S.5 | Ep. 9: Investing in People and Building Sustainable Leadership with Chris Calabrese

Welcome to Season 5 of the Unlock 360 podcast by Lead.Teach.Learn.360! In this episode, Wendy York Davoud is joined by Chris Calabrese, Superintendent of Benicia Unified School District, for a conversation about leadership development, district sustainability, and the power of investing in people.Chris shares the unexpected story that led him into education and the personal motto that has guided his entire career: “Invest in people’s lives instead of their money.” From teacher to superintendent, Chris reflects on his K–12 leadership journey and how developing leaders remains one of the most meaningful parts of his work today.The conversation explores the realities of leading a district through change, including leadership transitions, declining enrollment, financial pressures, and the challenge of maintaining strong academic outcomes while supporting students socially and emotionally. Chris also discusses the importance of helping leaders think long term, creating sustainable systems, and balancing district-wide coherence with school-level autonomy.Listeners will also hear how Benicia Unified is working to strengthen collaboration, close achievement gaps, and preserve the unique culture that makes the Benicia community special.Key Moments02:52 Investing in People Instead of Positions05:32 Supporting New Leaders Through Transition06:47 Building Sustainable Long-Term Systems07:22 Self-Awareness and Leadership Growth09:37 Using 100-Day Plans for Leadership Success13:25 Learning the Culture of Benicia Unified16:11 Addressing Enrollment and Budget Challenges17:45 Attracting Families Through Student Opportunities18:13 Extracurriculars Strengthen School Culture20:09 What Makes the Benicia Community Special22:19 Balancing District Alignment and School Autonomy26:55 Closing Achievement Gaps Through Collaboration29:07 Expanding Academic Intervention SupportsWhy You Will Love This EpisodeThis episode offers an honest look at what it takes to lead with purpose during times of transition and uncertainty. Chris shares thoughtful insight on leadership development, strategic thinking, and creating sustainable systems that support both students and educators. District and school leaders alike will walk away with practical ideas around collaboration, culture, and long-term planning.Connect with Chris CalabreseWebsite: https://beniciaunified.org/ LinkedIn: https://www.linkedin.com/in/chris-calabrese-b46079268 Email: [email protected] Follow UsWendy York Davoud LinkedIn: https://www.linkedin.com/in/wendyryorkLead.Teach.Learn.360 Website: https://leadteachlearn360.comLead.Teach.Learn.360 LinkedIn: https://www.linkedin.com/company/lead-teach-learn-360%C2%B0/About Unlock 360°Unlock 360° is the podcast where school leaders and instructional trailblazers reveal how they are turning bold vision into sustainable action. Powered by Lead.Teach.Learn.360, each episode brings you inside the systems, strategies, and human stories that drive school improvement, one leader, one learner, one breakthrough at a time.Enjoyed this conversation? Subscribe to Unlock 360° for more.