How to Maximize Your Conversations This Holiday Season

10 Questions You and Your Family Can Ask Around the Table

We are entering the holiday season, and that means a lot of great things: fun memories, good food, goofing off. But it might mean some awkward, uncomfortable conversations, too.

According to two economists from UCLA and Washington State University, “politically divided” families actually cut short their Thanksgiving dinners last year rather than wrangle over the table. “Our results suggest partisan differences cost American families 62 million person-hours of Thanksgiving time,” the pair wrote.

Hilariously, The Ellen Show recognized the same problem and created a spoof app called “The Mobile Moderator” that allows families to select their favorite cable news host to moderate family dinner conversation.

“You have five more seconds,” CNN anchor Wolf Blitzer warns one relative going on about her swollen feet. “That’s enough. Aunt Pearl, you are out of time.” Later, he interrupts a hotly disputed political question by saying, “If we could just please get back to the original question, ‘Could someone please pass the salt?’”

Unfortunately, real life doesn’t come with professional moderators to keep conversations on track. That means with all the parties and get-togethers between now and the end of the year, there’s almost no way to avoid dead-end discussions, off-the-wall observations, political posturing, and random rabbit trails that can leave you feeling like you need to leave early. Or is there?

Maximizing your conversations

Over the years I’ve learned a few critical elements for hosting great conversations. The big two are intentionality and great questions. These two come together in prepared questions.

I’ve seen this pay off at our yearly company celebration trips. We include not just our team members but also their spouses. The whole group gathers together every night for dinner as well as some focused time of vision casting. That means a lot of people getting to know each other for the first time—a.k.a., a lot of opportunities for awkward conversations.

To solve the problem, one of our team members creates several question cards for each time the whole group gets together. Instead of difficult conversations, we have a blast. I’ve seen a similar strategy work in other situations as well—even with total strangers. There are a handful of reasons this approach works so well at maximizing conversations.

First, it gives you a track to run on. One of the reason that conversations can be difficult is that it sometimes takes effort to find a topic that works. Sometimes it’s impossible to get past the small talk, especially when you’re trying to avoid controversial or heavy topics. But if you work up questions in advance, it can take the pressure off. It also reduces the ramp up. Instead of false starts, you can jump right in.

Second, it levels the playing field. We all like to talk about whatever comes most easily to us, but sometimes that means discussing topics that leave others out—or even alienate them. Crafting questions in advance gives you a chance to think through topics that everyone can discuss. Instead of a few people dominating the conversation, you can draw out everyone.

Third, it draws everyone together. Along with drawing everyone out, good questions can draw everyone in. Conversation can create intimacy and connection as people see their ideas and thoughts validated. Even people who start out on the edge of a conversation can feel included and appreciated.

Fourth, it filters out the weird. If you’ve got a track to run on and everyone can join in, you can also avoid a lot of the odd and awkward moments. Instead of feeling trapped, you can feel empowered.

10 questions to get you started

What kind of questions work best? Here are ten I’ve used that can give you a head start. I find these are perfect for getting things going in the right direction. And these are especially effective around the end of the year or when getting together with people you haven’t seen in awhile.

  1. How do you define a great holiday experience? What’s the best one you can remember?
  2. What are you the most grateful for this past year?
  3. What are you the most proud of this past year?
  4. If you had one million dollars to give to charity, how would you spend it?
  5. What are your top three strengths—and how have they benefitted others recently?
  6. What is your favorite trait in other people?
  7. As a child, what did you want to be when you grew up—and how does that relate to what you do now?
  8. When you think about the coming year, what are you most excited to accomplish?
  9. What new capability do you want to develop in the next year?
  10. What are the two biggest lessons you learned this last year?

Notice the one thing all these questions have in common? People usually find it easy to talk about themselves. The more you let people share about themselves, the simpler the whole situation will be. And chances are good you won’t need Wolf Blitzer to moderate.

Great conversations are like anything: Success is usually not an accident—it’s planned.

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