How to Understand Someone Better Than You Do Your Friends (in Just Three Minutes)
Excerpted with permission from chapter 3 of “The Art of People – 11 Simple People Skills That Will Get You Everything You Want” by Dave Kerpen

“Now you’re going to get to know the person next to you better than you know many of your friends, in just three minutes with just three questions!” said the tall, enthusiastic speaker on stage in front of 1,200 people.

I sat in the front row, excited but dubious about the claim that Larry Benet had just made at the Social Media Marketing World conference in spring 2013. Larry is a man on a networking mission. Often referred to as one of the “Most Connected People on the Planet,” Larry Benet builds much more than just passing friendships. He has earned a sterling reputation as a master relationship builder as well as a thought-provoking and highly entertaining seminar speaker.

But this was my first experience with Larry Benet, and I must admit that I was a doubter. Larry was the first keynote speaker at the conference, and I knew he was there to teach people how to network better. Still, the notion that he could teach me to understand someone better than I know many of my friends in three minutes seemed a bit far-fetched even for an expert.

“Question number one: What is the most exciting thing you’re working on right now?

On your marks, get set, go!” Larry said confidently. I turned to my left and very quickly introduced myself to the man next to me. We didn’t have much time, so I quickly told Steven about Likeable Local, the new company I was getting ready to launch, and he told me about a science project in a box his company was about to unveil. Whew, just under the deadline.

“Question number two!” Larry’s big voice bellowed from the center of the stage. “If you had enough money to retire and then some, what would you be doing?”

The pressure was on with only a minute to share answers, and so I quickly learned that Steven would travel the world with his wife, going to all seven continents, and I said that I would run for office, perhaps for mayor of New York City or governor of the state. Again, we made it in just under a minute. This was proving to be a very interesting experiment!

“Final question, and remember, you have just a minute to both answer it,” Larry announced. “What is your favorite charity organization to support and why?”

I insisted that Steven go first this time, because I had two organizations I wished to talk about and wanted to make sure he got his in. He told me about the Nature Conservancy (Nature. ​ org) and how passionately he felt about conversation and climate change, and I told him about the Multiple Sclerosis Society and the National Alliance for Mental Illness and how with multiple family members affected, my wife and I felt compelled to support both organizations.

And that was it. Steven and I didn’t immediately become best friends after this exchange. We didn’t continue the conversation over dinner or invite each other over to meet our respective families. Although Steven and I exchanged a few emails after the event, it’s been over two years since that first and only conversation I had with him. But here’s the really interesting thing: It’s been over two years, yet I still recall with ease the contents of that conversation. I still know more about Steven after three minutes over two years ago than I do about most of my casual friends from high school, college, and work.

After informally surveying the audience and smugly determining that the doubters like me had been persuaded, Larry continued with his keynote. He told the audience that life’s too short to waste precious minutes on small talk about the weather or where people are from or what they do for a living. He argued that if we could get to know the person sitting next to us as well as we had in just three minutes, why shouldn’t we give ourselves and the people we meet the same gift in future encounters?

Larry Benet was absolutely right. When we meet people “in real life” we may open up a conversation with a bit of small talk because it’s far more socially acceptable than asking pointed questions. But the truth is that by asking better, smarter questions, we can understand the people we meet much more quickly and determine rapidly whether they’re friend or foe, a potential business partner or mate, a future employee or casual acquaintance. Life is short. The less time we waste on the weather, the better.

The three questions Larry taught me are excellent ones. That said, there are lots of other questions you can ask early in a first encounter with someone to better understand that person and his or her worldview. Here are ten questions for your consideration:

1. What is the most exciting thing in your professional life right now?

2. What is the most exciting thing in your personal life right now?

3. If you had enough money to retire, what would you be doing today?

4. What’s one thing you would like to be doing or would like to have five years from now?

5. What’s your favorite charity organization to support and why?

6. If you weren’t doing what you do today, what would you be doing and why?

7. Other than a member of your family, tell me about your role model.

8. Who’s been the most important influence on you?

9. How would your favorite teacher describe you?

10. If you could choose to do anything for a day, what would it be and why?

These questions not only break the ice, they quickly get people talking about the things that really matter, the things that will reveal their true personalities: their values, their likes, their hopes, and their passions. Although you can’t administer a personality test to someone you’ve just met, you can ask better questions than the standard “Where are you from?” “Where did you go to school?” “What do you do?” and “How do you like this weather?”

At this point perhaps some of you are thinking, “Dave, you were told by a conference speaker to ask these questions. I can’t just come out to someone I’ve just met and ask these sorts of things without people giving me a crazy look.”

You may be right, and so when it comes time to put this experiment into action for yourself, you can simply open with, “I just read this crazy book that talked about asking better questions when you first meet someone. Mind if we try out a couple of these questions and each answer them?”

You’ll be surprised how easily the conversation goes and how valuable it is, just as I was surprised the day I met Larry Benet. And you’ll start understanding people a lot better and faster, too.


Dave Kerpen


Dave Kerpen is an entrepreneur, speaker and bestselling author.  He is the founder and CEO of Likeable Local, a social media software company, and the chairman and cofounder of Likeable Media, an award-winning content marketing firm for brands.  He is among the most popular writers in LinkedIn’s Influencer program, is one of the most read contributors for  You can visit him at  And you can purchase his terrific book “The Art of People” by clicking “HERE”


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