INTRODUCTION: Courageous conversations, commonly identified as conversations which are associated with some form of emotion, are features of many social workers' daily routine. In supervision, such conversations are typically required to address issues of supervisee professional competence, ethical issues or the supervision relationship and/or process. These conversations, which are challenging, are at times avoided and, at other times, may be poorly handled. APPROACH: Following identification of the obstacles which may impede addressing challenging issues in professional practice, this article focuses the supervisor's role in courageous conversations. The importance of building a supervision environment which can support robust conversations is highlighted. Here the contracting process, where the expectations of supervision are negotiated and the power inherent in the supervision relationship can be identified, is considered foundational. The skills and attributes needed by the supervisor to manage these difficult encounters are explored and three kinds of interventions are identified as helpful: relational, reflective, and confrontational. A framework for a courageous conversation is provided which highlights the need for clarity about the motivation, purpose and desired goals. Finally, a structure for the proposed conversations is presented.