How do you know whether you’re really listening to someone?
When I ask my friend Michelle how she is, she often begins explaining a problem one of her friends is having. (Only if they wouldn’t mind of course.) She can explain what the situation is, what her friend cares about, what the other relevant people care about, what’s making the decision hard for her friend, and so on.
I really admire this about her because it shows (1) how much she cares about her friends and (2) that she listens deeply.
People say that you’ve only ever learned a concept once you can teach it to someone else. Similarly, I think you’ve only really been listening to someone, if you can re-explain it to another person.