5 better questions to bring to your holiday gathering

Guest post by Taylor Buonocore-Guthrie, Co-Founder of Convers(ate)

The holidays are a time for gathering, catching up and conversation.

Whether you’re with loved ones over dinner or colleagues at a happy hour, conversation will be flowing.

And let’s be honest—sometimes a conversation is truly great; other times it feels like it’s missing something or just isn’t the kind of conversation you’d like to be having.

If that resonates with you, this year you might try something different - generously direct the conversation by using the single most powerful conversational tool you have—a good question.

As a facilitator, I led conversations with more than 150 groups in 2022. The data is clear - you can catalyze a meaningful, memorable conversation with a single powerful question.

In fact, asking interesting questions and really listening to the answers has always led me in the right direction.

So if you’re keen to connect more deeply and create space to really learn about those you’re with, even with people you know quite well or see often, here are 5 questions that I plan to use, that you might experiment with, too.

If you do, I’d love to hear how it goes!

1. Who is someone in your life who celebrated “the good stuff” well this year?
2. What did you intentionally invest your time in this year? What did you unintentionally invest a lot of time in this year?
3. What feels like a work-in-progress right now?
4. How do you feel about your relationship with technology this year? Or, more playfully….What part of your phone are you most hooked on?
5. Who is something you're looking forward to spending time with in the new year? What's special about them?
6. Book a Covers(ate) event.

Taylor Buonocore-Guthrie is the co-founder of Convers(ate) and facilitates some of Boompop’s most popular experiences, including “Goodbye Small Talk, Hello Connection” and “How to Ask Better Questions.” Convers(ate), an advisory firm that designs and facilitates team meetings, offsites and conferences, using great questions as a starting point. Before Convers(ate), Taylor built teams around the world as an independent consultant. She also speaks about how to elevate networking experiences and the most important factors for connection-oriented, memorable conversations.