In 1996, Dakin accepted a position within the Foreign and Commonwealth Office (FCO). He first lead staff groups involved in Russia and later on Counter Terrorism and, promoted to Director, he served on the executive board where he oversaw organisational transformation. Concurrently, he was invited by the then Chief of the General Staff, General Sir Nick Carter, to serve as the civilian Non-Executive Director on both the Army No. 1 Board and the Army Higher Honours Committee, a position he retained until 2019.[7]
In May 2019, the Foreign and Commonwealth Office announced that Dakin would succeed outgoing Governor John Freeman as Governor of the Turks and Caicos Islands.[10] As such, Dakin was the representative of Her Majesty Queen Elizabeth II and acted as the de facto Head of State responsible for appointing the Head of Government, and senior political positions in the territory.[10] Dakin was also responsible for chairing Cabinet and ensuring the good governance of the territory. The Constitution also reserved to the Governor responsibility for defence, external affairs, the regulation of international financial services and internal security, including the police force.[11]
Dakin's Governorship included: the COVID-19 pandemic, when he held emergency powers;[12] the challenges of mass irregular migration caused by a serious deterioration in the security situation in neighbouring Haiti;[13] a concurrent rise in gang related murder temporarily suppressed following the deployment of armed officers requested from The Bahamas and a package of UK support;[14] an election and resulting change of government during the pandemic;[15] a Royal Visit[16] and the impact of Hurricane Fiona.[17]
Dakin commissioned and oversaw the development of the Turks and Caicos Islands Regiment;[18] the establishment of a National Security Secretariat and accompanying Strategy[19] and the deepening of relationships with the USA and The Bahamas to deliver the inaugural North Caribbean Security Summit and the resulting uplift in regional security co-operation.[20] The decision to combine Immigration and Customs Officers to form a new Border Force was taken.[21] With UK support, the Royal Turks and Caicos Islands Police Force established a 'Guns, Gangs and Drugs' Team to tackle serious organised crime[22] and legislation was passed to provide the Police with a technical intelligence collection capability.[23]