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50+ Cheeky Ice Breaker Questions to Get Your Colleagues Talking

By Preethi Jathanna

Senior Writer for HR and Remote Work

Ice Breaker Questions

We have all been there – a cross-functional training session where you are in a room with people you have never met before. Or you have joined a new workplace and all you see are new faces. One thing that is common in scenarios like this is the presence of awkward silences and the inadvertent activity of “Break the Ice” with, well, icebreaker questions.

Shakespeare mentioned the phrase “break the ice” in his famed The Taming of the Shrew and it is relevant even to this day. 

Icebreaker questions are a fun way to break the rigidity in an unknown setting and to get the people talking freely. The topics can range from work to hobbies, personal life, view on values on life, etc. 

You can also explore our insightful article on icebreaker tools and discover how they can foster connections, and create a positive and collaborative atmosphere among your team members.

Here are over 50 of the extensively used icebreaker questions that would resonate with most offices.

1.What Are Icebreaker Questions?

What Are Icebreaker Questions

Icebreaker questions are defined as thought-provoking questions that can be used to encourage people to talk or open up. They are used in most social and work scenarios where there would be the presence of awkward silences or to break the monotony in a fun, light-hearted, and conversational way.

2.Why Are Icebreaker Questions Important in a Work Setting?

Why are icebreaker questions important in a work setting

Icebreaker questions are important especially in a work setting, as that’s one place with the most group-level awkward silences. We have noticed that in many organizations, icebreaker questions are heavily underrated. Apart from being designed to know more about your colleagues, cheeky ice breakers also help with these things – 

  • Break the monotony of lengthy meetings
  • Help re-engage, disengaged employees
  • Aid with team bonding and building rapport
  • Help create a relaxing environment, especially in the classroom setting
  • Prepare them for future collaborations

So yeah, this list will help you enliven any awkward or silent atmosphere in a slightly cheeky way.

3.The Best Icebreaker Questions for Work

The Best Icebreaker Questions for Work

3.1. Ice breaker questions for a smaller number of people

Ice breaker questions for a smaller number of people

Use these ice breaker questions for work as a quick starter for deeper discussions. Since the group is smaller, everyone will get a chance to share their opinion on these cheeky ice breakers, and this will help gain great insights into their school of thought with these fun work icebreaker questions. Also these are great questions to get to know colleaguesbetter.

  1. What did you think about the new cafeteria policies?
  2. How would you caption this image/cartoon/meme?
  3. What was the craziest request you had from a client/customer?
  4. You all survived a plane crash and stuck in the middle of the desert with few items. How would you collectively survive until rescued?
  5. Who among this group would you rather be stranded on an island with?
  6. Do you care about zodiacs?
  7. What can you do/say to impress <someone in the group> today?
  8. Which trend do you want to kill immediately? 
  9. All of you should pick one fantasy world to bring to life. Which would it be?
  10. You all have one hour to live. What would you do together?

3.2. Ice breaker questions for a larger number of people

Ice breaker questions for a larger number of people

Ice breaker questions for larger groups should be able to spark interest and remove monotony. You can study the group during the course of the meeting or training and set aside questions to ask your colleagues for funbased on the type of people without making them feel uncomfortable. Don't worry no embarrassing icebreaker questions here !

  1. What would you wish that people would stop assuming about you?
  2. If you were to, as a third person, ask your school principal about your attitude in school, what would your principal say?
  3. Imitate someone in this room as if they were heading this meeting
  4. Which place do you not want to go to at all?
  5. If you had the chance to be the company’s mascot, what would you be and why?
  6. What was the last movie you walked out of?
  7. What was the last book you quit reading halfway through?
  8. Who do you really admire in this company?
  9. What’s the best and worst thing about coming back to the office?
  10. What kind of person do you love working with on a project?

3.3. Ice break er questions based on daily life

Ice breaker questions based on daily life

What does your co-worker do on a daily basis? What do they like and dislike? These daily life-based ice breaker questions will help you unravel the (not-so-personal) details about your colleagues. We have even used some of these ice breaker questions for work and saved the answers so as to help us get them a gift later!

  1. What about you do people forget?
  2. Which show do you say you don’t watch, but secretly do
  3. If you were made boss for a day, what would you do?
  4. Best piece of advice you have ever received
  5. What is the most unexpected praise you ever received?
  6. What are your top 5 items on your bucket list?
  7. If you had a million dollars, what would be the first thing you buy?
  8. Did you ever have an imaginary friend? Describe him/her/it.
  9. What weird food combination do you really enjoy?
  10. What would you be doing if money was not a criterion?

3.4. Ice breaker questions to get to know them better

Ice breaker questions to get to know them better

First impressions matter! And what other situation can be better than during an icebreaker to hold a unique introduction round? This will especially set the tone for your training sessions if they are conducted virtually. Let go of the get to know your colleagues questions like “Tell me your name, and your work experience”. Get cheekier with these questions to get to know colleagues!

  1. What are your top 5 favorite songs/books, and why?
  2. What would you like to talk about that no one has ever asked you?
  3. Which fictional character can you relate to the most?
  4. What makes you excited to be alive right now?
  5. What hashtags would define you?
  6. What’s your mobile wallpaper?
  7. What nickname would you rather have?
  8. Two truths and a lie
  9. What is a peculiar habit that you have?
  10. What clubs were you a member of in high school?

3.5. Ice breaker questions for fun & entertainment

Ice breaker questions for fun & entertainment

Every group – small or large – would love some laughs irrespective of the progress of the meeting or training. Having fun and entertaining icebreaker questions in the middle of a (possibly) boring session can lighten up the room figuratively and wake up everyone literally. Try these fun work icebreaker questions next time you see bored, sleepy, or any kind of disengaged employees. But do remember to not ask any embarrassing ice breaker questions. Cheeky ice breakers are acceptable. Here are some funny questions to ask work colleagues;

  1. What whimsical world would you want to live in?
  2. Which person (dead or alive) would you want to go on a date with?
  3. “Would you rather…” questions
    • Tea or Coffee.
    • Small town or big city
    • Dog or cat
    • Invisibility or Superspeed
    • Freeze time for 30 secs or rewind time for 30 secs?
  4. You have an option to be half-animal half-human. Which animal and human would you choose?
  5. What’s the most awkward/embarrassing thing you have texted someone?
  6. What was the last internet quiz you took, and what was the answer?
  7. Have you ever forgotten to speak/spell your own name?
  8. What’s the pet peeve that you wish you had?
  9. If you could have an endless supply of one food item, what would it be?
  10. What would your entrance theme song be?

3.6. Unique ice breaker questions based on values


Time to get philosophical with some thought-provoking icebreaker questions. Get their innermost views on themselves and life, with these questions. Fun apart, these will also help you gauge if they will align with the company’s ethics and policies.

  1. What is one ability you never want to have?
  2. How would you break up with yourself?
  3. Which past war would you rather be a part of?
  4. What one thing would you like to say to the world?
  5. If you were me, what question would you ask
  6. What do you think about when you travel or drive?
  7. As a kid, what did you dream of working as?
  8. What advice would you give to your teenage self?
  9. If your future self visited you now, what would he/she advise to the present you?
  10. You have one whole day to be on the dark web. What would you do?



4.1. What is a good icebreaker question for work?

Icebreaker questions can be related to work or personal (not too personal esp in a work setting). Questions like “Tell me about yourself”, “where do you see yourself in 5 years”, and “Tell me about your work experience” are cliches. You can have your icebreaker questions in training sessions, meetings, or even in interviews by adding a personal touch to them. Questions like “What was the craziest customer/client you got and how did you handle it”, “Describe what you see out of a window now”, and work-related ‘would you rather questions can be great in knowing more about the person as well as evaluating how suitable they are to the role and company values.

4.2. How do you successfully ask icebreaker questions?

5 Asking an icebreaker question so as to beget great team bonding and a fun experience can be daunting. Esp when you are not sure if the question you are about to ask would be considered inappropriate or not. A few simple rules will ensure you get great responses

  • Be the first answerer
  •  Allow for self-expression
  • Keep it so that anyone can answer any question
  • There should be no right answer to any question
  • Keep it fun and light

4.3. What are some good 21 questions?

Some of the best 21 questions are based on “get to know you”. The best thing about 21 questions is you need not wait for a formal ice breaker questions session. This can be done at any place, any time. You can even walk by a new joiner by their cubicle or the water cooler and ask 21 questions to get to know them better as a person and as a colleague. Some questions you can ask are –

  • Why did you quit your last job?
  • Do you have any pets?
  • What do you find as the most challenging aspect of your work?
  • What’s your favorite team/movie/book?
  • As a kid, what did you want to grow up to be?
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