We have difficult conversations in critical care. We deal with sick and complex patients who may be at the end of life. The families we talk to may be in a state of shock and acute grief, unable to think clearly and make important decisions. Patient safety incidents and other challenging issues such as organ and tissue donation may further complicate the patient journey. We will follow the story of Leah and the difficult conversations that were needed in caring for her and her family. We will examine some of the key elements that can contribute to successful communication in difficult circumstances. As clinicians, our training in this type of communication may be limited to observing our mentors, and we may feel inadequately prepared. We will investigate how simulation training can be used to improve the quality of communication, increase our skill and comfort level so that we can guide patients and families through complex and challenging situations. We will also investigate how lessons learnt from simulation debriefing can be transferred to the conduct of difficult conversations in real life.