‘AI in Question, Part 1’: Can Donor Relationships Be Automated?

This is the first in a short series I’m calling AI in Question.

Over the next three weeks, I want to raise some flags about the rush to lean on AI to do too much in fundraising creative.

And today, I want to start with relationships.

Because donor development has always been about relationships… and the question we have to ask is whether those can really be automated.

A ChatGPT conversation that’s stuck with me

Not long ago, someone I loved was treated pretty poorly, so I naturally wanted to talk to the offender about it.

I wasn’t sure how to approach the conversation, so I did what a lot of us are doing these days. I opened ChatGPT and asked it for some talking points.

And you know what? It delivered. The lines were smooth, the tone was calm but firm, and honestly, ChatGPT Derek sounded better than I would have on my own.

But here’s what stuck with me afterward:

Chat never asked me whether I should talk to the person who hurt my loved one in the first place.

It didn’t pause and say, “Are you sure you should even waste your time on the guy?” It just gave me an answer I wanted it to give me, and it did it without any pushback.

That was the moment I realized something important:

AI is smart, but it doesn’t have wisdom.

It can give me words, but it can’t discern whether those words should be even be spoken in the first place.

Another ChatGPT conversation that struck me

Last week, I had another conversation with Chat that was… interesting. Here’s a snippet of it.

What a perfectly fine answer: a summary of what Christians believe!

But I pressed further…

Chat readily admitted what we sometimes forget:

AI doesn’t have the capacity for relationships.

It can mimic warmth, it can simulate empathy, and it can stitch together words that sound like care.

But it can’t really care.

Why this matters in fundraising creative

Producing effective fundraising creative is all about understanding relationships and human dynamics.

It’s about listening and building trust over time, and it’s about knowing how words and their design will make someone feel.

AI can’t do that. So here’s the flag I want to wave:

If we lean too heavily on AI for donor development creative, we’ll end up trading authenticity for automation.

Donors will feel the difference, and so will your organization’s bottom line—if not immediately, over time.


Next week in Part 2 of AI in Question: AI has data, we have experience. And in fundraising, that difference is everything.

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‘AI in Question, Part 2’: Can Data Replace Experience?

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Why You Should Kill Prepositional Phrases in Your Copy