A Guide for the Introvert to Thrive at Holiday Events

2 min read

December is a remarkable opportunity to connect with your people: past, present and future clients.  Enjoy the holiday season and take advantage of social, business, and fundraising opportunities to connect with people and build the high quality relationships that will be essential to thrive in the coming year.   

I have assembled a list of 36 questions you might consider asking people at holiday events.   Be sure to choose the ones that resonate with you and that are appropriate for the unique person you are talking with.   

The foundation of effective and deliberate conversations is a mindset of curiosity, an openness to learn and a solid foundation of cognitive empathy.    

Enjoy the holiday season.  

36 Questions to help you thrive at Holiday events.
 General Openers: 
“How are you enjoying the event so far?”
“How do you usually spend your holiday season?”
“Are you involved in any other local events or charities?”
“What’s been the highlight of your year so far?”
“What’s one thing you’re looking forward to in the coming year?”
“Do you know other local entrepreneurs or business leaders here tonight?”
“What kind of hobbies or activities do you enjoy during the winter season?”
“What makes you tick outside of work?What is your work?”

Holiday Specific (if they are Christmas people) 
“What’s your favourite holiday tradition or memory?”
“Have you tried any new holiday recipes or traditions this year?”
“What’s the most memorable Christmas gift you’ve ever received?”
“If you could invent a new holiday tradition, what would it be?”
“What’s the most unusual holiday gift you’ve ever given?”

Business Oriented: 
“What inspired you to start your business or choose your career path?”
“I’m always interested in collaborative ideas. Are there any projects you’re dreaming of pursuing?”
“Have you read any good books or listened to any interesting podcasts lately?”
“If you could have any fictional character as your business partner, who would you choose?    and why?”
“What’s been a significant challenge you’ve overcome in your career?”
“If you could give a piece of advice to someone starting in your industry, what would it be?”
“What innovation or change do you think will impact our community the most in the next few years?”
“If you could start a new venture in any field without any risk, what would it be?”
“If you were an entrepreneur in a parallel universe of your own design, what would your business be?”
“Have you noticed any interesting business trends recently?”
“Imagine you have unlimited resources to create the ultimate product or service. What would it be?”

Real Estate Oriented: 
“Do you live in the area, or did you travel in for this event?”
“What do you love most about your neighbourhood?”
“Have you noticed any interesting real estate trends in your area lately?”
“What’s on your wish list for the perfect home?”
“If you could change one thing about your current home, what would it be?”
“If you could decorate any home for Christmas, whose would it be and why?”
“Do you know others here who are involved in real estate or related fields?”
“Would you like to exchange contact information to discuss potential future opportunities?”

“If you could take a holiday trip anywhere in the world, where would you go?”
“If you could host a dinner party with any three people from history, who would you invite and what would you serve?”
“Suppose you found a magic snow globe that could transport you to any place and time. Where and when would you go?”

Using these as a motivator, create some of your own. Have fun and make some new friends! 



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