This article reports on what is at work during individual supervision of medical students in the context of teaching breaking bad news (BBN). Surprisingly, there is a relative lack of research and report on the topic of supervision, even though it is regularly used in medical training. Building on our research and teaching experience on BBN at the undergraduate level, as well as interviews of supervisors, the following key elements have been identified: learning objectives (e.g., raising student awareness of structural elements of the interview, emotion (patients and students) handling), pedagogical approach (being centered on student's needs and supportive to promote already existing competences), essentials (e.g., discussing skills and examples from the clinical practice), and enhancing reflexivity while discussing specific issues (e.g., confusion between the needs of the patient and those of the student). Individual supervision has been identified as crucial and most satisfactory by students to provide guidance and to foster a reflexive stance enabling them to critically apprehend their communication style. Ultimately, the challenge is to teach medical students to not only connect with the patient but also with themselves.