Today we welcome Will le Fleming who is the Founding Master of Thomas’s College in Richmond, an 11–18 day and boarding school rethinking the secondary journey with a three-year Sixth Form that begins in Year 11 and a hybrid pathway that blends GCSEs with Thomas’s Qualifications; Years 12 and 13 are reshaped to deepen scholarship, independence and readiness for life beyond school. Educated at Eton and Clare College, Cambridge, Will worked as a journalist and author before moving into teaching. He began at St Paul’s School, becoming Undermaster, then served as Deputy Head at St Paul’s Girls’ School. He went on to lead Fulham School as Headmaster and later became Head of The Abbey School in Reading, before his appointment to Thomas’s College. Alongside teaching, he is a published novelist. Will’s leadership blends rigorous scholarship with wellbeing, pupil agency and creative endeavour, fostering confident, curious and principled young people who achieve outstanding outcomes. In this conversation, Simon and Will discuss the innovative educational approaches at Thomas's College, emphasising the importance of a diverse school culture, student agency, and personal development. They explore the challenges of navigating academic choices and assessments, the need for reform in the current education system, and the role of technology in preparing students for an uncertain future. The conversation highlights the significance of kindness, confidence, and hope in education, advocating for a more holistic approach to learning.