Clinicians can, with training, improve their communication skills. In this chapter, we describe an interactive, evidence-based method for teaching clinicians to communicate with seriously ill patients. The programme, Vitaltalk, emphasizes small-group teaching with simulated patients and immediate feedback to allow learners to practice how to give serious news, talk about goals of care, and about what is most important to dying patients. This chapter describes common evidence-based principles used in developing an advanced communication skills programme based on Oncotalk experiences, identifies unique aspects of the learning context within an intensive retreat structure, and illustrates the lessons learned that can be tested in other settings. The programme is effective in improving learners’ communication skills in clinical studies. The growth of this programme in multiple specialties is discussed, as are our plans for disseminating the programme in the future.