This week I had a conversation with a nonprofit leader whom I respect greatly. His usual optimistic and friendly manner had a tone of exhaustion. The week before, another wonderful colleague shared anxieties expressed from many participants in a monthly fundraising roundtable. Despair is in the air.
It’s not been an easy couple of months for the nonprofit sector, and there’s a palpable fear over loss of funding.
The part of fundraising I love most is hearing people tell me what they care about in the world, and then helping them invest in it. (Social ROI – the chance to do work that does good – is why we’re all here, isn’t it?)
Talking to people is a distinctly personal way to connect around philanthropy. It’s also made me reluctant to use tools that feel impersonal, like AI. But I’m coming around.
Trends – and experts like Nathan Chappell – tell us that individual giving is down. Are people less generous, losing hope, or just overwhelmed by information?
Too many emails.
Too much negative news.
Too little time when we’re not in front of screens.
I’m an optimist at heart. I’d like to believe Allison Fine’s excellent article last month in the Chronicle of Philanthropy. She is a kindred spirit to Mr. Chappell when she says:
AI is just technology looking for patterns to free humans up to do what we do best: build relationships, solve problems and create communities.
I absolutely love that! (Which is not very surprising. If you read this, this or this, you know I am passionate about building community.)
But is it really possible for automations to add a “personal” touch in fundraising?
Ms. Fine believes that relational fundraising at scale prioritizes genuine connection and communications over efficiency. It’s a chance to recognize and empower individuals in roles beyond donors – as advocates, ambassadors and collaborators.
If using AI for relational fundraising involves a new set of habits and norms, then it’s time for me to challenge some of my old habits. Want to come along on the ride?

Two Assumptions
My work creating comfort for board members of small nonprofits to engage donors has focused on one-to-one connections. What if, instead, we assume that:
We can let AI help us learn what donors think about our nonprofit’s work (just like we do in a real, human conversation with a donor), and
Our definition of a great donor is one who just made their second gift (rather than someone we think may be “wealthy” because they give a lot to our organization or another).
It takes two to three years to cultivate a major donor for a much larger (say, 10x) gift. Testing this idea certainly won’t take that long.
All for One, or One for All?
A major gift strategy creates a journey for a single donor that always starts with learning why that specific donor gives. (There is only one certainty in fundraising. If you make an assumption about why a donor gives, you will be wrong.)
An approach that leverages AI feels like creating a path that many donors can travel – more like a customer journey. If we ask questions related to the kinds of impact we create (and the stories we tell to demonstrate that impact), then we’ll have a road map to guide us in matching each story to donors’ actual interests.
To learn this, Ms. Fine recommends asking: How do we make you feel as a donor? I’ll put a slightly different spin on what I’d like to learn from a bunch of donors:
What is it about our work that made you want to give?
It’s a priceless way to hone our messaging to what resonates with those who are funding the work. And it gives us the gift of thinking about the destinations where we want our donors to go. Let’s fill a whole bus with them! When they look out the windows, they’ll see things that are relatable because they connect with their personal interests for social ROI.
This is starting to feel a bit like real relationship-building. Maybe I could get to love this kind of fundraising too.
Got any easy AI donor engagement tales to tell? Inspire us!
Always pointing to the ❤️! This is where we live truly.