Board & Administrative Team Focus on Leadership, Culture, and Communication at Annual Retreat

The Board of Education and District administrators came together for the Chappaqua Central School District's annual July Administrative Retreat. The focus was on learning, reflection, and collaboration designed to prepare leaders for the year ahead.

Over the course of two days, three nationally recognized speakers explored different aspects of effective leadership. While each session offered a unique perspective, all emphasized the importance of building strong school communities through intentional leadership, meaningful relationships, and effective communication.

Dr. Joe Sanfelippo, former superintendent of the Fall Creek School District in Wisconsin and best-selling author of Lead From Where You Are, encouraged leaders to think about the small moments that shape school culture. Emphasizing that "we build culture 30 seconds at a time," he shared practical strategies for leading with intention, finding joy in the work, and fostering positive school environments through everyday interactions.

Tim McDonald, Associate Policy Researcher at RAND and Co-Director of the Systems Transitions Applied Research (STAR) Initiative, explored how education leaders can navigate increasingly complex and contested environments. Drawing on his work in systems analysis and negotiation, he provided tools and strategies to help leaders address challenging situations, build consensus, and guide organizations through change.

Michelle Kelley, U.S. Lead for the Listening Institute and former FBI Special Agent, concluded the retreat by highlighting the power of elite listening. Through stories from her FBI career, she demonstrated how intentional listening can strengthen relationships, improve difficult conversations, and help leaders build trust within their school communities.

Together, the sessions reinforced the important role school leaders play in shaping positive learning environments through thoughtful communication, strong relationships, and a shared commitment to supporting students and staff. The Board and Leadership team will meet again for their August retreat to prepare for the upcoming school year.