This research deals with role playing (RP) aimed at assisting learners to optimize their managerial style. While RP is often used in training sessions, contributions on its evaluations have decreased since the beginning of the 1980s. Although RP as a training method had been criticized for several reasons, RP has the advantage to conciliate theoretical knowledge and practical construction of meaning, based on the learners’ experiences, games and the group as a place of creation and growth. In this research based on the analysis of a reflexive exercise led by a trainer during 17 years of experiencing RP – it is argued that the socio-constructivist approach, by promoting awareness in the training process, allows trainers to develop relational skills and to gain behavioural flexibility in their sessions. The main results of our study indicate the need for learners to co-determine the parameters of the RP process (rules and security) in close collaboration with the trainer, in order to make this method effective.