Parenting with the End in Mind: Raising Children of Character with Chris Cleveland

In this episode of What Great Teachers Know That All Parents Can Use, Peyten Williams sits down with Chris Cleveland, President of Wesleyan School in Atlanta, to talk about what he has learned from more than three decades of working with students, parents, and families.Chris offers honest, practical wisdom for parents who want to raise children of character without falling into the trap of over-control, anxiety, or constant rescue. He reminds us that parenting is hard, children are resilient, and our job is not to manufacture perfect outcomes—but to guide, shepherd, and prepare our children to make wise decisions.Together, Peyten and Chris explore the difference between raising rule-followers and raising good decision-makers, why mistakes are valuable opportunities for growth, and how parents can shift from a “microscope” view of daily struggles to a “telescope” view of long-term character formation.This conversation is full of encouragement for parents who want to play the long game: investing deeply in who their children are becoming, not just what they are accomplishing.Guest BioChris Cleveland has served as Wesleyan School’s head of school since 2014. He originally came to Wesleyan in 2002 to serve as middle school principal, became principal of the high school in 2004, and assumed the role of assistant headmaster for advancement in 2010. Originally from Atlanta, Georgia, he earned a bachelor’s degree in history from Auburn University and a master’s in administration and supervision from the University of Tennessee-Chattanooga. A member of the Rotary Club of Atlanta, Chris serves on the boards of the Georgia Community Foundation, the Georgia GOAL Scholarship Program, the Cleveland Group, and the Executive Committee of the Council on Educational Standards and Accountability (CESA). Chris and Julie have been married since 1991, and they are proud parents of Kyle and Sam.00:00 Welcome and introduction to Chris Cleveland02:15 Why parenting is so hard04:00 What parents can and cannot control06:05 Parents as guides, not outcome-creators07:37 Parenting in today’s culture10:45 Helping children listen to trusted voices12:15 Raising decision-makers instead of rule-followers13:50 Letting kids make small decisions and experience consequences17:42 How teachers help students learn from mistakes19:37 “Never waste a mistake”22:30 Disappointed in the decision, not the child24:00 The microscope vs. telescope parenting metaphor27:43 Building a parenting toolbox29:26 The Graduation Game31:00 Character over achievement34:24 Parenting with backwards design35:36 ClosingTo learn more about Peyten Williams and Bowbend Consulting, visit bowbendconsulting.com.For parent coaching, school workshops, or speaking inquiries, reach out through Bowbend Consulting and explore resources designed to help parents and educators become strong and kind adults in the room.