The Question That Unlocked 25 Ideas

We'd been stuck at 3% member giving for years.

It wasn’t because we weren’t trying. In fact, we experienced a 1% growth and celebrated. We ran campaigns, made appeals. Still, the number didn’t budge.

But we hadn’t found the right question to ask.

When I Realized I Was Asking the Wrong Question

A few weeks ago, I wrote the following:

Each gift averages over $250, and our retention rate is 55 percent. Incredible. Yet the percentage of members contributing has remained flat for years. What resources do we already have, at minimal cost, that could help us improve beyond 4%?

That's Constrained Generative Thinking. You don't ask what you could build. You don't ask what you'd do with more budget.

You ask about what you already have but haven't fully used, and you build that boundary into the question itself.

The limitation is what turns the list into something you can act on, rather than just wish for.

What It Looks Like to Come Up With 25 Ideas

I shared the question with my team and let them brainstorm. They came up with 25 ideas.

The first ten ideas came quickly. They were the obvious ones we’d already thought about. The next ten were tougher. By the time they reached 25, we had moved into new territory.

One idea was to add a donation option to the conference registration checkout. This was an asset we already had—a moment of high engagement that we overlooked every year.

We had never tried this because we hadn’t thought to ask the question in this way before.

Sorting Is the Key to the System

Making the list is just the first step. The real work begins when you start sorting the ideas.

Three buckets:

Act now: These are low-effort ideas that use current assets and can be assigned to someone this week. Make sure to assign these before the meeting ends.

Build toward: These are good ideas that need more infrastructure or a conversation with a partner. Add them to the roadmap so they don’t get forgotten.

Set aside: These ideas aren’t right for now. They're too expensive or not practical. Write them down instead of throwing them out, because things can change.

If you don’t sort the ideas, you end up with 25 things that never get done.

What Surprised Me the Most

I emailed several colleagues about the act-now items, including the conference checkout idea, which involved a team outside of fundraising.

I expected some pushback—maybe questions about the budget, a promise to revisit it next quarter, or at least one gentle no.

But within days, every single person said yes without conditions.

The real barrier wasn’t resistance. No one was against growing revenue from member gifts. They just hadn’t been asked in a way that made it easy to say yes. A clear, specific, act-now invitation works better than a vague call for help.

We didn’t need a bigger budget or a new hire. We just needed to spend enough time with the question to see what was already available.

The Framework

There are three steps, and they work for any metric that’s stuck—whether it’s giving rates, major gift pipelines, corporate revenue, or board engagement.

Step 1: Identify the metric that’s stuck and provide context. Write down the number, the baseline, and what you know about the opportunity. Being specific keeps you honest.

Step 2: Add a constraint. Focus on current assets, minimal cost, existing relationships, or a time limit. Set this boundary before you start brainstorming answers.

Step 3: Come up with at least 20 answers and then sort them. Don’t stop at ten. The best ideas often come after the obvious ones. Sort the list before you leave the room, and assign someone to handle the act-now items right away.

On My Radar

James Schramko's 4-minute YouTube video, "Why Founders Who Know Everything Stay Stuck," made me rethink where I direct my attention. One story I like: a founder spent hours optimizing ad platforms while a 60% churn rate bled his business dry. The fix wasn't more acquisition; it was pointing at the leak already in front of him.

It's the same trap as our stuck member giving rate. We could have tried a bigger campaign. The real move was constraining the question.

Coming Next Week

Next Sunday: the four stages every gift moves through, and why the ask usually comes before the relationship can support it.

Your Turn

Choose one metric that hasn’t changed in at least two years. Write a version of the question with a clear constraint. Then, push yourself to come up with twenty answers before Friday. Don’t sort them yet. Just get more than ten and see what happens.

Cheers,
Christine

PS — I turned the three-step sequence into a worksheet for CFW readers. Name your stuck metric, build your constraint, and get to 20 ideas. ​​Grab it here​​. Free from one chief fundraiser to another.

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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.