Systematic evaluations are necessary to report on the true impact of continuing education on educational practices. The objective of this research was to assess the learning transfer of managerial functions among participants of a directive leadership training plan to the contexts in which they work in Chile. A mixed-methods methodology was employed to analyze the results of a survey administered to a sample of 47 participants, which showed the extent to which learning is being applied. A subsequent study of 12 cases provided a deeper understanding of the results of this first stage. Self-confidence and participant motivation – a product of the content validity of the course – were identified as key factors in the transfer process, while a lack of institutional conditions and difficulty in taking up managerial positions were the main obstacles.