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13 Intentionally Confusing Interview Questions (And How To Answer Them Perfectly)


Interviews are usually the toughest part of searching for a new job.

Even if you spend hours researching a company, fine-tuning your resume, and practicing your answers in front of a mirror, all interviews have an element of unpredictability.

For most job seekers, the worst-case scenario is something like this: your interviewer throws you a curveball question, and you have absolutely no idea how to answer it.

You draw a blank.

Even after you hurriedly rack your brain for anything halfway intelligent to say, nothing comes to mind.

And you go into panic mode.

These experiences not only rattle your confidence, but they can hurt your chances of landing the position. Although it’s impossible to prepare for every possible question that may come your way, there are some things you can keep in mind to make sure you don’t find yourself in one of these nightmare situations.

Here are 13 tricky interview questions—and how to answer them effectively—to familiarize yourself with so you can boost your chances of nabbing your dream job.

1. How would you sell hot chocolate in Florida?

Answer: This question challenges you to get creative.

It’s easy to sell ice cream in the summer, but how can you convince people in a warm climate to purchase a hot beverage? There’s no one right answer here, but you could conduct market research to determine if sales of coffee or other hot drinks spike during the winter, research places in Florida that have the greatest range in temperature between day and night, or check which cities in the state get the most tourists. You could also market a unique hot chocolate drink that incorporates Florida-related flavors like key lime or Cuban espresso.

2. What would you do if you were the sole survivor of a plane crash?

Answer: How you reply to this interview question, originally posed by Airbnb, reveals facets of your personality as well as your critical thinking skills.

It’s up to you how to answer, but you may want to focus on the basics: yell for help, check if your phone has reception, look for water, find food and shelter. As long as the plane isn’t on fire or too dangerous to be near, you can also confirm that there are in fact no other survivors, look for useful supplies on board, or bury the dead.

3. You’re shrunk to the height of a nickel and your mass is proportionally reduced so you maintain your original density. You’re then thrown into an empty glass blender, and the blades will start moving in 60 seconds. What do you do?

Answer: The devil is in the details with this interview question from Google.

If your density stays the same, that means your mass and volume (density = mass/volume) also remain the same. So although you’d be tiny, you’d also have more than enough strength to break the blending mechanism or propel yourself out of the blender before you get chopped up into a metallic mess.

4. If you woke up to 2,000 unread emails in your inbox, and you could only answer 300 of them, how would you choose which ones to answer?

Answer: This question gives you an opportunity to show off your ability to prioritize.

You could sort the emails by sender and only reply to the ones from your boss and clients, or you could quickly skim the subject lines to determine which emails require your immediate response.

5. How would you explain a database so a 5-year-old child could understand it?

Answer: The key here is to break down a complex topic into simple, easily understood language.

A database is like a box of toys. They both let you store and organize things in one place so they’re easy to get to later. Instead of toys, a database contains data stored on a computer. This data could be information about people, like their age or gender, or information about things, like the number of red socks sold in a month or the daily temperature in your city.

6. How much would you charge to wash all the windows in Seattle?

Answer: With this type of brain-teaser question, exact numbers don’t matter. Your interviewer simply wants to assess how well you can reason and estimate under pressure. So instead of getting caught up in the numbers, focus on showing off your logical progression of thinking.

First, estimate the number of windows in Seattle. Consider that there are windows on offices, houses, apartments, and even cars. To make the math easy, assume there are roughly 1 million people who live in Seattle, and 100,000 offices, 500,000 homes, and 400,000 cars there.

So how many windows is that? Well, if each office has 100 windows (100 x 100,000), each home has 10 windows (10 x 500,000), and each car has six windows (6 x 400,000), that means there are (10,000,000 + 5,000,000 + 2,400,000 = 17,400,000) just under 17.5 million windows in total.

Your final step is to choose a price to charge. We suggest something simple and round, like $10 per window. Multiply $10 by 17,400,000 windows to get your answer, $174 million.

7. Why are manhole covers round?

Answer: If you’ve never heard this question before, it’s time to put on your thinking cap.

Visualize a manhole, and ask yourself what its function is. Because these covers serve as a barrier between the street and the sewer underground, they’re designed to protect and separate. If the cover were any other shape than circular, it could accidentally fall into the hole. But since the round cover is a little bigger than the hole, there’s no way it can fall into the sewer.

8. How would you describe the color red to a blind person?

Answer: If you consider yourself an imaginative person who’s good with words, this is your chance to shine.

You can compare the color red to sounds and experiences a blind person might be familiar with. Red is hot, like a fire or a burn, and it’s vital to life like blood and hearts. If you feel embarrassed, you might blush, and the heat you feel on your face is red.

9. How would you determine the number of skis that are sold in Sweden every year?

Answer: Similar to the windows in Seattle problem, this question asks you to show how you would think through a problem, even if you don’t have access to the necessary research materials.

First, you could search for data on how many people live in Sweden, how many ski shops there are, and how many Swedes own skis. Then, you could look for sales data on winter sporting equipment. With that information, simply make an educated guess.

10. Tell me a joke.

Answer: Companies value their culture, and this question lets you reveal your dazzling personality.

Whether it’s a knock-knock joke or a pun-based quip, just make sure you choose something that’s not offensive. Here’s a good example: How many psychologists does it take to screw in a lightbulb? Just one, but the lightbulb has to really want to change.

11. What are five things you could do with a sharpened pencil other than writing?

Answer: Now it’s time for some out of the box thinking.

You can get as creative as you desire: erase mistakes, hold your hair bun perfectly in place, stake a small plant, remove mud from the bottom of your sneakers. Draw a face on it to create a little “pencil person” sculpture. Have fun with it.

12. Would you rather fight one horse-sized duck or 100 duck-sized horses?

Answer: This is an amusing question from Whole Foods.

If you prefer to approach big challenges one at a time, opt for the equine-sized duck. But if you’d rather tackle a bunch of smaller problems simultaneously, choose 100 duck-sized horses.

13. If you could have dinner with three people who are no longer alive, who would you choose?

Answer: Rather than list your deceased grandparents or family members, choose people who were visionaries in your industry to reveal your knowledge and passion.

If you’re in tech, for example, you might say figures like Steve Jobs of Apple, Charles Babbage (known as the father of computing), Grace Hopper (one of the first programmers), or Alan Turing (a forefather of artificial intelligence).

Now that you know how to answer these challenging questions, get out there and conquer your next interview. Good luck!

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