In our first post of this series, we talked about opening the conversation with the major gift prospect sitting in front of you—setting the tone, building rapport, and helping the donor feel comfortable and engaged. If you have done a good job of getting the donor’s attention in the opening, your task now is to keep that attention and deepen their involvement. That can be easily accomplished through questioning.
Good cultivation work means you already know a few things about their interests and philanthropic history, but prospect research only serves as a sketch. The questions you ask in this meeting add color, shading, and depth. They help you see where their motivations, lived experiences, and hopes intersect with your mission.
That’s the purpose of this part of the visit: to understand what the donor cares about, in their own words.
Questions That Open Doors
Questioning works best when it feels like an invitation rather than a technique. Some donors will talk freely. Others need a little time or a gentle prompt. And while no two conversations are the same, effective major gift officers tend to draw from a few distinct types of questions, depending on where the conversation naturally leads.
Questions rooted in values
These bring out the emotion behind their philanthropy.
- “What first inspired you to get involved with causes like ours?”
- “When you think about your giving, what gives you the most joy?”
Questions grounded in experience
These help you understand what they already know or have encountered.
- “What have you heard about our plans for the new program?”
- “Did you get a chance to visit the campus recently?”
Questions that look forward
These surface a donor’s hopes for the future.
- “What kind of change would you love to see over the next few years?”
- “What impact feels especially meaningful to you right now?”
You don’t need to ask all of these, and you certainly don’t need to follow a prewritten path or script. Often, the most effective questions arise from listening closely to what the donor has just shared and following that thread a little further.
How to Guide the Conversation
Before you show a donor how a need can be met, they need to understand the need itself and see how it connects to what they care about. Your role is to create awareness, spark curiosity, and help the donor see the landscape without telling them where to stand. In other words, your goal isn’t to steer them anywhere specific—it’s simply to learn what resonates.
That can sound like: “What can I tell you about our mission that you may not know?” or “Would you like to hear about some of our newest initiatives?”
Questions like these position you as a partner in their philanthropy instead of a solicitor with an agenda.
A Simple Questioning Framework
If it helps, here’s one way to move from rapport into deeper dialogue without forcing the conversation, using some of the questioning types mentioned earlier:
- Start broad: “What values were you raised with that still guide your giving today?”
- Go deeper: “When you think about the impact you want to leave behind, where does [cause] fit into that picture?”
- Connect to your mission: “I’d love to show you how our [specific project] aligns with those values—may I share a bit more?”
- Invite imagination: “If we were to double our reach in this area, what kind of legacy would that create for our community?”
This progression helps the donor clarify their own thinking. In many cases, they’ll begin articulating the very priorities and outcomes that will later shape your presentation.
No Matter How Tempting, Do Not Talk About Money
A common impulse in these meetings is to jump ahead at the first sign of alignment. The donor says, “That program sounds interesting,” and suddenly the conversation turns to budgets and naming opportunities.
Rushing toward the ask can interrupt that moment of discovery. Give it the space it deserves and stay in this stage long enough to understand the donor’s priorities as fully as you can. Good questioning gives you the information you need later to make a thoughtful, confident solicitation.
Where This Stage Leaves You
Of course, questioning doesn’t happen in isolation. The quality of the questions matters—but the way you receive the answers matters even more. Great major gift conversations move fluidly between asking and listening, curiosity and attention.
In the next post in this series, we’ll focus on listening: not as a passive act, but as one of the most powerful tools a fundraiser has for building relationships and guiding a donor toward a meaningful gift.
About the Winkler Group
Strong communities depend on strong nonprofits. When those organizations thrive, the people they serve do too. We help make that impact possible.
For over two decades, the Winkler Group has specialized in guiding organizations from vision to action through strategic planning, capital campaigns, and fundraising counsel that delivers results.
A national firm headquartered in Charleston, South Carolina, with offices across the country, the Winkler Group proudly walks alongside organizations committed to education, community impact, and serving the greater good.
