Tony Little has worked as a boarding housemaster and been head of three schools with a boarding dimension. He has been a head teacher for 26 years, successively at Chigwell School (from 1989), Oakham School(from 1996) and Eton College (from 2002-2015). Over the years he has been a governor of 9 secondary schools, both state and independent, as well as 6 primary/prep schools.