And if you must know the answers to the question above, there is really no correct answer because the interviewer is only testing if you can think outside the box. But if you must have an answer, you can charge by the window. With that in mind, here are the trickiest interview questions you may face and how to answer them.
How to Approach and Answer Challenging Interview Scenarios
Q: What would you do if you didn't have to work?
Any answer that doesn't involve sleeping or being lazy will do. The point of this question is to know the interests, hobbies, and passions that you enjoy doing outside of work. Here is the list of 10 classic books for seeking a better career if you need to get inspired on how to answer this question best. Google, Zappos, IDEO, and other agencies that value creativity and motivation can ask this question.
Q: How would you evacuate an entire city?
This question is all about how you would confront a problem, so instead of detailing an evacuation plan outright, start by asking the interviewer about the type of massive disaster that he or she has in mind, and then proceed from there. This classic interview question, which will reveal your systems thinking and organizational approach, can be asked by Amazon, Google, FEMA, and others.
Q: How many golf balls can fit in a school bus?
The way to answer this question is to dictate the bus's dimensions by assuming its length, width, and height in terms of golf balls. Assuming that the bus is 200 golf balls long, 50 balls high, and 50 wide (200x50x50), then you get 500,000 balls. This question is asked to evaluate your logical thinking, estimation, and how good you are with numbers. We can easily assume that Meta, Microsoft, or Bain would be asking this question during the interview.
Q: How many piano tuners are there in the entire world?
Here's another question where you can apply assumptions, such as that it depends on the demand for their services. You can start by assuming how often pianos need to be tuned. Let's say pianos need to be tuned once a week, and that the work takes one hour to complete. So, if a piano tuner works 8 hours a day for five days, then he can tune a total of 40 pianos each week. It is then safe to deduce that there's one piano tuner for every 40 pianos in a given area. Another classic Fermi question - it is designed to evaluate your logical thinking and math skills.
Q: If you were the CEO of your previous company, what would you have done differently?
When answering this question, you have to be careful not to sound like you think ill of your previous employer. The goal of this question is to see how well you can see the big picture and take an objective approach to the issues and challenges you have observed at your former company, and what strategies would you have used to minimize, if not eliminate, their negative impact.
Q: You want to confirm that your friend John hasn't erased your number from his phone book, but you can't ask him directly. What do you do?
Ask him to call you at a specific time. If he doesn't, then he no longer has your number. This question is there to evaluate your ability to think outside the box, indirect reasoning, and, of course, problem-solving.
Q: How many quarters would it take to reach the top of the Empire State Building?
A variation of the 'golf ball' question, so again, you have to set the parameters by assuming both the thickness of the quarter and the height of the Empire State Building-unless the interviewer can give you accurate measurements for each. Otherwise, you can say that if a quarter is about a one-tenth of an inch thick, and the Empire State is about 1,000 tall, and that there are about 120 quarters in a foot, then you will need 120,000 quarters stacked on top of each other to match the length of the famed New York City building. Just like the questions about the piano tuners and golf balls, this one is there to test your logic and math.
Q: If you were a commodity, why should I buy you?
This one isn't really a trick question as much as it is a veiled one. What the interviewer is really asking is, "Why should we hire you?" To close the deal and land the job, you must be ready with a short list of reasons why they should choose you. Whatever your answer, you need to convince the interviewer of three things: That you will be a productive member of the team, that you will deliver exceptional work, and that you possess skill sets and experiences that make you a valuable hire.
Q: How lucky are you, and why?
This question is designed to assess whether you appreciate what you have. If you're reading this, that means you are alive and in reasonably good health. You can read, you are educated, and best of all, you are able to look forward to a bright future. Regardless of whether you think that you are moderately or extremely lucky, the important thing is to show genuine appreciation for where you are in life.
Q: Sell me this pen!
This classic sales question tests your persuasion skills, ability to think on the spot, and how well you identify a product's value based on a customer's needs. Focus on asking questions to understand the buyer’s needs, then show how the pen solves their problem - commonly asked when hiring sales roles at companies like Salesforce, Oracle, and Goldman Sachs.
Q: What's your favorite failure, and what did you learn from it?
Why it's asked: Employers want to assess resilience, accountability, and how well you reflect and grow from setbacks. Pick a failure that led to growth, and highlight the specific lessons or changes you made as a result. Common in: Startups and innovation-driven firms like Amazon, Facebook, or Tesla.
Q: If you could have dinner with any historical figure, who would it be and why?
This reveals your values, curiosity, and thought process when choosing role models or sources of inspiration. Choose someone relevant to your field or character, and explain how they inspire your goals or work ethic. Consulting firms and culture-focused companies like Bain & Company, IDEO, and Google tend to ask this question often.
Q: How would you explain a complicated concept to a 5-year-old?
This tests your communication skills and how well you simplify complex ideas - a must in leadership, teaching, and customer-facing roles. Break the concept into simple, relatable parts using analogies or stories that a child would understand. Tech companies like Apple, Microsoft, or Palantir use this question during their recruitment process.
Q: What would you do if you were the only survivor of a plane crash?
Why it's asked: This gauges your problem-solving, survival instincts, and ability to stay calm under pressure. Stay calm and logical, explain step-by-step actions for survival, and demonstrate your composure and critical thinking. Common in creative agencies, leadership development programs, and high-stress industries like PwC, McKinsey, or Airbnb.
Q: How would you improve our product?
Why it's asked: This question checks whether you've done your research, understand the company's offerings, and can think critically and constructively. Share one thoughtful, user-centered suggestion, and explain how it adds value without criticizing what already works. Product roles at companies like Spotify, Netflix, and Dropbox will use this to evaluate job seekers.
Q: If you were an animal, what would you be and why?
While it sounds silly (and a lot of fun, to be completely honest!), it tests self-awareness, creativity, and how you link personal traits to symbolic qualities (e.g., eagle = visionary). Choose an animal that aligns with your work style or strengths (for example, ant for teamwork or wolf for drive and ambition) and explain why. Creative roles and personality-driven industries like Ogilvy, Wieden+Kennedy, and L'Oréal might ask this question.
Q: Describe the color yellow to someone who's blind.
This question tests your empathy, imagination, and communication. It is especially important in design, user experience, and education roles. Use emotional, sensory, or metaphorical descriptions like “Yellow feels like warmth from the sun on your face.” We can definitely see Adobe, IDEO, and Frog Design asking it for their design roles.
Q: How would you design a spice rack for the blind?
Just like the previous one, this question tests your design thinking. Focus on accessibility, innovation, and user-centric problem-solving is especially important in UX/UI interviews at companies like Google, Amazon, or IBM. To answer it, consider tactile features, Braille labels, and accessibility, and walk through your reasoning step by step.
Q: What would you do with $10 million?
This one assesses your priorities, mindset, values, and decision-making under abundance, not just constraints. Balance practical, ethical, and visionary uses of the money, showing maturity and alignment with your values. This question is common in finance, entrepreneurship, and leadership interviews at firms like Goldman Sachs, Y Combinator, and BCG.
Tips to Keep in Mind When Answering
On the surface, these questions may appear utterly unrelated to the job you're applying for. The key here is to understand that companies use these questions to evaluate your thought process and reaction. So, before you head off to that job interview, here are five tips to keep in mind when answering the trickiest interview questions.
✅ Never question the value of the inquiry. If you start asking what the question has to do with the job, then you may as well kiss your chances goodbye.
✅ Never give an "I don't know" answer. This response will make the interviewer think that you are lazy and unimaginative.
✅ It's perfectly fine to ask for a moment to collect your thoughts. Just make sure not to take too long.
✅ Consider why the question was chosen. If you can't think of a logical solution to a problem, try answering in jest, as the interviewer could be trying to assess if you have a sense of humor.
✅ Don't let any question stress you out. Remember that part of the reason trickiest interview questions get asked during job interviews is to see your reaction. How you react during the process is as important as giving your well-thought-out answer.
If you think you need more help with acing that interview, here is our list of some of the most common interview mistakes to avoid.
Conclusion
Job interviews can be tough, especially when you get hit with tricky questions that test your thinking and confidence. From “Tell me about yourself” to tough behavioral questions, knowing how to answer them can help you stand out. The key is preparation, and it starts with a strong resume. With a resume writing company like ours, you can make sure your document highlights your best skills and experience, giving you a better chance at landing an interview.
