He received his formal education at Cheadle Hulme School, and read Modern History at Sidney Sussex College, Cambridge, where he developed a life-long passion for rowing, before joining the Royal Air Force, initially as a conscript under the terms of the United Kingdom's National Service Act 1948,[1] being granted a temporary commission as a pilot officer in the Education Branch on 4 November 1948.
Education officer at RAF Ballykelly in Ulster, in West Germany, at the RAF Technical College, at RAF Changi, at the Air Ministry in London, at the Headquarters of Bomber Command (where whilst carrying out his duties he developed a scholastic interest in the controversial conduct of Marshal of the Royal Air Force Sir Arthur Harris's command of the arm in World War II), and at the R.A.F.
In 1976 Probert was appointment to the office of the Royal Air Force's Director of Education, which he held until his retirement from the R.A.F.
Bomber Command upon German cities during World War II, with their consequentially high civilian casualty rates.
Posthumously the R.A.F Historical Society created a bursary in Probert's memory, awarded to facilitate academic studies in the field of R.A.F.