19 head-scratching questions bosses have actually asked at job interviews

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Try your hand at solving these bizarre puzzles. GlobalStock/Getty Images
  • Think you’ve been asked some tricky job interview questions? We’ve compiled a list of some of the toughest prompts people have faced.
  • Examples include “How would you measure the weight of the earth?” (Facebook) and “Tell me a joke” (J.P. Morgan Chase).
  • Note that Google, and possibly other companies, have stopped asking brainteaser-type questions in the last few years – so lucky for you, there’s a chance you may not hear these at your next job interview.

Job interviews are stressful.

Even if the hiring manager is nice, and even if you feel you’re a perfect fit for the role, no one would fault you for breaking out in a sweat and fumbling a few questions.

But some job interviews are more nerve-racking than others. Over on Glassdoor, people have shared the tremendously tricky (and frankly, often bizarre) questions they have been asked during interviews at Amazon, Microsoft, McKinsey & Company, and elsewhere.

Google has said it’s banned brainteaser-y questions, with other companies following suit. So, you may not encounter these exact questions in your job interviews.

Still, it’s worth trying your hand at these puzzles to see how well you’d fare in these job candidates’ shoes.


There are 25 horses and 5 race tracks. How many races need to be run to select the top 5 horses?

Job: Business operations analyst at Google


You’re about to get on a plane to Seattle. You want to know if you should bring an umbrella. You call three random friends of yours who live there and ask each independently if it’s raining. Each of your friends has a 2/3 chance of telling you the truth and a 1/3 chance of messing with you by lying. All three friends tell you that yes, it is raining. What is the probability that it’s actually raining in Seattle?

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Job: Facebook data scientist


Having an infinite supply of water and two containers, one for 3 litres and one for 5 litres, how would you measure 4 litres?

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Job: Software development engineer at Amazon.com


You are on a game show. There are three doors. Behind one of them is a prize; the other two have coal. The host knows which door holds the prize. You choose door #1. Before it is opened, the host opens door #3 and reveals a lump of coal. You have the choice to stick with the door you chose originally or switch to door #2. What do you do?

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Job: Program manager at Microsoft


What would you do if your exec was on a plane to Germany to give a highly confidential presentation, and you realised that he forgot to take the presentation with him?

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Job: McKinsey & Company executive assistant


Three friends with different salaries need to find out their average salary without revealing individual salaries to each other. How?

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Job: Software developer at Bloomberg L.P.


How many scale measurements does it take to know which of eight balls weighs the most? How many would 28 balls take?

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Job: Software engineer at Cisco Systems


What is the exact angle formed by the hands on a clock when the time reads 9:30?

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Job: Bain & Company associate consultant


How have you ensured that you have kept Walmart’s image in the community?

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Job: Store manager at Walmart


Tell me a joke.

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Job: Investment banker at J.P. Morgan Chase


How would you measure the weight of the earth?

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Job: Facebook products


What would you do if you found someone stealing?

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Job: Sales associate at Best Buy


Estimate the revenue of M&M’s in the US.

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Job: Commercial due diligence intern at Ernst & Young


If I were to tell you that you aren’t ambitious, how would you refute me?

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Job: Associate consultant at Liberty Mutual


If you had to eliminate one of the 50 states, which one would it be?

Job: Senior project manager at HealthStream


You are a new manager at Burger King. On your first day, your senior manager tells you that sales have dropped 50% from the previous quarter. What are the three questions you would ask?

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Estimate the number of cell phones sold every year in the US.

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Job: Consultant at Strata Decision Technology


On a scale of 1 to 10, how confrontational are you?

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Job: Project manager/implementation consultant at Epic Systems Corporation


How many people can you fit into Texas?

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