In 1967, Woolcott drafted a speech for Prime Minister
Harold Holt that said Australia was geographically part of Asia and that it was "a basic tenet of our national policy to live in friendship and understanding with our Asian neighbours". Between 1967 and 1970, Woolcott was the Australian
high commissioner to Ghana. In the role, he regularly visited several capitals and cities throughout
West Africa. From 1975 to 1978 he was
Australia's ambassador to Indonesia, at the time of the
Indonesian invasion of East Timor. In a series of oft-cited and highly-influential cables throughout his ambassadorship, he urged his country to take a 'pragmatic' or '
Kissingerian' approach to the Indonesian incorporation of East Timor, largely due to the importance of the
Suharto regime to Australia's strategic and foreign policy goals and its relations with
ASEAN and the region, although also informed by the under-sea oil resources that Australia was claiming close to Timor. Subsequently, Woolcott was appointed Australia's ambassador to the Philippines between 1978 and 1982. American cables leaked by Wikileaks reveal that Woolcott had been an informant to the US, providing consular officials with information of internal government processes during 1974. Woolcott 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 position in Australia, from 1988 to 1992. As DFAT Secretary, he was involved in the establishment of the
Asia-Pacific Economic Cooperation (APEC) forum. On 4 June 2008, Australian Prime Minister
Kevin Rudd announced that Woolcott had been appointed an envoy to conduct discussions to form a new Asian regional forum. 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. ==Personal life and death==