Get curious about what they just told you.
Here's an example of the way I do it. I might ask, “Are you from around here?” If they're from somewhere else, I can ask, “How did you find your way here?” I haven't planned the whole conversation. I'm following the thing they gave me.
I've had long conversations with strangers where most of the questions were about them. That's okay with me. I wanted to learn how to be in a conversation, and being interested in the other person gave me somewhere to put my attention.
I was doing this before I read a Larry King book, and I later recognized that same idea there: get curious about whoever you're speaking to. The curiosity matters. I don't just want a list of questions to run through while I'm worrying about my next word.
In a work conversation, I also remember the small things someone tells me. A trip, a family detail, something they're looking forward to. When it comes up again, there's a natural reason to ask about it.
You don't need my exact wording. The useful part is hearing an answer and allowing that answer to shape what comes next. That's what I had to practice.
Were those follow-up questions deliberate?
Yes. I said the words I used were very intentional. I had tried a bunch of things. “Are you from around here?” and asking how someone found their way here were general kinds of follow-ups I used.
In that explanation, I also said I wasn't pre-scripting. You didn't have to use my exact phrase. I wanted to get the person talking about themselves and get curious about what they told me. Those were the kinds of questions I had learned to use.
What happened after my comment about the cookies?
At Publix, a man was looking at cookies. I said, “If that's on sale, then I'm in trouble.” I told him I used to eat a lot of junk food and that sometimes you see it and it calls to you. Then I asked, “How about you?”
He told me he couldn't touch it because he was diabetic. I said, “But you still look at it. Smart.” That was the exchange. We had something in front of us, I asked him a question, and his answer gave me something to respond to.
You can watch that grocery recording. Afterward, I pointed out that he had been looking at the cookies and that was what we had commented on. It was a natural way to start, and it stayed short.
A simple example in a store
I've explained it with an imagined trip to Target. An employee tells you the item is in the back corner. You could thank them and go. In my example, I also gave a possible follow-up: “I bet you walk like two miles here.”
I imagined the person laughing and saying it felt as though they walked forever. That gives you something else to respond to. You can go and get the product, or keep talking. That was an example I used to explain the choice.
How did I end one of my group calls?
I said, “Hey guys. So I think I'm going to peace out,” and told them it had been fun and that we'd done a good, solid chunk of time. Then I thanked them.
I also told them I knew it was hard and that I'd had a lot of bad days. That was how I began wrapping up that conversation: I said I was leaving, thanked the people I had been talking with, and left them with some encouragement.