My ultra-high-net-worth client was leaving an event when the development director of another nonprofit approached near the elevator. She introduced herself and said, “I would love an opportunity to tell you about our organization.”

My client responded warmly: “I love your organization. That’s fabulous. I’d be happy to support you.”

By the time my client reached their car, the interaction had been forgotten. The development director clearly left with a very different impression: that she had just landed a new major donor.

Three days later, my client received an email from the development director. It said, in effect: “I am so excited that you would like to support our organization. Attached please find the form to be the principal sponsor of our gala at the $1 million level.”

There had been no follow-up conversation, no effort to understand my client’s interests, and no attempt to build a relationship. A courteous remark at a crowded event had been converted into a seven-figure solicitation.

My phone rang shortly after the client received the email.

“I’m forwarding you an email,” my client said. “Who is this organization? I don’t remember speaking with them.”

The nonprofit believed it had secured a donor. The prospective donor did not even realize that a relationship had begun.

I advise both nonprofits and ultra-high-net-worth families, and I suspect many fundraisers and ultra-high-net-worth families have witnessed some version of this story. I also understand how it happens. Gala revenue targets are real. Boards ask, “Who did you meet?” Time with someone of significant means is rare, and the instinct to seize the moment is strong. That pressure is exactly what makes this mistake so common—and so costly.

Why It Went Wrong

Politeness was interpreted as commitment. Ultra-high-net-worth individuals are approached frequently, and many have learned to respond graciously. “I love what you do” may be sincere, but it is not necessarily an indication that the person is ready to make a gift. “I would be happy to support you” may mean that someone is open to learning more. It does not mean the organization has permission to send a $1 million sponsorship form.

The relationship was skipped entirely. The organization knew almost nothing about my client’s interests, priorities, or giving process. It did not know whether my client cared about galas, sponsorships, or the program the event would support. It moved straight from casual introduction to solicitation.

The method of asking compounded the problem. In my experience, a $1 million request, even when the prospective donor is a billionaire, should be made in person. In most cases, it should also be made through a peer: a board member, a current major donor, or someone else who understands both the organization and the prospective donor. If the organization has already developed a close relationship with the individual, there may be exceptions. At the very least, a request of that size should involve the CEO. It should not arrive as an unexpected email with a form attached.

There Is No Single Formula

Wealthy donors are individuals, not a fundraising category. Their interests, personalities, family circumstances, and decision-making processes vary enormously, and an approach that succeeds with one person may fail completely with another.

We are often taught that cultivating a major donor requires six, eight, or even twelve meaningful interactions before making an ask. That is a useful guideline, but it is not an absolute rule.

Sometimes one of my clients will call after a first meeting and say, “A friend introduced me to this organization. They are doing exactly what I care about. Can you research them? If everything checks out, I would like to send a small gift.”

For some of my clients, that “small gift” might be $25,000. It is often a feeder gift: a way to see what the organization does next. Does it acknowledge the gift thoughtfully? Does it report back on the work? Does it communicate without immediately asking for more? Does the experience match what the donor was promised?

The gift may follow a first meeting, but the difference is important. The donor has expressed genuine interest, a trusted person likely made the introduction, and the organization’s work aligns with an established philanthropic priority. The donor is deciding to take the next step. The organization is not manufacturing a commitment from a courteous exchange.

More Than a Checkbook

In my experience, ultra-high-net-worth individuals do not want to be treated solely as checkbooks. That does not mean nonprofits should be afraid to ask them for money. It means the relationship should not consist only of requests for money.

Ask for their perspective. Invite them to see the work. Seek their ideas about a problem they understand. Introduce them to the people leading the program. Give them an opportunity to become intellectually and emotionally invested before presenting a financial proposition.

What to Do Instead

When a prospective donor responds warmly, follow up to learn what they care about before proposing anything. Involve the CEO or a well-connected board member early. Offer a site visit before any proposal. And keep the first ask proportionate to the relationship, not to the donor’s net worth.

In this case, the development director could have asked the CEO to send a brief note thanking my client for the conversation and requesting a 20-minute call to learn what matters to them. My client might have accepted, and genuine alignment might have emerged. A meaningful philanthropic relationship could have developed.

Instead, the organization rushed to the ask and, in doing so, likely ended the relationship before it began.
I wish this were a one-off story. It is not.