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What you’ll get: a working playbook for nonprofit fundraisers who want to stop performing and start listening, built from a live conversation with one of the Upper Midwest’s most trusted philanthropic advisors.

The Problem Most Nonprofit Fundraisers Don’t Want to Admit

You’re talking too much.

Not in a rude way. Not in a bad-at-your-job way. In a trained way. Somewhere along the line, fundraising got framed as performance. You walk into a donor meeting with a pitch deck, three talking points, and an ask. You leave with a polite “let me think about it.” And you tell yourself the meeting went well.

It didn’t.

Scott Holdman has been in this work for more than two decades. He’s coached hundreds of nonprofits across the Upper Midwest. He founded Legacy Logic. And when he sat down with me live at the WellTold Conference, the thing he kept circling back to wasn’t strategy. It wasn’t tactics. It wasn’t even storytelling.

It was listening.

Here’s the gap most nonprofit leaders are stuck inside: good intentions on one side, real impact on the other, and a chasm in the middle filled with talking. Pitching. Performing. Trying to be impressive instead of being present.

This blog is the unpack. Everything Scott shared on that stage, plus the practical playbook to actually use it. If you run development at a nonprofit, sit on a board, lead a small team, or just care about doing this work better, you’ll leave with something to try this week.

Not someday. This week.

Why Listening Is the Most Underrated Skill in Fundraising

Scott opened with the two great Carls. Carl Jung and Carl Rogers. Rogers built an entire school of therapy around one practice: actually listening.

Scott put it like this on stage:

“I spent a whole career trying to be creative, and when I first learned the ability and a skill which has to be developed like anything else, I would start to listen and then realize that people didn’t need my ideas.”

Read that twice.

He’d built his career on having good ideas. Ten of them. Twenty. And then he learned that when you really listen, the answers are already inside the person across from you. Your job isn’t to deliver wisdom. Your job is to make space for theirs to surface.

This is hard for fundraisers. You’ve been trained to lead with your case for support. To anticipate objections. To close. And so you walk into donor meetings with a script in your head, half-listening to the donor while you wait for your turn to talk.

That’s not a conversation. That’s a sales pitch with extra steps.

What Story Listening Actually Looks Like

At Tellwell, we talk about story listening as much as we talk about storytelling. Same skill. Different direction.

Story listening means:

• You enter the meeting without a script in your head
• You ask one real question and wait for the real answer
• You don’t interrupt to connect their story to your mission
• You take notes on what they care about, not what you want to pitch
• You leave with a clearer picture of their world than your own

Bad version: “Thanks for meeting. Let me walk you through our impact report. As you can see on page three, our outcomes have grown 40 percent year over year, which is why we’d love to invite you to our $25,000 giving circle.”

Good version: “Thanks for meeting. Before I share anything about us, I’d love to understand what’s been on your mind this year when it comes to giving. What’s pulling at you?”

The first version is a monologue with a price tag. The second is a conversation that might actually lead somewhere.

The Sculptor Mindset: Why Removing Beats Adding

Scott shared a metaphor I haven’t stopped thinking about.

When you’re young, he said, you’re a painter. You add. More color. More texture. More everything. You believe more is the answer because you have the energy to believe it.

But as you get older, you start to realize the better posture is sculptor. You remove. You take away. And something beautiful gets revealed in what’s left.

This applies to your fundraising calendar. Your appeal copy. Your event lineup. Your board agenda. Your strategic plan.

Most nonprofits I work with are painting when they should be sculpting.

Where to Sculpt First

Pick one of these this week:

• Your year-end appeal. Cut it in half. Then cut it in half again. The donor doesn’t need every program. They need one story.
• Your event roster. Which two events are pulling the most weight? Which two could you stop doing in 2026 without anyone noticing?
• Your donor communications calendar. How many emails are you sending because you’re supposed to versus because they actually move someone?
• Your board meeting agenda. What’s on there because it’s always been on there?

Bad version of sculpting: “We trimmed our newsletter from twelve sections to ten.”

Good version of sculpting: “We killed the newsletter. We replaced it with one handwritten story per month from a Story Maker we serve.”

Sculpting is brave. Painting is safe. Donors can feel the difference.

The Fundamentals Conversation Nobody’s Having

Halfway through our conversation, Scott pointed at something most leaders skip over: we’ve lost respect for the fundamentals.

Not basics. Fundamentals. There’s a difference.

Basics are the entry-level stuff you learn once and check off. Fundamentals are the things you return to over and over, your entire career, because they actually produce results.

For a fundraiser, the fundamentals look like:

• Knowing your donors’ names, kids’ names, and what they care about
• Sending thank-you notes within 48 hours
• Following up when you said you would
• Asking better questions than anyone else in the room
• Showing up consistently, not just at gala season

None of this is sexy. None of it will get you a LinkedIn post with 400 likes. And that’s exactly why most organizations skip it for the latest dopamine hit: a new CRM, a new campaign theme, a weighted vest for rucking.

Scott named the trap directly:

“We’re dopamine fiends, just like our feed on our phone. It’s, well, what if the beautiful parts are actually in slowing down and being really good at the core skills?”

A Fundamentals Audit You Can Do in 15 Minutes

Open a blank doc. Time yourself. Answer these:

1. What are the three fundamentals of my role that, if I did them excellently, would produce 80 percent of my results?
2. When was the last time I did each of them well?
3. What am I currently doing that has nothing to do with those three?
4. What would I have to remove from my week to spend more time on the fundamentals?

That’s it. Fifteen minutes. Most fundraisers I’ve watched do this exercise come out of it embarrassed. Then energized.

Time-box CTA: Do this audit today. Before lunch. Don’t optimize it. Just do it.

Change vs. Evolution: A Distinction That Actually Matters

Scott dropped this almost in passing, and I’ve been chewing on it ever since:

“There’s a difference between change and evolution, and I think that’s a choice. A change is something we’re just doing to do something differently. Evolution is a great word, because we’re on our way to something different.”

Most nonprofit “change initiatives” are change for change’s sake. New logo. New website. New strategic plan. New tagline. Same organization underneath.

Evolution is different. Evolution means you’re actually becoming something. You’re heading somewhere specific, even if you can’t fully see the destination yet.

The question to ask your team this quarter: Are we changing, or are we evolving?

If you can’t answer where you’re evolving toward, you’re just changing. Stop. Get clear. Then move.

Eldership: The Missing Role in Your Nonprofit

This one hit hard in the room.

Scott referenced psychologist Bill Plotkin’s idea that as a culture, we’ve lost the role of the elder. In healthy tribes, elders went first. They named what younger people were experiencing. They gave them a path forward.

We don’t have that anymore. We have influencers. Which is not the same thing.

An influencer is performing wisdom for a feed. An elder is offering wisdom to a person.

In your nonprofit, this means something practical: you have a generational pyramid that you’re not using. The 30-year board member who’s seen four EDs come and go. The retired fundraiser on your committee. The Story Maker family who’s been giving for two decades.

These are your elders. And most organizations let them coast in the corner instead of inviting them to the table.

How to Invite Eldership This Quarter

Pick one person who fits the description. Schedule a 60-minute conversation. Ask them three questions:

1. What did you see this organization get right in its early years that we’ve drifted from?
2. What’s a hard truth about our donor base that nobody on staff is willing to say out loud?
3. If you were in my role for one quarter, what would you stop doing immediately?

Take notes. Don’t argue. Don’t explain. Just listen.

Bad version: “We’d love to pick your brain over coffee sometime!”

Good version: “I’m setting up six conversations this quarter with the people who’ve seen this work the longest. Could I have 60 minutes of your time on October 14th?”

One is a vague invitation that goes nowhere. The other is a real ask that signals you actually want what they have.

The TALK Framework for Better Donor Conversations

I shared this on stage with Scott because it’s been running my donor and BD meetings for six months. It comes from Alison Wood Brooks, a Harvard researcher who wrote a book called Talk.

The 30-second version:

• T – Topics. What are the things you’ll actually talk about? Have a few in mind.
• A – Asking. Ask genuine questions to build on the topics. Not interrogation. Curiosity.
• L – Levity. Have some fun. The best donor meetings have laughter in them.
• K – Kindness. Go in without expecting anything back.

That last one is the hardest for fundraisers. You’re trained to get to the ask. You have quarterly numbers. You have a campaign deadline.

But here’s the math: the donor who feels heard once is worth ten donors who feel pitched twice. Kindness without expectation is the long game. And the long game is the only game in nonprofit fundraising.

Your Next Donor Meeting, Run on TALK

Before the meeting:

• List three topics you think they’d find interesting (not about you)
• Write three real questions you actually want their answer to
• Pick one moment of intentional levity, a story or observation
• Decide ahead of time that you will not make an ask

During the meeting, run it. Watch what happens. Most fundraisers I’ve coached through this come back saying the meeting was the best one they’ve had in years, and the donor reached out to them afterward.

That’s not magic. That’s listening with a structure underneath it.

Life Tasks vs. Life Purpose: A Better Way to Prioritize

Scott closed with one more Carl. This time Carl Jung, and his concept of the life task.

We spend a lot of time chasing purpose. What is my purpose? It’s a big, abstract, paralyzing question. A life task is different. A life task is: what’s important right now?

Not forever. Right now.

For a parent of a sick kid, the life task is the kid. For a fundraiser in a capital campaign, the life task is the campaign. For someone navigating a health change, the life task is health.

Scott pointed out that researchers say we hit a “life quake” about every 18 months. A job change. A relationship change. A health crisis. A loss. Midlife crisis is a misnomer. It’s a rolling cycle.

For your organization, this means: your donors are in different life tasks at different times. The donor who gave $50,000 last year and went silent this year isn’t disengaged. They’re probably in a life quake. Your job is to notice, ask, and make space, not to chase them with another appeal letter.

This is donor engagement at its most human. And it’s how relationships last 20 years instead of two.

Your Action Plan: What to Do This Week

I don’t want you to close this blog and feel inspired and then do nothing. Inspiration is cheap. Action is the whole point.

Here’s a time-boxed plan:

Today, 15 minutes: Run the fundamentals audit. Identify your three.

This week, 60 minutes: Schedule one elder conversation. Pick someone who’s seen your organization across multiple eras. Send the email today.

Next donor meeting: Run it on TALK. Topics, asking, levity, kindness. No ask. Watch what happens.

This month, 90 minutes: Sit with your year-end appeal and sculpt it. Cut it in half. Then ask: would a stranger care? Cut again until the answer is yes.

This quarter, ongoing: Audit your top 20 donors for life quakes. Who’s gone quiet? Don’t send an appeal. Send a real check-in. No ask. Just presence.

That’s the plan. Five moves. None of them require a new budget line, a new vendor, or a new platform.

All of them require slowing down enough to listen.

The Bigger Idea: Donor Engagement Is a Listening Problem

If there’s one thing to carry out of Scott’s conversation, it’s this:

Donor engagement is not a messaging problem. It’s a listening problem.

The organizations that thrive in the next decade won’t be the ones with the best brand video, the slickest CRM, or the most clever year-end campaign. They’ll be the ones who built a culture of listening from the inside out.

That’s the work. It’s slow. It’s unglamorous. It compounds.

And the fundraisers who figure this out first are going to look around in five years and realize their donor base is steady, their team is healthy, and their mission is moving forward while everyone else is still chasing the next platform.

Sculpt. Don’t paint.

📚 Resource Hub

• Scott Holdman on LinkedIn: https://www.linkedin.com/in/scottholdman/
• Legacy Logic (Scott’s philanthropic advising practice)
• Talk by Alison Wood Brooks: the book behind the TALK framework
• Bill Plotkin’s work on the cultural role of elders, start with Soulcraft
• Carl Rogers on person-centered listening, foundational reading for anyone in donor relationships
• Seasons of Story: Tellwell’s framework for nonprofit communications across Spring, Summer, Fall, Winter
• Start with Story: Max’s weekly newsletter for nonprofit and mission-driven leaders at https://wetellwell.com
• WellTold Conference: the annual gathering for mission-driven storytellers in Fargo, ND
• Tellwell: The Podcast: subscribe wherever you listen