 He was the son of Rev Oscar Dan Watkins (1848–1926) - Archdeacon of Lucknow  , and Elizabeth Martha née Ferris (1846–1928) and was born in Allahabad.Educated at Marlborough and a 'bible clerk', that is undergraduate scholar at All Souls College, Oxford, by virtue of being a founder's kin , in 1899 Watkins cut short his study to enlist in the ranks of the Oxfordshire and Buckinghamshire Light Infantry in the Second Boer War; after the war subsequently joining the South African Police.In 1907 he moved to Kenya and as a junior District Commissioner in Kenya he was a magistrate in the Kenya Slave courts, freeing slaves from Arab slavers on the East African coast and developing a lasting interest in Swahili culture.