Sometimes in life you’re just walking along and happen to come across a cairn. Other times, it takes a little work to uncover a cairn that is in front of you.

One of my favorite ways of uncovering cairns from other people is by asking them sharp questions. If you ask a low-quality question like, “How’s it going?” you’re going to get a low-quality answer. I’m always on the hunt for a good question.

A question that has always yielded me good fruit is “What’s the biggest question you are wrestling with right now?” Sometimes I have to expand the definition of this question if I think the person thinks I’m asking exclusively about work or any other specific domain. The point is to get people to open up about what is top of mind for them.

Last night I asked one of my colleagues this question. Without further prompting, she told me that she’s been thinking a lot about the capacity people have to empathize. Her perspective, if I understood it correctly, is that people tend to overestimate their capacity for empathy and think they are able to do so deeper than they actually can. What they are doing instead is intellectualizing a response.

They might say, “Gun advocates say this while opponents say that.”

That’s not empathizing. That’s articulating other’s thoughts. Are you able to feel other people’s feelings? Really feel them?

This response challenged me because I’m sure that I have a tendency to overestimate my level of empathy. As a kale-eating, latte-sipping, Obama-voting, left-wing liberal loon, part of my worldview involves respecting many perspectives. More likely than not, I’m likely intellectualizing people’s emotions and not feeling them.