25 best questions
Get to know people in an interesting way
#1: What was your first job?
By far, this question has prompted the most interesting responses for the companies we work with. Employees are always find it hilarious to learn that their boss’ first job was as a pool boy, or find it fascinating that a coworker’s first job was working in her mom’s doctor’s office. While it’s an unassuming question, the responses stand out.
#2: Have you ever met anyone famous?
This question is a fun one, as it taps into the people that your coworkers admire. Folks bond over a mutual love for Jude Law, or have a laugh when a manager shares her story about meeting LeBron James at a gas station.
#3: What are you reading right now?
People are always looking for something new to read— and so swapping book recommendations are a great way for people to know each other. Learning what others are reading also provides insights into coworkers’ interests. David Heinemeier Hansson, CTO of Basecamp, shared his answer to this question here.
#4: If you could pick up a new skill in an instant what would it be?
With this question, you’ll learn how your coworkers want to grow or what they aspire to do. For instance, you might learn that a coworker would love to be able to pick up Italian instantly, or that your boss has always wanted to get good at woodworking.
#5: Who’s someone you really admire?
Understanding who someone looks up to reveals a significant amount about a person’s influences, preferences, and outlook on life. This is a great question to ask to help get a sense of what and who a person values.
#6: Seen any good movies lately you’d recommend?
Perhaps you’ve asked this question before — but don’t overlook it. Movies are a great shared conversation topic. It never fails to be one that people like to answer and like to see other people’s answer to. Often times, people will end up going to see them movies that are recommended and talking about it over lunch, etc.
#7: Got any favorite quotes?
Personally, I’m a sucker for a good quote. I think it can provide a fascinating look into a person’s point-of-view. Asking about a person’s favorite quote is a great way to break the ice and get to know them better.
#8: Been pleasantly surprised by anything lately?
While this question may seem vague, the answers to this question are often a delight and intriguing to read. Someone might share an excellent customer service experience that surpassed their expectations, or share a funny story about them liking squash soup despite their initial reservations. This is especially a great question to ask to a group of folks who might know each other a little better already.
#9: What was your favorite band 10 years ago?
This question always elicits a chuckle or two. You’ll find out that you shared a embarrassing favorite band from years ago, and also find the generational difference between coworkers humorous as well.
#10: What’s your earliest memory?
This is typically something that’s not shared even between close friends — so asking about it creates a special connection between folks. Hearing about an intimate, early part of someone’s life says a lot about who they are.
#11: Been anywhere recently for the first time?
Sharing a new, novel experience is a wonderful way to create a sense of connection between people. You’ll learn about a new restaurant, a fun out-of-the-city getaway, or a never-heard-about bookstore you might find interesting.
#12: What’s your favorite family tradition?
Cooking Korean dumplings together around the holidays is one of mine. When you ask this question, you get an inside look into your coworkers family’s heritage and the things that bring their family together.
#13: Who had the most influence on you growing up?
A mother, a sports hero, a grandparent, an elementary school teacher… This question is touching to hear the answer to. You’ll gain a sense of respect about who has shaped your coworkers.
#14: What was the first thing you bought with your own money?
Maybe it was a goldfish as a pet or a pair of Air Jordans. This is another great question that fosters a sense of nostalgia and provides insights into people’s interests of the past and what they valued when they were younger.
#15: What’s something you want to do in the next year that you’ve never done before?
I love asking this question instead of the stale, “Do you have any goals this year?” Rather, this is a great aspirational question that exposes people’s dreams and hopes they’d love to pursue.
#16: Seen anything lately that made you smile?
The answers from this question are often unexpectedly lovely. You’ll find yourself nodding your head as a coworker talks about his kids, or about a beautiful tree she saw on her walk recently.
#17: What’s your favorite place you’ve ever visited?
Responses to this are varied and fun — you’ll find that some folks have the same “favorite place” in Spain that they’ve visited, or a place that happens to be just 20 minutes from where you live.
#18: Have you had your 15 minutes of fame yet?
This is a cheeky question that turns up a variety of answers and interpretations. You might be impressed about how a coworker was in the newspaper one time or get a good laugh about how they were on the evening news.
#19: What’s the best advice you’ve ever heard?
I’m a big fan of this question, as you’re essentially asking a person about what wisdom they personally find most valuable. The best advice I’ve ever received, myself? “Trust yourself.”
#20: How do you like your eggs?
Our customers who ask this question are always shocked by how popular the answers to it are. They discover that colleagues are immensely passionate about scrambled eggs or are sunny-side-up diehards.
#21: Do you have a favorite charity you wish more people knew about?
This is a fantastic question to ask. One company I know took it as a way to make a small donation to each charity mentioned.
#22: Got any phobias you’d like to break?
Spiders, heights, the ocean… Sharing fears is always a great way to feel closer to someone.
#23: Have you returned anything you’ve purchased recently? Why?
Ask this question and you’ll unearth some interesting observations on why people buy things — and what they find unsatisfactory.
#24: Do you collect anything?
Skip the boring question, “What are your hobbies?” and ask this instead. You might find that someone is unexpectedly avid butterfly collector (my uncle does this), or enjoys finding a new postcard every time she travels (my mom does this). Regardless, it’s a more unique way to learn about a person’s interest.
#25: What’s your favorite breakfast cereal?
This question continually (and surprisingly) blows people away with the response when they ask it. One customer of ours had such an enthusiastic response on this from her staff, she created a Cereal Day for her team.
Longest list ever of icebreaker questions