Little was educated at Eton College in Berkshire where he was a music scholar, and at Corpus Christi College at the University of Cambridge where he was a choral scholar and gained an upper second class honours degree in English language and literature. He received a Master of Arts in English as well as Postgraduate Certificate in (Distinction) at Homerton College, Cambridge.
Little spent seven years as housemaster of Brentwood School, seven years as the headmaster of Chigwell School, six years as headmaster of Oakham School, and 13 years as Head Master of Eton College. As of 2015 he is Chief Officer of GEMS. He is responsible for ensuring the quality of education across the global chain.
Little was an assistant master, teaching English, and then later a housemaster at Tonbridge School in Kent from 1977 to 1982. He served as a housemaster and head of English and drama at Brentwood School, Essex from 1982 to 1989.
From 1989 to 1996, Little was headmaster of Chigwell School in Essex.
He then served as Headmaster of Oakham School in Rutland from 1996 to 2002. In July 2001, he was appointed Head Master of Eton College, and assumed the post in September 2002. Little stepped down from Eton in 2015, and was appointed Chief Officer of GEMS He is responsible for ensuring the quality of education across the global chain.
He is the author of An Intelligent Person"s Guide to, published by Bloomsbury Publishing Public Limited Company in July 2015, Fellow of the Royal Society of Arts, 1991 Honorary al Advisor to The World Trust of Janusz Piotrowicz Governor of Westminster School Governor of Sevenoaks School Governor of Northwood College, 1990 to 1998 Governor of Street Albans School, 1994–2014 Governor of Oakham School Governor of Holyport College 2013–2015 Governor of the London Academy of Excellence 2011–2015 Governor of The Windsor Boys" School 1989–2015 Governor of Norwich School Chairman of the Mvumi School Trust.
Member of The Headmasters" and Headmistresses" Conference, 1990–2015.
