Hi {{first_name|there}},

Last week, I was at the airport, waiting at the gate for my flight home, and I listened in on two coworkers meeting for the first time as they flew out to a sales conference.

The younger of the two seemed a bit nervous as they sat down. He was at the edge of his seat, his eyes scanning the waiting area, and he wouldn’t let go of his backpack. But the older coworker had a certain energy about him that seemed put the younger one at ease rather quickly, eventually getting him to open up about all kinds of things I wouldn’t have shared in my first meeting with a coworker.

By the time we all queued up to board the plane, you would’ve thought these two had been fast friends for a long time. It wasn’t too much of a stretch to think the older one was a superb sales rep.

Their interaction was a great reminder that some people just seem to know what to say.

You know the type. They glide into conversation with ease. Their questions are disarming and thoughtful, and their timing is natural. They ask things you actually want to answer, not just small talk, but questions that feel like invitations. Conversations with them feel expansive, not extractive.

If you’ve ever wondered how they do it, you’re not alone. I did some digging and discovered the good news. This is all a learnable skill. And it’s one that has immense value, especially as we enter another year where so many of us are craving better relationships, deeper belonging, and more satisfying conversations.

So how do you ask the kinds of questions that build real rapport?

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We default to surface-level questions (“What do you do?” or “How are you?”) because they’re safe. But they’re also overused and underwhelming. People answer on autopilot, and the conversation goes nowhere fast. If all we do is read from the small talk script, we’ll never get below the surface to where real connection lies.

But if we skip the small talk altogether, we fall into the awkwardness of rushed intimacy, so we have to at least spend a little time with the easy-to-answer questions as a formality.

Small talk isn’t something to avoid; it’s a necessary social exchange on the way to something better. Many people who complain about small talk feel that way because they never get past talking about the weather.

In a world of fractured attention and constant distraction, your goal isn’t just to get a response; it’s to spark reflection.

The best connectors don’t just talk. They create conversational space. And it starts with knowing what kind of questions to ask and why.

Once you’ve gone through the initial small talk questions, you’ve achieved the conversational clearance that allows you to connect in a deeper way. Believe it or not, studies show the quality of your connection depends solely on how many questions you ask.

As the one seeking connection, you know it’s your role to be the questioner, so the path to richer conversations comes from exploring one of these four lanes:

A great first question is only half the equation. The real magic is in the follow-up. That’s where relationships deepen. When someone answers, linger a moment on what they said. Ask questions that allow them to expand on their answer before you chime in with your own thoughts:

These follow-ups signal presence and let the other person feel seen. And they turn what could be a quick reply into a lasting moment of connection.

A conversational error I had to fix early on in my career was what I’ve come to know as the Boomerang effect. This effect happens when you ask your partner questions only until you find a topic to bring the conversation back to your turn to talk.

We all love to talk about ourselves. We love it even more when someone asks us to do so. We build rapport with those conversationalists who are masterful in asking questions to get us to open up. We hate it when someone drones on about themselves, always bringing it back to them. Thus, the boomerang.

Boomeranging feels like building rapport, but it’s not. As I practiced asking questions to establish common ground with strangers, I was too quick to seize on a common interest and chime in that we both liked the same thing, then I’d start waxing poetic about why that was also my thing, and dominate the conversation from there.

I remember vividly discovering someone I met at a conference was from New Mexico, the same state where I grew up. Once I learned this, instead of asking them what town they lived in, or their favorite memory of growing up there, I launched into my own recollections of growing up in the Land of Enchantment. It became a monologue about my life in New Mexico, and it didn’t last long before they found a reason to leave.

I still feel awkward when I think back to that exchange. I had boomeranged the conversation back to me. The focus should have stayed on them. If it had, I might have formed a better connection with this individual. After all, how many folks can say they grew up in New Mexico?

To correct that boomerang mistake, I learned to enjoy the little internal zing of finding a kindred spirit. Instead of chiming in with “me too,” I used the common interest to ask better questions and deepen the connection by getting them to open up.

It still takes effort to overcome the urge to boomerang, but I’ve found the conversation goes so much better if I hold onto the thrill of shared interest as a private celebration instead of gushing about my own experience.

A strong conversationalist will make their partner feel understood. However, there's a big difference between curious and nosy.

We’ve all been on the receiving end of what felt like a barrage of questions that felt invasive rather than inviting. There’s an easy way to avoid delivering that poor experience when it’s you leading the inquiry, and that’s through the type of questions you ask.

Good questions:

Bad questions:

If you’re not sure whether to ask something, try this litmus test: Will this question help them feel more known, understood, or valued?

If the answer is yes, proceed. Your conversation partner will appreciate you.

Conversation leading to connection is a skill you can build. And you have your whole lifetime to do so! You don’t need a formal networking dinner or event to get better at asking good questions. Try it out in everyday settings where the cost of mistakes is low:

Conversation, like any other skill, is something you can get better at if you work on it. The more you practice asking good questions, the more they’ll become second nature, and you’ll never have to worry about boomeranging again.

Before next week’s newsletter hits your inbox, start a “Questions Log” that will help you practice going that one level deeper with someone else.

(You might surprise yourself with what you hear, and how it deepens the connection.)

And here’s a bonus: each time you hear an interesting question in a podcast, article, or conversation, add it to your log. You’ll build a personal database of better ways to connect, regardless of who your target is.

Just don’t forget to start with, “How are you?”

Because the right question, asked at the right time, can change the entire arc of a relationship.

And you never know which one will be the start of your next great connection.

What’s been your experience as both the questioner and the questionee? Do you have something you’ve done that you think could help others? Just hit reply to let me know — I’m listening. 🙏

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