Crafting conversations

As you prepare for holiday gatherings with family and friends, think back on leaving previous gatherings and how you felt about your interactions with those closest to you.

I often leave those gatherings and realize I somewhat went through the motions of being affable and interested without actually having many substantive conversations. What if we were intentional especially this week about crafting excellent conversations and made a bit of an art of asking good questions and listening intently?

Ask couples to tell you the story of their relationship, how they met and courted. Ask older people about their greatest life adventures and any wisdom they want to pass on. Ask teenagers what music they’re listening to.

If you’re hosting, consider setting some guidelines and expectations for the conversation around the table. What if there were only one conversation at a time that everyone at the table was a part of, instead of people carrying on a lot of conversations separately? Or maybe you can use place cards to seat guests in combinations that might spark better conversations. Separate those who know each other well or spend plenty of time together already.

Avoid polarizing topics. Who wants to argue about opinions that most people are not willing to reconsider?

Here are some challenging, fun questions to spark memorable discussions:

  • What did you want to be when you were a kid?
  • What has been your greatest adventure?
  • Best vacation ever? Dream vacation?
  • If money were not a concern, what would be your dream career?
  • If you could spend a day with anyone on the planet, who would you choose?
  • What books have truly impacted you in a meaningful way?
  • Describe in detail what you imagine your ideal day would be.
  • What important truth do very few people agree with you on? (Potentially polarizing, though.)

Coming up with fun questions could be a group effort as well. You don’t need to treat a conversation like a job interview, though. One good, authentic question can start an organic flow of ideas that doesn’t need to be forced and can lead to a remarkable encounter.  The key is active listening and following up and probing for better understanding.

My wife is great at giving quality attention at family gatherings to her 90+-year-old grandmother. It’s a delight to see them engaged in a discussion. And too often the oldest people, the ones who have lived the most life and have the most stories, tend to be talked around rather than talked with.

My recent weeks of interviews at work reminded me how interesting it can be to just sit and inquire thoughtfully and listen carefully. In those 30-minute interviews I had more interesting discussions with complete strangers than I’ve had recently in many hours of gatherings with my closest family members.

Everyone wants to be heard, and there is so much untapped wisdom and insight we miss out on by just failing to have genuine conversations with the people who are most meaningful in our lives.

The truth is you don’t have to be particularly suave or charismatic or interesting to be known as a great conversationalist. You just need to care enough to make the effort to be interested in others and to listen intently.


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