Turn Small Talk into Meaningful Talk – ask this one question

by | Sep 9, 2025 | 2 comments

You’re sitting with people you like and have known for a chunk of time. Think a book club, a birthday lunch group, or an annual meetup at your professional association convention.

The value of small talk

Small talk serves a real purpose. It’s polite, light and superficial conversation that builds rapport and facilitates social connection.

You begin here. And, maybe that’s all you want. There are times when that’s enough.

But I get itchy if that’s all there is. Especially with close friends or people you’d like to get to know better.

How to turn small talk into meaningful talk.

You ask questions.

❓ The First Runner Up Great Question: “Can you tell us a highlight since the last time we’ve been together?”

I have a group of friends that I only see annually, over a lunch, at a professional convention. The first time we met I now know that the organizer felt concerned that it might not flow well. Not knowing this I asked the group the “highlight” question. We had a blast. Now, every year, this group gets together (for a three-hour lunch!) and shares, one by one, their stories from the year. We love it and it’s become meaningful.

❓ The Winner Question That Goes Deeper: “What have been some turning points in your life?” Warning: while this question will create memorable and meaningful dialogue, you want to do this in a trusting environment.

Recently I asked this question at my book club with longtime friends. You’d think that after 20+ years we knew all of these stories by now. Nope. Full disclosure, the book we were discussing, “I See You’ve Called in Dead” by John Kenney (great book that I’d recommend to you) lends itself to this type of question. Our conversation the other day went from interesting to deep in a heartbeat. My turning points ranged from traumatic (parents dying too soon) to fabulous (buying a ranch – the best adventure I never wanted).

Why meaningful conversations matter

  • To understand people’s lives it is fascinating to hear about their highlights and turning points / outcomes.
  • You learn more, you remember more, and you create stronger relationships.
  • From a professional angle, you’ll do more business with those you know, like and trust. These trusting relationships are the result of more meaningful interactions.

So, thank you to my DSC annual lunch buddies Suzie, Becky, Carolyn, Pat, Karen, and Rebecca for this great tradition.

And, thank you to Robin and Beverly for sharing meaningful turning points in your lives.

2 Comments

  1. Harry Hall

    Karen:

    My son Zane is high-functioning autism, and we have had many conversations about improving his communication skills. This will be part of the narrative. Thanks for the info.

    Harry Hall

    • Karen Cortell Reisman

      Hi Harry – it pleases me so much that this info will be helpful for Zane. If Zane can use these tools I know he can have more meaningful conversations. Yay.

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