How Would You Answer These Top 10 Most Difficult Job Interview Questions?

CultiVitaeCareer Advice, Interview Tips0 Comments

difficult job interview questions

How Would You Answer The Top 10 Most Difficult Job Interview Questions?

Curveball interview questions are becoming more common as interviewers sigh at the cookie-cutter, rehearsed answers to the standard “What are your weaknesses?” question. You know, the answer that is touted off as an actual strength (i.e. – too hard of a worker, too nice, too ambitious and willing to volunteer for every task). Sound familiar?

Hiring managers and recruiters started to ask these curveball questions, not because there is a right or wrong answer, but to assess:
1. How well does this person think on their feet or under pressure?
2. What is their stream of thought at deriving at an answer
3. Can I gather anything about their personality (creative, sense of humor, serious, logical, etc.)?

While some of these curveball questions might have you scratching your head and you may not know the answer, you should always try to think of a logical process on how you would find the answer. The worst answer is, “I don’t know” and not even attempt it.

What are the Top 10 Most Difficult Interview Questions?

I’ve decided to type out my answers without any advanced review time or prep time to look over these questions. I already am going to preface this post with, “I’m not a math whiz nor engineer, so don’t judge me!” 😉

Here are my answers to these top 10 difficult job interview questions compiled from GlassDoor’s 2016 survey. I’d love to hear your answers, too!

So, without further ado, let’s get started!

1. SpaceX asked, “When a hot dog expands, in which direction does it split and why?” 


My answer: I think the circumference at both ends of the hot dog are the first to split. Which direction? Maybe into a diagonal cut. Why? Because I swear the last few hot dogs I’ve eaten looked this way. The center has the most density so the ends break first.

2. Whole Foods Market asked, “Would you rather fight a 1-horse sized duck or 100 duck-sized horses?”

My answer: Definitely a 1-horse sized duck. If there were 100 mini horses running around I would have a hard time herding them and capturing them because they are so fast. I might also get kicked in the head several times if they were swarming from all angles. A duck on the other hand is much less threatening. I would attack it from the back to avoid it’s beak. Not to get too gruesome, but I would definitely hack it’s wings and legs first so it can’t move anywhere.

3. Dropbox asked, “If you’re the CEO, what are the first three things you check about the business when you wake up?”

My answer: The first, I would make sure there are no system issues or complaints overnight about any technical errors. The second item of business is to check urgent emails and messages. I like to get these out of the way to clear the day to focus on new business. Third, I would check in with my teams to make sure everyone had clear goals and direction.

4. Urban Outfitters asked, “What would the name of your debut album be?”

My answer: Cracking Toes. I have a Spotify playlist titled this and it’s filled with all of the relaxing songs I listen to over and over again on repeat and never get sick of. I came up with this name when I realized how alleviating it was to crack your toes. You know that moment when you are lying down and your toes scrunch against each other? That moment is a real pressure relief.

5. J.W. Business Acquisitions asked, “How would you sell hot cocoa in Florida?”

My answer: If it were summer time in Florida I would definitely make hot cocoa milkshakes or hot cocoa frappuccinos. Anything ice cold in a hot summer sells well and hot cocoa powder can be blended into anything. It just has to have the flavor, it doesn’t need to be hot. Serendipity for instance has got this recipe down. Their signature item is the frozen hot chocolate. It’s really delicious!

6. HubSpot asked, “If I gave you $40,000 to start a business, what would you start?”

My answer: I’m a fan of online e-commerce businesses because the overhead is minimal and you can operate 24/7. I would want to be a site known for best prices such as Alibaba and Amazon, but sell something very niche and be a one-stop shop. The money would be going to site development, marketing, and inventory.

7. Trader Joe’s asked, “What would you do if you found a penguin in the freezer?”

My answer: I would make sure to call the animal control line as I admit I have zero knowledge of penguins except that they are always in their Sunday best. Hopefully the penguin is able to survive until they come. I just might give it some fish in case it is hungry. Not without paying for it first, of course.

8. Boston Consulting Group asked, “If you were a brand, what would be your motto?”

My answer: Cultivate your life. It’s actually the motto of my career coaching service, CultiVitae. I came up with it because everyone has an opportunity to shape and grow their lives. I believe it is so incredibly to always continue growing in all areas of your life, relationships, career, self-development, interests, causes, etc.

9. Delta Air Lines asked, “How many basketballs would fit in this room?”

My answer: I would first take the measurements of the room for its volume, height x width, length. I would then measure all of the furnitures volume as well. Next, I would find the measurements of the ball, height x width. I would subtract furniture volume from room volume and divide it by the ball’s measurement.

10. Uniqlo asked, “If you had $2,000, how would you double it in 24 hours?”

My answer: I’d put it all on black. Just kidding. I would scour the internet for a really good deal on items like tickets or used electronics in great shape. I would then flip it at a discount, but a heavy mark up on what I paid. If I couldn’t find buyers in time, I would try a pawn shop and negotiate for the full $4K if it meant I needed to come back with more goods at a later date.

Would You Hire Me? 🙂

Phew! That was fun. Reflecting back on these, I can’t say I definitely walked away with a job offer, but I know the interviewer walked away with knowing a lot more about my personality, presence and thought process.

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