That Time We Got the Big Ask

Every major gift fundraiser has imagined it: the moment you’re sitting across from a donor, and a carefully orchestrated conversation builds toward the Ask.

I’ve been on the asking side countless times. But last year, I found myself on the receiving end.

My fiancé has spent 50 years collecting rare first edition books on Pacific exploration — journals, maps, and atlases from explorers like Captain James Cook and Captain George Vancouver, Canadian overland explorer Alexander Mackenzie, and well-known American explorers Meriwether Lewis & Willam Clark. In 2022, he donated his carefully curated collection to his alma mater: a seven-figure gift of cash and gifts-in-kind.

It was a significant gift, so of course we'd been in ongoing discussions for the last three years, including about the upcoming donation of his Pacific Northwest and British Columbia library of 1,200 volumes. We took it in stride when in late 2024 the library’s chief fundraiser and the head of library special collections asked for a meeting with us one afternoon.

What happened next? They made a more significant seven-figure Ask.

We invited them to our home, and they sat with us in the living room and shared how students were handling books from the 1700s and 1800s with delight, how academics were using them to study early encounters between European explorers and Indigenous peoples, and how the collection was shaping research and education in ways they’d never imagined.

And then, the fundraiser turned to the head of library special collections and said, “We have a wonderful opportunity we want to share with you.”

Now, I could see exactly where this was going. What fascinated me, as a fundraiser, was how they structured the ask.

• They aligned the gift with my partner’s passions. This wasn’t just about securing funds, it was about making the collection more accessible, creating an endowed position in special collections, and establishing a research role that would deepen public engagement.
• The Ask came from the right person. The head of library special collections — who had spent hours with my partner, helping transition his beloved antiquarian collection to the library — was the one to deliver it. She was a little nervous but her words were heartfelt, and she spoke to us in a way that no one else could.
• They painted a picture of the impact. This wasn’t just about rare first editions resting in a vault. It was about students learning how 18^th- and 19^th-century books were published and distributed. It was about how the journals and images from the voyages were brought back and prepared for printing. It was about expanding research and creating a legacy of discovery.

So what happened next?

After they left, I turned to him and asked how he felt. He was excited! The vision, the impact, the opportunity all resonated with him. But, of course, reality mattered. The full Ask wasn’t financially feasible at this moment.

And that’s where the real fundraising work began.

What followed was a series of conversations, adjustments, and strategy. A right-sized agreement took shape:

✅ Immediate funding for key initiatives

✅ A structured multi-year commitment

✅ A future bequest to complete the vision

This is what I love about major gifts fundraising — it’s never just a yes or no. It’s about shaping a gift that fits both the donor’s passion and their financial reality.

Why Am I Telling You This?

Because too often, fundraisers wait too long to make the big Ask.

Yes, timing matters. But waiting for a mythical perfect moment? That’s a mistake. Inspiration matters. Showing donors what’s possible right now matters. Even a simple question like, “Is now a good time to discuss a gift?” can move the conversation forward.

And when you make the Ask, make it count. Speak to values. Show impact. And put the right person in the room to deliver it.

That’s how transformational gifts can happen.