I just read a remarkable quote from Leslie Jamison, in her book of essays called The Empathy Exams (Garywolf Press, 2014). Jamison has taken the role of a standardized patient in medical school training sessions. One of the SP's tasks is to grade the students on item 31, "Voiced empathy for my situation/problem." She came to realize some important things about empathy. An excerpt:
Empathy isn't just remembering to say that must be really hard--it's figuring our how to bring difficulty into the light so it can be seen at all. Empathy isn't just listening, it's asking the questions whose answers need to be listened to. Empathy requires inquiry as much as imagination. Empathy requires knowing you know nothing. Empathy means acknowledging a horizon of context that extends perpetually beyond what you can see.
Empathy comes from the Greek empatheia--em (into) and pathos (feeling)--a penetration, a kind of travel. It suggests you enter another person's pain as you'd enter another country, through immigration and customs, border crossing by way of query.