Cultivating empathy requires imagination. Whenever you find another person’s point of view deeply confusing or nonsensical you have an opportunity to try to use your imagination to explore their situation more deeply. You don’t literally walk in their shoes, but try to imagine what those shoes would feel like on your feet.
This skill is important; but we often resist it because of fear. Fear that the other person will change our cherished perspective–or fear that listening to their point of view will reward and reinforce a perspective we believe to be dangerous. We leap too soon to attempt to influence. Or we defend too quickly because we are afraid of being influenced.
Counterintuitively, if you listen deeply, with discernment, you’ll probably have a greater chance of having a lasting influence in the end (and/or having your own position clarified).
Conversationally, this looks like being able to restate your friend’s position in a winsome way. If you use your imagination and actually improve their arguments, they will feel respected and heard. Have them nodding their head with you before you begin your counterargument.
Make sure you have permission (explicit or implicit) before offering the counterargument. Slow down. If the venue of your conversation doesn’t allow for patient, thoughtful, respectful, private (if necessary) discourse, change venues or don’t engage.