3 min

The Art Of Follow-Up Curiosity

God I hate small talk. 

“How are you?” “Good, you?” “Good.”

What I hate even more is when I’m an active participant on either side of these surface-level conversations. But it’s impossible to completely eliminate “How are you?” from our daily interactions. If I started with, “What are you obsessed with lately?” I might get a weird look. So rather than try to ask cool, clever questions, I can master the art of Follow-Up Curiosity.

Follow-Up Curiosity is what allows the other person to share more, open up more, and be specific. That initial question is just a warm-up, preparing you for the more meaningful conversation to follow when you ask the second, third, fourth, and fifth questions. It lets them know you’re listening and you care. And only then will they feel safe to say what’s really on their mind. 

Follow-up questions flow between me and my true friends. We genuinely care and really want to understand how the other person is feeling, so naturally, we ask questions. And then we listen.

I struggle to ask more questions of people I’m friendly with but not friends with - like my neighbors - because it feels like I’m prying or taking up too much of their time. But it doesn’t have to be invasive or inappropriate. A follow-up question could be anything to keep the person talking and to learn more. If they’ve just told you a story you could ask how it made them feel. If they’ve quickly made a comment and dismissed it so they could ask about you, you can go back to what they said and say, “Tell me more about that.” 

My friend is a school teacher. I asked how teaching was going and she shrugged. “It’s fine. I don’t love it but I get summers off so I can’t complain. What about you?” 

Instead of answering her question, I responded, “Have you always felt that way or is it a recent thing?” 

“Ever since I had kids.” 

“Totally. I get it.” 

It was still a brief conversation, but it felt more meaningful to know how she felt about her job and about being a mom, rather than a meaningless ping pong of Q&A where one person asks but doesn’t care and the other person answers but doesn’t think.

Better conversations don’t happen when we have something valuable or important or funny to add. They happen when we’re curious and more interested in what the other person has to say. 

So next time you find yourself switching on autopilot mode in a conversation, try Follow-Up Curiosity. What might you ask someone to learn more?


This essay would have been trash without help from my friends Florian Maganza and Scott Krouse.