The objective of much of contemporary management education is to transform middle managers from strategy implementers to strategic thinkers who can help guide their organisations through the relatively chaotic environment in which they currently reside. This requires the development of a vast range of skills and abilities to face the conflicting demands of the modern work environment. The current study tracks the development of deep learning and meta-competency development of 58 Human Resource (HR) managers pursuing a part-time postgraduate masters programme. The evidence collated from participant learning review logs (350 pages of written personal reviews) is presented. The shape and level of their learning and developmental experiences are depicted along a developmental continuum model reflecting the evolution of the process. The results indicate the levels of learning/change experienced by participants and how this is reflected in their work practices.