The Art of Chitchat

I hate chitchat. Hate it.

I know I am probably (not probably, definitely am) an overly intense person. I want to be engaged in something that is meaningful and “on purpose” at all times—even when I am “off” and not working. To sit around and shoot-the-(well, you know) and talk about the weather, football scores or the latest celebrity gossip pains me beyond belief. Ask my wife: A conversation goes shallow, and I’ll go in the other room and read a book or find something else “productive” to do.

So when I know I am going into chitchat terrain (like holiday parties and family functions) I gear myself up and review my chitchat strategy.

Here is what I know for sure:

People like to talk about themselves—a la Winning Friends and Influencing People.

I really don’t like talking about myself or what’s going on in my life—I already know all that, and it bores me to hear myself talk about it. (And I know most people don’t really care; they are just waiting for their turn to talk about themselves. Seriously, no joke, see above point)

I love to learn and am in constant pursuit of life’s distinctions. If I am going to engage in chitchat (heaven help me), I want to learn something. I want to walk away with a new idea, tip or distinction I didn’t have before the conversation. And I believe I can learn something from anyone.

It’s up to me to make the conversation interesting. Considering the above (people really only want to talk about themselves, and I don’t, but I want to learn something), the key is to be ready with interesting and inquisitive questions. Anyone who knows me knows I am always asking questions (and it isn’t about Britney Spears or Snoop Dog news). The key is to have a series of great and insightful questions ready.

Want some help with creating great questions that get people talking about their greatest passions, hopes, dreams, ambitions and ideas?

If so, I will now give you my “on purpose” chitchat formula…

In my head, this is the FORMat I use to organize and keep the questions coming:

F—Family and friends



M—Money and meaning

Another tip: Ask specific and insightful questions, not ones that can be answered with “fine” or “good.” For example:

Not good — How’s you family doing? Or, How’s the job going?

Good — How have you seen your 4-year-old daughter’s personality open up and evolve over the last year? How has she surprised you the most?

Or, What adjustments have you made to your business the past year because of the economy? What worked and what didn’t? Looking back, what do you wish you had done differently?

Think about who you are going to be engaging with, and arm yourself with insightful and interesting questions in advance of stepping onto the front lines of the chitchat theater.

The result? As Dale Carnegie proved, you will be revered as a great conversationalist (even though you won’t be doing any of the talking); your chitchat companion will feel fabulously enriched (they got to talk about the things they love—themselves and their life and observations); and you might just learn something you can walk away with and use to improve your own insights and life. Everybody wins!

What are some of your best conversational questions? Share with us in the comments below.

Wishing you and yours a safe and happy holiday: Merry Christmas, Hanukkah, Kwanzaa, Yule, Saturnalia and-or Boxing Day!


Darren Hardy is the former publisher of SUCCESS magazine, an entrepreneur and New York Times best-selling author of The Compound Effect and Living Your Best Year Ever: A Proven Formula for Achieving Big Goals.

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