Over the years, I’ve seen countless fundraising strategies in action. Some are transactional, focused on quick wins, while others take a more intentional, relationship-driven approach. One concept that has stuck with me—which I first heard at a training hosted by the Institute for Charitable Giving—is Dinners for Twelve. This idea was originally inspired by Dr. Richard “Dick” Wilson when he was president of Illinois Wesleyan University, and I believe it has the potential to transform donor engagement across all types of organizations.
The Power of Small Gatherings
Large-scale fundraising events and one-on-one meetings each have their place, but there’s something uniquely powerful about intimate gatherings that foster real connection. Dinners for Twelve strike the perfect balance—creating a setting that is personal and engaging while allowing for meaningful conversations that go beyond a simple appeal for support.
These aren’t just dinners. They’re carefully curated experiences designed to strengthen relationships, deepen engagement, and build lasting investment in an organization’s mission.
A Gathering with Purpose
The goal of a Dinner for Twelve isn’t to make an immediate ask. Instead, it’s about raising aspirations, fostering dialogue, and planting the seeds for deeper commitment.
At Illinois Wesleyan, these dinners were a way to engage high-end annual fund donors and gently introduce them to the idea of becoming major donors. But the concept applies far beyond higher education. Whether you’re leading a nonprofit, an advocacy group, or a faith-based organization, this approach can work for you.
The Role of the Host
The selection of the host is critical to the success of these gatherings. The ideal host is a committed donor or supporter who serves as a bridge between the guests and the organization’s leadership. This role isn’t just about logistics—it’s about setting the tone for the evening and fostering an environment where guests feel valued and heard.
The Four Phases of Connection
Each dinner is structured intentionally, ensuring that guests progress through a journey of engagement rather than passively listening to a presentation. Here’s how it works:
1. A Warm Welcome from the Host (5-6 minutes)
The evening begins with a brief introduction from the host, who shares their personal passion for the organization’s mission. They set the stage by explaining that the dinner is an opportunity to connect with leadership, hear about priorities, and engage in meaningful discussion—without pressure for a donation.
2. Sharing Stories (10-12 minutes)
As the first course arrives, guests take turns introducing themselves and sharing their connection to the organization. Some may recall personal experiences, while others speak to the impact the organization has had on their community. These unscripted, heartfelt moments create an immediate sense of belonging.
3. A Leadership Conversation (10-12 minutes)
Following the main course, the organization’s leader takes the floor—not for a lecture, but for a conversation. They highlight 2-3 key issues shaping the organization’s future and invite guests to share their thoughts. This dialogue is what makes the evening unique—it’s an open exchange, not a one-sided presentation.
4. Shaping the Future (10-12 minutes)
As dessert is served, the discussion shifts toward future opportunities. Rather than making a hard sell, the leader invites guests to reflect on how they might play a role in advancing the organization’s mission. Some may consider financial contributions, while others may express interest in volunteering, advocacy, or strategic partnerships.
The evening ends with a simple thank-you and a promise of follow-up from a development team member. No pressure, no pitch—just a continuation of the relationship.
Real Connections, Real Impact
What sets Dinners for Twelve apart is the sense of authentic engagement they foster. Guests walk away not just as potential donors, but as people who feel seen, heard, and valued.
Dick Wilson found that alumni and supporters who attended these dinners consistently increased their giving over time. But the real success wasn’t just in dollars raised—it was in the strengthened relationships and deepened investment in the university’s mission.
The Follow-Up: Where the Magic Happens
As Dick emphasized, you don’t let this sit. Within 48 hours, development staff reach out to thank guests and schedule follow-up conversations. This quick response ensures that the discussion doesn’t end with dessert—it continues, growing into a lasting partnership.
A Flexible Model for Any Organization
One of the great strengths of this approach is its flexibility. Some hosts prefer to open their homes for a warm, personal touch, while others opt for a private dining space at a restaurant. The organization typically covers the cost, but some hosts choose to sponsor the event themselves.
More Than Fundraising—A Lasting Tradition
At its core, Dinners for Twelve aren’t just about raising funds. They’re about raising aspirations and building a community of passionate supporters. Through storytelling, shared experiences, and open dialogue, these gatherings make an organization’s mission feel personal, tangible, and impactful.
The conversation doesn’t end when the dinner table is cleared. It continues—evolving into new relationships, deeper commitments, and opportunities to create lasting change.
Would this approach work for your organization? Let me know if you try it out!
From,
Kevin Gentry
