After earning a bachelor of science in law from the University of Minnesota in 1954 and then attending law school for two years, John Westerman was called up as a member of the ROTC to serve in the Air Force. When he returned from duty, he took additional coursework and earned a bachelor of business administration with a major in finance in 1958. He then attended the University of Minnesota for his Masters in Hospital Administration, which he earned in 1960. He then completed his administrative residency at University Hospital under Ray Amberg from 1959 to 1961. From 1961 to 1964, he served as assistant administrator, in a position akin to chief operating officer, at Strong Memorial Hospital in Rochester, New York, part of Rochester University. Westerman returned to the University of Minnesota to work with Dr. Richard Magraw, under Dean Robert Howard, on expanding the Comprehensive Clinic. As the project grew, he transferred to President O. Meredith Wilson's office as an executive secretary, serving as the coordinator of the Committee for Long Range Planning in the Health Sciences. After serving in this position from 1964 to 1966, he took over as general director of University Hospitals and Clinics in November of 1966. He served in this position until 1982.