Checkland was born 9 October 1916 in Ottawa, Ontario, and died in Cambridge on 22 March 1986. He was the second of three sons of Sydney Tom Checkland, itinerant preacher and journalist, and Fanny Selina Savory Mason. The household was strongly supportive but very strictly Baptist, weekly attendance at the First Baptist Church of Ottawa being an important feature of family life. Checkland's education began in two elementary schools, Slater Street Public School (1921–2), and Elgin Street Public School (1922–9). This was followed by High School at Lisgar Collegiate Institute, (1929–34). From school he took a position as a trainee clerk in the Bank of Nova Scotia, becoming an associate of the Canadian Bankers Association in 1937. By then he was employed as an accountant with the Ottawa Sanitary Laundry Company. His savings from this post, £250, allowed him to go to England in 1938 to study for the BComm degree at Birmingham University under Philip Sargent florence. There he became president of the Guild of Undergraduates (1940–1), president of the National Union of Students (1941) and President of the International Union of Students (1942). He graduated with first-class honours in 1941 and married Edith Olive Anthony, a geography student at Birmingham, in 1942. They had two sons and three daughters.
From The Biographical Dictionary of British Economists in Oxford Reference.