In the United States, it’s nearly Thanksgiving and that means, for many people, it’s time to join up with family and friends to enjoy a meal together. It also means it’s time for social conversation—which can be challenging or fraught for many people, particularly people who may or may not agree philosophically. The last two years, we’ve done a dinner-party game that I thought I’d share with you. These are conversation starters that help break the ice and change the typical family scene into a moment of introspection and reflection.

Dinner party conversations can be awkward if there isn’t a guided way to get through them, or if you don’t have experience with small talk. I’m not a fan of small talk (at all!) so I love picking a framework and going deeper when we have social events. Here are two of my favorites.

Conversation Starters #1: Tim Ferriss’ Eleven Questions

Last year I was reading Tribe of Mentors by Tim Ferriss, and he shares the questions he’s found work best for getting a great interview. I love these questions and asked my family if they’d be interested in playing along. Because Tim Ferriss is so well known, it was easier to get buy-in from my family to try this out. Here’s how we did it:

1. Get buy-in. First, I asked a few family members before dinner if they would be interested in trying a new conversation game with me during dinner. This is a classic move—if you’re trying to get buy-in for a new idea, don’t wait until the moment you’re on stage or in the spotlight. Run a campaign beforehand to get key players to buy in. (As an aside, this is what I do 90% of the time I introduce a new idea in any company or leadership meeting.)

2. Introduce the idea at the table. “Hey everyone,” I said. “Tim Ferriss is this great interviewer and he has a list of 11 questions he uses when he does his interview series. He’s the number-one business podcast on iTunes and the questions are awesome. I thought we could go around the table and each pick a question and answer it today!”

3. Pick a question. The way we played is we had each person randomly pick a number between one and eleven. “I want seven!” my sister said, for example. Then, I’d read the question out loud, and we’d hear her response.

It turned out to be a really beautiful way to get to know people and these conversation starters let me get a deeper look into their lives. I loved it.

One note: people aren’t always good at being put on the spot, so it can also be a great idea to write these on notecards and introduce the game early in the day, so people can see the questions and think about them in advance.

Here are Tim’s Eleven Questions:

1: What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?

2: What purchase of $100 or less has most positively impacted your life in the last six months (or in recent memory)? My readers love specifics like brand and model, where you found it, etc.

3: How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

4: If you could have a gigantic billboard anywhere with anything on it — metaphorically speaking, getting a message out to millions or billions — what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)

5: What is one of the best or most worthwhile investments you’ve ever made? (Could be an investment of money, time, energy, etc.)

6: What is an unusual habit or an absurd thing that you love?

7: In the last five years, what new belief, behavior, or habit has most improved your life?

8: What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

9: What are bad recommendations you hear in your profession or area of expertise?”

10: In the last five years, what have you become better at saying no to (distractions, invitations, etc.)? What new realizations and/or approaches helped? Any other tips?

11: When you feel overwhelmed or unfocused, or have lost your focus temporarily, what do you do? (If helpful: What questions do you ask yourself?)

Conversation Starters #2: Your Life Story in 3 Minutes

I was in a postpartum mom’s group, and every week we shared a new part of our stories with each other. The first week, we talked about pregnancy; then we talked about birth. We talked about our postpartum experience. And in one of our weekly meetings, we were given the prompt to tell our life story in three minutes.

The important added layer was picking a “filter” to use. Instead of trying to cram every detail in three minutes, we were tasked with picking a filter or a lens to tell the story through. For example, we could tell our life story in geographic locations (where we’ve lived and moved), or through the lens of education (where and what we studied). Here are some of the filters you can pick:

  • Geography
  • Education
  • Sports / athetics
  • Adventures
  • Spirituality or religion
  • Maternal lineage
  • Paternal lineage
  • Language
  • Food

You can pick any filter you want (the above are just ideas). Set a timer and go around in a circle and share a piece of your life story. When the timer goes off, wrap up the sentence or thought that you’re on, and pass it along to the next person.

This game works best if you kindly remind people at the beginning not to interrupt. It’s better to sit back and listen, even though the temptation to ask questions or chime in will be strong (“You went to Penn? Me too! What year?”). Let the follow-up questions happen after the sharing circle has finished.

What I love about this one is that it sparks deeper conversations after the group circle, and I find myself with a glass of wine, by the fire, hearing stories from aunts and uncles that I didn’t know about.

Enjoy your holidays, and your time with family members. Use these conversation starters at any time, whether at a social event or a dinner party, or in a team meeting with your crew.

Want more? Check out the podcast episode episode we did on journaling for clarity, all about reflection questions and using them to connect more deeply with yourself or others.


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