How to Have a Conversation That Deepens Connection

Sometimes it takes just a small amount of creativity and attention to spark surprising and important conversations.

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3 women celebrating thanksgiving

I’m in a lot of Zoom meetings these days. I find that the ones that are the most effective, productive, and nourishing are those that begin with getting everyone’s voice in the room. One way to do this is to propose a question that each person responds to via audio or chat. Here are a few examples:

– What do you love about your work?
– What are your biggest challenges?
– What do you do for wellbeing?

I often like to begin gatherings and meals in a similar way. I particularly like this tradition at special times and holiday meals, like Thanksgiving. Here are some possible opening questions that I find work at such occasions (and many can be used in other settings as well):

– What is one thing you are grateful for?
– Complete with one sentence: What surprises me about my life right now is…
– What brings you here; what really brings you here? (you can define “here” any way you choose).
– What do you love about your life and what are your biggest challenges?
– What is your favorite activity on Sunday afternoons?
– How did you celebrate Thanksgiving growing up?

David Brooks, a New York Times columnist, recently wrote an excellent article on this subject. In Nine Nonobvious Ways To Have Deeper Conversations he suggests asking elevating questions like:

• What crossroads are you at?
• What commitments have you made that you no longer believe in?
• Who do you feel most grateful to have in your life?
• What problem did you use to have but now have licked?
• In what ways are you sliding backward?
• What would you do if you weren’t afraid?

He also suggests that we approach conversations with a sense of awe (for more on cultivating awe, check out my recent post about awe walks).

Sometimes it takes just a small amount of creativity and attention to spark surprising and important conversations – especially with those we’ve worked with for many years, or with family members or people that we “know” well (I highlight the word “know” because it’s all too easy to stop being curious, to stop really listening to the people that surround us frequently). Most of us love to be heard, love to be able to tell stories. We love to surprise and be surprised.

Try opening a conversation by asking the person to tell you their story: “What was it like for you growing up? Tell me about your parents. Did you have a best friend as a child?”

In the workplace, some great conversation starters are:
• How do you think about creativity, learning, and problem solving?
• How did you get into this kind of work?
• What did you study in high school or college?
• Who were some of your mentors?

Business meetings, Thanksgiving gatherings, and meal times in general provide a great opportunity for getting everyone’s voice in the room, for asking open-ended questions, and most of all, for listening and connecting wholeheartedly, with care and curiosity. Listening with your full attention, both to the words and the feelings, creates an environment of learning and going deeper, while building the connective tissue of trust and understanding.

Happy Thanksgiving!

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