Volunteers serve in an organization because they believe in its mission. They see the impact firsthand—children thriving in after-school programs, families receiving critical resources, and lives being changed. But when it comes to fundraising, many feel unprepared to make the ask. The idea of asking for money can feel intimidating, even though donors are already invested in the cause. The good news? Fundraising isn’t about sales—it’s about deepening relationships and reinforcing a donor’s decision to give.
By understanding the WHY and HOW of fundraising, volunteers can reduce anxiety and learn to use their personal passions to start natural, engaging conversations with donors. These conversations—rooted in gratitude and mission alignment—can lead seamlessly to a meaningful and effective ask.
In this blog, we explore a real-world scenario that walks through how volunteers can approach donor conversations with confidence, turning their enthusiasm for the mission into authentic, impactful fundraising interactions.
The Art of the Ask: Training Volunteers for Meaningful Fundraising Conversations
When Emily first agreed to help with fundraising, she hesitated. She wasn’t a salesperson, and the idea of asking people for money made her uneasy. But as a longtime volunteer at ABC Youth Center, she had seen firsthand the impact of its programs—kids finding a safe space after school, teens discovering new passions in apprenticeships, families receiving support when they needed it most.
“You’re not just asking for money,” her mentor, David, reassured her. “You’re inviting people to be part of something bigger.” Emily’s training began with a simple but powerful exercise: understanding the donor list.
Step 1: Understanding the Donor List and Giving Patterns
David handed Emily a report with donor names and giving history. “First,” he explained, “we evaluate who’s already giving and how. Some donors support a specific program—maybe they care about after-school initiatives, while others focus on the annual fund.”
They looked at who gave consistently and who had lapsed. More importantly, they assessed mission-mindedness—which donors seemed truly engaged with the cause beyond just financial contributions? “See this?” David pointed to a donor who had given every year for a decade but had never attended an event. “She believes in what we do, but she might not feel connected. That’s an opportunity.”
Step 2: Identifying the Top 25 Donors
From the full list, they identified the top 25 donors, those who had given the most or most consistently.
“These are the people who already believe in us,” David said. “Now we need to understand why they give.”
Step 3: Running a Giving History Report
Emily ran reports on each donor, uncovering patterns. Some had donated large sums to capital campaigns, others supported specific events, and a few had given in memory of a loved one.
“This tells us how to approach them,” David explained. “Someone who gives because of a personal connection will respond differently than someone who values community-wide impact.”
Step 4: Creating a Moves Management Strategy
David introduced Emily to Moves Management, a structured approach to deepening donor relationships.
“Think of fundraising as building a relationship,” he said. “Every step matters.”
For each of the 25 donors, they planned a sequence of moves—intentional actions to strengthen their connection to the mission.
- Personalized Phone Call – A warm check-in, not an immediate ask.
- Handwritten Note – A genuine expression of gratitude.
- Invitation to a Mixer – A chance to engage with the impact of their giving.
- Formal Letter – A strategic opportunity to share the bigger picture and the need.
Emily realized fundraising wasn’t about pressure—it was about showing gratitude and creating opportunities for donors to say yes to making a difference. The donor is already invested in the organization, as demonstrated by their giving. Asking conversations should focus on what the donor is already doing and reinforce their decision to support the mission. Instead of feeling like she was convincing someone to give, Emily now saw her role as affirming their generosity, deepening their connection, and helping them see the tangible impact of their support.
Step 5: The Giving Pyramid and Strategic Asks
David showed Emily a Giving Pyramid, explaining that every successful campaign had donors at different levels:
- Major donors (Top gifts) – a few individuals giving large contributions.
- Leadership donors (Mid-tier) – several donors making significant commitments.
- General donors (Broad base) – many supporters giving smaller amounts.
They mapped out where their top 25 donors might land on the pyramid and tailored their asks accordingly. For example, one longtime donor, Mark, had given $5,000 annually to a specific program. Instead of a generic ask, they’d invite him to consider an increased commitment to sustain and expand that program.
Step 6: The Personal Conversation
Emily was ready. She picked up the phone and dialed a donor.
“Thank you for your commitment to those we serve. Your giving has totaled $15,000 over the years. In case we haven’t communicated enough, we deeply appreciate your financial support. Your gifts have allowed us to provide after-school enrichment for hundreds of kids in our community. I’m curious—what prompted you to give?”
She waited. The donor shared how his grandmother had been a teacher and how education had always been important to him.
“Thank you for sharing that,” Emily said. “What we want to do right now is thank you for your support. We can never thank you enough, and we appreciate your partnership. Is there anything you’d like to share that would help us as we move forward?”
The donor mentioned he wished he could see more firsthand stories of the kids benefiting from the program.
“That’s great feedback,” Emily said. “We actually have a student, Cindy, who struggled in school until she joined our after-school program. Now she’s thriving, and she just got accepted into an advanced STEM camp. Your gifts made that possible.”
The donor paused, clearly moved.
Step 7: The Ask
Emily continued, “We’re excited about the future. Supporters like you have helped us expand, but we have a big heart to serve more. In 2025, our after-school program will serve 50 more kids like Cindy. With $25,000, we can provide tutoring, meals, and enrichment activities to ensure they succeed.”
She pulled up the Giving Pyramid and asked, “Would you be open to considering where you see yourself in this? Your continued support at any level makes a real difference.”
The donor agreed to think about it and asked for more information.
A New Fundraiser is Born
After her first few calls, Emily realized fundraising wasn’t about asking—it was about listening, engaging, and inviting people to be part of something meaningful.
David smiled. “You see? It’s not about selling. It’s about helping people invest in something they already believe in.”
Emily nodded. She wasn’t just asking for money—she was inviting people to change lives.
And that made all the difference.
Angie Thompson is an independent consultant with 40 years of experience bridging the gap between for-profit strategy and nonprofit impact—helping organizations craft powerful messaging, engage supporters, and drive lasting growth.
Disclaimer:
The story of Emily and David is a fictional scenario created to illustrate effective fundraising strategies. Any resemblance to actual persons, living or deceased, or real-life events is purely coincidental. This narrative is intended for educational and illustrative purposes only, demonstrating best practices in donor engagement and Moves Management techniques.