Since 2011, the organisational and management process of the Italian Prison Administration has started to change. The Open section and Dynamic supervision measures introduced into the Italian penitentiary system, requires that all prison workers participate in the observation and treatment of the prisoners’ activities, carried out within a multidisciplinary perspective. This may imply a significant increase, in both the workload and possible sources of stress for prison workers and, therefore, hinder the organizational change. To enable the process of change, while monitoring the employees’ wellbeing, monthly multidisciplinary meetings have been planned, involving the ward staff of each prison. This study aims to both understand the impact of the organisational change on the employees of a prison in northern Italy and to explore the sustainability of the ward staff tool. Ten multidisciplinary meetings were analysed over a year, focusing on topics discussed within the group and relational positions assumed by the members. Content analysis has been performed through the T-LAB software, whereas the analysis of the interactive modalities has been carried out through the application of the Interaction Process Analysis grid. Results showed the group’s tendency to focus on the task, neglecting the relational dimension and moments of shared reflection related to the process. The study allows us to reflect on those aspects that may undermine the organisational and employee wellbeing and to assess the sustainability of a new organizational tool.