Leading with curiosity: How to ask good questions

By Jessica Lucadamo, Vice President, Client Services

When I work with fellow fundraisers, I often hear the same hesitation: ‘I’m not ready to reach out because I don’t know enough’. That could mean ‘I don’t know enough of the technical information—the work, the statistics, the facts’. Or, it could mean ‘I don't know enough about the donor’. 

It's easy to fall into analysis paralysis, focusing our time on mastering program details, memorizing numbers, refining the perfect pitch, and diving down research rabbit holes. While preparation is important, trying to know everything before we take the next step can lead to missed opportunities to connect with donors and secure funding for our missions. 

The best conversations with donors, though, are the ones where we, the fundraisers, talk the least. Getting ready for a phone call or meeting with a donor is less about preparing what to say and more about preparing what to ask.

Curiosity drives relationship‑based fundraising. As fundraisers, we are explorers. We learn about missions and all the ways our organization makes a difference. Then, we get to go out into the world and find our people—supporters who care about the same things we care about.

When we meet with prospective donors, we are both sleuths and guides. We find the overlap between our vision and the donor’s passions, then we connect the dots between our work and the donor’s philanthropy. 

To be effective, we have to listen more than we talk—which is why, rather than prepare what to say, we need to prepare what to ask. The good news is that there is a science behind questions—as well as an art. To intentionally strengthen relationships and move conversations forward, keep the following three types of questions in your toolbox:

• Exploratory questions

• Open-ended questions

• Closed questions

Exploratory questions: The conversation openers 

Sample exploratory questions:

• Tell me about your story. 

• Tell me about your philanthropy.

• Tell me about your experience with our organization. 

• Share with me how you got interested in this cause area. 

• Share with me what resonates with you about our mission/work. 

• Tell me how you’ve been. 

Each of these three types of questions invites a different kind of response. Exploratory questions prompt the most expansive responses. In fact, they are designed to create space for the donor to share whatever is on their heart and mind. 

Every conversation you have with a donor should start with an exploratory question, even if it’s just: ‘Tell me how you’ve been.’

The donor’s answer will provide a read on how the donor is arriving to the conversation—what they’re hoping to cover, what they most want to talk about, or even what they’re expecting. 

Giving the donor a chance to share what they’re bringing into the conversation offers two advantages: 

• The donor can relax into the conversation knowing they’ve already had a chance to share what (consciously or unconsciously) they wanted to share. 

• You can adjust your approach to the conversation based on what you learn.

Using exploratory questions often doesn’t feel like asking a question. There’s no question mark—and the construction can feel awkward for those of us who are most comfortable driving the direction of the conversation. When we first start using them, we’re tempted to pair them with open-ended questions (which we will explore next). For example, instead of saying “Tell me about your philanthropy,” we say “Tell me about your philanthropy. What causes do you focus on? How do you choose where to invest?” 

Resisting the temptation is worth the effort, though. Ask your question simply, in one sentence, then step back. You may be surprised by how much you learn that you can then build on to move forward the conversation, relationship, and your ask. 

Open-ended questions: The conversation propellers

Sample open-ended questions:

• Where are you focusing your philanthropy in this critical moment for our community? 

• What do you hope to accomplish next through your philanthropy? 

• How do you make your philanthropic decisions? 

• What inspires your generous philanthropy in our community?

• Why is [cause area] important to you? 

• What would you need to see in order to consider investment in our work? 

Exploratory questions kick-start the conversation and encourage robust responses. With some donors, asking one exploratory question can prompt a response that takes up half the meeting—which is great.

But at some point, you’ll want to intentionally move the conversation forward. That’s where open-ended questions come in. These questions can begin with any of the following—as long as the question cannot be answered with just one word. 

• Why 

• How 

• What 

• Who 

• When 

By asking thoughtful, open-ended questions in an intentional order, you will learn about the donor’s interests and where they align with your mission, and begin to see potential next steps. 

Typically, these kinds of questions should take up a large part of your meeting—so planning them in advance ensures you’ll get the information you need to guide the donor toward the next step in the process. Be mindful to: 

• Ask questions about their perspectives, goals, and philanthropy unrelated to your organization and its mission.

• Be curious about personal details and interests, but don’t get stuck there; your job is to lead a conversation about philanthropy.

Closed questions: The conversation closers 

Sample closed questions:

• What I heard is that you’re interested in…do I have that right? 

• Are you interested in [this initiative]? 

• Do you want to learn more about [this initiative]? 

• Would you be open to meeting again to continue the conversation? 

• Would you be interested in meeting with [leadership/program staff] to hear about the work first-hand? 

• Would you consider a gift of $X to this initiative? 

• Would you be open to a proposal? 

Going into any conversation with a donor, you should know what the next steps could look like. As the connector between the donor and your mission, it’s your role to build the relationship with purpose. Create forward motion in relationships by planning ahead: Where could we go next? 

Closed questions are those that the donor can answer in one word—and usually that word is “yes” or “no.” They typically begin with: 

• Do 

• Are 

• Would 

• (And sometimes) What 

In fundraising, we use these kinds of questions strategically to advance the conversation toward a next step. 

You can use them to confirm interest, suggest a next meeting, and, of course, make an ask.

Going into a conversation, line up a few options for various scenarios. That way, you can be sure you don’t miss the opportunity to guide the relationship to its next logical step. 

Then, in your next conversation, you can begin again…exploring, learning, and advancing a partnership that both you and the donor care about.