The value of learning from program management has not received full recognition in the workplace. The purpose of our study was to investigate whole life program management success and its link to leadership competency units to define meaning of true program success and motivation for learning. An inductive interpretive approach using open-dialogue interview technique was applied. Seventeen Defence leaders responsible for the acquisition and support of UK major defence programs in excess £50 Billion published in the UK National Audit Office (NAO) Major Project Report 2015 participated in this study. A case study of the UK Defence programs provides insights into what success is in a Defence context. The study suggests that whole life program management success, measured against capability outcome as against performance, cost and time (PCT), can be achieved through competent leadership. This can be a motivation for learning from the program success. The findings showed that success extended beyond baseline deliveries, and it is insufficient to measure success with PCT parameters. Our study defines what success is and propose its achievement has a direct correlation to program leadership competency and its non-achievement be understood by organisations for survival in a complex highly structured environment.