From Small Talk to Deep Conversation

Updated: May 5

A couple years ago I was at an outdoor gathering with a large group of friends and acquaintances. I was standing alone near the door of a pavilion watching my children play in the distance when a friendly woman who I had met a few times walked up and said, “I know you don’t like small talk, but isn’t it a beautiful day?”


It was a beautiful day, but I was struck most by what came before her question. She reminded me that I had once told her I struggle with small talk.


I do struggle when conversations linger in small talk too long, but I also recognize that being able to engage in small talk is important because it allows people to build rapport and open the door to move to deeper conversation. That’s why I was happy when Chad Littlefield, co-founder of We and Me, shared his thoughts about how to go from small talk to deep conversation on his YouTube channel.



At the heart of Chad’s advice lies three ideas I have written about but that are difficult to follow unless we are intentional about making them habits: being curious, asking questions, and listening.

  1. Aim for depth rather than breadth by increasing your curiosity. Before you find yourself stuck in the small talk zone, set an intention to be more curious in an upcoming interaction (e.g., networking event, office party, family gathering).

  2. Curiosity is enacted when you ask questions. Be curious about one thing the other person shares and ask open ended questions that help you dig deeper. Avoid questions that steer the topic toward things you want to share about yourself. Show genuine interest in the other person instead.

  3. Listen. Chad says, “When we listen really well we can get curious about many more things.” He goes on to say that when you listen with intention, what you are curious about will change because what you hear will be fundamentally different.

  4. Repeat. Chad encourages us to ask follow up questions and then follow up on follow up questions.

Reciprocity plays an important part in my ability to have deeper conversations. When I share deeply, others seem to be more willing to do the same. Likewise, when others share more deeply, I feel comfortable sharing on a deeper level as well. Not every conversation needs to be deep, but if you feel like something is missing in your life or if you want more meaningful relationships, being curious about others may be a good place to start.

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