Here’s something that might surprise you: The most effective fundraising conversations sound nothing like what most people think fundraising should sound like.

No PowerPoints. No glossy brochures. No perfectly polished presentations that wow donors into giving.

Instead, they sound like…conversations.

The Counter-Intuitive Truth About Fundraising

When I train nonprofit leaders on making asks, I often hear the same concerns:

“I don’t know what to say.” “I’m not good at sales pitches.” “I feel like I’m bothering them.”

Here’s what I tell them: Stop trying to pitch. Start asking questions.

This feels completely backwards to most people. We think fundraising means we need to have all the answers, deliver compelling presentations, and convince donors through the power of our words.

But effective fundraising is actually about having great questions and letting donors do most of the talking.

A Simple Framework That Changes Everything

I love Andrea Kihlstedt’s asking conversation framework. It has just six parts, and five of them are essentially questions:

1. Settle: “How are you doing?”
2. Confirm: “Is this still a good time to talk about your giving?”
3. Explore: “What have you enjoyed most about our work this year?”
4. Ask: “Because you’ve said [what they told you], would you consider a gift of…?”
5. Explore: “Would giving it quarterly be helpful?”
6. Confirm: “If I don’t hear from you by next week, is it cool if I follow up?”

Notice what happens in step 4? You’re not making up an ask from thin air! You’re connecting directly to what they’ve already told you matters to them.

Why This Works (And Why Pitches Don’t)

In the first Explore phase, you’re doing only 25% of the talking while they share 75%. This isn’t just being polite—it’s strategic.

When donors talk about what they love about your work, two things happen:

1. You get confident. You hear exactly what resonates with them, so you know how to frame your ask.
2. They get excited. They’re talking themselves into giving by sharing their own passion for your mission.

One fundraiser told me after making several seven-figure asks: “I don’t have to make up an ask anymore. By the time I’m ready to ask, I know exactly what to say because they’ve told me what matters most to them.”

This Approach Aligns With Your Values

Here’s why this approach feels so much better than traditional “sales” tactics: You’re genuinely trying to understand and serve the donor, not manipulate them.

Most nonprofit professionals got into this work to help people. But fundraising often feels like taking from people, which creates internal conflict.

When you shift from pitching to asking questions, you’re back to helping. You’re helping donors connect their values with your mission. You’re helping them find meaningful ways to make a difference.

That’s not taking from them—that’s serving them.

The Questions That Steer Conversations

Remember: The person asking the questions is actually the one steering the conversation.

Instead of hoping your pitch resonates, try starting the conversation with questions like:

• “What drew you to our organization initially?”
• “What would you like to see happen next in our work?”
• “How do you see yourself being involved?”

These aren’t just conversation starters. They’re steering the entire interaction toward understanding what matters to them.

And feel comfortable asking questions about their answers. These help you move from surface level “I like it here” answers to getting to what really matters to the donor.

This isn’t an interrogation. If you are sincerely curious, they’ll feel that. And they will anwer.

For Executive Directors Who Avoid Asks

If you’re an ED who’s been putting off that major gift conversation, remember: You don’t need to have all the answers. You just need to have good questions.

The pressure isn’t on you to deliver a flawless presentation. The opportunity is for you to have a meaningful conversation about something you both care about.

For Board Members Who Feel Uncomfortable

If you’re a board member who dreads fundraising, this approach can be a game-changer. You’re not selling anything. You’re asking about their experience and interests.

Most board members are much more comfortable asking, “What do you think about the new program?” than delivering a fundraising pitch.

The Ask Still Matters

Let me be clear: You still need to ask for money. Conversational questions alone don’t raise funds.

But when your ask comes after genuine listening — “Because you mentioned how much the youth program means to you, would you consider a gift of $25,000 to expand it?” — it feels natural instead of forced.

Your Next Conversation

The next time you’re preparing for a fundraising conversation, try this:

• Instead of planning what you’ll tell them, plan what you’ll ask them.
• Instead of preparing to convince them, prepare to understand them.
• Instead of hoping they’ll be impressed by your presentation, focus on being genuinely curious about their connection to your mission.

You might be surprised how much more confident and successful you’ll feel.

My advice? Save the pitches for baseball.