Making the Ask: Why Learning To Ask for Major Gifts Is Like Building a Plane in Flight
Scaling Major Gifts. Strategies, action steps, and ideas for scaling major gifts by Tammy Zonker, Major Gift Expert & Keynote Speaker.
If you’ve ever felt like asking for a major gift is “building a plane while flying it,” you’re not alone. After nearly 30 years in major gifts—as a Gift Officer, Chief Philanthropy Officer, consultant, and seminar leader—I can tell you the stakes are always high, the adrenaline always real, and the outcome never guaranteed.
Here’s the good news: you can make those high-stakes conversations feel less like turbulence and more like a smooth climb. In this edition of Scaling Major Gifts, you’ll learn strategies I wish I’d known before my first big “ask,” tips to re-engage ghosted donors, and how new tools—including AI—are changing the game for fundraisers.
The Stakes (and Why They’re High)
Major gifts are the lifeblood of most nonprofit missions, accounting for 80% of contributions or more for many organizations. Yet the AFP Fundraising Effectiveness Report tells us nonprofits retained only 67% of major donors last year —often due to gaps in engagement and stewardship. Layer on the pressure that even one “yes” could mean six or seven figures for your mission, and it’s easy to see why so many fundraisers feel their heart race before an ask.
My Big Early-Career “Ask” Mistake
Let me be the first to confess: I’ve stumbled—hard—when making the ask.
Early in my career, I walked into a meeting with a beautifully researched prospect, brimming with excitement. I’d rehearsed my talking points, confident I had the perfect pitch. But when the moment came, I rushed through the ask, focused almost entirely on our needs, and never paused to invite the donor’s perspective. The air seemed to leave the room. After an awkwardly long pause, they politely declined, later confiding to a board member that they felt like a “target,” not a partner.
It stung. I drove back, replaying every word, realizing I’d made it all about the plane I was building—and never about the passenger I wanted onboard.
The turning point came when I committed to listening first, asking second, and role-playing tough conversations with trusted peers. I learned that major gift work is not about a flawless pitch—it’s about authentic conversation, curiosity, and partnership grounded in shared beliefs and values.
The Common Pain Points I See
Over the years, I’ve seen even seasoned pros face these same challenges:
Getting ghosted after what felt like a great meeting.
Hearing “Maybe later” too many times.
Nerves that derail confidence right at the key moment.
Outreach that feels impersonal—or worse, formulaic.
Follow-ups that fizzle without moving the donor closer to “yes.”
Courageous Conversations Need Safe Practice
As a major gift fundraiser, you know that the most meaningful fundraising outcomes are born from courageous, purpose-driven conversations—moments where trust is forged and lasting impact takes root. Both new and seasoned fundraisers benefit from a safe space to refine their approach, build confidence, and prepare for pivotal donor interactions.
At the Modern Institute for Charitable Giving (ModernICG), our mission has always been clear: empower major gift fundraisers to ask bigger, scale faster, and lead with confidence—by blending timeless wisdom with modern tools to create true, lasting impact.
That’s why ModernICG has partnered with Practivated.
Practivated is your AI-powered practice partner, purpose-built for nonprofit fundraising professionals. At our Excellence in Major Gift Fundraising Seminar in October, you can practice donor conversations in a supportive, low-pressure environment where every scenario is tailored to the challenges you face in major gifts.
Engage with lifelike donor avatars that reflect a spectrum of personalities and giving behaviors, gaining immediate, actionable feedback in key areas, such as clarity, conciseness, storytelling, confidence, engagement, and building trust.
So you'll strengthen your skills in knowing not only what to say, but how to say it authentically and effectively.
And, with guidance from Coach Tivy, your personal AI-powered practice partner, you receive even more support along your journey. Coach Tivy offers personalized, empathetic guidance, delivering actionable strategies to overcome anxieties, listen deeply, handle objections, plan strategically, and strengthen donor relationships.
As part of your training in October, you’ll use Practivated during our three-day Excellence in Major Gift Fundraising Seminar, applying custom major donor role play scenarios created by yours truly. I draw on nearly 30 years of major gifts expertise and my proven ability to coach thousands of nonprofits to collectively raise over $1 billion.
My scenarios, coupled with live coaching —superpowered by Coach Tivy as your AI-powered practice partner—will help you navigate real-world challenges, hone your skills, and grow in confidence—right there in our virtual training room.
Turning “Maybe Later” Into “Yes!”
During the upcoming Excellence in Major Gift Fundraising Seminar, we'll share the essential re-engagement strategies for major donors who seem to vanish. You will learn how to:
Lead with value in your invitation—purpose, not pressure.
Personalize every touchpoint—don’t let templates do the talking.
Use multiple channels (calls, email, texting, LinkedIn) to land meetings.
Ask a question only they can answer to spark curiosity.
Follow up with persistence and purpose, not desperation.
Make their next step effortless.
Real-World Win
I recently coached a development director who’d been ghosted for months by a high-capacity prospect. We strategized outreach that combined bold vision, donor-centered language, and multi-channel persistence—a handwritten note, a LinkedIn connection request, and finally an email with a question tailored to the donor’s expertise: “If you could dream big with us, what would you want to make happen?”
The donor replied within days. Two weeks later, they committed to a six-figure gift.
We Fly Together
If you’ve felt that anxiety before a major “ask”—you’re in good company. I’ve been in that cockpit, gripping the controls, wondering if I could land the moment. The truth is, your skill—and your confidence—grow in direct proportion to the practice you put in and the community you lean on.
We also know the turbulence you face:
Prospect ghosting – Prospects who don’t return your calls after initial interest.
What You’ll Learn: Our tried-and-true major gift fundraising strategies and follow-up techniques that turn “maybe later” into a six- or seven-figure “YES.”
Ask anxiety – Afraid of saying the wrong thing or uncomfortable making big asks.
What You’ll Learn: How to build confidence using AI-powered practice tools and practical language to reduce stress and show up to donor meetings feeling calm, clear, and ready.
Limited prospect pipeline – Not enough qualified major gift prospects in your pipeline.
What You’ll Learn: How to use AI to uncover hidden prospects, craft custom stewardship journeys, and make data-driven decisions that move high-value donors from interest to investment.
Lapsed donors – Donors who give and then disappear into thin air.
What You’ll Learn: Our moves management system for intentional donor cultivation and stewardship to build lasting trust, strengthen connections, and dramatically improve donor retention.
You’re not alone in facing these challenges—and you don’t have to navigate them without guidance.
That’s why I invite you to join me, Tammy Zonker, and Coach Tivy for the “Art of the Ask Role Play” and "Securing the Visit & Making the Ask" sessions at our upcoming Excellence in Major Gift Fundraising Seminar—October 13–15, 2025.
You’ll leave with more than just strategies; you’ll leave with a flight plan to navigate every one of these pain points with confidence and skill.
→ Learn more and reserve your spot today!
Keep scaling,
Tammy Zonker
Author, Major Gift Expert & Keynote Speaker
President, Fundraising Transformed
President, Modern Institute for Charitable Giving
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