by Dr. Kevin Dean, President & CEO, Tennessee Nonprofit Network
It’s a truth universally acknowledged that fundraising can feel… awkward. But recently, the sheer absurdity of our donor interactions hit me like a poorly timed push notification. I was in Nashville, catching up over hot chicken with one of my dearest friends. Newly divorced, she was recounting the horrors of modern dating. Her tales of dating apps were a symphony of cringe: unsolicited NSFW photos, breathtakingly sexist opening lines, and an overwhelming sense that everyone was just… shopping. She had finally moved on from her ex and was ready to explore finding a lifetime love, but it seems everyone on the app wanted something a little less…long-term, if you catch my drift.
“It feels so transactional,” she lamented, swirling her sweet tea. “They say they want a relationship, but they treat it like a series of one-night stands. No real effort to connect, just swiping and hoping for a quick win.” She confessed that some days, the whole experience made her want to swear off romance entirely.
Suddenly, a rogue piece of Nashville hot chicken wisdom smacked me in the face. “Wait a minute,” I said, mid-bite. “That’s… that’s exactly how we treat our donors sometimes!”
Think about it. Do we only slide into their inboxes when we need something? Is our communication a barrage of desperate pleas for cash, devoid of genuine connection or interest in who they are? Do we treat them like walking, talking ATMs, swiping right only when their giving history looks promising? If a potential date sent you nothing but requests for money, you’d block them faster than you can say “catfish.” So why do we think our donors will stick around if our relationship feels equally transactional?
If we truly desire lasting, meaningful relationships with our supporters – the kind that weather economic storms and inspire sustained generosity – we need to ditch the dating app mentality. We need to create authentic connections that go beyond the ask. The difference between a one-time hookup and a long-term partnership about commitment yes, but it’s about mutual respect, shared values, and a genuine interest in each other’s lives. The dating app model of fundraising—where we broadcast generic messages to thousands, hoping for a match—is designed for speed and volume, not depth and loyalty. It promotes one-time gifts and superficial interactions, not the kind of deep-seated loyalty that turns a first-time donor into a lifelong advocate.
The Art of the Donor “First Date” (Beyond the Ask)
We all know the pressure of a first date. You want to make a good impression, but you also want to get to know the person. You don’t start the conversation by asking how much money they have in their bank account. So why do we do that with donors? The “ask” is important, but it shouldn’t be the opening line.
1. Research and Personalization: Beyond the “Dear Friend” Email
The first step to a successful “first date” is to do your homework. In the dating world, we might check their social media or ask mutual friends about them. In the fundraising world, this means using your CRM, annual reports, and publicly available information to truly understand a donor’s interests.
- Example: The Music Therapy Connection. Let’s say you have a new donor, Dr. Jones, who gave a modest gift to your youth education program. Instead of adding her to your next mass email blast about your annual gala, do a little digging. You might discover from a quick LinkedIn search that she’s a retired music teacher. Your first follow-up shouldn’t be a request for another gift. It should be a personalized email that says, “Dear Dr. Jones, thank you so much for your recent gift to our education program. I was so excited to see that your background is in music! We have a new music therapy initiative for children with special needs, and I thought you might appreciate this story about how a grant you helped us get has allowed a child named Leo to find his voice through a new violin.” This shows you see her not as a wallet, but as a person with a history and passions. There’s no ask, just a connection.
2. The “Just Checking In” Message: No Strings Attached
This is the equivalent of texting someone you’ve been on a date with, just to say, “Hope you’re having a great week!” without a specific agenda. These messages are critical for building trust.
- Example: The Story of the Scholarship Recipient. Imagine a donor who made a significant gift to a student scholarship fund. Six months later, you could send a short, personal email. “Hi [Donor Name], I was thinking about you today and wanted to share a quick update. The student you helped send to college, Maria, just made the Dean’s List! She wanted me to send you this photo of her in the library studying. Just wanted you to know how much of an impact your generosity is still having. No need to respond, just wanted to share the good news!” This is a powerful, non-solicitation moment that reinforces their value to your mission and shows that their investment is paying off.
The Long Game: Nurturing the Relationship
The goal of a healthy relationship isn’t a single, spectacular event; it’s the consistent effort and care that builds over time. Fundraising is the same. We need to move past the “one-time hookup” of a single donation and invest in a long-term partnership.
1. Celebrate Their Impact: Make Them the Hero
Donors aren’t just giving to you; they’re giving through you to a cause they believe in. You are the conduit for their generosity. Acknowledging this makes them the hero of the story.
- Example: The Personalized Impact Video. Instead of a generic thank-you email after a donation, send a short, personalized video. “Hi Mr. Smith, this is John from the community garden project. I wanted to personally thank you for your donation. Because of your support, we were able to install the new irrigation system last week. As you can see, the tomatoes are already thriving! We couldn’t have done this without you.” If possible, get a beneficiary or staff member to record a 30-second video message. A direct, human message like this is far more memorable than any form letter.
2. The Donor’s Report, with a Twist
Most organizations send an annual report filled with charts, graphs, and financial data. While this is important, it’s not exactly romantic. A more relational approach frames the report as a shared journey.
- Example: The “What We Did Together” Journey. Instead of a dry PDF, create a visually engaging, interactive digital report or a beautifully designed booklet. The title isn’t “2024 Annual Report,” it’s “Our Shared Journey: A Year of Impact.” Use powerful photography, infographics that tell stories, and testimonials from people whose lives were changed. Structure it around key themes like “Feeding Our Community,” “Inspiring the Next Generation,” and “Creating a Safer Tomorrow.” This narrative approach makes the donor feel like a collaborator, not just a line item on a budget sheet.
3. Invite Them Behind the Scenes: From Outsider to Insider
True relationships involve sharing experiences and giving someone access to your world. For donors, this means inviting them into your mission in a way that goes beyond a fundraising dinner.
- Example: Coffee with the CEO. Instead of a formal event with a thousand people, host small, exclusive gatherings. “Coffee with the CEO” is a perfect example. Invite a handful of key donors to an informal meeting. The agenda? No ask. Just a chance to share the vision, discuss challenges, and listen to their feedback and ideas. This makes them feel like a true partner, not just a source of funds. Other ideas include tours of your facilities, a virtual roundtable discussion with program directors, or a sneak peek at a new project before it’s announced to the public. These events build social capital and reinforce their status as a valued member of your inner circle.
Avoiding the “Ghosting” and “Breadcrumbing” Traps
Just as in dating, nothing kills a donor relationship faster than disappearing after you get what you want (ghosting) or sending vague, non-committal messages that never lead anywhere (breadcrumbing).
- Ghosting: This is the most common sin in fundraising. A donor makes a gift, you send a thank-you note (if they’re lucky), and then you don’t talk to them again until your next campaign or gala invite arrives a year later. This signals that they were only valuable to you for their money.
- Solution: The Year-Round Communication Plan. Create a simple, year-round communication schedule. It doesn’t have to be a daily email. It could be a quarterly newsletter focused on impact stories, a holiday card with a mission-related message, or a simple call from a board member to say “thank you.” The key is consistency and showing that you’re thinking of them even when you don’t need anything.
- Breadcrumbing: This is sending out generic, vague communication that doesn’t build a real connection. “Your support matters,” “We couldn’t do it without you,” etc. These phrases are nice, but they’re hollow if they’re not backed up with specific, personalized examples of how their support is making a difference.
- Solution: Be Specific and Transparent. Be an open book. If a donor asks a question about a program or where their money went, give them a clear, detailed, and honest answer. Share a specific success story, a specific challenge you’re facing, or a specific goal you’re working toward. This transparency builds trust and shows them you’re serious about the relationship.
In the end, it all comes down to a fundamental shift in perspective. Our donors are not just checkbooks or living ATMs. They are people with passions, stories, and a deep desire to make a difference in the world. Our job isn’t to take their money; our job is to facilitate their generosity and build a relationship that honors their trust and passion. So, let’s put the dating apps away. Let’s stop swiping right for a quick win and start building some real, long-term partnerships. The kind that last a lifetime.
What’s one small, non-monetary action you can take this week to show a donor you genuinely care about them as a person?