Designing a Better Conversation
Throughout my career, I've learned to carry better conversations and build relationships by honing my listening skills and asking questions. Listening is such a rare skill that learning to do so had an outsized impact on my ability to occasionally fake charisma. But still, I'm not immune to the sting of a clumsy conversation, the kind you think about for the rest of the day and wonder just how much the other person thinks you're a spazz.
Self-consciousness deserves much of the blame for awkward conversations. Being hyper aware of what you're asking and how you're responding — and what your hands are doing and where your eyes are and if you're standing straight or if you have something in your teeth — only locks up the machinery.
Self-consciousness is born of inexperience, which causes over-analysis of everything that comes out of your mouth and then creates the self-fulfilling prophecy feedback loop.
My conversations are at their best when they are plentiful. Whenever I find myself stuck in long periods of isolation parked in front of my laptop, the return to human connection tends to feel more inept. Practice makes perfect.
Talking to Strangers
Nick Epley, a behavioral scientist at the University of Chicago, has research that says we're all craving more conversation than we let on. He advocates talking to strangers on the bus or in line or any number of places most of us would say sound like terrible ideas. It seems, though, we're afraid of these conversations not because the other person will be insufferable — though it's possible — but because we're scared of rejection. His same research also shows we're craving more intimacy in our daily conversations. We want depth instead of small talk. Genuine intrigue over surface-level platitudes.
It got me thinking about how to design a better conversation. After researching the topic, it's admittedly risky and potentially counterproductive to ascribe a framework to a skill that only gets worse the more you try to focus on it. But I think it's worth attempting to provide a starting point for those who want to know exactly how to be more social, make friends, or at least not regret their next conversation with the barista.
From the research, the guide to starting and holding better conversations is:
- Introduce yourself
- Skip the small talk
- Ask 2x more questions
Step 1: Introduce Yourself
Scenario: You sat down at the stool next to someone pretty, then felt like it was your window to say hi as they glanced at you and shuffled their things — except you didn't say hi. Now the initial window has passed. You look for a new window, but then actively critique yourself for having missed the first one, and the longer you stew, the more awkward it feels to just say hi now that you've already been sitting there for a few minutes in silence.
Sound familiar?
What the data shows is that the way a conversation starts is extremely forgivable. Barring aberrant or insulting behavior, any way you start the conversation is good enough because it gets things moving. It's like going skydiving. Even if the instructor had to pull you kicking and screaming out the door a few minutes past the drop-off point, once you're in the air, you're skydiving and there's no turning back.
So what's the easiest way to start?
"Hi, my name is [First Name]."
That's it. That's all you need.
Saying your name is a trick pulled from expert conflict facilitators. If the other person knows your name, it immediately humanizes you and makes you more relatable.
Step 2: Skip the Small Talk
How can we push the accelerator past small talk into relationship building without moving so fast as to make the curious question-asker seem like a weirdo?
Small talk is our way of dipping our toe into the conversational waters. It's like saying, "Hey, I'm maybe interested in a conversation depending on how you react to this average question I'm about to ask."
The problem with small talk is that it assumes the other person doesn't really want to have a conversation in the first place. This pessimistic attitude, according to Nick Epley, is what prevents us from having more connections throughout the day.
So we throw out a lame insight like "nice weather" because we're scared, then the other person answers benignly because they think you're just being polite. Conversational stalemate.
The weather feels like the right conversation starter because it's safe. It's inoffensive and unintrusive. But it's also completely uninteresting. And just like a hit movie where the lead dies, the follow-up is hard to pull off.
Here are some small-talk question alternatives. Yes, they feel like higher stakes. That's the point.
Instead of "Nice weather we're having," try any of these:
- "Are you a summer person or do you live for fall?"
- "What's your favorite activity this time of year?"
- "What's something you are looking forward to this week?"
- "What's the best part of working here?"
- "What does a good day off look like for you?"
Bonus Tip: Share a sincere compliment.
"I love your glasses / tattoo / hat / hair…"
Keep it focused on something they chose.
Step 3: Ask 2x More Questions
Good communicators ask about two times as many questions as the rest of us. Asking good questions requires good listening. When the other person offers insight or a clue into their life, notice it and follow up with the goal of finding common ground and exploring passions.
"I'm really a summer person. I love the beach!"
"Me too! What's your favorite beach to visit?"
Final Thoughts
I rarely have conversations on airplanes. Like everyone, I sit down, smile, and then push in some headphones. On a recent trip, halfway through the flight as the drinks were being served, I glanced at the gentleman next to me watching The Shawshank Redemption.
"What do you think — is that one of the greatest movies ever made?"
I asked one line that started a conversation lasting two hours. It was a wonderful conversation, everything you'd hope for with a stranger. And sure, it could have gone badly, but it went better than expected. We exchanged contact information, but it didn't really matter. It was the kind of conversation that makes you optimistic about humanity.
Our technology isn't making it any easier to make friends and connect with others. It's too easy to opt out and let the fear of a bad interaction color our entire view of conversations with others. And the more we opt out, the worse we get at holding conversations and predicting their outcome. But there's magic — a new friend, a future partner if that's what you're after — on the other end of the conversation. All it takes is a few moments of courage. I'm trying to get better myself. I look forward to running into you out there and saying:
"Hi! My name is Adam."
What else am I working on?
