Why Asking Is So Scary

Have you ever found yourself dreading that moment when you need to ask a donor for a gift?

You’re not alone.

For many mid and major gift fundraisers, the ask is the biggest emotional hurdle in their work. I’ve known hundreds of fundraisers who can build authentic relationships, hold deep conversations with donors, and share great impact stories—but when it comes time to invite that donor to invest, fear sets in.

Why is asking so scary?

I think there are two major reasons. First, most fundraisers don’t truly believe that asking a donor for a gift actually helps the donor. They see fundraising as “taking” rather than “giving.” Second, they haven’t been trained in how to ask in a way that feels authentic and aligned with the donor’s passions and interests.

What do I mean by this?

Asking Is Helping Find Joy

When you ask a donor to make an investment in your mission, you are not taking something away from them—you’re offering them an opportunity to live out their values. You’re helping them experience the deep joy that comes from giving.

Think about it: most donors you talk to want to make a difference. They long to see a world that looks more like the one your organization is trying to build. When you invite them to join you, you are facilitating that joy. You’re helping them help change the world through the work you are doing.

But this shift in perspective takes work. You may carry a mindset of scarcity or fear. You worry about being too pushy, too bold, or somehow alienating the donor. But when you truly see yourself as serving the donor, asking becomes a natural part of the relationship.

The Power of Permission-Based Asking

At Veritus Group, we teach what we call Permission-Based Asking (PBA)—a simple but powerful structure for communicating and soliciting gifts in a way that builds trust, removes pressure, and aligns everyone around shared purpose.

Here’s how it works:

1. Align with the Donor. Make sure you truly understand your donor’s passions and desires. What inspires them most about your mission? What impact do they most want to make? Here you are making sure the donor is aligned with the purpose of your meeting and how much time you have.
2. Be Curious. Ask thoughtful questions. Let the donor talk more than you. The more you learn, the better you can connect their values to your organization’s work.
3. Solicit. Once you’re aligned and the time is right, invite the donor to give a gift. Do it clearly, confidently, and with permission. You might say, “Would it be OK if I shared an opportunity that matches what you just said matters the most to you?”
4. Align Again. After the ask, check in: “How does that feel to you?” “How would you like to fulfill your gift?” You’re still partners in this process.
5. Celebrate. Whether the donor says “yes,” “no,” or “not yet,” celebrate the relationship. Gratitude and respect build long-term connections. 

Taking the Fear Out of Asking

When fundraisers learn to use Permission-Based Asking, everything shifts. The fear dissolves because you are no longer “pushing” a gift—you are inviting participation. You’re aligning with the donor instead of persuading them.

So, if asking feels scary, know that it doesn’t have to. See your role as guiding the donor toward joy. Remember: you are on the same side of the table, working together to create impact and meaning in the world.

When you do that, the ask becomes the most life-giving part of your job.

Jeff

Want to learn how to use Permission-Based Asking in your donor conversations? Download our free guide!