Discussing serious news can be difficult and a skilled clinician can improve their patient’s care and feeling of being cared for. Communication is central to the effective medical practice, and the data shows that clinicians can learn to improve their skills. This book will focus on the broad domains of communication skills and cognitive roadmaps. Through personal reflection as well as honing communication skills and using roadmaps, clinicians can cultivate internal psychological capacities that lead to more skillful and authentic conversations. Our basic principles at VitalTalk are to start with the patient’s agenda, track emotional and cognitive data, stay at the patient’s pace, express empathy explicitly, discuss what can be done before the things that can’t, cover big picture goals before specific interventions, pay true attention, and ask for the patient’s take away. In addition to reading about serious illness communication, these skills are best learned through observation, practice, and feedback.