Charles Duhigg’s book “Supercommunicators” has many great insights in it, and a big thread through the book is about how to more deeply engage with those that you’re talking with.

A great way to do that is to simply ask more questions about the person you’re with. From the book:

Ask open-ended questions and listen closely. Get people talking about how they see the world and what they value most. Even if you don’t learn, right away, what others are seeking—they might not know themselves—you’ll at least inspire them to listen back. “If you want the other side to appreciate your interests,” Fisher wrote, “begin by demonstrating that you appreciate theirs.”

As I shared a few weeks ago, this can come from the idea of using your gift of curiosity to learn more about others.

That said, it’s easy for people to feel like they did this when they actually do the opposite. In Adam Grant’s “Give and Take“, he shares how people who talk a lot can feel like they understand others:

Logically, learning about the people around you should depend on listening. The less you talk, the more you should discover about the group. But Pennebaker found the opposite: the more you talk, the more you think you’ve learned about the group. By talking like a taker and dominating the conversation, you believe you’ve actually come to know the people around you, even though they barely spoke. In Opening Up, James Pennebaker muses, “Most of us find that communicating our thoughts is a supremely enjoyable learning experience.”

Avoiding that trap is the first key, and then simply “appreciating their interests” is likely to lead to a much better conversation and connection.

I talk about empathy quite a lot (here are 160+ other posts on it), as I feel it’s one of the most important skills we can develop. Understanding the feelings and experiences of others is one of the best ways to connect and learn.

One of my favorite books from the past few years is Mónica Guzmán’s “I Never Thought of it That Way“, which explores ways to better understand those around us, particularly those that we disagree with. Her main premise of the book is:

“That’s because, to be totally frank with you (and if it isn’t already obvious), one of my deepest personal convictions in life is that understanding the people who confound us is always, always worth it.”

When recently digging back into Chris Voss’ “Never Split the Difference“, he had a similar take. His goal comes from the angle of negotiation, and he puts a nice twist on it, saying:

“The beauty of empathy is that it doesn’t demand that you agree with the other person’s ideas”

Guzmán thinks similarly in her book. She encourages you to work hard to understand the other person, but that doesn’t mean you need to agree with them. You should work to understand and see things from the other person’s point of view and it’ll really open up your eyes, but that doesn’t mean you need to agree with them at all.

I was recently listening to an episode of the “You Are Not So Smart” podcast where they were chatting with Mónica Guzmán (author of the excellent book “I Never Thought of it That Way“), and Mónica got into some interesting thoughts regarding curiosity.

She shared a story of when someone considered her curiosity to be selfish. As she explains, they didn’t mean it in derogatory way, simply stating that “you’re learning because you want to make yourself better“.

While they didn’t mean it in a bad way, she still felt it wasn’t accurate. In her case, she sees curiosity as a gift and a way to make deeper connections with others. From the show:

“And now I know why it bothers me, actually. Now I have realized why it bothers me, because curiosity is a gift. The gift of your interest in somebody else. It’s unexpected. We’re all running around. We’re very busy. You know, I’ll even meet friends and … I’m so touched when they actually care enough to ask like more than two or three questions about my day.”

I’ve never really thought of curiosity that way, and I think that’s an angle of it that I sometimes lack. It’s one thing to be curious about science or politics or whatever, but another to be intentionally curious about those around you. As she says, people tend to be “so touched when they actually care enough to ask like more than two or three questions about my day”.

I suppose curiosity can be selfish, but if you focus it outward it can be an amazing superpower.

Compassion often requires work on the side of the person giving it, but sometimes the best work is to do nothing at all. Similar to the idea of avoiding the trap of “we have to do something“, compassion can sometimes be best served by becoming an empty vessel.

The book “Orbiting the Giant Hairball” shared a deep insight into this that really struck me. From the book, they said:

Compassionate emptiness. The two words seized me and would not let go. Compassionate emptiness. To me that meant a state of nonjudgmental receiving. I thought:

“I will try to be in that state when people come to me to recount their burdens.”

From that day on, whenever somebody would come by to pour out their company woes, I would listen. In silence.

I would imagine myself to be an empty vessel only to receive. As fully as possible. Without judgment.

This is something I tend to not do well with, as I like to see myself as a problem solver. How can you solve a problem if you’re listening in silence? Many times, that silence might indeed be the very best way to help solve the problem.