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The central challenge of management development is to control and manage the learning process of managers, focused on individual development and career success and/or reaching organisational goals. This article examines the two seemingly opposed assumptions that either management development comes with experience, job‐rotation and learning on the job or as a result of coaching, mentoring and tacit development programmes that tend to attract younger recruits. It concludes that each assumption includes a part of the truth. Thus, the job, the work environment, and the individual employee characteristics play a role. The article seeks to improve the understanding of the influence of these factors. It focuses on the interaction between developmental characteristics of the job, the learning behaviour of individuals, and the consequences of this interaction for career success of managers.