Use the Holidays to Master the Lost Art of Conversation

April 27, 2026

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I was at a seated holiday dinner party this week and decided to play one of my favorite games. It’s called, “How long can I get my dinner partner to talk by asking one question?”


I think I set a personal record. I asked one question. My partner talked for 20 minutes almost non-stop with me throwing in the odd comment or two. We had a great time.


I tell you this because as the holiday party season stretches into football party season, now is the time to hone our relationship building skills by practicing the art of conversation. If you can make interesting conversation with a dinner guest, you can build the relationships that build business.


Great conversationalists live by the adage “The key to being interesting is to be interested.” Indeed, the only tools you need to be a great conversationalist are some good questions and a willingness to really listen.

Great Conversations Start with Great Questions

First, good conversationalists understand that to get a conversation going, you need to have some good open-ended questions that prompt a story or an opinion. Around holiday season, here are a few of my favorites:

Are you planning to go anywhere for the holidays? Most people have holiday plans. If your partner doesn’t regale you about his annual ski trip, maybe you’ll get the scoop on his crazy parents.


Does your family have any holiday traditions? One friend always sets up an old model train set and makes a gingerbread house. One year the house was so elaborate that it was entered in a magazine contest (It didn’t win).


Perhaps the best practice is simply to ask for an opinion. Ask a real estate developer what she thinks about property values or new Mercedes-Benz Stadium. Ask a Coca-Cola executive what he thinks of energy drinks.

At my holiday party this week, I was seated with a former Georgia Tech running back. As a Georgia Tech fan, I asked “What do you think of the quarterback?”


Asking about Tech’s quarterback was like saying the magic words. “Shazzam!” The opinions flowed and we began a passionate discussion. We solved Georgia Tech’s gridiron problems and soon did the same for the Falcons.

Listening Comes Next

Asking questions isn’t enough. You must listen. You need to find it in your heart to be genuinely interested in your partner’s opinions and show that interest so that your partner can tell.


The best listeners do a couple of things. First, they make great eye contact. Poor listeners constantly look around at others. One local attorney is well known for what I call the “better deal look”. That is, he looks around for someone he would consider a “better deal” to talk to you than you.


Great listeners also react verbally and facially. They smile or nod or do whatever else seems natural for the moment. They throw out such brilliant chestnuts as “Wow. That’s interesting.” Trite. But it works if it’s sincere.

I’ve spent an embarrassing amount of time working on my “listening face.” Sometimes when I’m listening carefully I tend to look bored, even if I’m not at all. And when chatting with my Georgia Tech dinner partner, I made sure that I was smiling, nodding and giving him a clear sense that his ideas interested me.


The art of conversation isn’t hard. It just takes a few questions and a willingness to really listen, the same things it takes to build relationships that turn into business.


Joey Asher

A smiling professional wearing a tan blazer over a multi-colored floral top and a pearl necklace against a white background.

Joey Asher has worked with thousands of business people helping them learn how to communicate in a way that connects with clients. His new book 15 Minutes Including Q&A: a Plan to Save the World from Lousy Presentations” is available now. He is also the author three previous books including “How to Win a Pitch: The Five Fundamentals That Will Distinguish You from the Competition”, “Selling and Communication Skills for Lawyers” and “Even A Geek Can Speak.”

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