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Can You Answer This CEO’s Favorite Interview Question (That Everyone Gets Wrong)?

Before your next interview, heed the advice of 16 CEOs and business leaders and learn how to answer the tricky questions that stump everyone.

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Be prepared for anything

A job interview is an incredibly stressful situation, and that’s before your potential employer throws a curveball at you. Correctly answering a tricky question that’s designed to be tricky can be a sink-or-swim moment for hopeful job applicants dreaming of landing a new, well-paying gig. It can seem impossible to do that in the moment, but it isn’t—not if you know the questions that may be coming and have some insider information on what you should and shouldn’t say. Here is the infamous interview question the CEO of Duolingo asks, along with 15 other tricky questions that CEOs and business leaders spring on candidates, and smart advice that will help you ace the answers.

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What would someone who doesn’t like you tell us about you?

Because no one knows you quite like your enemies, the CEO of Doulingo, Luis Von Ahn, asks this tricky interview question to all prospective employees. As you might imagine, the wrong answer is that everybody likes you. According to Von Ahn, that shows you’re either unrealistic, lying, or clueless. Another big no-no? Blaming other people for misunderstanding you and not taking responsibility for your actions. Instead, be honest (with your potential employer and also yourself), and try your best to explain something you need to improve upon. For example, maybe you sometimes get short with people during crunch times, which, Von Ahn says, is common and understandable. Just make sure to keep your answer short and simple, without sugarcoating your flaw or getting defensive. That’s also good to keep in mind when answering the question, “So, tell me about yourself.

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Manager Table with Desktop Computer and Business Notes Inside the Office.

Where do you see yourself five years from now?

In general, the truth will serve an applicant better than saying anything simply to please the interviewer, says Pratibha Vuppuluri, chief blogger at She Started It!, an online resource guide for working moms. Regarding this tricky interview question, Vuppuluri would like to hear an answer along the lines of: “In five years, I see myself as team leader.” Why? “This may sound too aspirational for some, but for me, it’s being honest with your personal career goals,” she explains. Additionally, it’s not necessary to commit yourself to that particular company by saying, “I still see myself working here,” because nobody really knows if they will still be in the same place in five years’ time.

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How do you see yourself contributing to this company?

It sounds simple, but it can definitely trip people up. But that’s not why Jeremy Ong, founder and CEO of the personal-finance blog HUSTLR, asks this question to all potential job candidates. The best answer he has received to date is: “If you want me to perform my role at its best, I would like to have a lot of autonomy and less micromanagement. I would like a company that judges me based on the impact that I bring to the table, not by the hours I sit at my desk.” He believes this is the perfect answer because it demonstrates the confidence, personality, and culture fit of the candidate.

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What’s the worst job you’ve ever had, and why?

Jaime Chapman, founder and CEO of the career-services company Begin Within, always starts with this interview question that “knocks candidates off course and makes them demonstrate their level of professionalism, often revealing red-flag behaviors.” She follows it up with: “What was the best job?” There’s not really a right or wrong answer to either, but Chapman says she’s looking for “top-notch work ethic, authenticity, and coachability.”

How a person deals with an unexpected question is also telling. “I like to see a people’s brains hard at work and get to know their process,” she says. “When someone wants to work at my company, given the nature of our work, I expect a lot from interviewees because if hired, the candidate will literally be helping other people learn how to interview for jobs. I can’t hire a pot to call a kettle black. I need skilled interviewers on my team.” If you’re looking for jobs with the greatest growth potential, check out this list of the highest-paying jobs in every state.

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How do you like to be managed?

Patrick Algrim is an experienced executive who has spent a number of years in Silicon Valley hiring and coaching some of the world’s most valuable technology teams. He’s also the author of a tricky interview question guide. His ideal answer to this question would go something like this: “The best managers that I’ve worked with always set clear goals, paths to achieving those goals, left the door open in terms of being able to ask questions, and had patience with us when we needed a helping hand in getting the job done. Because of that, I felt like growth was achievable both on a personal level and on a company level.” This answer is ideal because it’s focused, it sets the candidate’s expectations, and it demonstrates a clear understanding of what they need to succeed (and an ability to communicate it). What else do you need to succeed? Employers are looking for these 17 soft skills right now.

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At your last job, what’s a time when you screwed something up, and what are the first three things you did in response?

Both as a leader and a coworker, Karen Bussen, CEO of Farewelling, is influenced by the energy of her managers and team members. In interviews, she “likes to ask candidates questions that probe their style and perspective when it comes to stress, conflict, and communication.” Bussen doesn’t want to hear a rote answer to this question. Instead, she’s looking for “a thoughtful reply that shows the candidate is someone who takes responsibility, is a self-starter, has some self-awareness, and maybe knows how to organize a project as well.” Interviewees will score bonus points if they can tie their responses back to the business.

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Why do you want to leave your current job?

The purpose of this question isn’t to put you on the spot, says Jon Hill, CEO of The Energists, a management consulting and professional search firm for the energy industry. Instead, it’s “to see how someone responds when given the chance to talk bad about someone. After all, many people have complaints about their bosses, coworkers, and the organizations they work for.” Hill says that if the response involves a series of gripes about their current employer, the applicant is not right for his company. The key is to keep things professional and appropriate. By the way, here’s how to look for a job while you still have one.

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What do you enjoy doing in your spare time?

You bring all of yourself to a job, not just one specific part. And that’s why Shawn Breyer, owner of Breyer Home Buyers in Atlanta, wants to know what potential employees do after hours. “The answers to this question tell interviewers whether or not you’re going to be an asset to the company or not,” he says. “Do you spend your free time in front of the TV, going out and eating unhealthy, playing video games, and sitting around the house? Or do you spend your time pursuing a hobby, exercising, reading and studying, and spending meaningful time with friends and family?” Breyer says he would prefer the latter. Why? He believes that a person like that will be recharged after fun, fulfilling weekends and come to work with positive energy and new ideas, ready to lead and to grow personally and professionally. Should your hobby be your job? Here are 9 signs you’re in the wrong career.

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What should I know about you?

Sometimes, an interviewer may do away completely with traditional interview questions. Carisa Miklusak, CEO of tilr, will ask candidates an open-ended question like this because it gives the applicant “an opportunity to sell themselves by outlining some of their accomplishments at previous positions and highlighting what they are passionate about.” The ball is in your court, which can feel like a lot of pressure—but is actually a huge opportunity.

Plus, Miklusak likes that this question leads to a conversation, as opposed to a Q&A session. “The best interviews are often conversations because you can have a thoughtful dialogue and really get a feel for someone without the pretense of a formal interview or without them reciting back memorized answers,” she says. “It’s tricky because many interviewees feel the need to break the awkward silence and will just keep talking. However, it’s through this type of engagement where you really get to know who someone is and what they’re thinking. You also get to see how they handle pressure.”

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If I asked your colleagues or current boss, how would they describe you?

Vasyl Dzesa, Chief Operating Officer of Coding Ninjas, always starts an interview with this question. What does he expect? “An honest and adequate evaluation of the person’s strong and weak sides.” For future reference, here are 8 ways to build trust with your coworkers. Additionally, Dzesa asks candidates what they are currently reading and what the last book they finished was. “Lots of candidates can name only something from the school program, which is always a bad sign,” he says. So pick up a new book and be ready to talk about it and the impact it is having on you as an informed, interesting, and well-rounded person.

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Tell me something you have learned or discerned during your interview process that you think I may not want to hear?

Adrienne Cooper, Chief People Officer at FitSmallBusiness.com, concludes her interviews with this doozy of a question because she “values coworkers who aren’t afraid and are well-adept at addressing uncomfortable feedback out in the open.” While Cooper actually dislikes trick questions, she does “want to challenge desirable applicants with the task of providing feedback that might make them, or myself, uncomfortable—all the while viewing how they think on their feet.” There’s no perfect answer to this tricky interview question, but, she says, “it’s important to hear the ‘why’ behind the applicants’ feedback as they deliver constructive criticism about the interview process.”

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What can your hobbies tell me that your résumé can’t?

Company Folders has made Inc.‘s list of the 5,000 fastest-growing private companies in America for three consecutive years, so founder and CEO Vladimir Gendelman knows a thing or two about the hiring process. He considers this question crucial to understanding a candidate, but not for the reason you might think. “I don’t care about the candidate’s hobbies, but when they have one, it’s a good sign because people who have hobbies are more likely to have goals and a love of learning new things,” he explains. Plus, how serious candidates are about their hobbies can provide insight into leadership, learning, and problem-solving skills. If their passion doesn’t come through when discussing a hobby, it likely won’t come through at work either.

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What’s your biggest weakness?

Jill Gugino-Panté, director of the Lerner Career Services Center at the University of Delaware, knows full well that this question “causes a lot of clients to panic because you’re supposed to put your best self forward in an interview and not talk about your weaknesses.” But it cuts to the chase and reveals a lot about a candidate. “We all have weaknesses, and no one is going to match 100 percent of the job requirements listed,” she says. “And having self-awareness of your weaknesses is a good thing, and something employers look for in a candidate.” It is a smart idea, however, to flip your weakness into a strength by discussing in clear terms what demonstrable steps you are taking to improve.

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What do you think about our company’s values?

The CEO of Transformify, Lilia Stoyanov, is looking for a candidate who’s done his or her homework. That’s what a person’s answer to this tricky question will reveal. “If the candidate has not done any research and has no idea what our brand stands for, s/he is not a match,” she says. “Lack of engagement and curiosity early on is a red flag. [This question] also reveals the values of the candidate and if s/he can express these values openly.” So, before you sit down for an interview, spend some time on the company’s website, reading about its philosophies, values, and history. Then use your newfound knowledge during the interview to demonstrate your thoughtfulness and commitment. That said, it’s important to be curious about the right things.

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If you could work anywhere, where would it be?

According to Kate Zabriskie, founder and CEO of Business Training Works, an HR consultancy in Maryland, answering this question can be tricky because “unless you are interviewing at your dream company, you can give an interview-ending answer.” For example, “I’d be a Broadway star” could easily lead to a potential employer saying, “You do realize this is an accounting firm, right?”

Zabriskie suggests answering this question by “focusing on the kind of place you want to work rather than a specific company.” Speak in broad brushstrokes, saying things like: “I have an entrepreneurial spirit, and I like challenge and change. For that reason, start-ups are where I do my best work. There is something about building an organization that gets me excited each morning when I work in a start-up environment.” Of course, that only works if you are indeed applying to such a business.

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What questions do you have for me?

While Gary Fortier, the Chief People Officer at Cengage, may not actually ask this question outright, it is one of the things he pays attention to most. He’s not looking for a particular response to a particularly tricky question; he’s looking at the process and logic that a candidate applies when crafting a response. “It’s very rare for me to set up a question that has a distinctive pass/fail answer associated. Rather, I pay attention to people’s ability to apply reason to difficult situations,” he says. “[I want] candidates who think critically about the components of a question, and in return, ask me questions—a lot of questions.”

Jeff Bogle
Jeff Bogle is an Iris Award–winning photographer, avid traveler and English football fanatic who regularly covers travel, culture, cars, health, business, the environment and more for Reader's Digest. He is the proud dad of teen daughters.