Woolcott was educated at Geelong Grammar School, Cranbrook School and the University of Melbourne, and became a member of the Australian Diplomatic Service. He held positions as Australia's ambassador to Indonesia and The Philippines, as well as High Commissioner to Malaysia, Ghana and Singapore. He was the Australian Ambassador to the United Nations from 1982 to 1988, and served as the President of the United Nations Security Council for Australia's term in November 1985. Woolcott also served as Secretary of the Department of Foreign Affairs and Trade (DFAT), the most senior diplomatic posting in Australia, from 1988 to 1992. As DFAT Secretary, he was involved in the establishment of the Asia-Pacific Economic Cooperation forum. On 4 June 2008, Australian Prime Minister Kevin Rudd announced that Woolcott had been appointed as an envoy to conduct discussions to form a new Asian regional forum.
Since 1997, Richard Woolcott has been the Founding Director of the Asia Society AustralAsia Centre.
In 2003 Woolcott wrote a personal memoir entitled The Hot Seat: Reflections on Diplomacy from Stalin’s Death to the Bali Bombings, and he also wrote a book called Undiplomatic Activities in 2007.
For his services to diplomacy and international relations, he was made an Officer of the Order of Australia in 1985, and appointed a Companion of the Order in 1993. Woolcott's son, Peter, is also a diplomat and has served as the ambassador to Italy.
In July 2008, Richard Woolcott was selected as one of the inaugural fellows of the Australian Institute of International Affairs to highlight his very high level of distinction in and distinguished contribution to Australia's international affairs.
- On Line Opinion (2008). Richard Woolcott. Retrieved 5 June 2008.
- "Richard Woolcott and Mandyam Srinivasan". The Backyard (Australian Broadcasting Corporation). 29 August 2007. Retrieved 17 December 2007.
- Maley, Paul (5 June 2008). "Old warhorse Richard Woolcott back in harness to smooth regional ties". The Australian.
- HarperCollins (2008). The Hot Seat: Reflections on Diplomacy from Stalin’s Death to the Bali Bombings. Retrieved 5 June 2008.
- Scribe Publications (2008). Undiplomatic Activities. Retrieved 5 June 2008.
- It's An Honour (2008). WOOLCOTT AO, Richard Arthur. Retrieved 5 June 2008.
- It's An Honour (2008). WOOLCOTT AC, Richard Arthur. Retrieved 5 June 2008.
- Away with the Anachronism: A Republic will serve Australia's Domestic and International Interests. Retrieved 31 July 2008.