How to Have More Meaningful Holiday Conversations

Improve the Time Together with Thoughtful Questions

Having meaningful holiday conversations can be one of the more stressful things about holiday gatherings.


Whether the event is an office party, a neighborhood celebration, or a family meal, for many, the crucial question is, “What do we talk about?”

Years ago, I made a commitment to myself that I would be a person who works to bring out the best in others around me. Applying that commitment to the topic of meaningful holiday conversations is crucial.

  • There are people in and outside of our families that we only see at holiday gatherings.
  • The benchmarking nature of holidays creates unique opportunities to have serious discussions with others.

In rearing our children, and in serving as mentors for young married couples, Tammy and I have learned the value of some deliberate, strategic planning before such events.

When we want to have meaningful conversations with others, we often ask ourselves:

  • “What would we most like people to take away from our time together?”
  • “What do we hope to get them to think about?”
  • “Are there ways that others can leave our company feeling better about themselves and their life-situations?”
  • “What good things do we see in their lives? Do THEY recognize those things?”
  • “What dangers do we see in their lives? Are THEY aware of their existence?”


4 reasons creating questions in advance helps promote meaningful holiday conversations

Michael Hyatt recently addressed this topic on his blog site with a post titled, How To Maximize Your Conversations This Holiday Season.” 

His reasons were:

  1. It gives you a track to run on
  2. It levels the playing field
  3. It draws everyone together
  4. It filters out the weird

9 open-ended questions to help create meaningful holiday conversations

Hyatt called them, “perfect for getting things going in the right direction” and “especially effective around the end of the year or getting together with people you haven’t seen in a while.”

Here’s his list of leading questions:

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


Maybe you are a person who wants to have a greater impact on others you interact with.

Maybe you want to stretch a bit and offer more of yourself to others socially.

Or maybe you just want to feel a little less uncomfortable in the “conversation game” at parties.

Regardless, I wish for you more relaxing and enjoyable sets of meaningful holiday conversations this year. May God richly bless your efforts to interact with others in meaningful ways.



Please note: I reserve the right to delete comments that are offensive or off-topic.

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2 thoughts on “How to Have More Meaningful Holiday Conversations

  1. How true that forethought in conversations will deepen relationships and foster a connection between people. Especially doing the holiday season with good cheer and somewhat a time of relaxation if all the madness of making the spirit right is done; people should be more opened to meaningful conversations.

    As a follower of Christ, I feel compelled to interject God’s glory in my everyday encounters. Such as when I sneeze and people will respond with a “Bless you,” I will say, “Yes, God does bless me.”
    Even while walking outdoors on a beautiful day, people greet you with a hello and I would add that God made this beautiful day for me to enjoy. Taking the time for forethought in daily speech encounters are opportunities to give testimony to God’s grace and goodness in our lives.

    • Thanks for sharing Betty.

      I too think that being “salt” and “light” as Jesus told us means being so especially in the “little things” of life.

      Didn’t he say that something as small a a cup of cold water could have a lasting impact?