The Association ‘Maestri di Strada’ (MdS) undertakes socio-educational interventions to promote the well-being of young people in the ‘high-risk’ suburbs of Naples. The socio-educational work is not a mere ‘technical-rational’ activity and it relies on the use of ‘self’, which is not an unlimited resource. MdS places great emphasis upon reflexivity after the action and adopts the ‘Multi-Vision Group’ (MVG), which is a modified Balint group, as a support mechanism for its staff. Before trainees begin working, they attend the MVGs, observe them, and provide narrative accounts of the process. In this study, 61 reports prepared by the trainees during an academic year underwent a textual analysis. The aim was to evaluate the reflexive function of the group and the results indicate that, within the MVG, the practitioners express emotions, doubts, and difficulties linked to the job and its high-risk contexts. They show both self-awareness and awareness of the importance of the team, thinking as a community in a cooperative way. These are features related to reflexivity, which is recognised as being crucial for practice; the process of observation and recording also has a high educational importance for the trainees and social work students.