Exploratory Conversations, Part 2: The Art of Forging Strong Relationships

Have you ever walked into an initial meeting with a transformational gift prospect and felt both excited and a little unsure? You know this conversation could lead to something incredible, but you’re not quite sure how to steer it.

Here’s the thing: Exploratory conversations aren’t about pitching or persuading—they’re about connecting. They’re about discovering your prospect’s motivations, aspirations, and philanthropic interests – the “heart” of their philanthropy – so that, later, in your pursuit of a big gift, you can show them how their passion aligns with your mission.

The magic happens when you cease talking at your prospect and start engaging with them. And it all boils down to two simple things: asking great questions and really, truly listening.

Let’s dive into how you can master the art of strategic questioning and active listening and turn your exploratory conversations into the foundation for a strong relationship.

 

Step 1: Be Curious

We’ve all heard the phrase, “People give to people, not causes.” Let’s expand on that a bit: People give to causes that align with their values, but they do it because someone took the time to connect with them on a human level first.

This is why you want to start every exploratory conversation with genuine curiosity. You want to ask questions that help you learn what interests your prospect, what drives them (i.e., their motivations and aspirations), and how your mission might fit into their world. To uncover these insights, you’ll need a mix of open, probing, and knowledge questions.

 

Open Questions: Getting Started

Open-ended questions invite your prospect to share their story. These questions set the tone for a thoughtful, two-way conversation. They’re perfect for kicking things off in a way that feels natural and engaging. For example:

• How are things going with your business?

• What do you strive to achieve with your philanthropy?

Open questions create space for your prospect to share what’s most important to them. Their answers often reveal clues about what they value and where your mission might align.

 

Probing Questions: Digging Deeper

Once the conversation is flowing, probing questions help you uncover details that add depth to your understanding. These questions show you’re truly interested in their perspective and encourage them to expand on what they’ve shared. Examples include:

• Can you tell me more about that?

• What led you to prioritize this cause over others?

• How did that experience shape the way you think about giving?

Probing questions demonstrate that you’re actively seeking to understand the “why” behind their answers. This level of curiosity strengthens trust and opens the door to meaningful dialogue.

 

Knowledge Questions: Getting Specific

Knowledge questions help you gather specific information that will inform your pursuit and strategy. These are more direct but equally important for gauging their interest and setting the stage for a philanthropic partnership. For instance:

• How familiar are you with our work in [specific program or initiative]?

• Have you had a chance to attend one of our [name of event]?

Knowledge questions not only give you insight into their level of interest and engagement but also highlight opportunities to deepen their connection to your mission.

When you approach your prospect with curiosity instead of leading with the list of talking points you want to communicate about your organization, you create space for them to share their story. And that’s where the connection begins.

 

Step 2: Really Listen

Most of us think we’re good listeners, but if we’re being honest, how often are we just waiting for our turn to talk?

Active listening isn’t about nodding along while waiting for your turn to speak. It’s about giving someone your full attention – mind, body, and spirit – so that you can hear what’s being said (and what’s not). It’s a skill, and like any skill, it has clear components you can practice and master.

 

1. Acknowledge

Start by acknowledging what your prospect shares. This is your way of showing them you’re paying attention and that their words carry weight. Simple phrases like these can go a long way in making your prospect feel heard.:

• I see.

• That makes sense.

• I appreciate your perspective.

Acknowledgment is about creating an emotional connection—letting them know they’re not just talking to you; they’re connecting with you.

 

2. Clarify

Sometimes, your prospect might share something that sparks curiosity or leaves you wanting to know more. This is where clarifying questions come in. They not only ensure you fully understand what they’ve said, but they also invite the prospect to expand their thoughts. Try asking questions like these:

• Can you give me an example of what you mean?
• Would you say more about that?

Clarifying helps prevent misunderstandings and demonstrates your genuine interest in understanding them at a deeper level.

 

3. Validate

Validating means recognizing and affirming the prospect’s feelings, ideas, or experiences. It’s not about agreeing with everything they say but acknowledging that their perspective is valid. You might say:

• I understand why you feel that way.
• What you’re describing sounds really meaningful.

Validation builds trust and reassures your prospect that their voice matters in this conversation.

 

4. Summarize

Summarizing ties the key points you discussed together and ensures you’re on the same page. After your prospect shares something significant, reflect it back to them in your own words. For example:

• It sounds like your goal is to make a real impact on education in your community.
• So, what you’re saying is that you want to focus on initiatives that empower young women in STEAM fields?

This step not only reinforces your understanding but also helps clarify any miscommunication. It shows your prospect that their thoughts have been received and respected.

When you combine these four components – acknowledge, clarify, validate, and summarize – you’re not just collecting information; you’re building a relationship. Active listening makes your prospect feel valued and understood, which opens the door to other meaningful conversations and an increasingly stronger connection.

 

Step 3: Begin Connecting the Dots (Their Passion to Your Purpose)

Once you’ve listened deeply, you can reflect the prospect's motivations, aspirations, and philanthropic interests back to them in a way that begins to show how your organization can help make their vision and goals a reality.

For the prospect who’s passionate about giving young people opportunities to thrive in STEAM fields, that’s your cue to share a story about Leila, the competition winner you sponsored who created an AI-powered image recognition system to sort plastic waste more efficiently and reduce contamination in recycling facilities.

The goal isn’t to sell them on your mission—it’s to show them how they can be part of something bigger. How their passion, paired with your organization’s purpose, can bring about something truly transformational.

 

Step 4: Keep the Door Open

Not every exploratory conversation will end with a big “aha!” moment. And that’s okay. Again, the purpose of these conversations isn’t to close a deal—it’s to plant a seed.

So, after the call or meeting, send a heartfelt thank you note. Not a generic “thanks for your time” email, but something that shows you were paying attention to what they had to say. Reference something specific they shared, or express how inspired you were by their vision.

Do this, and you will have established the foundation for a robust relationship—one that will hopefully lead to big gifts down the road.

 

Why This Skill Matters

Here’s the truth: Ultimately, fundraising isn’t about money—it’s about impact. It’s about helping people step into their legacy by supporting something they care about deeply.

And as a fundraiser, you’re the bridge. Creating impact starts with the first conversation—the moment when you choose to be curious, to listen deeply, and to connect authentically.

Every exploratory conversation, and every other conversation after that, is a chance to help a prospect step into their greatness. So go out there and start building those connections one conversation at a time by asking great questions, really listening, and connecting the dots.

We wish you great fundraising success!

 

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References

From our research, it appears that ‘strategic questioning’ was coined by activist and educator Fran Peavey in the 1980s. Peavey developed this approach as a tool for fostering dialogue, encouraging deeper thinking, and facilitating change by asking open-ended, thought-provoking questions designed to uncover possibilities and inspire action. Her work emphasized the power of questions to engage people in collaborative problem-solving and drive social transformation.

The term ‘active listening’ was coined by Carl Rogers and Richard Farson in their 1957 work titled Active Listening. Rogers and Farson introduced the concept as part of their client-centered therapy approach, emphasizing the importance of genuinely understanding and responding to what the speaker is communicating, both verbally and non-verbally. Their work highlighted active listening as a critical skill for fostering meaningful communication and empathy in various contexts, including counseling, education, and relationships.