This paper presents the results of the monitoring of the activities implemented under measure 5 ("Extracurricular Internships") of the Youth Guarantee Programme, funded by Regione Campania and reserved specifically for undergraduates and graduates with disabilities under the age of 35. After developing a questionnaire to identify the internship opportunities that best matched both the expectations and the characteristics of each graduate/undergraduate, the professionals of the Sinapsi University Center (University of Naples Federico II) monitoring the Youth Guarantee project have studied, with the help of a conversational and reflexive device, how the selected young people gave meaning to both the internship experience and the intertwining of professional and biographical transitions. The conversational reflexive device was implemented to detect behavioural and relational aspects, the role of interpersonal relationships in the training context, the knowledge and skills implemented. Inclusion in working life is in fact a key factor for people with disabilities: over the course of their lives, individuals may often face 'pivotal' transitions that challenge personal balances. These transitions do not represent a simple passage from one condition to another but involve the performance of certain functions and the fulfilment of a series of developmental tasks in the emotional, cognitive and fulfilment areas.