In this episode of Expressions of Leadership, Michele Kawamoto Perry sits down with Bob Riddle, a lifelong educator whose nearly four-decade journey, from math teacher to Head of School, offers a powerful perspective on what it means to lead with purpose, courage, and authenticity.

Together, they explore the defining moments of Bob’s leadership, including coming out and leading with greater authenticity, as well as bold institutional decisions like eliminating AP courses, launching a transformational capital campaign, and founding the Equity & Justice Institute to embed inclusion and impact into the fabric of the school. Bob also reflects on leading through complexity and crisis, the importance of building strong, values-driven communities, and his continued work in the nonprofit sector to expand educational access and support community healing. This conversation is a thoughtful look at leadership that is centered on relationships, integrity, and a commitment to the greater good.

Connect with Bob Riddle on LinkedIn: https://www.linkedin.com/in/bob-riddle-171a94298/

Learn more about Crossroads School for Arts & Sciences: https://www.xrds.org/

Don't miss an episode! Be sure to click on the follow and subscribe buttons. Follow Expressions of Leadership on YouTube and Instagram @ExpressionsOfLeadership. You can also catch the show on Radio Evolve at www.radio-evolve.rocks every Saturday and Sunday at noon PT.

Discover more about host Michele Kawamoto Perry and The Forward Project’s expertise in culture transformation and leadership development at www.theforwardproject.co.