Educated at Eton College, Sir Henry spent most of his career either farming or working in broadcasting. He worked on his father's farm until 1972 when he took over the tenancy. The same year he joined BBC Radio Oxford as a freelance presenter working shifts whenever they were available. In 1987 he joined the board of FOX FM, the company awarded the Independent Local Radio licence for Oxfordshire. With others, he went on to found another seven independent radio stations throughout central and southern England, retiring from the radio industry in 2006. He was Deputy Chairman of the National Trust 2002–05 and President of the Country Land and Business Association 2008–10.
Sir Henry and Lady Aubrey-Fletcher now run a number of companies in Buckinghamshire, including Chilton House Residential Home and the Chilton Business Centre.[2]