AI can rebuild your whole plan this weekend. That's the problem.

4-minute read

You could redo your whole development plan this weekend. Give your draft to AI, and in 15 minutes, you’ll have a polished, formatted plan ready to go.

That’s what makes me uneasy.

Last week, I came across a document I hadn’t seen in 20 years: my strategic fund development plan for the YWCA of Metropolitan Chicago. I wrote it by hand in June 2005, when I was working to double our revenue from $1.6M to $3.2M.

Looking at it now, I can see exactly what has changed over two decades and with AI, and what hasn’t.

What I’d Keep

More than I thought I would.

The gift range chart is still on page 6: 10% of donors give 60% - 80% of the dollars. That math hasn’t changed. It was true in 2005, and it’s still true now.

The moves management approach for major donors is still the same.

Board give-or-get expectations and full participation are still just as important.

Bequests remain the easiest entry point into planned giving. That’s how we still focus our time.

The Donor Bill of Rights was stapled to the back then, and we still follow it now.

The fundamentals don’t get old.

What I’d Remove

The plan used a Nine-Point Performance Index to measure results. Nine numbers, most just tracking activity.

Today, I’d toss out eight of them and keep the four I use now to predict revenue. (Issue 45 has the details.)

One line made me laugh: under corporate goals, it says, "The Development Committee has not yet set its goals." I sent out a plan with a blank section. I wouldn’t do that today.

What AI Can Do in the Blink of an Eye

This part would have seemed like science fiction to the person I was when I wrote that plan.

Back then, prospect research meant outsourcing 3,000 names for screening, then holding manual sessions with board members to fill in the gaps.

Now, AI can screen for capacity and giving patterns in minutes, and draft the first version of a prospect brief before I finish my coffee.

For institutional proposals back then, I started each one from scratch.

Now, AI drafts the first version tailored to the funder, so I can focus on using my judgment.

And here’s what I would have wanted most in 2005: I can give the whole plan to AI and ask where we’re over-concentrated, which ratios aren’t realistic, and what systems the plan assumes are working but never mentions. That kind of pressure-test used to require an expensive consultant and six weeks of meetings.

What I Got Right Without Realizing It

That 2005 plan included a section called Assumptions—what needs to be true for the plan to work. Things like board participation and having an honest prospect pool.

That’s the same question I focused on in Issue 39, Your Forecast Won't Warn You: what must be true? I was asking it in 2005, but back then, I had to answer it by hand and hope for the best.

The important questions haven’t changed. What’s different now is that answering them, conducting the research, and drafting no longer take a month.

That’s the real meaning of the “do more with less” promise.

The Plan Pressure-Test

So I turned my old consultant-and-6-weeks routine into something you can do this week.

The Plan Pressure-Test: five prompts I use to now to review my development plans before calling it final. They cover concentration risk, hidden assumptions, ratio reality, missing systems, and wrong sequence.

Take your current plan, run it through these five prompts, and you’ll see where it’s weaker than you thought.

Get it here: The Plan Pressure-Test. If you’d rather have it sent straight to your inbox, just reply and I’ll send it.

One caution before you start: a plan can look finished in minutes, but it can still miss the judgment that only comes from real experience with donors. Creating the document is easy now, but the discernment behind it still takes years to develop. The Pressure-Test is where your judgment really matters.

Your Turn

Take your plan and use prompt #2: list one assumption it relies on but never mentions. Circle the one that would cause the most trouble if it’s wrong. Start with that.

On My Radar

Ruben Hassid’s newsletter, How to AI, is the one I actually open every week. It’s full of step-by-step, screenshot-heavy guides for using AI tools—no jargon, nothing theoretical. If you want your team to use AI rather than talk about it, this is what I’d read.

Coming Next Week

Next Sunday, I handed AI a plain read of my week — the meetings, the sign-offs, the decisions landing on my desk — and asked it where I'm the bottleneck in my team's progress.

It got the diagnosis right. It got the fix wrong, in a way that would've made things worse if I hadn't caught it. I'll share the four-bucket audit I built to catch it.

Until next Sunday,
Christine

PS - The Plan Pressure-Test is ready for you. Run it on one section of your plan first, the one you're least sure about, and see what surfaces. Let me know what surprises you.

This newsletter grows one fundraiser at a time, and mostly by word of mouth. If it's useful, forward it to one Chief Fundraiser who'd get something out of it.

I’m Christine Bork, Chief Development Officer at the American Academy of Pediatrics.

I write CFW to share what I’m learning as I lead a growing team and try to do the work in a way that’s sustainable and thoughtful.

The Fine Print

Sometimes I include links from affiliates. If you click and buy, I may receive a small commission or a discount on my own purchase, no markup to you. I only link to things I'd tell you about over coffee anyway.

© 2026 Christine Bork / Chief Fundraiser Weekly. All rights reserved.