Parenting Teenagers: Boundaries, Consequences and Building Trust With High School Dean, Anthony Thomas

In this episode of What Great Teachers Know That All Parents Can Use, we sit down with Anthony Thomas, a high school dean, to explore how to discipline teenagers, set healthy boundaries, and build trust during the challenging high school years. Anthony draws from his experience overseeing student discipline, attendance, and wellbeing, and explains how the role of a dean often overlaps with that of a parent: acting as a mediator, counsellor, cheerleader, and crisis responder for young people navigating adolescence. Together, we explore accountability, responsibility, and the importance of clear rules, especially for high school students living in an era shaped by social media and blurred boundaries. Anthony shares practical insights on setting boundaries and building trust with teenagers, enforcing consequences with care, and building strong relationships through proactive conversations. He speaks about the idea of using structures and expectations as “guard rails” designed to catch young people before they fall.  Whether you’re struggling with discipline or simply looking for better ways to connect with your teen, this conversation offers grounded advice from both an educator and a parent who understands the pressures families face today.Anthony Thomas currently serves as Upper School Dean of Students and Head Boys Basketball Coach at Woodward Academy in College Park, Georgia. Born in Atlanta and raised in College Park, Anthony Thomas is a 1998 graduate of Woodward Academy. He went on to earn his degree in Political Science from Furman University in 2002, where he was a four-year basketball letterman. He received his Juris Doctor from Georgia State University in 2005 and later completed a Master’s in Educational Leadership from Harvard University in 2024.A licensed attorney with the Georgia Bar Association since 2005, Anthony has been a dedicated member of the Woodward Academy faculty since that same year. He is committed to student development both in and out of the classroom and the court. Anthony is passionate about connecting with students and supporting their growth as they find their stride.A selfless, lifelong learner and self-described “ultimate teammate”, Anthony continues to seek out ways to empower young students each day. Outside of his professional life, Anthony enjoys spending time with his wife and two daughters and is a passionate supporter of all things Atlanta sports.Anthony’s successes can be traced back to one phrase: “to God be the glory!”