The not-so-obvious ways to have a more in-depth conversation with anyone

I rarely peruse through the New York Times for management and leadership insights. Not that I don’t expect any from their incredible panel of award-winning journalists, but the idea of finding a useful piece (for me) amidst all that content feels like an arduous task.

Every once in a while though, I bump into something that’s not just sharable but life-changing. And boy, the paper does a shoddy job to promote these pieces.

Anyway, I think I was lucky enough to find this fantastic piece by David Brooks that elaborates on the subtle ways to have a deeper conversation. While David calls these “non-obvious” reasons, the ideas resonated with me for obvious reasons — as a leadership coach, listening, building trust and rapport are the foundation of every coaching relationship.

What I loved about the piece were the simplicity and overall functionality. You don’t have to be a leadership coach, a manager or a consultant to use these ideas. They are more-or-less principles that anyone willing to invest in a relationship can embrace.

So, here are David Brooks’ non-obvious ways to have a deeper conversation.

Approach with awe. The people who have great conversations walk into the room expecting to be delighted by you and make you feel the beam of their affection and respect. Lady Randolph Churchill once said that she thought him the smartest person in England when sitting next to the statesman William Gladstone. Still, when she sat next to Benjamin Disraeli, she felt she was the most intelligent person in England.

Ask elevating questions. Some questions, startling as they seem at first, compel us to see ourselves from a higher vantage: What crossroads are you at? What commitments have you made that you no longer believe in? Who do you feel most grateful to have in your life? What problem did you use to have but now have licked? In what ways are you sliding backwards? What would you do if you weren’t afraid?

Ask open-ended questions. Many of us have a horrible tendency to ask questions that imply judgment: Where did you go to school? Or we ask yes/no questions: Did you have a good day? Which shut off exciting answers. Better questions start with “What was it like. …” or “Tell me about a time. …” or “How did you manage to cope while your wedding was postponed for a year?”

Make them authors, not witnesses. The critical part of people’s lives is not what happened to them, but how they experienced what happened to them. So many of the best conversations are not just a recitation of events. They involve going over and over an event, seeing it from broader perspectives coating it with new layers of emotion, transforming it, so that, say, an event that was very hard to live through is now very satisfying to remember.

Treat attention as all or nothing. In a conversation it’s best to act as if attention had an on/off switch with no dimmer—total focus. I have a friend who listens to conversations the way congregants listen to sermons in charismatic churches — with amens and approbations. The effect is magnetic.

Don’t fear the pause. Most of us stop listening to comment about halfway through so we can be ready with a response. Businesspeople are more likely to hear the whole comment in Japan and then pause, sometimes eight seconds, before responding. That’s twice as long silence as American businesspeople conventionally tolerate. (SN: that’s a generalisation, I believe cutting off silence is a global phenomenon now.)

Keep the gem statement front and centre. Amid many difficult conversations, there is what the mediator Adar Cohen calls the gem statement. This is the comment that keeps the relationship together: “Even when we can’t agree on Dad’s medical care, I’ve never doubted your good intentions. I know you want the best for him.” If you can both seize that gem statement, it may point to a solution.

Find the disagreement under the disagreement. In the Talmudic tradition when two people disagree about something, it’s because there is some deeper philosophical or moral disagreement undergirding it. Conversation then becomes a shared process of digging down to the underlying dispute and then the underlying disagreement below. There is no end. Conflict creates a cooperative effort. As neuroscientist Lisa Feldman Barrett writes, “Being curious about your friend’s experience is more important than being right.”

The midwife model. Sometimes people talk to solve a person’s problem. The Rev. Margaret Guenther wrote that a good conversationalist in these cases is like a midwife, helping the other person give birth to her child. That means spending a lot of time patiently listening to the other person teach herself through her narration, bringing forth her unthought thoughts, sitting with an issue as it slowly changes under the pressure of joint attention. “To influence actions,” neuroscientist Tali Sharot writes, “you need to give people a sense of control.”

Don’t just read these ideas—Mull over them. If possible, take a print out and go through it at least once every day for the next couple of weeks. The ideas above are among the best compilations on listening I’ve read or studied in my 20-year career.

And you should check out the original piece by David for the whole picture on the NYT website. If possible, share this or the source with others who might benefit. It might be the best year-end gift you can give to your loved ones.

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