Elected in 1886 to the council of the government of Malta, Strickland began to take an active part in Maltese politics at an early age and in December 1887, he accompanied Dr. Fortunato Mizzi – founder of the Maltese Nationalist Party – to the first Colonial Conference in London to submit a scheme for a legislative assembly. The result was that the new Maltese Constitution of December 1887 was largely based on the joint Strickland-Mizzi proposals. In the following year, he was appointed as Assistant Secretary to Malta in 1888 and held the office of Chief Secretary of Malta in 1889, a post which he held till July 1902 when to avert more trouble in Malta which were created by his orders in councils to increase taxation, he was appointed as Governor of the Leeward Islands in the Caribbean.