How to Avoid Awkward Holiday Conversations

By John Millen

Ah, the holidays.

It’s that special time of year when we slow down, eat too much food and…engage in awkward conversations.

Whether your business and family holiday gatherings are in-person or virtual, you'll face the same old challenges in communicating during this season.

While it can often be nice to mingle, sometimes meeting new people or chatting with people we rarely see can leave us feeling uncomfortable and dreading these visits. It can exacerbate social anxiety.

Here are eight tips for surviving the holiday conversation gauntlet:

1. Leave politics at the door

It should go without saying, but particularly here in the United States, avoid talking about politics. The polarized political environment makes it an untenable topic for holiday cheer.

Some people think they can persuade others to change their views, but that will not happen, since we all seek to confirm our own beliefs. (If you want to break out of that narrow mindset yourself you should challenge your beliefs.)

If someone tries to get you to focus on politics, don’t take the bait. Likewise for other controversial topics like vaccines and the shape of the earth. Smile and say you’re going to check out the refreshments.

2. Don’t reach for your phone

For many of us, the solution to feeling awkward at a public event is to reach for our smartphones. When we are left standing alone, feeling like a lonely middle-schooler, the answer is to grab for our smartphones.

By palming our phone and checking for email, text or notifications we reassure ourselves: “I’m not a loser, standing around by myself with no one to talk to,” we tell our inner critic. But we also cut off the possibility of meeting someone new, of catching the random set of eyes and making new friends.

3. Prepare ahead of time

Who will you be seeing? Old friends? Colleagues? Random strangers? Think about who will be there and scribble a few notes on a card about what you might want to share or avoid.

Will there be a particular person you want to make sure to connect with?

Someone you should avoid? A little planning can help you maneuver through the emotional minefield we often face during the holidays.

4. Share your stories

A great way to avoid awkward moments is to think ahead of time about some of your favorite stories. As human beings, we are hardwired for stories. Just take a few minutes to look through your story bank to refresh your memory. You do have a story bank, don’t you? If not, check out my article How to Collect Your Favorite Stories.

5. Be vulnerable

By opening up and sharing your personal stories or passions, you will encourage others to do the same. You’ll be amazed at what you hear and the bond that can be forged in a few minutes with someone by sharing yourself.

I recently met someone who told me he grew up in a small town in Texas. Though I’d never been there, that obscure town has special meaning in my life; so I shared my personal story with him and we came to understand one another at a much deeper level.

6. Ask questions

People love to talk about themselves when given the right space and opportunity. Ask open-ended questions (those that can’t be answered with “yes” or “no”) and ask questions that are more specific. In other words, not “how was your year?” but “what’s the best thing that happened to you this year?” A question like this will usually bring out a great story.

7. Be an active listener

We all like to think of ourselves as good listeners, but in most cases, that’s just not true. If you monitor your listening skills you’ll find you spend a lot of time thinking about what you want to say next. We often just listen for keywords that generate thoughts that will turn the conversation in our direction.

Instead, listen without intent. Listen with empathy. Listen for what’s not being said. Listen for the attitude behind the answer and ask follow up questions to go deeper.

8. Stay focused

There’s nothing worse than the person who pretends to be listening to you but keeps looking over your shoulder or at their phone. Don’t be that person. See if you can stay completely focused on the person in front of you while truly listening.

These simple practices can make a huge difference in the quality of your communication and your relationships.

While some awkwardness during holiday conversation cannot be avoided, a bit of planning and thought can make a challenging season a whole lot less stressful.

Happy Holidays!

John