Why My Elementary School Dating Strategy Is Terrible Fundraising Advice

Back in elementary school—in the glorious awkwardness of the 1980s—I had a pretty sweet dating strategy. Maybe you remember it (or are guilty of using it) too.

I’d scribble a note that simply asked, “Will you go with me? Check yes, no, or maybe,” then fold it neatly and pass it along, my heart pounding like I’d just diffused a nuclear bomb.

Fast-forward a few decades, and thankfully I learned a crucial fundraising lesson early in my career: Never phrase your donation ask as a yes-or-no question.

Turns out, what was terrible dating advice in the ‘80s remains terrible fundraising advice today.

Why a yes-or-no donation ask creates an easy exit

Let’s talk behavior psychology for a moment because as fundraisers and marketers, we’re essentially professional students of human decision-making.

Renowned behavioral economist Daniel Kahneman explains that our brains are designed to minimize effort and friction (Kahneman, 2011). Given an easy out, most people naturally take it.

Robert Cialdini, a leading expert on persuasion, reinforces this idea, suggesting clear, authoritative statements move people to action, whereas questions often give them permission to pause—or worse, decline (Cialdini, 2006).

Think about how this plays out in fundraising. If your appeal asks, “Would you consider donating today?”, you give donors a comfortable off-ramp.

Even if a donor is feeling generous, their brain seeks the path of least resistance. “Would you consider…” introduces friction: the donor must actively weigh reasons, find justifications, or rationalize hesitation. Suddenly, saying “no” becomes the simpler, faster option.

But what happens when you shift to, “Give today to save a life”? There’s a stark contrast. It’s directive, clear, and purposeful.

You no longer ask the donor to do the hard work of making a decision. You just point out the correct action for them to take.

Thankfully, I learned this lesson early on

I’m grateful my early career included a mentor who helped me sidestep costly fundraising missteps.

Rick Dunham drilled into me the art and science of a successful ask, and he explained early on why yes-or-no phrasing was fundraising poison.

Since then, I’ve applied (and taught) this principle repeatedly, and have seen similar results across hundreds of campaigns.

I wasn’t just grateful for this fundraising best practice—I was sold for life.

Neuroscience agrees: Donors need clear direction. Choices? Not so much.

Neuroscience strongly supports this principle.

As I’ve mentioned in an earlier post, Daniel Kahneman describes two distinct cognitive systems: System 1 thinking (fast, emotional, instinctive) and System 2 thinking (slow, rational, cautious) (Kahneman, 2011).

Effective fundraising taps directly into System 1: your message must bypass slow deliberation and quickly trigger emotion-driven action.

Directive statements like “Give now to provide clean water” resonate quickly and emotionally. They spark instinctive responses.

This isn’t manipulation—it’s smart, thoughtful communication.

Imperative statements tap directly into emotion, urgency, and subconscious triggers. They reduce cognitive strain and allow donors to act without hesitation.

When you help donors clearly see what matters, you remove unnecessary friction and guide them toward actions aligned with their values.

Exactly how to phrase your donation ask (so the donor can’t easily say no)

Enough theory. Let’s get practical.

Here are some quick, actionable guidelines you can use right away:

❌ “Will you give today?”
✅ “Please give now to feed hungry families.”

❌ “Could you support this important cause?”
✅ “Give now to protect endangered animals.”

❌ “Are you able to join us in supporting this work?”
✅ “Ready to save lives? Give today.”

See the difference? Remove hesitation. Replace ambiguity with clear imperatives. Then your ask becomes powerful, confident, and much harder to dismiss.

If only Don Draper had written my elementary school notes…

Let’s revisit my elementary-school romantic life one last time.

Imagine if, instead of timidly passing a yes-no-maybe note, I’d channeled my inner Don Draper. Rather than an uncertain “Will you go with me?”, my note would’ve boldly proclaimed:

“You. Me. Let’s be boyfriend and girlfriend. You won’t regret it.”

Okay, so Elementary-school Derek probably couldn’t have pulled that off, but Fundraising Derek? For sure he can—and so can you.

Ditch the yes-or-no habit. Be confident, direct, and clear.

Your donors—and your results—will thank you.

Sources:

• Kahneman, Daniel. (Thinking, Fast and Slow.) Farrar, Straus and Giroux, 2011.

• Cialdini, Robert B. (Influence: The Psychology of Persuasion.) Harper Business, Revised Edition, 2006.