How to turn small talk into real talk
Not too long ago, I boarded a quick flight for a speech, and a gentleman sat down in the seat next to me.
He was on the phone as we waited for takeoff, so we didn't exchange anything more than polite nods. I heard him mention New York on his call and order a water with no ice, and that was that.
The next day, I took the same flight back to Houston. Once again, a gentleman sat next to me—and just before takeoff, he leaned over and said, “This is strange, but I think you were my seatmate yesterday.”
I recognized his voice immediately. Sure enough, it was the same man. He joked that he recognized me by my notoriously loud and heavy backpack (there are all kinds of metal airline tags hanging from it, so you can always hear me coming).
I’d planned to work or maybe even squeeze in a quick nap on that flight. But then, I thought about the challenge I’d set for myself about being kind to strangers. My seatmate seemed to be in the mood to chat, so I took off my headphones, told myself my work (or nap) could wait, and struck up a conversation as we taxied down the runway.
The first thing I asked was if Houston was home for him. He said yes; we had that in common. And then I said, “So, tell me your story.” (That’s my favorite way to strike up a conversation with someone I don’t know.)
Next thing I knew, we’d talked the entire 45-minute flight. We kept it going even after we landed and didn’t part ways until we reached the end of the jetbridge.
We talked about . . . everything:
His work (he's a tax attorney) and mine.
His daughter, who shows horses competitively; his son, who is a teenager in high school; and my bonus daughter, Evie. We passionately discussed how hard it can be to empower your kids and how things have changed since we were children (he’s about 15 years older than me).
We talked about travel: He said he goes to New York often (which is why he’d been talking about it on the previous flight). We found that we’d both traveled like crazy before the pandemic, and being forced to take a break revealed how unsustainable that lifestyle was. We’re grateful to have found more balance.
He told me he’s dabbled in public speaking and has learned how to connect with audiences at tax conferences (he joked that it doesn't take much to be engaging at a tax conference). I shared how I prepare for my own talks.
We explored the topic of AI and the things that it will never replace. We agreed that we want to challenge ourselves to evolve with technology while staying true to the things that make us human.
We talked about where we live: He’s been in the same house for more than 30 years with his family; Spiros and I moved into our home two years ago and hope to be in it for a long time.
We gushed about our spouses. I told him about Spiros and his work as a surgeon; he told me about his wife, who is an educator.
We shared our feelings about aging parents. He told me about his mother-in-law, who’s living with him, and I told him that I hope my parents will live with me when we get to that point in our journey.
We discussed retirement. I told him about my dad, who just retired at 77, and he said he hopes to have the energy to do the work he’s doing for at least another 10 years.
I told him about the early days of Student Maid and how I didn't know anything about taxes or tax law back then. I shared some of our funny-not-funny mess-ups, and he laughed and cringed, especially as he imagined the reactions of my dad, who is also a lawyer.
My favorite topic we explored was mentorship. He told me that he’s realized his job as a leader now is to help others succeed. He said it makes him sad when successful people forget about those who helped them get there, and he never wants to be that way. He shared a story about missing a meeting due to a flight delay: He asked a team member to lead it in his place, and it launched her career. That led to us talking about how some of our most fulfilling moments have come from watching those we lead thrive.
And then . . . we landed.
Not as strangers, but as two people who had a meaningful conversation and might even stay friends.
And all of that happened in just 45 minutes.
Before we left each other, he gave me his card. I sent him an email as soon as I got home and thanked him for our conversation. He wrote back immediately and said he couldn't believe how many topics we’d covered in just 45 minutes! We joked that maybe we'll sit next to each other again someday and promised to get together with our spouses for dinner in the future.
The next evening, Spiros and I went on a double date with some dear friends. I shared that story, and it led to a conversation about how to turn small talk into a meaningful conversation with a stranger.
My friend shared that because she’s so introverted, she sometimes has trouble getting past the pleasantries and taking conversations deeper when she doesn’t know much about the other person. She said it’s even tougher at work because she’s in a male-dominated industry and isn’t always sure how to find common ground with her colleagues. She was surprised that I’d had such a deep, wide-ranging conversation with a stranger and said she admired the fact that I’d built a connection with him in such a short amount of time.
“How did you do that?” she asked. “What do you say to someone you don’t know to get them to open up?”
I began by pointing to a clear difference between me and my friend: I’m more extroverted than she is, and I’m also used to going to events where I meet people for the first time and work to build connection with them. I get a lot of practice.
“But let’s say you were teaching a crash course on how to take small talk deeper,” she said. “What advice would you give?”
I mentally retraced the steps of my conversation with the tax attorney and realized I could sum up my answer pretty simply: “Ask questions and genuinely listen to the answers.”
The key to a great conversation, I’ve found, is to listen. Don’t just wait to respond; seek to understand and look for opportunities to ask followup questions. Stay curious. That’s how you can start to find areas where you have mutual connections or things in common.
As for what questions you could ask, I told my friend that my favorite is, “What's your story?” It’s totally open-ended, which means your conversation can go anywhere from there.
In the case of the gentleman on the plane, I decided to start by asking about Houston because we seemed to have that in common. When I know something about someone, I like to start there. I might say, “I have to know: How did you get into XYZ?” or, “What led you to the work you're doing now?”
Asking the first question always feels a little shaky, maybe even risky, but once you get an answer that seems to have some passion or energy around it, you’re off to the races.
The world needs all the kindness it can get, and striking up a conversation with a stranger is a great place to start. So now, I want to ask you: What’s been your experience connecting with strangers? Do you tend to stick to small talk, or do you try to move the conversation toward something more meaningful? Is there someone you see regularly but don't know much about? What could happen if you had the courage to ask them to tell you their story? Reply to this email and tell me all about it. My team and I love reading your responses!
Before I sign off on today’s post, I’ve got an important announcement:
I’m taking a short break from the blog!
Writing to you every week is one of my favorite ways to exercise my creativity. But the thing about creative capacity is that we only have so much of it.
For months now, my team and I have been hard at work behind the scenes on a HUGE creative project, and we’re in the home stretch. To make sure it turns out the best it possibly can, we’ve decided to step back from the blog for a few weeks so that we can focus all of our creative energy on this other thing that I am bursting at the seams to tell you about! (Soon, I promise!)
I always say that our energy is something we have to protect. We only have so much of it! I see this as a moment to practice that “out loud.” If you’ve been craving space for yourself or thinking about shifting your priorities, I hope this post gives you permission. I mean, you don’t need my permission, but I know that sometimes, when I see someone else do something, it makes me feel like I can do it, too. I hope that by taking a break from the blog, I will inspire you to honor and protect your own energy so that you can show up as your best—for you and for those you want to impact.
And with that . . . see you back here on April 28th! Can’t wait to be reunited with you when that day comes.
Big hugs,
