I recently stumbled on a technique for making empathy easier: Get the other person to talk about something that has nothing to do with me.
By default, they'll talk about stuff that involves me, or interests me, for the obvious reason. If I'm not deliberately attempting empathy, talking about something that doesn't involve me in any way will in fact bore me.
But when empathy is a primary goal, I'm a distraction to myself. If I ask them about their experience of the interview I helped them prepare for, or about principles of mind design, or about the time when we went to the Exploratorium with mutual friends, then I can't help spending a lot of precious cognitive resources on things besides empathy.
But if I get them to talk about a time when they went out to dinner with their family, there is nothing whatsoever interesting about what they have to say except what the experience felt like and meant for them.
