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20 Interview Questions Smart Bosses Never Ask Job Candidates

Unless you don't want your interviewee to work for you.

We've all been there before: You've got an important opening for a position on your team you'd like to fill quickly. You've got the budget you want. You've narrowed down the candidates to a few highly sought-after, deeply talented individuals who can help your company achieve success. When they come in for a meeting, you want to challenge them with your interview questions—but not so much that you turn them off. Assuming you know what to ask, what are the questions you definitely shouldn't?

These 20 questions right here. We spoke to more than ten of the brightest minds in business—CEOs, HR managers, entrepreneurs—to compile the greatest hits of interview questions that are worse than useless. (Bonus! In most cases, we've also included what questions you should be asking instead. You're welcome.) And for more tactics for upping your boss game, check out these game-changing strategies that every boss should know.

"Where do you see yourself in five years?"

Man Interviewing a Woman

A terribly unhelpful cliché. "Companies change as do candidates," says Sol Garger, senior director of product at ZipRecruiter. "It is unfair to ask this question especially if there is no long-term hiring path for this position."

Geoff Scott, a career adviser and resume expert at, agrees. "Most of us don't know what we want in five years—that's why the turnover rate is so high nowadays," he says. "If an interviewee says they see themselves at your company in the future (as management or otherwise), it's impossible to tell if they are being sincere or not. They are simply telling you what they think you want to hear."

Instead, interviewers should get what they are trying to learn through other questions. Scott says you should opt for, "What areas of this field excite you?" or "What intrigues you most about working for our company?"

"If the interviewee is sincerely interested in working for you, they'll know about your products and the kind of roles they would fill as your new hire," says Scott. "Measure their enthusiasm with such questions—legitimate passion is a better indication that they'll be a long-term employee than their answer to the 'five years from now' question." Now, if you're on the other end of the job interviewing table, make sure you don't give one of these answers.

"What is your biggest weakness?"

Job interview, Business man

"This is not a good question as the candidate usually will give a false negative such as 'I work too hard,'" says Garger. "The intent of this question is usually established to see if the candidate has self-awareness."

This is one of the interview questions that makes it hard for the candidate to answer in any way that isn't a terrible cliché. "Think for a moment," says Jameson Slattery, vice president of global marketing for health-science company Colorescience. "If you were to openly and honestly speak on your biggest weakness, what are the odds that you're hired by that company? If a candidate has done any sort of interview preparation, they will have thought about their answer to this question, which will most likely not be entirely truthful." And for more advice, here's how to be a better leader (and man).

"Can you work well under pressure?"


"Of course, the interviewee is not going to say no to that," fumes Jesse Harrison, founder and CEO of Zeus Legal Funding, who oversees the company's recruiting and hiring. Any questions where it is obvious the interviewer is looking for a specific answer is not going to get you any added understanding of the candidate. For more great leadership advice, here's what every first-time boss needs to know.

"Will you speak up in a meeting if you think it's going off track?"

Business Meeting, Interview

"Closed-ended (yes/no) questions are of virtually no use in interviews, because candidates know what the 'right' answer is," says Mikaela Kiner, founder of Uniquely HR. Even if the answer to some of these are not as obvious as "Do you work well under pressure?," they still create a sense that there is a right or wrong answer and dampen the possibility of getting any real insight into a candidate or his or her interests and abilities. And speaking of business meetings, make sure yours run as smoothly as possible with these secrets.

"How would you deal with a frustrating coworker?"

Annoyed Coworkers,

"If I ask you a question like 'What would you say to an unhappy customer…,' it's easy enough to make up a perfect response," says Kiner. Instead, she says interviewers should focus on behavioral interview questions such as, "Tell me about a time when…," which gives the candidate a chance to describe an actual event in their work life and how it was handled. "The difference is not subtle," she adds. "The behavioral question tells you if the candidate has actually been in this situation before. Their feelings about the situation are bound to come through too, and you can see if they were frustrated, irritated or patient when dealing with that customer." For more insight into how to be the best business leader possible, read through the wisdom of successful startup founders.

"Are you married? Have kids?"


"Personal questions about family or marital status should be avoided since they are not relevant to the job," says Kiner. If such details arise from the conversation organically, it's fine to discuss them in a friendly way, but asking pointed personal questions is rarely a good idea. If you are trying to determine if family commitments might impact the candidate's availability, simply ask if they are available to work overtime—don't put it in the context of their personal life. Now while you're thinking about questions to ask in your next interview, check out what one leading C.E.O. always asks his applicants.

"What race/religion are you?"


"From my experience, I advise to always play it safe and keep the interview questions on a professional level," says Slattery. "If you happen to bring up one of those topics, it could trigger an emotional response, or it could just supply you with information that doesn't help in making a hiring decision. You can always get to know the person after you hire them." And we compiled even more business and leadership advice from leading C.E.O.s here.

"Tell me about yourself"


"Of course, you want extra information on a candidate to get a feel for what they are like and what they have achieved in the past," says Steve Pritchard, HR consultant for Anglo Liners, a road marking company. "However, this question is not focused enough and opens up the opportunity for candidates to panic, waffle, and consequently, waste time."

Instead, an interviewer is better off focusing on a specific topic. Pritchard gives the example of asking interviewees to describe a challenge they faced and overcame, or simply a favorite brand and what they love about it. "Remember, candidates should feel relaxed at all times during an interview because this is when you see the true side of their personality," he says. And if you want to project power, buy one of these office chairs that executives swear by.

"Why do you want to work for us?"

Job Interview

"Candidates feel they have already answered these questions previously and then rack their brains for more information, which can be off topic and irrelevant to the role available," says Pritchard.

It's better instead to get more specific during an interview, asking things like, "What is it about this role that appeals to you?" or to ask them if there was a particular campaign or product of the company's that they admire. "These types of questions are a subtle way of testing a candidate's genuine enthusiasm for the role, as an applicant who truly wants the job will have thoroughly researched your company," he adds. And here is one top C.E.O.'s advice on how to run a company that people will want to work for.

"What would your worst enemy say about you?"


This variation on "What's your biggest weakness" that has become one of the more popular interview questions in recent years sets a negative tone in an interview that should be focused squarely on the strengths of the company and individual. "From my experience, companies that capitalize on the strengths of their employees, instead of trying to change their 'biggest weakness,' have the most success," says Slattery. "Instead of asking what their worst enemy would say about them, ask "How would your best friend describe you?" And don't miss more advice on how to run a positive workplace here. 

"You're among eight candidates for this position. Why should we hire you?"


A little pressure and healthy competition can bring out better performances from workers. But turning an interview into an episode of The Apprentice is unlikely to give you any insight into how a prospective employee would actually perform in his or her work. "Not only are you asking the interviewee to compare him or herself to people they do not know, but you're putting them in a position where it's difficult to look good," says Slattery.

Instead of creating a zero-sum situation, he says it's better to frame the question like, "Based off what you know about the company, and what we've discussed today, how do you think you would be able to help us?"

 "We expect hard workers here. What kind of worker are you?"

Pair of hands on a desk, Interview

"Don't ask any behavioral question that prefaces the question with a statement of how things are around here," says Fletcher Wimbush, CEO of The Hire Talent, an employment assessment company. "By telling the candidate what the situation is and what you like or dislike you basically are handing over the correct answer, so unless the candidate wasn't listening then they will know exactly how to respond in a way you will like them."

Instead, it's better to ask them slightly more open-ended questions, such as "What is a work project of which you are particularly proud?"

"What motivates you?"

Interview, casual

"This question is a fail because 90% of respondents will reply that their kids for family are their motivator," says Danielle Kunkle, vice president at insurance supplement company Boomer Benefits. "I suggest changing the verbiage to 'What motivates you to do your best at work?' This wording will then usually result in an answer closer to what the interviewer is looking for: money, recognition, chance for advancement."

"What has been your greatest accomplishment?"

Application, Interview

Similar to the previous one, this interview question tends to elicit heartwarming answers about one's kids or family, but doesn't tell you much about how the candidate would be as an employee. Kunkle suggests instead modifying the answer to speak specifically to employment history: "Tell me about the one thing you are most proud of in your work history?"

"If you were an animal, what animal would you be?"


"Nontraditional interview questions can be a fun way to break up the monotony of an interview and learn something interesting about a candidate," says's Scott. But "this worn-out interview staple has outlived its usefulness."

Originally devised to get interview subjects thinking creatively, this has now become a question as cliché and predictable as "What do you expect to be doing in five years?" Feel free to ask more creative questions, but be sure they are relevant to the position the candidate is applying for—and that it's actually a creative question.

"What were you earning in your last position?"


Whatever the candidate was earning at his or her last job does not actually have anything to do with this current position. Their previous organization may have been paying them much more than they expect in this new position, or perhaps much less. Any salary questions should focus on the current position, what they expect, and what your organization can afford. Anything else is a distraction. Also, If you need to negotiate salary details, make sure you know how to negotiate anything and win.

"Do you drink socially?"

Handshake, Interview

"Your team may love Thursday night cocktails together, but you can't ask an applicant if they intend to participate," says Francine E. Love, founder and principal attorney of Love Law Firm, PLLC. "This can run afoul of disabilities legislation. A similar type of question to avoid is 'Do you do drugs?' This can go to disabilities and other protected health information (i.e., the applicant takes daily medication for a chronic illness). The EEOC (which enforces the federal anti-discrimination statutes) considers prior alcohol and drug addiction to be disabilities that are protected." If you're currently working at a place that loves company happy hours, be sure you know how to drink with your boss.

"Are you a team player?"


This is another of those yes-or-no interview questions that will get you a canned answer. Instead, ask the candidate to tell you about a time when they had to collaborate with a few colleagues to solve a problem.

"What do you bring to our team?"

Interview, Job Application

You're much better of asking them interview questions about what aspects of the work most interest them or where they have notched up the biggest successes.

"Wow! You're tall. I bet you played basketball in school, right?"

Any interview questions about candidate's physical appearance treads onto dangerous territory.

"It may seem like just a continuation of March Madness excitement, but it can lend itself toward disability-type responses," says Love. "For example, someone may be tall or short based on a genetic condition. This line of questioning should also avoid weight or other appearance inquiries."

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Alex Daniel
A journalist based in Brooklyn, New York. Read more
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