Beyond The Smalltalk: 50 Questions I used to bring my Stanford class closer together

A list of questions I used on a Stanford school trip in Colombia

A few years back, I organized a trip to Colombia for 260 of my business school classmates. It was a massive project, but one of the coolest parts was figuring out how to help people connect in a meaningful way. You know how it goes with big groups: lots of surface-level chatter, the usual “Where are you from? What do you do?” stuff. I wanted more than that.

That’s when I had the idea of creating conversation cards. Back when I gave my TEDx talk on “Breaking the Habit of Smalltalk,” I talked about the power of better questions. So, I decided to take it one step further. I crowdsourced a bunch of fun, quirky, and deep questions from my friends and network—everything from “What’s a random skill you’ve always wanted to learn?” to “What’s a moment that changed your life?” Pretty soon, I had over 150 questions. For the trip, I narrowed it down to 50 and printed them onto cards.

When we kicked off the trip, we handed out the cards and told everyone to give them a try. The idea was simple: use them during meals, bus rides, or whenever you felt like breaking the ice in a fun way. Everyone got at least three cards to start with.

Not everyone used the cards—and that’s fine—but I heard so many stories about how they helped people have real, memorable conversations. One night, I sat down to dinner with three classmates, and we decided to give the cards a shot. What started with a few laughs over silly questions quickly turned into a very meaningful conversations that we still reference to this day. We shared stories about embarrassing moments, personal challenges, and things we’d never really talked about with others – especially not people we had just met. It was vulnerable, raw, and deeply connecting.

Looking back, it’s clear to me how powerful the right question can be. It’s such a simple tool, but it has the potential to completely change how we connect with the people around us. If you want to try it out yourself, here’s the list of the 50 questions we used in Colombia.

1. When was the last time you did something for the first time?

2. What's your passion project these days?

3. What’s something about you that others tend to get wrong?

4. What’s the strangest thing about where you grew up?

5. Which of your scars has the most interesting story to tell?

6. What did you buy with your first salary ever?

7. What part of your life are you most grateful for?