Cleland received his bachelor's degree from the University of Pittsburgh in 1954, his MBA from the University of Pittsburgh School of Business in 1958, and his Ph.D. from Ohio State University. He started working at Wright-Patterson Air Force Base, Dayton, Ohio as a project manager in the development of weapon systems. He was also very active in Project Management at the Air Force Institute of Technology (AFIT). He eventually retired as Lieutenant Colonel In 1967 he started his academic career, teaching Project Management for 35 years at the Swanson School of Engineering, University of Pittsburgh.