Since 2012, the Deans' Roundtable Conference has provided independent school deans with professional development resources. As deans, our jobs are all encompassing; requiring us to oversee the day-to-day running of faculty, student, and school life. We are also tasked with building a cohesive learning environment that is both challenging and fun. The conference creates a forum in the summer where deans can get together to reflect, share best practices, collaborate, and laugh. Participants also gain an expanded professional network, actionable ideas, a greater understanding about how other schools operate, and an online forum for continued insights.