201 Icebreaker Questions for Work: Melt Away That Office Awkwardness

Looking for a few icebreaker questions to help people connect with one another at work? Or wondering how to improve employee engagement at work through the power of conversation? This is the post for you!

Is this your face when someone asks you for a good icebreaker question for work?

Let’s be real — not everyone is good at starting conversations. Some of us feel awkward about being the first to speak up in groups. Maybe we’re introverted or reserved. Maybe we’re shy or afraid of saying the wrong thing. Maybe we’re more listeners than talkers. Maybe we think we are too new to understand the culture and don’t want to jump in first.

All of that is totally understandable — especially if you’re working with employees who are new to the team or company. But it does make things very awkward for a facilitator or leader when you want people to connect and all they do is blink at one another.

What Even Are Icebreaker Questions?

Icebreaker questions are fun, light-hearted prompts designed to get people chatting and breaking the ice in any setting. They’re perfect for kicking off conversations and helping everyone get to know each other in a relaxed and informal way. Whether you’re at more of an informal social gathering or a business meeting, icebreaker questions for work can reduce tension, spark interaction, and build rapport among participants.

Just last year at our annual staff meeting, we used the icebreaker question “What’s a little-known fact about you?” to generate more than 6,000 connections across Enboarder. Check out the video below about the Connection Networking Game:

Icebreaker questions for work can range from sharing memories, to giving your opinion, to surfacing business ideas to super deep philosophical thoughts — but at every level, they have something to offer. By encouraging open communication and sharing, icebreakers create a collaborative work environment and melt away the anxiety that often comes with new beginnings. They also boost connection and belonging by allowing everyone to learn about each other’s experiences, interests, and personalities, promoting a sense of inclusivity and unity.

Why Use Icebreaker Questions at Work?

Icebreaker questions are a clever way to get employees quickly engaged in a group setting that might otherwise feel very awkward. They are especially handy during meetings, team-building activities, and onboarding sessions to help new employees feel right at home. That’s because they are excellent at making people think or laugh — or both.

Icebreaker questions for work give people structure and permission to speak, which can really help new employees feel welcome in your groups, and ease jitters. Good icebreakers help get people talking without feeling so self-conscious.

Icebreakers also help people learn things about their co-workers they otherwise would have never known. Check out this video featuring an off-site at OVO Energy, where they used icebreakers and Enboarder’s Connection Networking Game:

“I’ve shown the photo of myself and my daughter at the Eurovision final last year and the amount of people that didn’t know that about me and how passionate I was about women’s football. It’s just been amazing that I’ve been able to connect with people at a different level,” Neil Watson, head of people services and operations at OVO Energy.

As part of an engagement-led onboarding process, icebreakers can also help new hires quickly understand company culture and team dynamics. They create a positive atmosphere where everyone feels valued and connected right from the start — the kinds of human connection that are the future of connection at work.

201 Icebreaker Questions for Work: Melt Away Office Awkwardness

Whether you’re onboarding or just looking for some fun icebreaker questions for your next meeting, we’ve got you 100% covered. Here is a collection of 201 of the best icebreaker questions for work we’ve seen.

Get-to-Know-You Questions

If you could live anywhere in the world, where would it be?
Do you have any pets? Tell us about them.
What languages do you speak well enough to get around in that country?
What’s the most interesting documentary or book you’ve read recently?
What’s the most unique place you’ve ever traveled to?
What’s a quirky habit or ritual you have that makes you happy?
Have you ever performed in public? What did you do?
What’s a talent you have that not many people know about?
Are you an introvert or an extrovert? Ambivert?
Where did you meet your best friend?

Work-Related Questions

What was your very first paid job?
What’s the most unusual job you’ve ever had?
What job would you be terrible at?
What’s the most challenging project you’ve ever worked on?
What is your favorite office supply?
If you could master any skill overnight, what would it be?
What’s your favorite work-related book or podcast?
What’s the best team-building activity you’ve ever participated in?
What’s your favorite productivity tool or app?
Who is your most memorable mentor?

Virtual Team Building Questions

What’s your favorite virtual meeting background?
What’s the most interesting thing in your home office?
What’s the funniest thing that’s happened during a virtual meeting?
What’s your preferred video conferencing platform and why?
What’s your favorite virtual team-building game?

Seasonal and Holiday Questions

What’s your favorite family holiday tradition?
What’s your go-to holiday movie?
Which holidays do you decorate for? How?
What’s your favorite way to spend a snow day?
What’s your go-to summer vacation spot?
Do you have any New Year’s resolutions?
What’s your favorite holiday song?
Is Die-Hard a Christmas movie?
Holiday songs and decorations – when is too early?
What’s your favorite holiday? Least favorite?

Personal Growth Questions

What’s the skill you’d most like to develop or improve?
What’s a book or resource that has significantly impacted your personal growth?
What’s the biggest lesson you’ve learned in the past year?
What’s one habit you’ve developed that has positively impacted your life?
What’s the best piece of advice you’ve received for personal development?
What’s the professional advice you’ve most often given to others?
What’s a quote or mantra that inspires you?
How do you maintain a work-life balance?
What’s one thing you do every day for your personal growth?
When you have a day where you do nothing — do you feel good, or bad? Why?

Inspirational Questions

Who has been your biggest inspiration and why?
What’s the most inspiring book you’ve ever read or movie you’ve seen?
Where is your happy place?
What’s a moment in your own life that inspired you?
What’s an inspirational story you’ve heard recently?
Who is a historical figure you find inspiring and why?
What’s an act of kindness that inspired you?
What’s the most inspirational place you’ve visited?
Who is an artist or musician that inspires you?
What’s a cause or movement that inspires you?

Technology and Gadgets Questions

What’s your favorite smart gadget and why?
What’s the most useful app on your phone?
What’s a piece of technology you can’t live without?
What’s the coolest tech innovation you’ve seen recently?
What’s your favorite tech-related hobby?
What’s a tech gadget you regret buying or wish didn’t exist?
How do you use technology to stay productive?
What’s a piece of tech you’d like to learn more about?
What is your favorite way to communicate at work? Email, video, Slack, call?
What’s the most futuristic tech you hope to see in your lifetime?

Current Events and Environmental Questions

What’s a current issue, event, or cause that you’re passionate about?
What’s a recent development in your field or our industry that excites you?
What’s a recent piece of good news you’ve heard?
What’s a current trend you find to be particularly exciting or troubling?
What do you think of generational cohorts? Is age just a number?
What’s a recent scientific discovery that fascinates you?
What’s a small change you’ve made to live more sustainably?
What’s an environmental issue you’re passionate about?
What’s your favorite eco-friendly product?
What’s an inspiring environmental project you’ve heard of?

Pop Culture Questions

What’s your favorite TV series of all time?
Who’s your favorite celebrity and why?
What’s your favorite movie quote?
What’s your favorite book series?
Who’s your favorite musician or band?
What’s the most recent movie you watched and loved?
What’s your favorite game?
What’s the last book you read?
What are your favorite podcasts?
What’s the most memorable concert or live performance you’ve attended?

Hobbies and Interests Questions

What’s your favorite hobby and how did you get into it?
What’s a hobby you’ve always wanted to try but haven’t yet?
Do you collect anything? If so, what?
Do you play any musical instruments?
Say we’re raising money for our favorite charity. What’s for sale at your booth?
Do you have any DIY projects you’re working on?
What could you teach us to make?
What’s your favorite sport to watch or play?
What’s the most challenging hobby you’ve ever taken up?
If you had a day to volunteer, where would you spend it?

Travel Questions

What’s the most interesting place you’ve ever visited?
If you could travel anywhere in the world, where would you go?
What’s your vacation vibe? Beach lounge, mountain spa, culture excursion, city lights, sporty getaway or staycation?
Do you like traveling alone?
How light or heavy do you pack?
Planes, trains, ships, bikes, feet or automobiles?
What’s your favorite travel memory?
How do you like to document your travels?
What’s the longest trip you’ve ever been on?
What’s one place you’d never visit again and why?

Food and Drink Questions

What’s your go-to comfort food?
If you had to eat one cuisine for the rest of your life, what would it be?
What’s the best meal you’ve ever had?
What’s your favorite restaurant?
What’s your signature dish to cook?
What’s the weirdest food you’ve ever tried?
Do you prefer sweet or savory foods?
What’s your go-to drink order (alcoholic or non-alcoholic)?
What’s the best food you’ve tried while traveling?
What’s your favorite 3pm munchie?

Childhood and Family Questions

What’s your oldest childhood memory?
Did you have an imaginary friend?
What was your favorite subject in school?
What’s the best family vacation or trip you had as a kid?
What posters did you have on your wall as a kid?
Did you ever enter a science or state fair? What was your project?
What’s your favorite childhood movie or TV show?
Did you ever win a ribbon, medal, or trophy as a kid? In what?
Did you have a favorite superhero or character?
If you could have any animal, even mythical, as a tame pet, what would you choose?

Would You Rather Questions

Would you rather travel to the past or the future?
Would you rather be able to fly or be invisible?
Would you rather live in the city or the countryside?
Would you rather have unlimited free time or unlimited money?
Would you rather be able to speak all languages or play all instruments?
Would you rather have a personal chef or a personal trainer?
Would you rather be always a little too hot or a little too cold?
Would you rather explore space or the deep sea?
Would you rather be famous or be the best friend of someone famous?
Would you rather always have to sing instead of speak or dance everywhere you go?
Would you rather live without music or without movies?
Would you rather be a master of every skill or know everything?
Would you rather have more time or more money?
Would you rather always have to tell the truth or always have to lie?
Would you rather fight one horse-sized duck or a hundred duck-sized horses?

Deep Questions

If you could change one thing about the world, what would it be?
What’s the biggest risk you’ve ever taken?
If you could meet your future self, what would you ask?
If you could meet your past self, what would you share?
What’s the most significant challenge you’ve overcome?
What’s your biggest fear and why?
What’s something you’re passionate about and why?
If you could have any job, regardless of pay, what would it be?
What’s the best thing you ever did?
What’s one thing you still want to accomplish in your lifetime?

Fun and Silly Questions

What is your everyday superpower?
If you were an actual superhero, what superpower would you have?
What’s the weirdest food you’ve ever eaten?
Are you a good witch or a bad witch?
If you could transform into any animal which would you choose and why?
What’s your favorite go-to joke or pun?
Can you recite any part of a poem or verse by heart? Share it now!
If you had a time machine, what event would you love to witness in person?
If you could only listen to one song for the rest of your life, what would it be?
What’s the funniest prank you’ve ever pulled or had pulled on you?
If you could create your own reality TV show, what would it be about?
If you were a professional wrestler, what would your stage name be?
What’s your favorite ridiculous conspiracy theory?
If you could turn anything into an Olympic sport, what would you win gold in?
If you could live in any movie universe, which one would it be and why?

Lightning Round Questions

Coffee or tea?
Cats or dogs?
Morning person or night owl?
Winter, Spring, Summer, or Autumn?
Summer or winter?
Netflix or HBO?
Text or call?
Beach or mountains?
Book or movie?
Ice cream or cake?
Pancakes or waffles?
Pizza or burgers?
Music or podcasts?
Sneakers or sandals?
Mac or PC?
Early bird or night owl?
Is a hotdog a sandwich?
Dark mode or light mode?
Best day of the week?
Favorite word?

Hypothetical Questions

If you could have any superpower, what would it be?
If you could live in any fictional world, where would you live?
If you won the lottery, what’s the first thing you’d do?
If you could time travel, where and when would you go?
If you could meet any historical figure, who would it be?
If you could switch lives with anyone for a day, who would it be?
If you could speak any language fluently, which one would you choose?
If you could instantly become an expert in any field, what would it be?
If you could teleport anywhere in the world right now, where would you go?
If you could relive any moment in your life, what would it be?
Would you want to permanently feel zero pain if given the chance?
If you could erase one thing from existence, even the memory of the thing, what would it be?
If you had an animal or plant renamed for you, what would it be?
If you could make any one species go extinct, what would it be? Any?
You can anonymously send one text of <160 characters to everyone’s phone in the world. What does it say?
If you had to prove you were human and not an AI in 5 minutes via a text conversation, how would you do it?

Want more ideas on how to help new employees feel at home and connected from day 1? Learn more about Enboarder’s Connection Cards that spark joy and deep relationships at scale.