3 Tips for Successful Family Conversations

7 Simple Questions That Will Make Your Family Gatherings More Meaningful

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Let’s kick off this holiday season with a pop quiz: What’s the most important ingredient of a successful family gathering: The food? The company? The gifts?

Answer: None of the above.

The most important ingredient of a successful family gathering is the conversation. That’s why news outlets are filled with articles like What not to talk about at the family table? and How to handle difficult conversations at the holidays.

Fine. Everyone agrees on what you shouldn’t talk about—politics, war, tattoos, college admissions.

But what should you talk about?

As it happens, I’ve had a crush of questions on this topic in recent weeks. First, the great folks at Modern Elder Academy and Generations Over Dinner invited me to participate in an online discussion, “Elevate Your Holiday Conversations.” Second, the founders of Remento, a wonderful new app that allows users to capture family stories through conversation, asked me to recommend some questions that could promote meaningful interactions.

Here, based on what I’ve learned from years of studying family conversations, are three tips to make your holiday gatherings more successful:

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1. Start with Easy Questions

I love questions with staged conflict in them—prompts that produce different opinions invariably lead to better conversations. But that’s never the way to start a good conversation. Instead, you need to build slowly.

For a few years now, I’ve offered a gift service where I email grandparents questions about their lives so they can collect their family stories before they’re lost. The #1 lesson I’ve learned in this process: Always begin with a safe question. My go-to choice: Tell me about the toys you played with as a child. Everybody has a story; the question is non-threatening; the storyteller can feel good about themselves and then be off and running.

The same rule applies to family gatherings. Start with questions that everyone can answer, and that build confidence, camaraderie, and trust.

Here are three evergreen questions that I love:

What was your favorite part of the holidays when you were a child?

What’s the best piece of culture you consumed this year? It could be a book, movie, play, album, museum exhibition, or the like?

What app do you use most frequently?

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2. Focus on Failures

OK, everybody’s warmed up. Now go for the disasters! As I told the folks at Remento in my recommendations for conversation starters, a little nostalgia is good for setting the mood, but a little burnt pie or falling holiday decorations is just what a family conversation needs.

Some recommendations for fun embarrassments that I’ve found useful:

Tell us about a holiday fail.

What kooky or non-traditional food did your family eat when you were young?

What’s one holiday tradition you hope never comes back?

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3. End with Gratitude

My final tip is that after going for the mishaps and comedy, end with pure emotion. Gratitude has become a bit of a buzzword in recent years. And no wonder. In a comprehensive study of gratitude literature published in The Wiley Handbook of Positive Psychology, four distinguished scholars, led by Robert Emmons of the University of California, Davis, showed that gratitude does three things: 1) it protects from stress, 2) it improves sleep, and 3) it increases well-being.

I want all of those, but sometimes I feel reluctant with forced exercises that compel me to be earnest when I don’t want to be. My sister, however, feels no such resistance! She has insisted for a number of years that at family gatherings at the holidays, we all go around the table and say what we’re grateful for. Oh, please. Here come the butterflies and platitudes, I always think.

But here’s the thing: People like butterflies! They like platitudes! And they like hearing that people appreciate their many blessings in life.

So, my final recommendation is to give people what they want. Ask, “What are you grateful for this holiday season?”

You might be surprised when someone says, “I’m grateful for my family.”

Happy holidays, everyone! I wish you many meaningful conversations.

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Thank you for reading The Nonlinear Life. Please help us grow the community by subscribing, sharing, and commenting below. Also, you can learn more about me, read my introductory post, watch my latest TED Talk, or scroll through my other posts. And if you'd like to do a storytelling project with a loved one similar to the one I did with my father, click here to learn more.

You might enjoy reading these posts:

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Or check out my books that inspired this newsletter: Life Is in the Transitions and The Secrets of Happy Families. Or my new book, The Search: Finding Meaningful Work in a Post-Career World.

Or, you can contact me directly.

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