The list of things I love is long. Of course, it includes a whole bunch of people. It also includes many of the typical things people adore, like sea salt caramel, a Thursday night happy hour, pink sunrises, and sleeping babies, along with knowing the right answer and being asked for advice. Oh, and I love learning new things. That said, I'm less and less interested in classrooms (in person or online) as I near midlife, and more interested in one-on-one interactions. I want to glean as much as I can from conversations with someone who knows more or has a different perspective than I do.

Great conversations, though, can feel like finding $5 on the sidewalk--rewarding but random. In the past, I felt like great conversations just happened. I didn't know why or how, but I loved it when I came across one. Just like there's no strategy for increasing the number of times you find money on the ground, I didn't think you could increase your chances of having a great conversation. But I was wrong.

Some people are just great talkers, no matter the topic or who they're talking to. But it's more than just the other person's social skills that make for a great conversation. It's all about asking good questions.

Here are a couple of keys to coming up with great, provocative questions: First, stoke your curiosity by assuming everyone you talk to knows something you don't. Second, start easy, and be open to following where the conversation naturally leads. Trying to force something profound out of somebody turns awkward fast.

Of course, there are also a handful of good go-to questions that will always be helpful in getting the most out of any conversation. The simplest place to start is simply asking "why?" Why do you think that happened? Why do you think so-and-so said that? Why do you think they made that decision? There are endless forms this question can take--see if you can come up with the best for the given context.

Another interesting angle is asking someone about a turning point. When did they start feeling or acting the way they do now on a specific topic? For example, if you're talking with somebody about running, you might ask when they started adding track workouts. What prompted the change?

You can also ask people to draw parallels. There are often interesting insights to be found when comparing one event or situation to something else. What does this remind you of? Has there been another time you felt the same way? What was happening then?

And if you're just looking for facts from an expert, you can gently pull each string for more information. These are the how and why questions behind what you observe--remembering that there's no such thing as a stupid question. For example, when talking to an electrical engineer, you see the lights are on but how exactly does electricity travel through the wires? How is energy generated in your town? What is the biggest issue they encounter in their work? What solutions are professionals in their industry debating?

You can increase the chances of sparking something interesting during your next conversation by diligently asking questions. These questions have the added bonus of letting the person you're talking with know you're genuinely interested in them and their work--which is a surefire way to get them to open up and get to the juicy details. Try asking a few more targeted questions in your next conversation, and see what results you get.

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Published on: Apr 24, 2018