4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts

4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts

As a college freshman, I responded to an announcement on the Honors College listserv (that may give you a clue how long ago this was) for a job talking on the phone to alumni. I thought this was a dream job. All I needed to do was talk to people and make money. As an extrovert who had been trained by her manners-minded Southern mother to “make good conversation” my whole life, I had no qualms about keeping the conversation going and making folks like me on the phone.

After becoming a student supervisor in the call center, I quickly realized that most folks needed more structure and examples of what to say to have success at building rapport in conversation. It was indeed an art. I’ve now spent a couple of decades helping to systematize and teach the process of successfully talking to someone new. Over the years, I’ve learned that the secret to great conversations is the same whether you're a college student, a seasoned fundraiser, or even a 7-year-old girl chatting with her great aunt. It all comes down to asking the right questions.

Questions help us connect and connecting with a donor is essential before you ever ask for a gift. The right questions remove roadblocks and pave the way for a strong, lasting relationship between the donor and your organization. People give to people they like. As a fundraiser, you’re the bridge connecting the donor to your institution. Your goal in a discovery visit is to listen, learn, and understand what truly motivates them.
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Bad rapport-building does more harm than good. Questions should always stimulate a lively back and forth. Think dialog, not monologue. The best questions also extract valuable information, make the donor feel appreciated, and naturally lead to the next step in cultivation.
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Here are my favorite questions to ask during a discovery visit:

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1. How did you become involved with our organization (or mission)?

This simple yet powerful question invites the donor to share their personal story. Did they have a life-changing experience? Was a loved one impacted? Did they connect with your work through a friend or colleague? Understanding their “why” gives you insight into what matters most to them and helps tailor your approach moving forward.

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2. What are your philanthropic priorities, and where does our organization fit in?

This question helps you understand where you stand among the causes they support. Are you a top priority, or do they view your organization as one of many they give to? It also gives you a glimpse into their overall generosity and what drives their giving decisions.

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3. Who else should I be talking to?

Your donors often have strong networks of like-minded individuals. Asking this question uncovers potential new prospects and champions for your cause. It also signals that you respect their influence and see them as more than just a financial contributor.

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4. How do you prefer to communicate and stay involved?

Some donors want regular updates, while others prefer to give quietly without much engagement. Some enjoy receiving physical mail, while others prefer a quick email or social media updates. Understanding their preferences ensures you’re communicating in a way that resonates with them, making cultivation and stewardship more effective.

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The key to a successful discovery visit isn’t just asking great questions – it’s truly listening to the answers. Take notes, follow up thoughtfully, and use what you learn to deepen the relationship. Building real rapport makes every future conversation easier and more meaningful. When the time comes to ask for a gift, you’ll know exactly how to approach it in a way that aligns with their motivations and values.

What’s your favorite discovery question to ask donors? Drop it in the comments—I’d love to hear what works for you!
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Cheers!

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