I’ve been working in the nonprofit sector since 1977. Through CharityChannel Press, which I founded in 1992, my publishing house has published more than a hundred books, most of them for nonprofit professionals, covering everything from capital campaigns to board governance to planned giving. I’ve built and administered fund development programs, and founded a few thriving nonprofits, too. I’ve served as legal counsel to nonprofits since 1981.
For most of those decades, the technology conversations in fundraising followed a predictable arc. A new tool arrived: the Internet, online giving platforms, social media, mobile. The early adopters rushed in. Conference sessions filled up. Vendors made promises. Then reality set in. The technology was useful, sometimes very useful, but the fundamentals of fundraising didn’t change. You still needed to know your donors. You still needed to make thoughtful asks. You still needed to say thank you like you meant it.
AI breaks that pattern. It operates in territory that previous technology never touched.
Now Available
In Holding Fire: A Skeptic’s Framework for the Fundraiser with AI at Your Side, Stephen Christopher Nill, JD, lays out the Human-Centered AI Framework—his five-principles approach to keeping humans at the center of every donor interaction, even as AI quietly does the work no one fundraiser could ever do alone.
This book was written by a skeptic, for skeptics.
AI Changes What “Knowing Your Donors” Means
Previous fundraising technology handled transactions. Databases recorded gifts. Email platforms delivered messages. Online giving pages processed donations. These were all important functions, but they operated at the edges of the relationship. A typical CRM held a great deal of information on donors: giving histories, contact records, event attendance, program designations, even notes added after meetings and phone calls. But connecting all of it, seeing the patterns across hundreds of relationships and figuring out what each donor needs this week, still required a human being with enough hours in the day to sit down and think it through. Most development offices never had those hours.
AI works differently. Give it a donor’s complete record and it can synthesize everything: the giving trajectory, the program interests, the event attendance, the conversation notes, the engagement signals you might not have connected on your own. It can draft a personalized thank-you note in seconds that draws on all of it. It can prepare a donor visit briefing that reads like something a colleague who’s known the donor for years would put together.
That’s a fundamentally different kind of tool. A database stores information. AI reads it, connects it, and helps you act on it.
In preparing to write my book, I spent considerable time building and testing a system that puts this to work. After trying various approaches, I built a working online practice environment for a fictitious food pantry where you can see exactly how it operates: donor pages with structured data alongside free-form notes, dashboards that flag what needs your attention each week, and an AI assistant that reads all of it and drafts communications you can review and send.
The results surprised me. The drafts were more thoughtful than I expected. They referenced the right details, connected giving patterns to program impact, and in many cases identified opportunities I would have missed. A Monday morning review of an entire donor portfolio, something that would take hours of manual work, consistently took about twenty minutes.
Relationships Lead, Technology Follows
Every time I tested the system, the most important moment came after the AI finished its work.
A donor’s giving has been growing steadily, and the AI catches the pattern and drafts a note that connects the trajectory to program impact. The draft is a good start. But when the fundraiser reads it, she adds a coffee invitation because she knows, from a conversation that never made it into the notes, that this donor is looking for a deeper connection to the mission. The AI prepared the ground; the fundraiser made the relationship move.
The pattern showed up everywhere I looked. A board member’s visit briefing was remarkably thorough because the fundraiser had been diligent about logging notes after every board dinner and committee meeting. The AI pulled those notes together with giving history and engagement data to produce a preparation document that captured the full arc of the relationship, connections and context that would have taken hours to compile manually. The fundraiser then made the strategic call about what to emphasize in the conversation and how to frame a sensitive budget discussion. A lapsed couple’s reengagement letter pulled in their full history with the organization, but the fundraiser rewrote the closing because she knew this couple responds to warmth and the AI’s tone was a touch too formal.
That’s the book’s central premise: relationships lead, technology follows. AI handles the synthesis, the pattern recognition, and the drafting at a scale no human can match. What it gives back is the most valuable thing a fundraiser has: time to build relationships with the people who support the mission.
Why This Book, Why Now?
I’m writing Holding Fire because I think the fundraising profession needs a new framework right now, and my book offers one that my experience tells me is the right one. AI capabilities are being added to every major donor database platform. Fundraisers are going to use these tools whether or not anyone shows them how. The risk, if we get this wrong, isn’t that AI replaces fundraisers. The risk is that AI becomes another layer of impersonal automation between organizations and the people who care about their missions.
The book walks through a complete system: a Monday morning review that takes twenty minutes and ensures no donor falls through the cracks, communication workflows that turn AI drafts into messages donors actually remember, and strategic frameworks for major gifts, annual giving, stewardship, and lapsed donor recovery. It meshes perfectly with the free online Practice Portfolio I created; you can set up in your own workspace to follow along with every example.
What Comes Next
Starting next week, I’ll be writing every Tuesday about how to use AI in a way that puts the focus on the human side of the equation. Some weeks will cover specific AI techniques. Others will get into fundraising strategy, donor communications, or the organizational questions that come up when a team starts using these tools. Every piece connects back to the same idea: AI is at its best when it serves the very human relationships we have with our donors.
Next Tuesday I cover what AI actually does well in fundraising, where the technology runs out, and why that boundary deserves more of our attention than the capability does.
I’m glad you’re here. Let’s get to work.
Stephen Christopher Nill, JD, founded CharityChannel in 1992, building it into one of the largest online communities of nonprofit-sector practitioners in the world. He has edited, designed, and published dozens of books for the nonprofit sector through CharityChannel Press. Over four decades, Stephen has built, administered, and advised fundraising programs in the United States and internationally that have raised billions of dollars. He has served as senior vice president of development at a hospital system, chief advancement officer at a West Coast university, director of development at a parochial school he helped to found, and founder and executive director of a charity that feeds the homeless in Southern California.
The Grant Professionals Association presented him with its first President’s Award. The Grant Professionals Certification Institute later honored him with the Pauline G. Annarino Award for foundational contributions to its existence. Stephen has been a frequent commentator on charitable giving for CNN, Fox News, MSNBC (now MS NOW), and other news shows.
He has provided training to attorneys on advanced charitable gift planning techniques on behalf of the State Bar of California’s continuing legal education program. As a lawyer and consultant, he advised hundreds of nonprofit organizations and educational institutions.
Stephen’s engagement with artificial intelligence reaches back to the 1970s, decades before the current wave. Holding Fire: A Skeptic’s Framework for the Fundraiser with AI at Your Side draws on that long history and on his career inside development offices.
He writes weekly to development professionals at charitychannel.com. These days he’s busy writing his first novel and composing symphonic music in his music studio.
