In this episode of Leading Voices in Education, we sit down with educator, author, and digital learning leader Dean Shareski to explore one of the biggest shifts facing schools today: the rapid rise of artificial intelligence. Drawing on decades of experience as a classroom teacher, district consultant, and global thought leader in digital learning, Dean shares how his deep commitment to joy, humanity, and curiosity shapes the way he approaches AI in education. Dean reflects on his journey from teaching grade one to supporting districts across North America, and how his early love of technology has evolved into a nuanced, sometimes uneasy, but ultimately hopeful stance on AI. Together, we dig into the tensions educators are wrestling with—loss of human connection, new skill development, ethical concerns—and the powerful possibilities AI offers when used to amplify creativity, reduce workload, and give teachers more time for what really matters. We also explore the essential role of school leaders in building cultures of transparency, critical thinking, and responsible innovation. Dean shares practical insights about conversations teachers need to have with students, the importance of guided use over avoidance, and the value of embracing uncertainty as we navigate this unprecedented shift.