Early in my fundraising career, the organization I worked for had an immediate funding need. I sat down with a very successful businessman and asked him for a significant gift, say $100,000, to cover this deficit. I was confident his wealth made the request reasonable.

He looked straight at me and said, “Why would you think I have $100,000 in cash to simply write you a check? I keep whatever money I make working for me.”

That moment changed how I think about donors. Wealth and liquidity are not the same thing. Most donors, even very wealthy ones, have cash flow constraints. Their resources are tied up in businesses, investments, and property. Just because someone can give does not mean they can give now.

One of the biggest problems in fundraising isn’t lack of effort or even lack of generosity. It’s what we think we know. Assumptions feel efficient. They save time. They help us move faster. And they’re wrong more often than we’d like to admit.

I’ve made plenty of them. Each one cost something.

The Loyal Donor Who Left Nothing

Nonprofits often assume that long-term, faithful donors will naturally include the organization in their estate plans. Certainly, that can be the case. But that assumption can be an expensive mistake.

I worked with a university whose board chair had faithfully supported the school for years. He believed in the mission. He even encouraged them to start a planned giving program. When he passed away, the university was shocked to learn he didn’t leave them a gift.

He had an estate plan, and two other charities were included. Just not them. They hadn’t asked.

When he was making decisions, the university wasn’t part of the conversation.

Assumptions often take the place of conversations, and conversations create legacy gifts.

That wasn’t a financial planning failure. It was a relationship miss. Assumptions often take the place of conversations, and conversations create legacy gifts.

How We Measure Success

Sometimes the most experienced development professionals are the most vulnerable to assumptions. They’re under pressure to produce results that are impossible to guarantee, so they rely on patterns they’ve seen before. The problem is, every donor’s story is different.

A lot of nonprofits set goals in dollars instead of activities –– visits, conversations, questions asked. When we’re chasing numbers, it feels faster to fill in the blanks ourselves. But we can’t control when someone gives or how much. We can only control the quality and consistency of our engagement. These communications build relationships. And deeper relationships tend to lead to greater generosity.

When we stop meeting with people and start working spreadsheets, assumptions multiply.

What’s the Alternative?

My dad used to say, “God gave you two eyes, two ears, and one mouth. Use them accordingly.”

The best way to avoid assumptions is to listen more than you talk.

When I first started in fundraising, I thought that the more I talked, the more successful I would be. I figured if I explained the organization’s needs well enough, I would convince people to give. I eventually learned the opposite was true: my effectiveness was directly related to how much I listened. The best fundraisers I know are curious people. They’d rather ask another question than prove they’re right.

Part of my approach is permission solicitation. I ask questions that I’d be comfortable answering myself. But the real work is listening without deciding ahead of time what their answer means. Even if they’ve given you an answer, it may not have been thorough.

Relationships don’t end after a gift is made, and conversations don’t end if a gift is not made. If I call on a donor and they choose not to give, I ask four questions:

1. Is it the amount?
2. Is it the timing?
3. Is it the project the gift would support?
4. Is it the organization?

The answers to these questions help me understand the person better, while further molding me into a better professional for future conversations and relationships.

Curious Fundraisers

Great fundraisers aren’t the ones who are always certain. They’re the ones who stay curious. Assumptions may never disappear entirely, but when relationships come first, they lose their power to do damage.

You don’t lose gifts because donors don’t care. More often, you lose gifts because you never really knew what they cared about. And the only way to know that is to ask and then really listen.

 

©2026, Eddie Thompson, Ed.D., FCEP
Founder and CEO, Thompson & Associates

“If we merely aim for the industry standard, then our goal is mediocrity. Emulating the average nonprofit, we are destined to live with all the problems the average nonprofit faces. So, we suggest you aim to be exceptional in your approach to fund development.”