18 Unusual Job Interview Questions Top CEOs Ask (And Why They Ask Them)

As a job candidate, you‘ve likely spent hours preparing for the classic interview questions that get asked at almost every company – "What are your greatest strengths and weaknesses?", "Why do you want to work here?", "Tell me about a time you faced a challenge and how you overcame it."

But if you‘re interviewing with an iconic, innovative company like Zappos, Facebook, Birchbox or Capriotti‘s Sandwich Shop, you‘d better come prepared for the unexpected. Because to build disruptive, industry-changing organizations, today‘s top CEOs need employees with very particular skills. Skills that your average, garden-variety interview questions simply can‘t assess.

So to separate the creative geniuses from the merely competent, elite executives have developed their own arsenal of tricky, surprising, and downright weird interview questions. And if you want to impress them, you‘d better have some genius answers prepared.

Why Are CEOs Getting So Creative With Interview Questions?

The short answer? They‘re fighting a war for talent, and the stakes have never been higher. Research from Korn Ferry shows that by 2030, there will be a global human talent shortage of over 85 million people. Companies will be battling for a limited supply of high-performing employees. And the organizations that snag the best and brightest minds will be the ones that win.

Moreover, in an era when artificial intelligence can handle many routine cognitive tasks, CEOs know that the human skills their employees bring to the table are more important than ever. Skills like:

Skill	Why It Matters
Creativity & Innovation	Generating novel ideas to stay ahead of the competition
Critical Thinking & Problem Solving	Analyzing complex issues and finding strategic solutions
Emotional Intelligence	Collaborating, communicating and leading effectively
Adaptability	Staying agile in the face of constant change

By asking unexpected, thought-provoking interview questions, CEOs gain valuable insights into a candidate‘s abilities in these pivotal areas that a run-of-the-mill Q&A session simply can‘t provide. Let‘s take a closer look at some CEO favorites and what they reveal:

"On a scale of 1 to 10, how weird are you?" – Tony Hsieh, Zappos

What makes this question brilliant is its ability to assess several important traits in one query – self-awareness, individuality, and culture fit. Tony Hsieh built Zappos into a customer service powerhouse by celebrating weirdness and encouraging his employees to march to the beat of their own drum.

When a candidate ranks their weirdness, the interviewer isn‘t just looking for a number. They‘re looking for the reasoning behind it. Does this person embrace their own unique quirks? Can they laugh at themselves? Would they mesh well in a workplace that values off-the-wall thinking? There‘s a "Goldilocks" principle at play – you don‘t want to come across as too conformist, but you also don‘t want to be so eccentric that you‘d have trouble fitting into the team. Answering in the 6-8 range and giving a witty, self-deprecating example of your own weirdness is a great approach.

"What would you do in the event of a zombie apocalypse?" – Ashley Morris, Capriotti‘s

While the chances of a zombie outbreak impacting your job duties are (hopefully) low, this zany hypothetical is a great way for an interviewer to test a slew of professional skills, such as:

• Strategic planning – how would you secure resources and protect your team?
• Decisiveness under pressure – what swift actions would you take to contain the threat?
• Adaptability – how would you adjust strategies as the situation evolved?
• Leadership – how would you inspire and mobilize others amidst the chaos?
• Creative problem-solving – could you find innovative solutions with limited resources?

A candidate with strong survival instincts in a fictional crisis is more likely to remain cool, clearheaded and resourceful when real-world challenges strike. To ace this question, walk the interviewer through your thought process and emphasize how you‘d leverage your professional strengths to guide your team through uncertain times.

"A hammer and a nail cost $1.10. The hammer costs $1 more than the nail. How much does the nail cost?" – Jeff Zwelling, ConvertRO

On the surface, this question tests basic algebra skills. But its real purpose is to provide a window into how a candidate‘s mind works. Do they have strong analytical abilities? How do they approach solving problems? Can they admit when they‘ve made a mistake and adjust accordingly?

The correct answer is that the nail costs $0.05 (if the nail is x, then x + (x+1) = 1.10). But the interviewer cares less about getting the right number and more about the reasoning process. They want to see the candidate break the problem into steps, consider all the information carefully, double-check their work, and demonstrate the humility to acknowledge and fix any flaws in their initial calculation. Talking through your approach out loud allows you to showcase your smarts even if you don‘t land on the right answer right away.

"Tell me something that‘s true, that almost nobody agrees with you on." – Peter Thiel, Clarium Capital

This doozy of a prompt from billionaire investor Peter Thiel, who‘s known for his contrarian views, is designed to identify original thinkers who aren‘t afraid to voice unorthodox opinions. Thiel knows that the business leaders who change the world often have perspectives that fly in the face of conventional wisdom.

A great answer demonstrates that you‘ve thought deeply about an issue, have unique insights to share, and can back up your beliefs with logical arguments and examples, even if they‘re unpopular. Maybe you believe that unlimited PTO policies are counterproductive, or that open office plans actually stifle collaboration. The key is to take an uncommon stance you genuinely believe in and build a compelling case for why you hold that view.

Other Dastardly Difficult Questions to Prepare For

• "What‘s the last costume you wore?" – Katia Beauchamp, Birchbox
  • Assesses: creativity, sociability, cultural fit
• "Are you the smartest person you know?" – Miranda Kalinowski, Facebook
  • Assesses: confidence, self-awareness, humility
• "How much do you charge to wash every window in Seattle?" – Scott Thurell, Emerald Technology Partners
  • Assesses: analytical thinking, ambition, salesmanship
• "What kind of tree would you be?" – Barbara Corcoran, Shark Tank
  • Assesses: personality, self-perception, storytelling ability

Mastering the Curveball: Your Interview Question Playbook

The strategies for knocking unexpected interview questions out of the park are simple in theory, but take practice to execute with poise. Below is a step-by-step playbook for wowing your interviewer with an unforgettable answer to even the weirdest question:

1. Don‘t panic. Take a deep breath and consider the question carefully before responding. Saying "Let me think about that for a moment" buys you precious seconds to formulate a thoughtful reply.

2. Clarify if needed. If any part of the question is unclear, don‘t be afraid to ask for more details. Answering the wrong question won‘t impress anyone.

3. Identify the intent. Think about the deeper qualities or skills the interviewer is likely trying to assess with their quirky query, such as creativity, logic, values, or personality.

4. Break it down. Tackle complicated questions piece by piece. Identify the key points you need to address, or steps you‘d take to solve a hypothetical issue.

5. Apply relevant examples. Even if the question is abstract, try to ground your answer with brief, concrete examples of how you‘ve applied the skills in question in your past work.

6. Admit what you don‘t know. If asked to do complex calculations or answer something you‘re unsure about, be upfront about it rather than fumbling your way through. Honesty is always the best policy.

7. Have fun with it. Many wild card questions are designed to let your individuality shine. Don‘t be afraid to answer with humor or a charming personal anecdote if it feels natural.

8. Practice makes perfect. Prior to any CEO interview, review some of the most out-there questions they‘ve been known to ask. Practice answering out loud until you can do so with confidence and flair.

Ultimately, answering unexpected interview questions is about applying the same skills CEOs want to see in their employees every day – the ability to think on your feet, solve problems creatively, communicate persuasively, and adapt to novel challenges. Do all that while letting your unique personality and passion shine through, and any CEO would be crazy not to hire you.

The Bottom Line

No matter your industry or experience level, preparing for curveball interview questions is essential in today‘s competitive job market. By combining diligent practice with strategies to keep your cool and showcase your strengths, you‘ll be ready to bat a thousand at your next high-stakes interview.

So the next time a CEO asks you how your life experiences have prepared you to survive a zombie apocalypse, you‘ll be ready to respond with a story that knocks their socks off. In this battle for talent, a creative, quick-thinking candidate is the ultimate secret weapon – and with the tips above, that candidate is you.