The true measure of fundraising success isn’t landing the first major gift—it’s turning that milestone into years of partnership and impact. In my experience, donor retention is where the real transformation happens, yet it’s often overlooked by busy teams focused on acquisition. In this edition of Scaling Major Gifts, I want to talk candidly about why donor retention matters and lay out proven steps any nonprofit leader can take to nurture lasting relationships.

Whether you’re writing a book, launching a capital campaign, managing a major donor portfolio, or facilitating a board retreat, the challenges are universal: time scarcity, emotional toll, and sacrifices and trade-offs. Sound familiar? This article is for my fellow executive directors, major gift officers, development directors, fundraisers, volunteers, and board members who are striving to make a difference while balancing the many hats you wear.

As someone who’s spent nearly 30 years in the trenches of major gift work—building relationships, bridging tough divides—I know firsthand just how challenging it is to honor both your donors and your community. If you’re a major gift officer, development director, executive director, or board member, you’ve likely felt this tension yourself. In my experience, the “fundraising divide” isn’t just a headline—it’s an exhausting reality. And right now, it’s deepening.

What if you could practice high-stakes donor conversations in a safe space before the real thing? In this edition of Scaling Major Gifts, I share the strategies I wish I'd known before my first big ask, plus how new AI tools are changing the game for fundraisers like us. Read this edition and share it with your team—because we all need to fly together in this mission-critical work.

In this edition of Scaling Major Gifts, I want to share some hard-earned insights on upgrading major donors, drawing from both my own journey and the many talented professionals I’ve had the privilege to work alongside.

After nearly three decades in the world of major gifts, I can say with absolute certainty: securing that first major gift is a triumph, but transforming that initial generosity into a lifelong partnership is where the real magic—and challenge—happens. Whether you’re a major gift officer, development director, executive director, or board member, donor retention isn’t just a metric; it’s the heartbeat of your mission’s sustainability.

My book, Calling All Heroes, is my invitation—and my challenge—to all of us who believe in the transformative power of philanthropy. I wanted to offer a roadmap that blends the best of donor-centered and community-centered fundraising, grounded in real-world experience and a profound respect for every stakeholder in our missions.

After nearly three decades in the world of major gifts, I can say with certainty: the journey to securing transformational support begins long before a check is written. It starts with that very first impression—an interaction that can set the tone for a relationship that lasts years, even decades. Whether you’re a major gift officer, development director, executive director, or board member, how you approach those initial moments with a potential donor can make all the difference.

After nearly 30 years in major gifts, I’ve seen our field transformed—sometimes overnight—by technology. But one thing has never changed: major donors want to feel seen, valued, and connected to our missions.

Today, as executive directors, development leaders, and board members, we face the challenge (and opportunity) of building authentic relationships in a digital-first world. Let me share what I’ve learned, the pitfalls I’ve witnessed, and the practical solutions that keep donors engaged, loyal, and inspired—no matter the medium.

After thirty years in major gifts, I’ve seen the transformative power of strong donor relationships. But I’ve also seen the pitfalls when those relationships cross from professional stewardship into personal friendship. Let me share why, in my experience, maintaining professional boundaries isn’t just best practice—it’s essential for the health of both your organization and your own well-being.

After nearly three decades in major gift fundraising, I’ve seen countless trends come and go. But few have reshaped the landscape quite like donor-advised funds (DAFs). If you’re a major gift officer, development director, executive director, or board member, understanding DAF donors isn’t just a “nice to have”—it’s essential for your organization’s future.

If you’ve been in the nonprofit trenches as long as I have—nearly three decades—you know that economic and political uncertainty isn’t new, but it always brings fresh challenges. I recently read in The Chronicle of Philanthropy (by Ben Gose) that online donations have dropped sharply since President Trump’s latest tariff announcements. This year, President Trump’s tariffs and the resulting stock market volatility have sent a chill through online giving. As major gift officers, development directors, executive directors, and board members, you’re likely asking: Should we pull back on fundraising appeals, or is now the time to double down?

After nearly three decades in major and planned giving, I’ve learned that our work has always been built on three pillars: trust, timing, and tailored conversations. Relationships are the heart of what we do. But today, artificial intelligence (AI) is giving us new tools to deepen those relationships—by helping us uncover hidden prospects, personalize stewardship, and make data-driven decisions that move high-value donors from interest to investment, all without losing the human connection that matters most.

If there’s one truth I’ve learned in nearly three decades working in major gifts, it’s this: nothing moves the needle for a nonprofit quite like a well-executed major gift ask. As Jerold Panas famously said, “If you get the visit, you’re 85% on your way to getting the gift.” That single meeting—securing it, preparing for it, and making the ask—remains the most pivotal moment in our work. Whether you’re a development director, executive director, or board member, mastering this process is essential to your organization’s growth and impact.

As someone who has dedicated nearly three decades to major gift fundraising, I can tell you that the landscape of donor engagement and stewardship has evolved tremendously. One of the most transformative shifts I've witnessed—and embraced—is the move toward a data-driven moves management process. If you’re a major gift officer, development director, executive director, or board member in the nonprofit sector, this approach is not just a buzzword; it’s an essential strategy for building deeper, more fruitful donor relationships and sustaining your organization’s mission.

As much as we honor the past, we know the world of major gift fundraising is changing. Donor expectations are evolving, technology is racing ahead, and the challenges we face are more complex than ever. That’s why, as of January 13, 2025, my company, Fundraising Transformed, has acquired the Institute for Charitable Giving, also lovingly known as ICG. And together, we’ve launched the "Modern" Institute for Charitable Giving (ModernICG). It’s a dream come true for me. And I believe, a turning point for our sector. This isn’t just a name change or a rebrand — it’s a bold leap forward for our sector, and I believe it’s exactly what we need right now.

After nearly three decades in the world of major gifts, I can say with certainty: the way we steward our major donors is the single most important factor in achieving lasting fundraising success. Whether you’re a major gift officer, development director, executive director, or board member, your role in donor stewardship directly impacts your organization’s ability to retain and grow its most significant supporters.

After nearly 30 years in this field, I’ve seen firsthand how the right major donor strategy can propel an organization’s mission to new heights. But I’ve also seen the common pitfalls that can stall even the most passionate teams. In this edition of Scaling Major Gifts, I want to share the most persistent challenges major gift officers face when implementing a major donor strategy—and, more importantly, the practical solutions I’ve found to move past them. Whether you’re building your program from scratch or looking to take your results to the next level, these insights are for you.

Struggling to invite grateful patients and families to share their stories without crossing sensitive boundaries? In this week’s edition of Scaling Major Gifts, I’m drawing on nearly 30 years of experience to unpack the real challenges (and big opportunities) of authentic storytelling in healthcare fundraising. I share practical strategies, a real-world success story, and actionable tips you can use right away to create safe, meaningful pathways for patients and families to get involved. 

In this week’s Scaling Major Gifts newsletter, I sharing practical strategies, real-world examples, and actionable tips to help you engage next-gen donors effectively. Whether you’re a major gift officer, development director, or nonprofit leader, this is your roadmap to building authentic relationships with the changemakers of the future.