Patients undergo multiple transitions during the course of their cancer care. Oncologists are uniquely positioned to help patients through these transitions. When patients' situations change, they must cope with loss and associated negative emotions. They then are able to redefine hope. During transitions, patients want their oncologists to provide biomedical information, show that they care about and understand them as individuals, and balance hope and realism. Eliciting concerns and expressing empathy shows patients that their oncologist cares about and understands them and also helps patients to cope with the loss and negative emotions that transitions create. Oncologists can maintain hope by being sensitive to what patients are ready to hear when, and by helping them discover and identify realistic hopes. This is accomplished with the Ask-Tell-Ask and Hope for the Best, Prepare for the Worst techniques, and most importantly by being curious about patients' hopes and fears.