What Else Would You Like With That?

Using Leading Questions in Fundraising 

Every time I go to Starbucks, I think about fundraising.

Weird, I know — but hear me out. Because what happens is a masterclass in guiding a conversation.

You walk up, place your order: “I’ll have a tall soy vanilla latte, please.”

And then, almost without fail, the barista replies:

“What else would you like with that?”

It’s a simple question. Cheerful. Routine. But it’s also brilliant.

Because it’s not if you’d like something else. It’s what else.

It assumes you might want more, and it opens the door to possibility. It’s a classic leading question — gentle, guiding, and highly effective.

That simple phrase — so natural, so effective — made me realize something:

In fundraising, the way we phrase questions can dramatically shape the responses we get.

But are we using them well? Are we thinking about how they shape the answers we get?

What Is a Leading Question?

At its core, a leading question nudges the responder in a particular direction. It can be subtle (“What else would you like with that?”) or more overt (“Don’t you agree this is a smart investment?”). The key is that it frames the response and assumes a point of view.

In fundraising, we tend to be wary of leading questions—we don’t want to come off as pushy.

But let’s be honest: we’re not neutral.

We believe in our missions. We’re inviting people to do something meaningful.

And done with intention and integrity, a leading question can be a powerful tool to help donors articulate their values and align with impact.

The best leading questions aren’t about closing a gift. They’re about expanding the conversation — about helping donors articulate their values and see where they fit in the bigger picture.

When I ask, “What else would you like with that?”— in donor terms — I’m not trying to see if I can get you to buy a lemon loaf. I’m offering deeper engagement. Greater alignment. A chance to go beyond the initial transaction into something that actually transforms lives (including the donor’s).

Here’s how that might sound:

“What kind of legacy do you hope your giving will create?”
(This invites them to talk long-term, beyond the now.)

“Does this project reflect the kind of change you’ve said matters most to you?”
(You’re reinforcing alignment with their own stated values.)

“Would it feel meaningful to be involved in shaping how this initiative grows?”
(You’re guiding them toward ownership, not just support.)

“Can you see how your gift could inspire others to step up, too?”
(This plants the idea of leadership and influence.)

These aren’t manipulative. They’re intentional. And that’s an important distinction.

So… Is It Ethical?

Let’s name the discomfort. The phrase “leading question” can feel like something out of a courtroom drama or a sales training manual. It can sound like we’re trying to trap someone.

But ethics in fundraising isn’t about pretending we don’t care what people say. It’s about respecting their agency while offering a meaningful invitation.

Here’s the gut check I come back to:

• Am I using this question to serve them or me?
• Am I genuinely open to their answer — even if it’s no?
• Am I inviting, not pushing?

If the answer is yes across the board, then I’m on solid ground. Great leading questions help a donor explore something that might bring them meaning.

Try This Instead of That

Here are a few swaps to help you shift into effective leading questions.

These small shifts matter. They invite more discussion, more clarity, and forward momentum.