Case Study

How 16 CEO’s came together to transform their businesses and communities.

Instead of spending another year organizing the retreat themselves, Vistage partnered with Wilder to create a seamless experience focused on connection, conversation, and shared learning.

CEO’s

100+

New Perspectives

Future retreat planned

Client

Vistage

Duration

3 days

Location

Charleston

Number of people

16 CEOS

The Challenge

What Was Getting in the Way

Vistage is a peer network of CEOs and business owners who come together to learn from one another and return to their companies with fresh ideas, stronger perspectives, and practical solutions. Their annual retreat provides one of the few opportunities to step away from the demands of running a business and focus entirely on leadership, reflection, and peer learning.

The previous year’s retreat had been planned internally by members of the group. While the experience was worthwhile, organizing transportation, activities, and logistics meant time and energy that could have been spent participating in the conversations themselves. This year, the goal wasn’t simply to make the retreat easier to organize, it was to create an environment where every attendee could be fully present, learn from one another, and leave with ideas that would make them better leaders.

The Approach

What We Did Together

Together, Wilder and Vistage designed a retreat that balanced structured leadership conversations with experiences that encouraged relationships to develop naturally. Charleston provided a relaxed setting where discussions could continue long after the formal agenda ended, allowing members to connect as peers rather than simply as business owners.

Rather than treating activities as breaks from the meeting, each experience was selected to reinforce the purpose of the retreat. Wilder developed discussion prompts and leadership metaphors that tied directly into the group’s conversations, giving members opportunities to reflect on their own businesses while learning from one another’s experiences. Whether during a shared meal, a curated activity, or a self-led discussion, every part of the retreat supported meaningful dialogue and practical takeaways.

The Outcome

What Changed

By the end of the retreat, members left with more than stronger relationships—they returned to their businesses with new perspectives. Conversations throughout the week challenged assumptions, introduced fresh approaches to leadership, and gave CEOs the opportunity to think intentionally about the future of their organizations alongside peers who understood the unique challenges of running a business.