Simon Henderson, Head Master of Eton College, on balancing tradition and modernity at the near 600-year-old school
“Some of the rules around tech became too liberal – and trying to rein that in is like trying to put toothpaste back into the tube.”
Our next guest on Heads & Tales needs little introduction. As Head Master of Eton College for the last decade, Simon Henderson is at the helm of one of the world's most recognisable, and scrutinised, schools. In a Heads & Tales first, Simon joined us in person in the studio, speaking to Walter Kerr about the reality of running a near 600-year-old institution whilst preparing teenage boys for a world changing faster than any generation before them. In another first, Simon isn't the first member of his family to appear on our podcast, following in the footsteps of his wife Ali Henderson who joined us this time last year. When he asked what advice she could offer ahead of recording the episode, he was told in no uncertain terms: "don't tell any jokes".
Simon traces the journey that brought him to the top of Eton's ladder, from his early days teaching in post-apartheid South Africa to early leadership experiences at Sherborne and Bradfield. He reflects on the shifts that he has overseen at Eton – a kinder culture, increased bursary provision and a viral policy on smartphone use at the school. His episode is the portrait of a leader intent on balancing heritage with modernisation, and leading an iconic school determined to broaden who it serves and what it stands for.
🎙️ Episode highlights
Balancing 600 years with the next ten: Simon's discusses the balancing act between tradition and modernity, protecting Eton's heritage whilst ensuring its curriculum is relevant to the world boys are stepping into.
Expanding bursary provision: he details the school's massive annual bursary programme and why it's central to Eton's core mission.
Smartphone policy and wellbeing: Simon shares why Eton tightened its rules on phones and its impact on social life, focus and mental health.
The future of exams and skills: Simon reflects on the mismatch between traditional assessment and the skills required for a evolving workplace.
His human approach to leadership: from safeguarding to culture change, he speaks candidly about his headship and why every decision ultimately comes down letting the talents of others come to the surface.