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How to Maximize Your Conversations This Holiday Season

9 Questions You and Your Family Can Ask Around the Table

We are almost in the holiday season, and that means a lot of great things: fun memories, good food, and more. But it also means a few challenges.

You know one of my big ones? Let’s visit the Honest Planet for a minute. It’s awkward conversations.

You probably know what I mean. With all the parties and get-togethers, there’s almost no way to avoid those dead-end discussions, off-the-wall observations, and random rabbit trails that leave you feeling like you need to leave early, is there?

The Power of Great Questions

It doesn’t have to be like that. Over the years I’ve learned a few critical elements for hosting great conversations. The big two are intentionality and great questions.

I just saw this on our recent company celebration trip. I was committed to including not just our team members, but also their spouses. We gathered together every night for dinner as well as some focused time of vision casting.

That meant a lot of people getting to know each other for the first time—a.k.a., a lot of opportunities for awkward conversations. So we solved that problem before we even got started. One of our team members created several question cards for each time the whole group got together.

Guess what happened? Instead of difficult conversations, we had a blast.

4 Reasons to Create Your Questions in Advance

I’ve seen this 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. I want to share four with you now:

  1. 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. 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 just jump in.

  2. 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. Crafting advance questions gives us a chance to think through topics that everyone can discuss. Instead of a few people steering the conversation their way, we can draw out everyone.

  3. It draws everyone together. Along with drawing everyone out, good questions can 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.

  4. 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.

What kind of questions work best? Here are nine I’ve used to give you a head start.

9 Questions to Try out This Holiday Season

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 getting together with people you haven’t seen in a while.

  • How do you define a great holiday experience? What’s the best one you can remember?
  • What are your top three strengths—and how do they benefit others?
  • If you had one million dollars to give to charity, how would you spend it?
  • What is your favorite trait in other people?
  • As a child, what did you want to be when you grew up—and how does that relate to what you do now?
  • When you look back on the last year what are you most proud of?
  • What are the two biggest lessons you learned this last year?
  • When you think about the coming year, what are you most excited to accomplish?
  • What new capability do you want to develop in the next year?

Did you 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.

Great conversations are like anything. Success is usually not an accident. It’s planned.

What is the best—and worst—conversations you can remember? What went right and what went wrong?

Disclosure of Material Connection: Some of the links in the post above are “affiliate links.” This means if you click on the link and purchase the item, we will receive an affiliate commission. Regardless, we only recommend products or services we use and believe will add value to our readers. We are disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.

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