Brett Williams,1 Christine King,1 Tanya Edlington,21Department of Community Emergency Health and Paramedic Practice, Monash University, Franskton, VIC, 2The Conversation Clinic Pty Ltd, Melbourne, VIC, Australia Background: Clinical supervisors are responsible for managing many facets of clinical learning and face a range of challenges when the need for "difficult" conversations arises, including the need to manage conflict and relationships. Methods: Spotlight on Conversations Workshop was developed to improve the capacity of clinical supervisors to engage in difficult conversations. They were designed to challenge the mindset of clinical supervisors about difficult conversations with students, the consequences of avoiding difficult conversations, and to offer activities for practicing difficult conversations. Preworkshop, postworkshop, and 4-month follow-up evaluations assessed improvements in knowledge, intent to improve, and confidence along with workshop satisfaction. Results: Nine workshops were delivered in a range of locations across Victoria, Australia, involving a total of 117 clinical supervisors. Preworkshop evaluations illustrated that more than half of the participants had avoided up to two difficult conversations in the last month in their workplace. Postworkshop evaluation at 4 months showed very high levels of satisfaction with the workshop's relevancy, content, and training, as well as participants' intention to apply knowledge and skills. Also shown were significant changes in participants' confidence to have difficult conversations not only with students but also with other peers and colleagues. In follow-up in-depth interviews with 20 of the 117 participants, 75% said they had made definite changes in their practice because of what they learned in the workshop and another 10% said they would make changes to their practice, but had not had the opportunity yet to do so. Conclusion: We conclude that the Spotlight on Conversations Workshop can improve the clinical supervisor–student relationship as well as build general difficult conversation capacity for a range of stakeholders in clinical settings. Keywords: clinical, education, supervision, communication