The 36 Best Icebreaker Questions for Work in 2022

I saw a great list of interview questions in the book Talent by Tyler Cowen and Daniel Gross. These can be used as icebreaker questions at the office or in the workplace.

See the later section for advice in asking these questions the right way.

Icebreaker Questions for Job Interviews

  • “Why do you want to work here?”
  • “What are ten words your spouse or partner or friend would use to describe you?”
  • “What’s the most courageous thing you’ve done?”
  • “If you joined and then in three to six months you were no longer here, why would that be?” (Ask the same question about five years as well, and see how the two answers differ.)
  • “How did you prepare for this interview?”
  • “What did you like to do as a child?”
  • “Did you feel appreciated at your last job? What was the biggest way in which you did not feel appreciated?”
  • “Who are our competitors?”
  • “What are the open tabs on your browser right now?”
  • “What have you achieved that is unusual for your peer group?”
  • “What is one view held by the mainstream or as a consensus that you wholeheartedly agree with?”

If you’re doing this interview at a restaurant, you could also ask:

  • “What do you think of the service here?”
  • “Do you usually find rooms to be so noisy?”

Interview Questions

  • “Which of your beliefs are you least rational about?”
    Or maybe better: “What views do you hold religiously, almost irrationally?”
  • “Which of your beliefs are you most likely wrong about?”
  • “How do you think this interview is going?”
  • “How successful do you want to be?”
    And a variant is: “How ambitious are you?”
  • “What would you be willing to trade to achieve your career goals?” Or “How do you think about the trade-offs that might be required to achieve your career goals?”
  • “In the context of the workplace, what does the concept of ‘sin’ really mean? And how does it differ from a mere mistake? Can you illustrate this from the experience of one of your co-workers?”
  • “In which ways might a Skype or Zoom call be more informative than a person-to-person interaction?”
  • “In what ways are you not WYSIWYG [what you see is what you get]?”
  • “Is this person so good that you would happily work for them?”
  • “Can this person get you where you need to be way faster than any reasonable person could?”
  • “When this person disagrees with you, do you think it will be as likely you are wrong as they are wrong?”
  • “How would you rate yourself on a scale of 1-10 on X?… And why is that rating the right number for you?”

Icebreaker Questions with Longer Answers

Here are some questions that not only will elicit stories but also might yield relatively interesting answers:

  • “How did you spend your morning today?”
  • “What’s the farthest you’ve ever been from another human?”
  • “What’s something weird or unusual you did early on in life?”
  • “What’s a story one of your references might tell me when I call them?”
  • “If I was the perfect Netflix, what type of movies would I recommend for you and why?”
  • “How do you feel you are different from the people at your current company?”
  • “What views do you hold religiously, almost irrationally?”
  • “How did you prepare for this interview?”
  • “What subreddits, blogs, or online communities do you enjoy?”
  • “What is something esoteric you do?”

Facilitation Advice

The book includes this helpful note about asking these questions, and how to implement them.

Buyer beware: When asking these uncommon questions, you'll often get a long silence, followed by an unrelated answer. This is a great sign! It means the candidate wasn't prepared and needs time to think. You'll want to give the candidate, who may well be nervous, time to contemplate before blabbering. One strategy is repeating the question: "That's great. What's another reason you want to work here?" Another is to be explicit about the situation: "Now, you might not have an answer prepared. That's fine! While you think, let me tell you about something esoteric I do…”
Once the words are streaming out of their mouth, your real task begins: assessing their response and what it reveals. And to do that you need to draw on a broad variety of knowledge about cognition and personality as well as on your own trained intuition.


Asking good questions during a job interview is an incredible skill to have. The book Talent is a killer resource for this!

For more icebreaker questions, and to understand exactly how to facilitate an icebreaker, see these other articles:

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About the author

Howdy! I'm Nick Gray. Most people know me as the Founder of Museum Hack. I wrote a book, The 2-Hour Cocktail Party, about making new friends and building big relationships through small gatherings.