Tony was educated at Eton and Cambridge. Following teacher training at Homerton College, Cambridge, he was appointed to the staff at Tonbridge School. He was appointed Head of English and Drama at Brentwood School where he also served as a House Master. From Brentwood he was appointed Headmaster of Chigwell School in Essex.
He was Headmaster of Oakham, a co-educational day and boarding school of 1,050 pupils aged 10-18 before taking up his post as Head Master of Eton College in 2002, a full boarding school for 1300 boys. From 2015 - 2018 he was Group Chief Education Officer for GEMS Education, an international schools’ group serving 250,000 children worldwide. He has been President of the International Boys’ Schools Coalition, President of the Boarding Schools Association and Chairman of the Mvumi School Trust, Tanzania. He is currently President of WLSA Fudan Academy, Shanghai, chairs a multi-academy trust in the Manchester area and is governor of four UK schools.