What I Learned About Donors in 20 Years of Nonprofit Work

I started working in nonprofit development when I was 26 years old. I thought I understood generosity. I had given money to things I believed in. I understood tax deductions and charitable giving.

What I didn't understand was donors.

Twenty years later, I've learned that donors aren't what most nonprofit leaders think they are. They're not ATMs with feet. They're not guilt-driven or obligation-driven. They're not checking a box.

They're people. Complicated, generous, sometimes messy people who want to matter.

Here's what I've learned the hard way.

1. Donors Don't Leave Because They Can't Give—They Leave Because They Feel Forgotten

This is the biggest lesson, and it might be the one that saves your nonprofit.

Over the years, I've had dozens of donors stop giving. And I used to think it was about circumstances. Their finances changed. They were supporting something else. Life got busy.

But when I finally asked them directly, the answer was almost always the same: "I didn't feel like you remembered me."

One woman told me, "You called when I gave a large gift. You sent a thank-you note. But for the three years after that, I heard from you only when you wanted money. I felt like you only cared about me on giving day."

That destroyed me. Because she was right.

The donors you're losing aren't losing interest in your work. They're losing the feeling of being known. They're losing the sense that they matter to you.

Here's what changed for me: I started treating donor relationships like friendships. Not once a year. Ongoing. Checking in. Remembering the details they told me. Asking about their life.

The donors who feel remembered are the ones who stay. Not because you guilted them. Not because they have extra money. But because they feel valued.

The practice: Set a reminder to reach out to 3-5 donors a month, just to say hello. No ask. No agenda. "I was thinking about you and wanted to catch up."

2. A Handwritten Note Beats a $500 Gala Every Single Time

Nonprofits spend thousands of dollars on galas. Fancy events. Impressive venues. Catered dinners. Silent auctions.

I'm not saying they don't work. But I am saying they're not your highest-ROI investment in donor relationships.

The highest-ROI investment is a handwritten note.

I learned this because I was terrible at sending handwritten notes at first. Too busy. Too many donors. Too hard to scale. So I focused on events and emails and phone calls.

Then I started asking major donors what made them feel most valued. The most common answer? "When [executive director] sent me that handwritten note after my mother passed away."

Not the gala they attended three years earlier. Not the recognition plaque. A handwritten note.

I've sent thousands of handwritten notes in my career. And I've never once regretted it. I've had donors tell me, years later, that they still have a note I sent them.

You can't scale that. You can't automate that. And that's exactly why it works.

The practice: Every time someone gives, send a handwritten thank-you note. Not a printed letter. Your handwriting. Your pen. "Thank you for believing in this work. It matters."

3. The Donor Who Gives $25 Monthly Is More Valuable Than the One Who Gives $1,000 Once

This one took me years to truly believe.

We always focused on the big gifts. The donors who could write a $5,000 check. They got special treatment. Personal meetings. We celebrated their gifts loudly.

But the donors who gave $25 a month, year after year, quietly? We took them for granted.

Then I looked at the lifetime value. The person who gave $25 a month for ten years gave $3,000. Plus, they stayed. They told their friends. They believed in the work even when times were hard. They felt like family.

The $1,000-one-time donor felt special. But they often disappeared. We never heard from them again. The relationship was transactional.

I started looking at monthly donors as the real treasure. Not because they gave the most, but because they committed the longest.

Everything changed when I started treating monthly donors like VIPs. Checking in with them regularly. Making sure they knew their monthly gift was building something. Inviting them into the community in special ways.

Some of those $25-a-month donors eventually became major donors. Not because I asked them to give more, but because they felt so valued that they wanted to.

The practice: Segment your donors by commitment type, not just gift size. Monthly donors get special, ongoing communication. They're your most valuable asset.

4. Never Assume You Know Why Someone Stopped Giving

This is a mistake I made more than once.

A longtime donor would stop giving, and I'd tell myself a story about why. "Oh, they must be having financial troubles." Or, "They probably switched to supporting a different cause." Or, "They're probably annoyed with our new direction."

So I'd either avoid them or approach them in a certain way based on my assumption.

Then one day, I decided to just ask. "I noticed we haven't heard from you, and I wanted to check in. Is everything okay?"

The answer surprised me: "I didn't know if you still needed my support. I thought maybe you had found bigger donors and didn't need people like me anymore."

My assumption was completely wrong. And because I'd been avoiding them, they'd been feeling abandoned.

This happened multiple times after that. Each time, the real reason was different. And each time, it had nothing to do with what I'd assumed.

The lesson: Don't tell stories about your donors' intentions. Ask them.

The practice: When a donor goes quiet, reach out within three months. Say, "I noticed we haven't heard from you, and I want to check in. Is there anything I should know?" Listen. Don't assume.

5. Donors Want to Believe in Something Bigger Than Themselves

I've learned that people have a deep, spiritual need to be part of something meaningful.

This is true whether they're Christian or not, religious or not, wealthy or not. Everyone wants their life to matter. Everyone wants to know that their choices made a difference.

When you ask someone for money, you're not really asking for money. You're asking them to join a movement. You're offering them a way to participate in something bigger.

If you're a church or faith-based organization, this is easier to articulate. But even secular nonprofits are doing this. The food bank is asking people to join the fight against hunger. The education nonprofit is asking people to join a movement for justice.

When donors understand that they're not just giving money but joining a mission, everything changes. They become invested. They become evangelists. They tell other people.

The donors who feel like they're part of a movement stay. The ones who feel like they're funding a budget line don't.

The practice: In every communication, remind donors why this work matters beyond the organization. What movement are they joining? What is becoming possible because they're involved? Help them see their role in something bigger.

6. Stewardship Is the Greatest Untapped Opportunity in Nonprofit Fundraising

Most nonprofits are terrible at stewardship.

They're excellent at asking. They're good at receiving. They're organized about thank-yous.

But stewardship—the ongoing work of showing donors what happened with their money, inviting them deeper, keeping them informed—that's where nonprofits fail.

Because stewardship is invisible work. It doesn't produce an immediate gift. It's long-term relationship maintenance. It's the nonprofit equivalent of tending a garden instead of planting seeds.

But here's the truth: the most successful fundraising I've ever seen was built on stewardship, not appeals.

When you truly steward a donor—when you show them impact, invite them into the story, ask for their wisdom, celebrate milestones together—they stop being donors. They become partners. And partners don't need to be asked to give.

I've seen donors increase their giving 300% when they felt truly stewarded, without us asking for more.

Stewardship is where the long-term sustainability lives.

The practice: Spend 30% of your time asking and 70% of your time stewarding. Tell donors about impact. Send stories. Invite them to see the work. Let them feel part of the solution.

7. Your Donors Are Usually More Generous Than You're Brave Enough to Ask

This last one is humbling.

I used to be conservative in my asks. I'd think about what someone could afford and ask for less. I didn't want to presume. I didn't want to make them uncomfortable.

Then a major donor friend sat down with me and said, "You're insulting me. You're asking for $5,000 when I can give $50,000. You don't even know me."

She was right. I was letting my fears limit what my organization could receive.

Over the years, I've learned that donors appreciate being asked boldly—especially when the ask is thoughtful and connected to their values.

The most generous people I've met are not afraid of big asks. They're afraid of small ones. They want to know that their generosity can actually make a real difference.

This doesn't mean you should ask every donor for their maximum capacity. But it does mean you should be thoughtful about matching the ask to the donor.

For major donors, do the homework. Know what they can probably give. Ask for that, not less. If they want to give less, they'll tell you.

The practice: For your top 10 donors, research what you think they could give. Make an ask that matches that capacity. You'll be surprised how often they say yes.

8. The Work Matters More Than Your Feelings About the Donor

This is the final lesson, and it's personal.

Over 20 years, I've worked with donors I didn't particularly like. Wealthy people with egos. People who were difficult or demanding. People with political views I didn't share.

For years, I let my feelings about the donor interfere with my stewardship. If I didn't like them, I wasn't as warm. If I thought they were arrogant, I was more formal. If I disagreed with them politically, I kept distance.

But here's what I realized: my feelings are not relevant.

What's relevant is that a child without clean water needs your program to get clean water. That a mom in poverty needs your job training program. That your mission is bigger than my opinion of any individual donor.

So I learned to separate the person from the partnership. I could steward donors I didn't personally love because the work was more important than my comfort.

This changed everything. I became more generous with people. More patient. More kind. Because I wasn't taking their quirks personally.

And something surprising happened: most of the donors I'd struggled with became friends. Because I stopped judging them.

The practice: When you feel frustrated with a donor, pause. Remember the person your organization serves. Remember that this donor's generosity is serving them. Let that be enough.

What's True About Your Donors Right Now

As I finish writing this, I'm thinking about the donors in your organization right now.

Some of them are struggling with finances and won't tell you. Some of them feel forgotten. Some of them don't realize how much their gift matters. Some of them want to give more but don't know how to ask.

Some of them are thinking about leaving because they don't feel seen.

And some of them are absolutely committed to your mission and will follow you anywhere—if you just remember to tell them that they matter.

My 20 years of experience can be boiled down to one truth: donors are not problems to solve or budgets to maximize.

They're people. Generous, complicated, hopeful people. People with their own struggles and dreams. People who chose you because they believe in something bigger.

If you treat them like people—remember them, honor them, keep them, steward them—they'll change your organization forever.

Not because of their money. Because of their partnership.

About DonorShepherd: The practices I've learned over 20 years are only possible if you have a system that helps you remember. DonorShepherd is built for this. It helps you track donor history, set reminders for follow-up, remember personal details, and steward relationships over time. The best nonprofit leaders don't rely on memory or luck—they rely on systems that let them do what actually matters: genuine relationship. If you want to apply these lessons but need better tools to support you, visit DonorShepherd.com. We're here to help you shepherd your donors the way they deserve to be shepherded.