How this Thank-You Call Unlocked a $100,000 Gift

In 2021, I was coaching Cristina Fragale, Senior Director of Recruitment and Development at Preston High School, a Catholic girls’ high school in the Bronx. At the time, Cristina was juggling those two very different roles, which may feel familiar to many nonprofit leaders and frontline fundraisers wearing multiple hats.

Preston had a small but loyal donor base made up of alumnae who gave year after year, with most gifts landing between $250 and $1,000. Letters went out every year asking alumnae to give, and Cristina and board members made phone calls of thanks - but only to local donors.

I asked how many donors were from outside the region (thinking of how many of my own high school classmates live all over the U.S. and around the world). There were some, she felt, weren't worth calling. I immediately thought she might be missing opportunities.

Thank-You Calls: With a Twist 

I suggested to Cristina that she start making thank-you calls to all the donors. And since the country was coming out of the pandemic, I wanted to give her something else that would create a connection. “After thanking them for the gift, why don’t you ask them, ‘Which of Preston's four values are you leaning into most these days?'"

Preston is grounded in four core values: Dignity, Honor, Respect, and Compassion. I knew that whatever year the donor had graduated they likely knew the values by heart.

That question did something important. It invited donors to remember why Preston mattered to them in the first place: not as donors, but as women. It helped them connect back to their high school experience and that important threshold in their lives.

One of those calls went to an alumna living on the West Coast who had been giving $1,000 a year for more than 15 years. A steady, faithful supporter. Appreciated. Respected. Thanked by letter. And never once asked for more, or inspired to do more.

Cristina left the voicemail of thanks along with the suggested question.

About ten minutes later, Cristina’s phone rang.

The donor said, “I’m so glad you called. I’ve been thinking about Preston a lot lately - and I’d like to make a $100,000 gift to the school.” (Needless to say, Cristina was floored!)

That donor went on to make that $100,000 commitment as her annual gift the next year and continues to do so. And, she made a significant gift to Preston’s recent campaign as well. Over time, Cristina has continued to deepen the relationship, moving from gratitude, to trust, to partnership.

What changed wasn’t the donor’s capacity. That had always been there.

What changed was the connection.

When we thank donors in a meaningful way — and invite them to reflect on shared values — we activate something deeper than memory. We invite them back into their own story with the organization’s mission.

This kind of remembering is powerful. It draws on personal experience, identity, and meaning. When donors reflect on the values they embody—dignity, compassion, respect—they’re not thinking like “a $1,000 donor.” They’re thinking like the person they want to be in the world.

And generosity often follows—not because they were persuaded, but because they were seen.

This is where assumptions quietly cost us.

We assume donors are giving at the level that feels right to them – or that they may even be giving at their capacity.

We assume they’ll raise their hand if they want to do more.

We assume asking for a larger gift might make them uncomfortable.

But if we’ve never invited them to consider a deeper level of engagement, we don’t actually know.

In this case, a donor who loved her school deeply had never been asked - and never inspired - to consider what was possible. Until a thank-you call opened the door.

This is why I offer this strategic advice:

Stop searching for wealthy strangers and start getting into coversations with supporters who already love your mission.

Stewardship isn't the end of a transaction

This is why stewardship is never just about closing the loop.

Meaningful thanking opens a path forward. It builds trust. It creates space for conversation. It lays the foundation for future generosity that is aligned, joyful, and sustained. 

This is the heart of connection-based fundraising.

Not scripts for the sake of scripts, but conversations rooted in shared values and genuine curiosity.

If you’re a frontline major gift officer or a development director, I’ll leave you with this gentle invitation:

Who might surprise you if you called simply to say thank you—and asked a question that helped them remember why your mission matters to them?

Sometimes, the most powerful fundraising begins with a thank-you.