The Ask for a Transformational Gift: A Framework for Success

Picture this: You’re sitting across the table from someone whose philanthropy has the potential to change the trajectory of your organization and those you serve. You know their passion aligns with your mission, and they are expecting you to ask for their financial support. Your pulse races. You’ve prepared, yet this fifteen-second moment still feels monumental… Because it is.

The ask for a transformational gift isn’t about luck—it’s about preparation, process, and purpose. 

With the right framework and mindset, you can structure a solicitation meeting that puts your donor at ease, makes them feel great about the ask, and provides a unique opportunity for them to partner in doing something extraordinary for the community you serve.

 

TGP Consulting’s Three Cs of a Solicitation Meeting

Your ask for a transformational gift begins with a simple, three-part framework: connection, check-in, and commitment.

 

1. Connection

Before you ever mention the gift, focus on building or strengthening rapport. Whether this is the first time you’re meeting with your prospect in person or the Nth time, people give to people they trust and to missions that resonate with their personal values, interests, motivations, and aspirations—i.e., their passion.

Start by asking questions that put your prospect at ease and remind them that you and your organization are sincere, authentic, and genuinely interested in them as a person. Ask about their family. Acknowledge their past support and share your gratitude. Then transition with a statement along these lines:

“Thank you for meeting with us today. We’re here to ask for your support.”

A warm connection lays the foundation for trust, which makes the “big moment” possible.

 

2. Check-In

Once you’ve established a personal connection, it’s time to shift to the details of the solicitation. 

Confirm that the prospect has reviewed the materials you shared (e.g., a proposal) and address their initial thoughts or questions. You might say:

“I hope you had a chance to review the proposal. What questions can I answer for you before we dive in?”

If the prospect has read your proposal and doesn’t have questions, move immediately to the next step.

If the prospect has read your proposal and has questions, provide honest, thoughtful, and appropriately vulnerable responses. If there’s a question you don’t know the answer to, that’s okay. No one expects you to be perfect. You can always say you don’t know, but you’ll circle back with an answer. Continue with the next step if the answer isn’t required to proceed with the ask.

If the prospect hasn’t read the proposal, you’ll need to walk them through your request before moving to the next step.

 

3. Commitment

Now comes the pivotal moment: the ask. 

You want to outline the potential impact of their gift right before you make an ask for the highest amount you believe the donor can give. Your ask should directly connect to their passions and be specific. Here’s an example:

“Thank you for the privilege of asking for your support. I have enjoyed every interaction we've had thus far, and it’s clear that your commitment to education aligns deeply with our mission to challenge the graduation status quo in the United States. We have a once-in-a-generation opportunity to change the trajectory of hundreds of thousands of students. Under what circumstances would you consider a transformational gift of $1,000,000 to make this possible?”

After you ask this question, you wait.

As long as it takes.

For an answer.

The words “under what circumstances” and your silence afterward are absolutely essential. 

Silence can feel uncomfortable, but it’s essential because it allows the prospect to reflect without pressure. Whether you’re waiting for one minute or ten while the prospect paces the room, trust that their response will come.

By beginning the ask with, “under what circumstances,” you empower your prospect to tell you exactly what circumstances need to be in place for them to do something transformational for your organization. That’s information you need to know in the event you don’t receive a “green light” immediately.

We recognize there are no guarantees in fundraising, but we know from experience that prospects are more positively inclined to support you and your organization when you follow this framework.

So go out there and ask for what your organization needs with confidence!

We wish you every success!

 

P.S. Want to Master the Art of Asking?

If you or your team could use support in learning even more about the art and science of making bold, impactful asks, we invite you to connect with us. We teach a ½ day workshop that helps Development teams take their asks from good to great.