10 Follow-Up Questions You’ll Need to Deepen Your Conversation with Major Donors (and One to Avoid)

Fundraising is not an operation. It’s a conversation.
It’s a conversation that can either build or diminish trust.

Trust is the cornerstone in the foundation of every relationship. And it’s especially important for major gifts and planned giving fundraising.

However, one conversational element needed for building trust is often overlooked. And that’s too bad because it’s actually your most powerful tool for taking your conversations with donors to the next level. It is the follow-up question.

Follow-up questions build trust because they prove to your supporter that you’ve been listening and you’ve thought about what they were saying. You’ve considered their perspective and processed their fears, worries, aspirations, and desires.

Hall of Fame fundraising researcher Dr. Russell James calls follow-up questions “magical,” because they show donors that you care and want to understand them. In his latest series of books, he found that, “People who ask more questions, particularly follow-up questions, are better liked by their conversation partners…”

Suffice to say that seasoning your donor conversations with follow-up questions is good fundraising. If you learn to use them wisely, you will forge deeper, more meaningful relationships that will lead to larger gifts for your organization.

Here are 10 follow-up questions you can use to elevate the experience of your donors and show them that you sincerely care about delivering the best possible value to them.

1. “Would you tell me more about that?”

Sometimes people say something in answer to a question, but you know there’s more there. This question also works well when the donor takes a strong position on a particular issue. Use this to get them to keep talking. When people feel heard, they increase trust in the listener.

2. “What do you mean?”

This is a good clarifying question. Sometimes people say things and it’s almost like they’re testing the waters. They’re used to being ignored or having wrong assumptions made against them. This question gives them a chance to express more of what’s on their mind, and to clarify a word or phrase they may have used.

3. “How so?”

This follow-up question expresses interest in what they’re saying, and asks for more details and more explanation.

4. “How did you feel about that?”

Sometimes donors share facts or details from a narrative, but they’re neglecting – on purpose or because they’re not used to ‘going there’ – the emotional component of the story. How did it affect them? Asking this follow-up questions shows you care not just about the facts and details, but also their emotional well-being. It shows concern for them, not just what they’re saying.

5. “How did you feel when that happened?”

Similar to the last one, this question pertains more specifically to an event or incident, whereas the other one could also apply to something a person said, or to an external situation.

6. “What happened next?”

Unlike the last two, this one focuses on the narrative itself that a donor is sharing about. It shows you are interested in whatever they’re talking about. It also refocuses and keeps the conversation moving if the donor may be stalling a bit or running off on a rabbit trail.

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7. “Really! Tell me more.”

This is a more emotional type of response than the first question on this list, but in a similar vein. You’d use this follow-up question when the donor shares something that’s a bit more surprising or shocking.

8. “What else?”

This simple open-ended follow-up question works especially well when a conversation seems to have hit a point of closure, but you know there is more there. It also works when you want more details or insights about something a donor is saying.

9. “Can you give me an example of that?”

Some donors make statements that aren’t always clear, or they are too broad and vague. They need a little prodding to share some details. Even if you understand the general idea of what they’re saying, this question lets them share more personal information, experiences, feelings, and interpretations. It gives you a window into how they see the world, and it shows you value their perspective.

10. “What led you to that?”

This follow-up question reveals a bit about how the donor makes decisions and how they prioritize. In certain contexts, it will also reveal motives. It provokes self-reflection.

And Here’s One Follow-Up Question to Avoid!

This rule isn’t written in stone of course, but in general it is probably worthwhile to steer away from asking “Why?” as a follow-up question. Or, at least be very careful when you ask that question.

Dr. James’ research found that asking “Why?” or “Why did you do that?” can at times feel like an attack. It’s a bit too direct, and sometimes triggers defensiveness because the person feels like you think what they did or said wasn’t smart, or makes no sense. You don’t want to make them feel inferior. So be careful with that one!

More Questions… for Yourself

Asking questions of the donor is one thing. But sometimes you need to ask questions of yourself too.

Before meeting with a donor, you need to know if they are qualified as a potential major donor. Here are 7 donor qualification questions to ask yourself before meeting with a donor.

As mentioned earlier, getting answers to those kinds of qualification and cultivation questions isn’t easy, and often isn’t cheap. But with the right technology, you can actually automate the qualification process at scale (through tech-enabled donor discovery) and get answers to those seven questions without having to invest the valuable time of your gift officers.

Schedule a free demo of MarketSmart’s software and see how it works.


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