As a former radio show host and conversation-based podcaster, I have had some experience in figuring out how to navigate discussions with strangers. I’ve talked to comedians about their religious experiences and to writers about their favorite bands. I ‘ve heard stories about mental hospital stays and divorces and discussed parenting and diet regimens with celebrities. But when people ask me to distill the hundreds of candid conversations I’ve pursued down to a single take-away, I never hesitate.

It all comes down to this for me: Keep asking questions.

I know it sounds simple. It almost sounds like a trope. But my proudest moments in conversation are the times that I didn’t chicken out and decided to ask one more question.

I was interviewing a friendly comedian from the West Coast a few years ago and we were early in the back-and-forth. I asked him about touring and traveling and upcoming plans and he gave me standard answers. 

“It’s been a long year,” he said at one point. “When I get back home I plan to spend some time working on a project that isn’t comedy related and then I am going to…”

The natural flow of conversation moved on, but I hung on to that tidbit and when there was a lull a few minutes later, I returned to the statement. 

“You said you have a project you are taking on that isn’t stand-up comedy,” I recapped. “What is it you want to do?”

“I am working on a book project,” he told me. 

Here I could have quit. I could have assumed he was writing a book about being a comedian or some aspect of being a guy who drives around the country and tells jokes. But something told me to keep asking questions. 

“What is the book going to be about?”

“My dad,” he answered. 

Again – this would be an easy place to quit. Dads are usually pretty good subjects. There are lots of emotional and psychological issues to examine in any father and son relationship. I figured this would be a fun book by a comedian about his funny dad who inspired him. But something told me to keep asking questions.

“Cool. Your dad? What was he like?”

The comedian took a breath.

“I thought he was dead until I was 17. And then I found out he was a hitman for the mob.”

Yes. This happened. And thus commenced 20 minutes of jaw-dropping conversation. 

And to think I almost didn’t ask him about that new project…

I was reminded of this concept again a few weeks ago when on a business call with a co-worker. She noticed a rock in a small glass case on the desk of the man we were meeting.

“Sorry. I have to ask,” she said bluntly. “What is the story with that rock on your desk?”

I was a little embarrassed for the poor guy. It looked like a trinket he might have gotten at a museum or his kid might have created in science class. I would have made some assumptions and just pushed on to the business purpose of this meeting. But when she asked about the rock, his face lit up and he launched into a story.

“A friend of mine was in Germany,” he started. “She was at an outdoor café and heard some commotion and saw people running towards her table from far down the street. She could tell something big was happening…”

It turns out that “something big” was the destruction of the Berlin Wall. She walked that direction and watched this monumental event happen in real time. And when she left, she grabbed a few pieces of the debris as souvenirs and gave one to this guy. It was in a glass case because it’s since been discovered to contain asbestos. 

And I was not going to ask about the rock.

Some will tell you that to achieve remarkable conversation one needs a plan, a map, a landscape. But often all you need is the curiosity to ask a question. 

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