CONTEXT: Difficult family conversations are a challenge for even the most seasoned clinicians. Teaching the skills of successful communication between providers, family members, and patients is a vital component of medical education. However, traditional teaching methods using didactics and expert role modeling are often inadequate. OBJECTIVES: The train-the-educator workshop aimed to teach educators how to create and conduct workshops on facilitating difficult family conversations that target their own learners’ needs. METHODS: This three-hour workshop included instruction on scenario writing and on the use of standardized actors as patients and family members. Workshop leaders presented examples of commonly encountered clinical scenarios where difficult information is discussed. The session used experiential teaching techniques. Outcomes were measured by qualitative discussions and a questionnaire to demonstrate communication skills learned from the sessions. RESULTS: The workshop was well received by participants who consisted of educators attending the annual meeting of the Pediatric Academic Societies in May 2016. Evaluations revealed that 92% of participants agreed or strongly agreed that the workshop achieved the learning objectives. All participants believed that the workshop increased their knowledge, competency, and skills in teaching and facilitation as an educator, with 86% of participants planning to apply the skills toward curriculum development. The major themes that participants learned centered on facilitation skills as an educator and techniques on how to communicate during challenging family meetings (86% of comments). CONCLUSION: This train-the-educator workshop addresses a critical need in both palliative care and general medicine by enhancing the educators’ skills in designing and implementing a curriculum on communication skills of health care providers using experiential techniques with formative feedback. The authors hope that by outlining the implementation of this three-hour interactive format, future educators will adapt and use this workshop as it works best for their learners.