This chapter focuses on the communication challenges that may be present when dealing with patients and their families in the intensive care setting. This has been identified as a key role of the intensivist, and these conversations may be stressful to lead in the context of the acuity of the setting, uncertain trajectory of patient illness, morbidity and mortality, and other complexities such as volatile or challenging family dynamics or where there is a lack or loss of trust. Sharing devastating news can be difficult, and the spectrum of acceptance is wide. Navigating responses and explaining multi-disciplinary management decisions is part of the challenge of being an intensive care doctor, and these issues are explored using 12 quotations relevant to some of the issues.