At the 2026 Virginia Advancing Main Street Director Retreat in Luray, 32 local program executive directors gathered for a session titled Appreciative Inquiry: Leading with Strengths, Purpose, and Possibility. These directors lead local nonprofit Main Street organizations—each a 501(c)(3) that partners closely with its municipality to strengthen downtown districts and advance community vitality. Appreciative Inquiry is a strengths-based approach to leadership that focuses on what works, why it works, and how to build more of it. Instead of troubleshooting problems, it mines success for insight—and the results were energizing.
The opening icebreaker, Who You Are as a Main Street Leader, revealed a powerful pattern: today’s directors are connectors, visionaries, communicators, mediators, marketers, and relationship-builders. Many described their “superpower” as bringing people together, keeping momentum alive, and helping partners see what’s possible. Pride moments centered on tangible community impact—revived theaters, thriving events, new businesses, successful grant wins, and hearing residents say they feel excitement downtown. When asked what brings them joy, directors spoke of legacy, community pride, business success, and seeing their hometowns flourish.
During the Appreciative Inquiry Peer Discovery activity, paired interviews uncovered shared success factors across communities. When stories were harvested, five themes emerged:
- Leadership Behaviors: vision, positivity, empowerment, and leading by example
- Relationship Strategies: trust, transparency, collaboration, and consistent communication
- Community Strengths: leveraging networks, local traditions, and unexpected assets
- Advocacy & Storytelling: using data and impact stories to guide decisions
- Conditions for Success: having the right people at the table
Taken together, these insights point to a clear takeaway: the most effective Main Street leaders don’t operate as solo problem-solvers. They act as ecosystem builders. They listen deeply, amplify others, and align partners around shared possibility.
The session closed with a collective realization—Main Street leadership isn’t just about projects or programs. It’s about cultivating belief: belief in place, in people, and in what can happen when communities work together with intention. Several directors left inspired to learn more about Appreciative Inquiry, seeing it not just as a facilitation tool, but as a leadership mindset. Curious about Appreciative Inquiry? This one-page cheat sheet gives Main Street leaders the quick scoop.
If this gathering proved anything, it’s that the future of Main Street is bright—because the people leading it already know how to find, grow, and celebrate what’s working.
Virginia Main Street 