Teaching advanced communication skills requires educators who are not only excellent communicators themselves but have the ability to deconstruct the components of the interaction and develop a cognitive approach that can be used across a variety of learners, diverse content, and under different time constraints while helping the learner develop the skill of self-reflection in a 'safe' and effective learning environment. The use of role-play in small groups is an important method to help learners cultivate the skills required to engage in nuanced, often difficult conversations with seriously ill patients. To be effective, educators utilizing role-play must help learners set realistic goals and know when and how to provide feedback to the learners in a way that allows a deepening of skills and a promotion of self-awareness. The challenge is to do this in a manner that does not cause too much anxiety for the learner. In this article we outline an approach to teaching communication skills to advanced learners through the use of different types of role-play, feedback, and debriefing.