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What you’ll get: A practical guide to building board fundraising confidence through storytelling and consistent training. Drawn from a conversation with nonprofit board development consultant Christal Cherry on Tellwell: The Podcast.

There is a moment that almost every executive director recognizes.

The board meeting ends. The financials are reviewed. The development report is presented. And then someone mentions fundraising, and the room goes quiet in a very specific way. Eyes drop to phones. People shift in their chairs. The person who was just passionately defending the mission two minutes ago suddenly has nothing to say.

Why won’t they just ask?

It is one of the most common frustrations in nonprofit leadership. And according to Christal Cherry, it has a cause that most organizations are completely overlooking.

Christal has spent more than 20 years working at the intersection of nonprofit fundraising and board governance. She has worked with grassroots organizations, hospital foundations, libraries, and everything in between. And she has arrived at a clear diagnosis for boards that go silent around fundraising.

“Your board members aren’t afraid to ask for money,” Christal says. “They’re afraid because nobody gave them the story to tell.”

Start there. Everything else follows.

Why Your Board Goes Quiet When Fundraising Comes Up

When boards disengage from fundraising, most executive directors assume the problem is motivation. They decide board members don’t care enough, aren’t committed enough, or aren’t the right people for the role.

Christal disagrees. After six and a half years of working directly with boards across every sector of the nonprofit world, she says the real problem is almost always preparation. Or the lack of it.

Board members show up to their first meeting excited to contribute. Then they sit through a presentation full of acronyms they don’t recognize and systems nobody explained. Six months later, the executive director wonders why engagement has dropped off.

Of course it has.

“CEOs will say to me, ‘My board is lame. They’re not doing anything,'” Christal says. “And I’ll ask, what kind of preparation did they get? What kind of training? Was there any orientation? And they’ll say, ‘We have a board book.’ And I’ll think, yeah. The one nobody read.”

The fix starts with better onboarding. But it doesn’t end there.

How Do You Fix Board Disengagement?

Start with the story before you start with the ask.

This is the foundation of what Christal teaches, and it’s what she’ll be bringing to the WellTold Nonprofit Storytelling Conference in Fargo on April 30th. Before you ask board members to go out and raise money, make sure they have a story worth telling.

Here is what that looks like in practice.

Christal sits down with board members who are convinced they could never ask anyone for money. She doesn’t argue with them. She asks a couple of simple questions instead.

Why did you join the board?

What moment from your service has stuck with you?

And then she watches what happens. People start telling stories. Real ones. Specific ones. Stories with names and details and feeling behind them. Stories that make you want to find the link to give.

“That’s it,” she tells them. “That’s the story. Tell me that.”

The ask becomes something different when it comes from that place. Board members stop thinking of it as a transaction and start thinking of it as an invitation. That shift in framing changes how people carry themselves going into a donor conversation.

What Stops Board Members From Sharing Their Stories?

The Midwestern Problem (and Its Nationwide Cousin)

Host Max Kringen put it plainly in their conversation: Midwesterners are raised to believe that talking about the incredible things you’re doing is rude. You don’t brag. You put your head down and do the work.

It’s a value that produces genuinely humble people. It also quietly limits board members from saying the thing that most needs to be said.

Sharing your story about why you love this mission is not bragging. It’s saying, this thing changed me, and it might change you too. That’s an invitation, not a sales pitch. And board members who understand the difference tend to have much easier conversations with donors.

Fear of the Ask Itself

Board members often imagine the moment of asking as uncomfortable, even aggressive. They picture themselves imposing on someone.

Christal has a different image she offers them.

“Asking is not imposing. It’s usually a yes or a no. And if it’s no, it’s not the end of the world.”

She uses a frame from the episode that is hard to forget. Think about the last time you drove to traffic court over a $55 ticket you felt was wrong. You could have just paid it. Instead you went in there, made your case with full conviction, and maybe still paid the ticket. But you showed up because the principle mattered.

A fundraising ask, done well, has that same energy. You’re not asking for yourself. You’re asking because a kid needs school supplies, or a family needs services, or a community needs the work your organization does. When board members start thinking about that instead of their own nerves, the ask gets easier.

The First Misstep Executive Directors Make

Most boards aren’t disengaged by choice. They’re disengaged by default, because nobody set them up to succeed.

Think about what it’s like to walk into your first board meeting. You are excited and ready to help. Then someone starts talking about CRM systems or a capital campaign timeline, and you realize you have no context for any of it. Nobody oriented you. Nobody showed you around. Nobody made sure you felt prepared before expecting you to perform.

“I don’t know what they want me to do,” Christal hears from board members constantly. “I want to help. I went to the board meeting. But now what? What am I supposed to do between meetings? No one’s communicating with me.”

Give board members a real onboarding. Introduce them to staff. Take them to the program site. Let them feel the mission before you ask them to fundraise for it. And make sure every board member gets the same experience, not just the ones who happened to be around during a more organized season.

What Consistent Board Development Actually Looks Like

Board Bites: The Two-Minute Habit

Christal has a concept she calls board bites. At every board meeting, a small item on the agenda, just two or three minutes, covers some aspect of board training or development.

It might be a quick conversation about board recruitment. It might be a heads-up about how to talk to donors at an upcoming event. Whatever it is, small and consistent beats occasional and comprehensive. Over the course of a year, those bites add up.

“You have to prepare them,” Christal says. “Give them the tools. Give them the knowledge. Give them the scripts, because they don’t know what to say.”

The annual board retreat matters. But the board bites in between are what keep the learning from evaporating.

Role Play Before the Real Thing

Role play is one of the most underused tools in board development. It feels awkward. People resist it. It is also extraordinarily effective.

Before you send board members into donor conversations, give them a framework. Something that helps them understand what the conversation is meant to accomplish and why. Let them practice. Let them make the stumbling mistakes in a low-stakes room rather than in front of a major donor prospect.

Then encourage them to make the language their own. Every board member should be able to say something that sounds like them and still points toward the same mission.

How to Reframe Accountability So It Feels Like Support

The word accountability makes a lot of people tense up. It sounds like surveillance, or a performance review from someone who has already made up their mind.

Christal’s version looks different.

In her framework, accountability looks like a board chair who picks up the phone on a random Tuesday and calls the executive director to say: I know things are hard right now. Is there anything I can take off your plate today?

It looks like a board member who sends a thank-you note without being asked, who shows up to the volunteer event even though attendance wasn’t required.

“It shouldn’t be burdensome,” Christal says. “It should be something you enjoy doing.”

She also offers something that sounds almost too simple. Use your phone. Set a recurring reminder every six weeks to check in with your executive director or a board colleague. Thirty seconds to set up. It costs nothing. And over time, that habit builds the kind of relationship where people actually show up for each other.

That is accountability. And any board can start doing it this week.

The Scholarship Story That Still Drives Christal’s Work

At the close of every episode, Max asks guests to share a story that still guides how they show up.

Christal’s answer is worth sitting with.

Early in her fundraising career, she discovered a scholarship fund that had been sitting dormant in an account for years. The money had been given in honor of a young woman who had passed away, a former student at the university where Christal worked. The family had intended to endow the scholarship but had never quite raised enough. And somehow, the effort had stalled.

Christal decided to restart it.

She tracked down the woman’s professors. She called alumni who had known her. She pieced together a real portrait of a real person, and then started sharing that portrait across campus, with current students who had never met this woman but who came to care about her name.

“The day that the check was cut and we were able to present it to the college president, that whole family was in the room,” Christal says. “And they were crying and just thanking me for bringing this to fruition.”

Then she says the part that stays with you.

“I remember thinking to myself, this is why I do the work.”

A great story does more than raise money. It restores something. It says to a family, your person mattered, and we haven’t forgotten. That kind of impact outlasts the check.

How to Apply This: Your Action Plan

This Week (30 minutes)

Pick one board member who you know has a story about why they joined. Reach out and ask them to share it. Don’t frame it as fundraising prep. Just say you’d love to hear more about their connection to the mission. Listen for the specific details that make it real.

This Week (20 minutes)

Look at your next board meeting agenda. Find a two-minute slot and add a board bite. It can be as simple as a discussion question: What’s one thing a donor has said to you that you’ve never forgotten?

This Month (2 hours)

Design a simple onboarding checklist for new board members that includes a site visit and a staff introduction. Make sure every future board member goes through it, not just the ones who joined during a well-organized season.

This Month (ongoing)

Set a recurring reminder on your phone to reach out to your board chair or executive director once every six weeks. Make it a habit before you need it to be.

Resource Hub

Christal Cherry, The Board Pro — theboardpro.com — Board development consulting, speaking, and coaching for nonprofits of all sizes.

Christal on LinkedIn — Search Christal Cherry — Connect directly and follow her ongoing work in governance and fundraising strategy.

The Board Pro on Substack and Facebook — More resources and community for nonprofit board leaders.

WellTold Nonprofit Storytelling Conference — welltoldconference.com — April 30th in Fargo. Christal will be there in person. One day of practical, story-focused learning built for nonprofit leaders.

Tellwell Resources — wetellwell.com — Guides on nonprofit storytelling, donor engagement, and brand strategy for mission-driven organizations.