This paper discusses the findings of a case study concerning a rarely investigated learning process in a police supervisor course (PSC) in Sweden. The paper argues that the educational design of reflective activities stimulates the course participants’ self-awareness and professional development in their new tasks as supervisors. By using written course evaluations and longitudinal focus group interviews, the study facilitates the identification and articulation of the supervisors’ learning processes during the PSC course. Results of the study emphasise the importance of well-educated supervisors to empowering the learning process of the police probationers creating sustainable professionals in a complex environment. The findings are thematised in three sections: Elucidating the Context, Changing Perspectives and Considering Consciously, which can be viewed as a general model for explaining similar learning processes in other occupations.