Richard Woolcott was educated at Geelong Grammar School, the University of Melbourne, Canberra University College and the London University School of Slavonic and Eastern European Languages. He joined the Department of External Affairs (later called the Department of Foreign Affairs and Trade) in 1950. He held posts in Africa, Asia and North America and with the United Nations. From 1988 to 1992 he was Head of the Department of Foreign Affairs and Trade.