Two years after graduating, he entered the
Colonial Office as a second class clerk. In 1887, he was Bacon Scholar of
Gray's Inn, and in the following year, he was the
Inns of Court student. He proceeded with Sir
John Frederick Dickson in 1891 to
Gibraltar, in order to inquire into the matters connected with the Registry of the Supreme Court. He was next appointed as the private secretary to
Sir Robert Meade, Permanent Under-Secretary of the State for the Colonies, in 1892 he served as the British Agent for
Bering Sea Arbitration. From 1883 to 1897 he edited the
Colonial Office List, later he appointed as the principal clerk. He became the secretary to the Conference between
Joseph Chamberlain and the Colonial Premiers in that year he had considerable opportunities of gaining an intimate knowledge of the feelings of the self-governing colonies. For the second time, he was despatched to
Gibraltar in 1899, on this occasion to inquire into the rates of pay of the Civil Service there. He returned to
London in the same year and remained until 1901, where Chamberlain chose him as
Colonial Office representative to accompany T.R.H. the Prince and Princess of Wales, then the Duke and Duchess of York, on their famous tour around
British Empire on board
HMS Ophir. It was during that trip that Sir John saw for the first time the colony over which he would preside. In 1902, again he acted as the secretary to the Colonial Conference, and in 1903, he received thanks of the Canadian Government and the Confederation medal for services rendered in connection with the
Alaska Boundary question and other matters. In 1904, he was appointed as
Governor of Straits Settlements where he served till 1911. In 1916, he was appointed as
Governor of British Ceylon. In Ceylon, he played a major role in settling many problems and riots that started in 1915 and suppressed harshly by the British. He suddenly fell ill at
Queens Cottage,
Nuwara Eliya in 1918 and died on 24 March 1918. It is recorded that his
Maha Mudaliyar,
Sir Solomon Dias Bandaranaike, who happened to be at his bedside, wrote: ==Honours==