What If the Big Ask Happened Today? Why Timing and Donor Confidence Matter

After writing my last post, The Time We Got the Big Ask, I read it aloud to my partner, the collector and donor at the heart of that story.

We recalled how well they made the Ask: how the fundraiser and the head of special collections were pitch-perfect. It was one of those moments fundraisers hope for: a meaningful, values-driven Ask that connected on many levels.

Then I said, almost offhandedly, “It would’ve been different if they had asked right now.”

Without missing a beat, he replied, “It would’ve been a No.”

Same Story. Same People. Different Timing. Different Answer.

That struck me. Nothing else would’ve changed: the relationship between us, the alignment of the (verbal) proposal, the brilliant framing of the Ask. But if the same conversation happened today, the answer wouldn’t be a hearty "Yes!" And he said he wouldn't have suggested a restructured gift. "It would have been, 'I really like the project, but not now, and I'm not sure when.'"

Why? Because timing matters.

We are in a particular period. Near the end of a condo renovation. A wedding this summer. More travel to see my new granddaughter.

And the world feels unsettled.

Economic uncertainty, political instability, markets in roller coaster mode. Here in Canada, there’s a growing concern about how the U.S. is flexing its muscle: that the U.S. at the least wants to economically knee-cap Canada and at this most has questioned the sovereignty of Canada.

And like many families, we’re thinking about our aging loved ones, possible job losses, and what support may be needed for them.

The Wealth Effect: Feeling Rich vs. Being Rich

My partner's reaction is such a good reminder for all of us working in major gifts fundraising: 

Donors don’t give based on what’s in their bank account or investments.
They give based on how wealthy they feel.

High-net-worth individuals are often defined as having $1 million or more to invest. Very high-net-worth as having $5 million or more to invest. Ultra-high-net-worth as $30 million or more to invest. for the HNW and VHNW, a 10% drop in investment value likely will be felt. But for UHNW, there is less risk.

But for many people with resources, this unsettled economic period can affect their sense of wealth and their confidence in making big commitments.

And that’s what we’re seeing: uncertainty creates hesitation. Not because the project isn’t worthy. Not because they don’t care. But because they’re scanning the horizon and wondering, “Is this the moment?”

So, Should You Stop Asking?

No. Absolutely not.

Because here’s the truth: The impact of the mission of your nonprofit hasn’t stopped. The desire to be part of transformation your mission promises hasn’t stopped. And most importantly, your donors’ values haven’t disappeared; they may just be buried under layers of worry right now.

As a major gift fundraiser, your job isn’t just to Ask. You work is to inspire. To show your donors how their previous gifts are still creating ripples of impact:

• The students learning
• The land preserved
• The new program launched
• The lives healed and lifted

And yes, you need to invite the donor or prospect into a conversation about what’s next. Not a series of yes/no questions you call a conversation, but a genuine discussion about possibilities.

Timing is Real. But So is Imagination.

The most carefully researched prospect profile, or even the deepest wealth screening, can’t predict how a donor feels when you make your ask.

That’s why every major gift ask is a confluence of facts, values, timing, and imagination, yours and theirs. And sometimes, the answer is “Not right now.”

That doesn’t mean never.

(If you want a refresher on what “no” means for fundraisers, I wrote about that right here.)

So What Do You Do in Times Like This? 

• Keep the conversations going.
• Show impact (reporting, stewardship, behind-the-scenes storytelling).
• Be ready to ask—but listen more than you speak.

Because sometimes, the most important thing we can offer a donor is the space to say, “I love this — but not now.”

And when the world feels steadier, when they feel their wealth again—you’ll be there, ready to help them dream big and give big once more.