December 14, 2023

The Essential Holiday Toolkit for Mastering the Art of Small Talk

The season for holiday socializing is upon us and many find small talk challenging or the most dreaded part of what should be a fun event.

Small talk leads to big talk and it paves the way for building a stronger sense of “community”, particularly with your customers. This is critically important these days given that many of our interactions are virtual.

Below I share some of my all-time favorite advice for getting through the rest of the year (and beyond) with shining executive presence and grace.

  • Adopt “host” behavior. As a host it’s natural to showcase warmth, approachability, and genuine interest in others. Treat everyone like they are a guest in your own home and your personality will shine.
  • Reserve judgement.
    • Some people may be shy or reserved at the beginning of a conversation, perhaps distancing themselves from dialogue. Introduce a light topic that has an element of humor to help people feel more at ease.
  • Leave a memorable impression, by treating each person you talk to as if they are a celebrity. Use their name. Be present, make sincere eye contact and smile. Remember that it’s more important to be interested than interesting!
  • Understand that people like to talk about themselves.
    • The words of Maya Angelou have great power,  “People may not remember exactly what you did, or what you said, but they will always remember how you made them feel”. When you encourage others to talk about themselves, you will make them feel special.
  • Ask engaging and personalized questions that spark meaningful conversations.
    • Instead of simply inquiring about someone’s occupation, initiate with “what” questions that inspire individuals to share. For example: What’s on your bucket list you’re eager to achieve?”, or “What do you feel most proud of accomplishing this year?” or “What are you looking forward to in the upcoming year?” In short, be genuinely curious without being intrusive and you’ll create a much more positive and enriching interaction with others.

Other small talk “what” questions you might use:

“What’s the most daring or exciting thing you’ve ever done?”
“What life event have you had that you would turn into a movie?”
“What movie can you see again and again?”
“What front row seats would you like to have for a concert?”
“What brand names do you swear by and never switch from?”
“What’s something you’d like to do but struggle with discipline?”
“What are some of your favorite rituals or traditions?”
“What famous person has most inspired you?”
“What’s one thing you would you do if fear wasn’t a factor?”

  • Actively seek common ground. At the onset of a workshop last week, I was chatting with George who mentioned that he loved a little-known, off-the-beaten-track restaurant in town. As he described it, my ears perked up, I immediately smiled and said: “I know that place and I go there often.” It was a great moment of connection. Think back to when that has happened to you. It could be about a movie, a song, a book, or even where you went on vacation. Sharing similar experiences creates a bond of comfort and familiarity that opens the door to expanding rapport and trust.

In the event that you’ve tried all of the above and the person isn’t particularly responsive to you, introduce them to someone you know and say: “You two must meet! I bet you have so much in common!” And then run…

Happy hosting and wishes for a joyful holiday celebration!


p.s. I highly recommend “4000 Questions for Getting to Know Anyone and Everyone” by Barbara Ann Kipfer, who inspired many of the questions above.

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