He has held staff appointments at 82 Wing (F-111) HQ, as the Assistant Defence Adviser at the Australian High Commission in Singapore, and in Force Development in the field of capability analysis.

His last official function was to be the Reviewing Officer of the Officer Training School Graduation Parade, held at RAAF Base East Sale, however due to unwanted weather conditions the Parade was cancelled.

He was given one final stairway guard by the young men and women of the Australian Air Force Cadets, who were on a camp at RAAF Base East Sale at the time.

Shepherd is known throughout the RAAF for calling out "Cooee", a distinctive Australian vocalisation used mainly in the outback, with which he ended his first address as Chief of Air Force.

His interests include gardening, rugby league football, travelling and understanding other cultures.