One glance at the balance sheet and I knew I had no time to waste. The organization needed a big swing as they approached the end of the fiscal year, and I had parachuted in to solicit a high-value donor.
Apparently, I was so confident in my persuasive powers that I did not do all the research I should have.
When we sat down, I launched into my bold ask. She looked a little abashed as she explained how hard her business had just been hit. I asked again, naming a number larger than any gift she had made before. Why wasn’t it working? I pushed harder, until she finally had to explain that her kids did not have money to go to college.
That shut me up pretty quickly.
This isn’t a fundraising story I love to discuss. But honestly, we have to discuss our mistakes. Relationship missteps break trust and result in lost support. And I’m not the only one who has regrets. Lack of stewardship (as I wrote about here), forgetting an acknowledgment, inadvertently offending a donor: these errors contribute to the massive gap in donor retention (nearly 60% of first-time donors never give again).
So let’s air the dirty laundry. By discussing our most embarrassing moments as professional fundraisers, we can learn what to avoid—and how to recover. Recognizing a mistake and taking thoughtful steps to make amends can transform a potential loss into long-term loyalty.
Here are a few for your schadenfreude pleasure:
The Ruinous “Reply All”
Here’s one I will remember until the day I die. I was feisty, young, and full of mission-driven ambition for an organization I absolutely loved. I was on a path to bring back every lapsed dollar of the past three years, and surpass any fundraising goals we had set.
And I had just scored my biggest win: regaining the attention of a former supporter whose gifts had once hit six figures, but had since fallen away. I helped to orchestrate a series of stewardship moves that recaptured his attention.
My first mistake was checking my emails at 3am. He sent a note to me, our president, and the chair of the board sharing the news that he had made a gift. It happened to be half the amount of his last gift, but who was counting? Apparently I was.
I typed my response: “Yes! We got a gift from Dylan. I will bring back the other half, even if it means I have to camp out on his front lawn.”
And as soon as I hit 'Send,' guess who’s name I saw in the CC line?
You got it. Dylan.
Talk about a pit in my stomach. It felt more like a gaping hole…that I had just dug myself into.
The No-Notification Nightmare
A colleague was working at a well-established, mid-sized nonprofit organization, helping the board of directors launch a “friends ask friends” campaign. Each board member pledged to secure three gifts of $1,000 or more, with the goal of building a community of new donors who, with careful stewardship, would give more over time.
Two weeks went by. Board members were discouraged at the radio silence.
So my colleague looked at the automated system that was supposed to send notifications to them—and realized a mistake in the set-up.
It turned out a lot of their friends had given. But since the board was not told about them, they had not been acknowledged. Some of them had even interacted with their new donors since the gifts.
Not exactly a model of relationship management.
The “Anonymous” Apocalypse
Another colleague shared this one with me: they were on the advancement team for a small college, and a new, young donor wanted to fund a new initiative, anonymously. The process of getting this commitment had been extensive, filled with hours of thoughtful dialogue and excellent research, resulting in a significant number of scholarships for students in need. This individual wanted every detail spelled out—but not who they were.
The admissions and advancement departments were so excited when they finally made their commitment. The team shared the news with palpable exuberance.
To their profound regret, in one of their posts, they blurted out the first name of the donor.
It was a unique name. The damage ran deep.
Turning the Egg On Your Face Into An Omelet
As harmful as these snafus were, these stories all have happy endings—out of luck, in my case. After the Ruinous Reply-All, I tried to go back to sleep, but all I could do was watch the hands move on the clock. I couldn’t wait any longer. I finally gave in at 5am and I called the president, explained what I had done, and apologized over and over. She laughed.
“How could I be angry with a fundraiser who cares as much as you do?”
I was fortunate it was Dylan, it turned out; I got an email from him later that morning saying I was welcome to camp out on his front lawn, but that I might want to wait until the spring when the snow is gone. Phew.
Meanwhile, the No-Notification Nightmare embarrassed my colleague’s hard-working board members, who had gone out of their way to engage their friends and felt they had failed in their obligation to them. They couldn’t go back in time to thank them. But the chief development officer took the reins to make sure there were plenty of thanks to make up for it.
She called each board member to explain the problem and tell them personally the names of their friends who had given, followed by a written list over email. Then she called each of those donors to thank them herself. For good measure, she sent a card to each donor a few weeks later.
The Anonymous Apocalypse was averted by the way my colleague and her team responded. Immediately, the head of development wrote and the president of the college called, saying they knew they had made a mistake and that the whole team was going to be behind whatever repair work was necessary. Over a few discussions and correspondences, the donor and team decided that since it was obvious that the donor made the gift, it was better for them to make a short statement about the importance of the scholarship. Then they gave the endowed fund a different title so as not to associate the donor with it over the long term.
Oh, and the story I started with, when I was overconfident with a donor who was in rough financial shape?
I took a deep breath, and I apologized—genuinely—for my insensitivity. I acknowledged that I had not listened to her situation, and assured her that I understood that now wasn't the right time.
Honesty and humility can help repair the damage we cause inadvertently. In this case,it took some time. She couldn’t give that year, but we stayed in good touch, and she remained a loyal supporter.
Eventually, she made a significant gift to the organization.
Cautionary Takeaways
Our most embarrassing failures are also powerful learning moments. They point to habits and systems we can all invest in as preventative measures. If you want to avoid being in a future newsletter like this, remember these lessons learned the hard way:
Build a Culture of Donor Awareness: Beginning with the leadership team and the development team, embed the appreciation of donors into your organizational values. The whole staff should understand deeply that gratitude, stewardship, and relationship-building drive their success. When everyone is in tune with them, it’s more likely you’ll be on top of how interactions are going.
Slow Down and Pay Attention: In this world of multiple distractions, it’s easy to rush through whatever we are doing, including relationships with donors. But doing it right is almost always better than doing it quickly. Double check your work. Have a colleague read your thank you letters before they go out. Test technology and processes. Yes, even holding an extra meeting is sometimes worth it. “Okay, let’s go over it one more time…”
Celebrate Mistakes: Not the results of the mistake, of course. But make sure you're an organization where people feel that, when they do mess up, they know they can come clean quickly and get help to make things right. When I made my donor CC mistake, I was amazed by the organization’s reaction. They saw how much I cared, how invested I was, and how bad I felt. Knowing that my organization believed in my skills, even when I was not at my best, made me want to do an even better job in the future.
So, what’s your most embarrassing fundraising moment?
And, just as importantly, what did you learn?
Not My First Rotary
A few weeks ago, I completely forgot my friend’s birthday, so I sent an apology card. “I hope you’ll forgive me,” I (thought I) said.
Instead, apparently, I wrote, “I hope you’ll forget me.”
She called me up laughing. “I’d never forget you,” she said. “Especially for making such a memorable mistake.”
When it comes to rebuilding donor trust, a heartfelt apology, even if it comes out a little awkwardly, can leave a lasting impression. We’re all going to make mistakes. But if you own them, you can make your relationships even stronger.
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