A guide to the trickiest interview questions that the world’s top CEOs ask
Securing a job interview is your chance to shine.
But what happens if the interviewer throws a curveball of a question?
Researchers at Resume.io collated questions that some of the world’s most successful business leaders ask during interviews – and created actionable tips on how to answer each one of them.
The result is a handy guide that gives readers the knowledge to answer even the most challenging interview curveballs.
Get ahead of the competition whatever the question asked!
Here’s a preview of the first section of the guide:
When smart leaders ask tough questions, they’re usually more interested in how you figure out your answer than whether you get it right. They’re not trying to trick you; they’ve sat in that interview seat, too, and they’re hoping your answer will prove you the perfect fit for your dream job. Resume.io has gathered 13 thought-provoking examples of such questions from top bosses, complete with analyses and tips, in a new infographic.
This infographic was created by Resume.io The source of the study can be found on the following link: https://resume.io/blog/interview-questions-by-successfull-business-leaders
13 Interview Questions Asked by Successful Business Leaders (And How to Answer Them)
1.
| Business Leader: | Elon Musk, CEO at Tesla |
| Question: | “You’re standing on the surface of the Earth. You walk one mile south, one mile west, and one mile north. You end up exactly where you started. Where are you?.”[1] |
| What it uncovers: | This question shows whether candidates can think and resolve issues quickly after being presented with data. The answer is often irrelevant, what matters is the process undertaken to reach a conclusion. [1] |
| How to answer: | The correct answer is the North Pole. Using the directions would take you in a triangle from the North Pole back to your starting position. Pro tip: If you can’t answer the question, you can still demonstrate your suitability by: Being honest instead of trying to talk around it. Asking follow-up questions to show curiosityBreak the problem down to demonstrate your processes[1] |
2.
| Business Leader: | Jules Walter, Product Lead for Monetization at Slack |
| Question: | “Among the people you’ve worked with, who do you admire and why?”[2] |
| What it uncovers: | This question will demonstrate your values without being directly asked about them, as what you admire in others tells a hiring manager a lot about what you find important. [2] |
| How to answer: | If a name doesn’t immediately come to mind, choose someone who is relevant to the role you are applying for or a former colleague who matches the company’s values. |
3.
| Business Leader: | Chad Dickerson, Former Etsy CEO |
| Question: | “Tell me about a time you really screwed something up. How did you handle it and how did you address the mistake?”[2] |
| What it uncovers: | An interviewer may ask this question to assess your humility, self-reflection, problem-solving, and communication skills.[2] |
| How to answer: | Go over the mistake and take responsibility for it, but don’t dwell on it. Be honest about how the situation made you feel. Explain how you resolved the issue to show your problem-solving skills. Share any steps you took to ensure it wouldn’t happen again.[5] |
4.
| Business Leader: | Laura Behrens Wu, CEO of Shippo |
| Question: | “What are some things outside of work that you’re irrationally passionate about?”[2] |
| What it uncovers: | By asking this question, a hiring manager can discover how you motivate yourself and how driven you are through hearing you talk about your hobbies and passions.[2] |
| How to answer: | Select hobbies that showcase values that align with the company, particularly community or charity volunteering or something health and fitness-related. Pro tip: Avoid making it seem like you won’t be focused on the role you are applying for by all-consuming extracurricular activities.[6] |
5.
| Business Leader: | Luis Von Ahn, CEO of Duolingo |
| Question: | “What would someone who doesn’t like you tell us about you?”[7] |
| What it uncovers: | Interviewers ask questions like this one to assess how honest and self-aware you are, and whether you are open about your shortcomings. [7] |
| How to answer: | Don’t try to avoid answering the question, as this will be noticed. Instead, use your answer to show that you are self-aware and open to improving yourself. [8] Pro tip: Use this as an opportunity to reframe your qualities in a positive light and show off your personality. If you identify a weakness, demonstrate what you have done to address it.[8] |
6.
| Business Leader: | Lilia Stoyanov, CEO at Transformify |
| Question: | “What do you think about our company’s values?”[9] |
| What it uncovers: | An interviewer may ask this question to find out how much research you have done about the company as well as whether you’d be a good fit for their culture.[9] |
| How to answer: | Map the company’s values against your own experience and find clear examples of where you have demonstrated their values in the past.[10] Pro tip: As part of your research before the interview, make sure to visit the social media profiles of the company for hints of their culture and values. |
7.
| Business Leader: | Sara Blakely, CEO at Spanx |
| Question: | “Describe yourself in three words.”[11] |
| What it uncovers: | By asking this question, hiring managers can get a sense of your self-awareness, your decisiveness, and whether you will fit with the company.[11] |
| How to answer: | Select three words that showcase:[12] How your mind works: Creative, curious, analytical, methodical Your character: Kind, honest, resilient, friendly, quiet Something interesting about you: tidy, optimistic, calm, generous |
8.
| Business Leader: | Porter Braswell, Co-founder and CEO at Jopwell |
| Question: | “What does success mean to you?”[2] |
| What it uncovers: | This question is often asked to open up a more free-flowing conversation where you will reveal more about yourself, your values, and goals.[2] |
| How to answer: | Give detail of what success means to you in a way that highlights your talents. Is it about great teamwork or giving back to the community or doing something you’re passionate about?[13][14] Pro tip: Before the interview, pick out examples of your greatest successes and identify why they meant so much to you. Even if you don’t get asked this question, it’s a good exercise to help you understand what matters to you. |
9.
| Business Leader: | Sarah Fetter, Founder & CEO at 121 Ventures |
| Question: | “When was the last time you changed your mind about something important?”[2] |
| What it uncovers: | By asking this question, the interviewer can get a feel for how your belief system or core values have been changed and what impact this had on you.[2] |
| How to answer: | Showcase your flexibility in changing your belief system or core values by giving an example and using the SARI formula to explain it:[15] Situation: What happened to make you change your belief? Action: What actions did you take as a result? Result: What impact did these changes have? Interesting Features: Go into more detail about what the impact of this change has had on your career, including how it would influence you in this role. |
10.
| Business Leader: | Roli Saxena, President at AdRoll Business |
| Question: | “What are you better at than most anyone else? What’s your superpower and how will you leverage that to make an impact at this company?”[16] |
| What it uncovers: | Interviewers ask questions like this one to hear in your own words how you will help them as a company.[16] |
| How to answer: | DO: Focus on a key strength that aligns with what they have identified in the job description. Give examples of this superpower in action. DON’T: Brag about yourself or your achievements. [17] Compare yourself to other candidates, or existing staff at the company.[17] |
11.
| Business Leader: | Tim Chen, Co-founder and CEO at NerdWallet |
| Question: | “If you were in my shoes, what attributes would you look for in hiring for this role?”[2] |
| What it uncovers: | By asking this question, the hiring manager will be able to identify what you consider are the keys to the role’s success. This is especially insightful if the role you’re applying for includes leading a team.[2] |
| How to answer: | Use this question as an opportunity to highlight your strengths and any specific skills you know will be useful to the company. Pro tip: If you have experience hiring, you could also briefly explain your thought process when looking for the right candidates.[2] |
12.
| Business Leader: | Pema Lin-Moore, VP of People Operations at WRA |
| Question: | “What’s one critical piece of feedback you’ve received that was really difficult to hear? Why was it difficult and what did you do with that information? What did you learn about yourself?”[2] |
| What it uncovers: | This question helps the interviewer assess how you respond to feedback that is out of line with how you see yourself, testing your resilience.[2] |
| How to answer: | Be sure to pick constructive criticism and walk the interviewer through the process you went through as clearly as possible. Pro tip: Use the STAR method to explain the situation:[18] Situation: How did you receive this feedback? When was it and who was it from?Task: What was the negative feedback? Action: How did you respond in the moment and what did you do to make improvements? Results: What happened as a result? How has this helped you in your career since? How could it help this company if they hired you? |
13.
| Business Leader: | Cindy Smith, Head of Strategy and Partner Operations at Upstart |
| Question: | “Tell me about a topic that you’ve taken it upon yourself to learn about.”[2] |
| What it uncovers: | An interviewer may ask this question to test your curiosity, assess your tenacity around learning and evaluate how you tackle hard topics.[2] |
| How to answer: | Walk the interviewer through the topic you’ve learned making sure to cover why you decided to study more about it, how you went about learning it, and what impact did this new knowledge have on yourself and your career.[2] |
Whether you’re facing Elon Musk or Sara Blakely across the table in the interview room, you now know how to answer their toughest questions while showcasing the skills that you can bring to any organization. Time to start applying for your dream job!
Sources
1. Kohler, C. (2021). Elon Musk’s Favorite Job Interview Question (Plus How to Answer It). topinterview.co.uk
2. First Round. (2021). 40 Favorite Interview Questions From Some of the Sharpest Folks We Know. firstround.com
3. Smith, J. (2016). Here’s the perfect response to 9 tricky interview questions. businessinsider.com
4. Cheary, M. (2017). Five character questions, and the answers that will get you hired. reed.co.uk
5. Doyle, A. (2020). Interview Question: Tell Me About A Time You Made A Mistake. thebalancecareers.com
6. Indeed. (2020). Interview Question: What Are Your Hobbies and Interests? indeed.com
7. Cain, A. (2017). A CEO shares his favorite job interview question — and the reason why people answer it wrong. businessinsider.com
8. White, J. (2021). How to Answer the Interview Question: “How Would Your Worst Enemy Describe You?”. wikijob.co.uk
9. Bogle, J. (2021). Can You Answer This CEO’s Favorite Interview Question (That Everyone Gets Wrong)? rd.com
10. Indeed. (2021). Values Interview Questions: What They Are and How To Answer Them (With Examples). indeed.com
11. MasterClass. (2021). Sara Blakely’s Tips for Hiring a Team: How to Hire Employees. masterclass.com
12. Connley, C. (2019). Suzy Welch: What to say when an interviewer says, ‘Describe yourself in 3 words’. cnbc.com
13. Indeed. (2021). Interview Question: How Do You Define Success? indeed.com
14. Torres University, Australia. (2018). What does success mean to you? torrens.edu.au
15. Fisher, N. (2017). Behavioural Interview Question – Tell Me About A Time You Changed Directions Quickly At Work. nataliefisher.ca
16. First Round. (2021). 20 Underrated Qualities to Look for in Candidates — And 50+ Interview Questions to Suss Them Out. firstround.com
17. Doyle, A. (2022). How to Answer “What Can You Do Better Than Other Candidates?”. thebalancecareers.com
18. Indeed. (2021). How To Answer “How Do You Handle Criticism” (With Tips and Example Answers). indeed.com
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