The Strategy That Has to Wait

Issue #48
3-minute read

Hi Reader,

I found an AI vendor to build something perfect.

Not a chatbot. A real AI tool that could tell me how mid-tier donors were engaging with our content — in real time — and customize communication based on behavior signals, not just gift history.

We have thousands of prospects in that segment. The lifetime value implications are huge.

I wanted to run a cost-benefit analysis on whether to hire the vendor. I couldn’t. Because we don’t have an AI policy yet.

Here’s the part that’s hard to sit with: the strategy is right. The organization isn’t ready to run it.

You can see further than the systems around you. You can design strategies that the infrastructure isn’t built to execute.

That gap between what you can see and what your org can execute isn’t a strategy problem.

It’s a readiness problem.

And it requires a different response.

What Waiting Costs

The instinct is to treat this as a pause. File it away. Come back to it when the conditions are right.

But waiting has a price, and we don’t always name it clearly.

In our case:

Slower engagement with people who are ready. Lifetime value that compounds in the wrong direction when we’re managing these relationships with blunt instruments instead of sharp ones.

The cost of waiting isn’t just the revenue we don’t raise this year. It’s the relationship equity we don’t build, the upgrade cycle we don’t accelerate, the donors who deepen their engagement elsewhere because someone else’s system read them better than ours did.

Naming that cost matters.

When the Gap is the Problem

This is a different kind of stuck.

Most Chief Fundraisers have a version of it.

The hire they couldn’t make because the budget structure didn’t support it. The campaign they designed but couldn’t launch because internal alignment wasn’t in place. The procedural change that would have fixed the gift-processing system, but it didn’t sync with finance's work plan.

What those situations have in common: the strategy was sound, but the org wasn’t ready. That distinction matters because it changes what you do next.

You don’t fix a readiness problem by pushing harder on the strategy.

You fix it by being honest about what needs to change and who needs to know the cost of the wait.

In our case, the AI policy is underway. Most importantly, my team found a stopgap solution that gets us started on customizing communications.

That’s not giving up on the original AI project. That’s how I'm leading from the gap.

On My Radar

I’ve been reading Chenelle Basillo’s 30 Days of Growth series on email list building. There are so many transferable ideas we can use for our donor or newsletter lists. Here's a great one.

A creator shared a Google Doc draft with his list and asked for feedback. People showed up, left comments, and collaborated in real time. What if mid-tier donors were invited to offer feedback on the next newsletter? That’s co-creation. And co-creation builds ownership that stewardship rarely does.

Your Turn

Before Friday, name one strategy you’ve been sitting on and do the math to figure out what it’s costing you to wait. That’s the number you need to have ready when the time is right to present to your CFO or CEO.

Coming Next Week

Next Sunday: The opportunity I built for months — and then killed. What the research taught me about our most important asset.

Cheers,
Christine

PS — If you’re building the case for an investment your org hasn’t said yes to yet, the System Six playbook walks through exactly how we do it.

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

Full disclosure:

Some links in CFW are affiliate links. If you click and buy, I earn a small cut or a discount — no markup to you. I only link to things I'd tell you about over coffee anyway. The commission is just a bonus for not keeping my opinions to myself.