Pickford was born in Manchester, son of the Manchester merchant Thomas Edward Pickford and his wife, Georgina, daughter of Jeremiah Todd-Naylor, and grandson of Thomas Pickford II of the Pickfords carriers. He was educated at Liverpool College and went to Exeter College, Oxford in 1867. He entered the Inner Temple in 1871, reading under Thomas Henry Baylis, and was called to the bar in 1874. Going the Northern Circuit, he had chambers in Liverpool.^[1]

As a junior Pickford appeared in the trial of Florence Maybrick. He took silk in 1893. He was made Recorder of Oldham in 1901, and then of Liverpool in 1904. He also represented the British government in 1905, in the inquiry after the Dogger Bank incident when Russia sunk some Hull trawlers.^[1]

Pickford was appointed a judge of the High Court in 1907 and a Lord Justice of Appeal and sworn of the Privy Council in 1914.^[2] In 1916 he was chairman of the Dardanelles Commission.^[3] He was made President of the Probate, Divorce and Admiralty Division and raised to the peerage as Baron Sterndale, of King Sterndale in the County of Derby, in 1918.^[4] The following year he became Master of the Rolls, a post he held until his death.

Lord Sterndale married Alice Mary Brooke, of Sibton Park Suffolk, on 18 August 1880. They had two daughters, Dorothy Frances Pickford (b. 1881) and Mary (Molly) Ada Pickford (b. 1884). His wife Alice died after childbirth on 5 September 1884. Sterndale's daughter the Hon. Mary Ada Pickford sat as Conservative Member of Parliament for Hammersmith North from 1931 to 1934. Lord Sterndale died in August 1923, aged 74, when the barony became extinct. He is buried at King Sterndale Church near Buxton, Derbyshire.