Edward Pickering was King's Assistant Private Secretary from 1929 to 1938. He is mentioned frequently in the diary and, like other members of King's staff, worked long and irregular hours.
King commented about Pickering: "He is not happy about coming to work part of the time at Laurier House, & I do not want anyone around who is not happy in this environment & what it affords of association & opportunity." (Diary, September 15, 1930) In spite of the tension implied by this comment, King appears to have liked Pickering and had confidence in him, and Pickering continued to work for King for another eight years.
Pickering travelled to the United States with Prime Minister King in 1935, and he was a witness to the swearing-in of Vincent Massey as Canadian High Commissioner to the United Kingdom. (Diary, November 2, 1935) When former Dominion Archivist Sir Arthur Doughty died in 1936, Pickering prepared the first draft of an appreciation of Doughty for King to give to the press. (Diary, December 1, 1936)
When Pickering resigned, King recorded the event very briefly: "Pickering's connection with the department was severed yesterday, ... the end of 9 years' association together." (Diary, August 2, 1938)