave the donor hanging. They don’t invite a response. And they definitely don’t feel like the moment of decision that a real ask should be. Compare that to: ✅ “Would you be willing to make a gift of $5,000 to support undergraduate research?” ✅ “Can we count on you for support at the $25,000 level this year?” ✅ “Will you help our students with a $1,000 gift to the Dean’s Fund?” These are direct. Respectful. And clear. By ending your ask with a question, you’re signaling that it’s now the donor’s turn to speak. That subtle shift sets up a healthy, balanced fundraising conversation. ✅ 2. Mission Moment + Dollar Amount This is where you tie the ask to purpose. Don’t just ask for money—anchor the ask in something that matters. This is what moves the donor from “How much?” to “What for?” Instead of: ❌ “Would you consider a gift this year?” Try: ✅ “To help provide book scholarships for every student in the program, would you make a gift of $10,000?” Instead of: ❌ “We’d love your support.” Try: ✅ “To allow faculty to attend national research conferences this year, would you be willing to give $2,500?” You are the bridge between the mission and the donor’s capacity to make something good happen. That’s your role. You’re not begging. You’re inviting them into something meaningful—with clarity. And don’t shy away from being specific. A donor can always say no to a number. That’s okay. But if you ask, “Would you consider helping us out?” and they say “No,” you’ve left yourself no room to move. When you name a number, you create the chance for a real conversation. They might say, “That’s higher than I was thinking,” and now you can respond: “What would feel more comfortable for you?” or “Would you like to stretch that over a multi-year pledge?” Specificity unlocks possibilities. Vagueness shuts them down. ✅ 3. End. Pause. Listen. This is the part that makes or breaks it. Once you’ve made the ask—STOP TALKING. I know. It’s awkward. It feels like an eternity. But it’s crucial. The silence after the ask gives your donor time to process. It allows them to think. It gives them space to share what’s really on their mind. And what you learn in that silence? That’s gold. Maybe the timing’s off: “I just paid my kid’s tuition bill.” Maybe they need buy-in: “I’d have to talk it over with my spouse.” Maybe they’re passionate—but about something else: “I’d rather support the scholarships instead of the building fund.” If you rush in to fill the silence, you will miss all of that. You’ll speak from your own nervousness instead of their reality—and you’ll never know what part of the ask didn’t work for them. Practice the pause. Get comfortable sitting in it. It’s where the most honest parts of the conversation live. Bringing It All Together: Here’s a strong ask, built using the Magic Formula: “To help us provide every student in our department with book scholarships, would you be willing to make a pledge of $25,000—$5,000 a year for five years?” [PAUSE] If they say yes—celebrate and affirm it. Then let them know next steps to document and facilitate the gift payment. If they say no—that’s your cue to start the conversation. “Would it help to spread the gift out?” or “Is there a specific area you’d like to support instead?” But don’t jump ahead. Let them answer first. Want More on What Amount to Ask For? I’ve got a whole system for deciding how much to ask for—based on donor history, capacity, engagement, and more. If you'd like me to write about that next, leave a comment or shoot me a message. I'm happy to dig into that in a future post. Cheers! PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
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Jessica Cloud, CFREI've been called the Tasmanian Devil of fundraising and I'm here to talk shop with you. Archives
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