10 Ways to Get to the Heart of People

When I was at Art Basel in Miami a few months ago, I was mesmerized by the work of artist Juan Genoves, specifically his piece “Duel,” that was shown by the Malborough Gallery in New York. Here’s why: From far away, the painting appeared to be very detailed images of pedestrians from above.

But the closer you got to it, the more you saw…

…they were really just little blobs of paint that, in a quick glance, appeared to be something else entirely! It’s the way we see others in life, isn’t it? We make assumptions about people from across the street, the room or the restaurant table. And we’re missing out on so much because of it.

The art made me think about how often we let our quick glance or five-minute conversation with someone be all we use to get to know who someone is. But I’m sure you’ve had an experience, like I have, when talking to someone a little deeper reminds you that getting to the heart can change everything. Wow, you think, they weren’t at all what I expected. And we’re always for the better when we get to the heart of knowing someone.

So here are ten ways you can get to know someone better in a short time.

1. Ask them their life’s purpose. Maybe it’s “to have a good time.” Maybe it’s “to be a good friend and mother.” I’ll never forget how much my opinion changed of a man I met who worked in banking when he told me his life’s purpose was to create a school with his sister for disadvantaged youth. Don’t assume their core beliefs, ask them about it.

2. Say, “Tell me. What’s the best thing that happened to you today?” Every day doesn’t have a promotion, great date or baby’s first steps. And you’ll learn a lot about someone by hearing what means “best” for them on a daily level. And you’ll raise their day by letting them tell you about it.

3. Ask, “What’s your biggest fear?” I asked this question at a party one night to everyone who entered the kitchen, and it led to the fastest bonding you’ve ever seen between strangers. From “heights” to “failure” to “being average” to “not being able to have kids,” hearing someone answer this question is like seeing into their soul.

4. Ask what movie they can’t turn off if they come across it on cable. For me, it’s Escape from Alcatraz and Something’s Gotta Give, and I think those both say something about me in a breaking-free-of life-and-wanting-to-write-in-a-huge-house-in-the-Hamptons kind of way. Like the cable TV world’s dream analysis, let the person you’re with tell you what draws them to the movies they love.

5. Have them tell you what their best skill is. We all want to be noticed for what we’re best at, but we don’t always get the chance to show it or talk about it. In this case, give someone else that chance. What a gift, letting someone share their best—and it will shift the energy of your conversation in a profoundly positive way.

6. Have them tell you what they wish their best skill was. Sure they’ve mastered ventricular endoscopic neurosurgery, but they never could hula-hoop. Funny, that.

7. Ask, “What are you absolutely awful at?” I had a friend who, in every conversation, was always claiming the final expert word on everything from cooking to fitness to art to bike maintenance. But one day, after I admitted something I was terrible at (probably how I’ve become so bad at math, I literally use my fingers to tally up the tip on a restaurant bill), she shared a weak spot, too. And I’d never liked her more. Open the door for a hilarious and revealing topic and guide them to the welcome mat.

8. Ask about their most exciting moment as a kid. When you get someone talking about their childhood, they will be transported back to that place of innocence, eagerness and genuine feelings. Whether it was meeting a baseball great, singing the lead in the school play, or being picked first for a team, the flashback is likely to bring out their playful, softer side.

9. Find out what they’re most proud of today. Their children? The table they built by hand? Re-gaining use of a leg doctors said would never walk again? What sets off beams of pride says a lot about the person.

10. Ask, “So…what makes you happy?” You may find yourselves making Charlie Brown lists of how happiness is everything from a warm puppy to a strong morning coffee to a kayak at sunrise on a calm bay. And while everyone else in the room is griping about their work day with wrinkles on their foreheads, you’ll be smiling, relaxed and feeling as happy as if you were experiencing what you’re talking about. Bring out the good parts of life.

Don’t accept the rash judgment your eyes or mind are quick to make for you. Dig deeper with the people you meet. Find out what makes them tick, what moves their soul. The more we learn about each other, the more real our connections and relationships can be.

Get to the heart of people. That’s where the good stuff is.

Big love,