The Most Common Mistake Fundraisers Make

“We would love to!”

A huge wave of relief washed over me.

I was sitting at coffee with a wonderful couple, who I’ll call Jeff & Barb to respect their privacy, when Barb said the words every fundraiser longs to hear: “We would love to!”

Jeff & Barb had just agreed to give a gift to the nonprofit where I had recently begun my tenure as lead fundraiser. It was my first “big-time” fundraising job, and this was my first major ask on behalf of the organization.

Hearing Barb say those words brought such joy and confidence. I had done it.

For context: I had been cultivating a relationship, and a genuine friendship, with Jeff & Barb for quite some time. My wife and I had spent a lot of time with them: getting to know their kids, sharing meals in one another’s homes, and even attending other nonprofit fundraisers where they were sponsors.

Jeff & Barb were a lovely couple. Retired, with several adult children and a handful of grandkids, they were among the most philanthropic and hospitable people I’ve ever met. Jeff had spent his career as a top executive at a global transportation company. Born into a lower middle-class, blue-collar family, he joined the company right after school and worked his way up to overseeing all North American operations by the time he retired in 2015.

In retirement, Jeff & Barb kept a home base in Kansas City and owned several homes across the U.S. that they visited regularly. With some light prospect research, I estimated their personal net worth to be somewhere in the mid-eight figures.

Our relationship started innocently. My wife and I met them at church, and they invited us to attend a gala shortly thereafter. Over the next two years, we built a genuine friendship, and during that time, I never once sought to ask them for a gift.

But once I stepped into my new role, I knew the timing was right.

I texted them and asked if they’d be willing to meet for coffee the following week. They accepted immediately.

Based on our relationship and their existing philanthropic activity, I knew they were likely to give—as long as I didn’t screw it up. I also knew that, if handled well, they were easily capable of making a transformational gift to our organization. A gift like that would equate to several times my new salary. Securing something that significant so early in my tenure would be a massive win.

So I prepared.

I spent nearly four hours that week perfecting my “pitch.” I reviewed materials, studied financials, and even did a little Facebook research to see where they’d been traveling recently.

I walked into the coffee shop that morning with a familiar mix of emotions most fundraisers can relate to: excitement about the opportunity, nervousness about relational missteps, and confidence that I was well prepared.

Jeff & Barb joined me, and we caught up on kids, grandkids, travel, and holiday plans. Eventually, they asked how my new job was going.

Perfect, I thought. Here’s my chance.

I jumped right in, telling them about my new role, the organization, and all the amazing things we were doing and planning to do. The conversation flowed naturally. Barb had volunteered with several nonprofits over her lifetime with similar missions, and they were both passionate about the work.

Then came the question every fundraiser hopes for:

“So how can we help?”

It felt like a slow pitch right down the middle.

I explained how much their financial support would mean and what their gift could help accomplish. Without hesitation, Barb said, “We would love to!”

Relief.

We wrapped up the meeting in great spirits, and I told them I’d send instructions to their DAF manager on where and how to submit the gift.

I got into my car and immediately texted my boss, who had been tracking the meeting. I walked through the rest of the week feeling like the greatest fundraiser alive.

One week later, their gift arrived in the mail.

$2,500.

Don’t get me wrong, $2,500 is a generous gift.

But… what?

I had seen Jeff & Barb write $50,000 checks on a whim at galas we’d attended together. Where had I gone wrong?

This turned out to be one of the most formative lessons of my fundraising career, and a mistake I now see repeated constantly.

They simply didn’t know what to give, because I never told them.

I had fallen into a trap that even seasoned fundraisers make.

I gave Jeff & Barb zero specifics.

No organizational budget.

No fundraising goals.

No campaign targets.

All they knew was our programming.

Based on my explanation, they had no way of knowing whether we were a brand-new $100K-per-year nonprofit, a $5M organization, or in the middle of a $2M campaign. For all they knew, they might have thought they were covering a full month of operating expenses with that check.

I left them completely in the dark.

And that was 100% on me.

I had fumbled on the one-yard line.

So what’s the lesson?

Tell your donors exactly what you want, assuming they can reasonably accommodate the request.

If you’re seeking a $1,000 gift, ask.

If you’re looking for a $100 monthly commitment, ask.

If you’re sitting across from people who could write a six-figure check without blinking—and who have shown genuine interest in you and your organization, ask for the gift you’re actually seeking.

Otherwise, you may learn the same lesson I did.

But here’s the deeper challenge for nonprofit leaders:

Stop hoping generosity will guess your need.

Clarity is not pressure. Specificity is not manipulation. And confidence in your mission is not arrogance.

When you fail to define the opportunity, you shrink it.

When you fail to name the number, you cap the gift.

When you avoid the ask, you limit what your donor might have joyfully done.

Your donors want leadership.

They want direction.

They want to know what difference their gift can make, and at what level.

So before your next meeting, answer this question clearly:

What exactly am I asking for?

Write it down. Practice saying it out loud. Attach it to a rea

l outcome.

And then ask. Confidently, clearly, and unapologetically.

Your mission is too important to leave generosity to guesswork.