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7 Killer Interview Questions Managers Should Ask Prospective Hires ?

Forty-six percent of new hires don't last longer than 18 months, primarily due to "poor interpersonal skills," according to a study by leadership training company Leadership IQ, despite the fact that candidates are arguably more qualified than ever before. Certainly, they're more educated: 873,000 Americans are projected to earn master's degree in 2016/17 (a more than 50 percent rise since 1997), according to the U.S. Department of Education. The bottom line is that a candidate's resume isn't the only — and at times not even the most important — predictor for staying power or long-term success.

Forty-six percent of new hires don’t last longer than 18 months, primarily due to “poor interpersonal skills,” according to a study by leadership training company Leadership IQ, despite the fact that candidates are arguably more qualified than ever before. Certainly, they’re more educated: 873,000 Americans are projected to earn master’s degree in 2016/17 (a more than 50 percent rise since 1997), according to the U.S. Department of Education. The bottom line is that a candidate’s resume isn’t the only — and at times not even the most important — predictor for staying power or long-term success.


(Photo Credit: BAM Corp/Flickr)

Your goal, as a manager, is to cut through the sea of buzzwords, degrees, and bullet points to see the potential employee within – and to determine how well he or she will fit with the rest of your team.

Do You Know What You're Worth?

“If [an employer] find[s] a candidate who has less experience than their competition, but has stronger growth potential and seems to be a better cultural fit, the employer may feel encouraged to hire that person,” notes recruitment expert Edward Fleischman.

The interview is the most logical forum to make this sort of assessment of a candidate’s cultural compatibility, and specifically, the particular questions asked in the interview are what allow an interviewer to get a sense of his or her personality.

While there is no one “right” or “wrong” answer to a question like “How would you describe yourself in one word?,” looking out for certain uniformly positive traits (or red flags), is never a bad thing, and insightful, open-ended interview questions provide a good lens through which to do so. 

As Fleischmann explains, “Though the specific personality traits that employers are looking for are subjective to the role and the organization, some qualities that are a good indication of success in a role include organizational and communication skills, great team player, strong leadership skills, an ability to think on your feet, drive, and initiative.” 

While instincts play a big role in determining a candidate’s integrity, certain questions can shine a light on compatibility better than others. To this end, we’ve compiled a roundup of some of the most interesting personality, soft skill-oriented interview questions asked by some of the country’s most desirable companies to help identify a potential hire’s best not-on-paper skills.

“Why Shouldn’t I Hire You?”

One of the most compelling questions we came across comes from Jay Gould, CEO and cofounder of Yashi, a New Jersey-based video-ad tech firm.

“Everything you need to know can be learned in the moment when you look a candidate in the eye and ask them, ‘Why shouldn’t I hire you?’” Gould explains in an interview with Fast Company.

For Gould, the point of the question is to assess the three most crucial traits he looks for in a new hire: “integrity, self-awareness, and transparency.”

“How they answer the question is just as, if not more, important than the answer itself,” he explains. “If they they think too long, or can’t answer the question at all, they may be hiding something. If their answer is genuine then you have a contender,” he says.

According to Gould, an emotionally intelligent interviewer can tell whether an interviewee is being forthright and sincere by paying attention to “eye contact, body language, and voice inflections.”

Furthermore, he says, “People who are upfront about their shortcomings possess the element of humility that makes them a likable person you want to work with.” 

More Zingers

1. “Are you driven by the determination to succeed or the fear of failure?”

Source: Tom Koulopoulos, author and founder of the Boston “biztech” think tank, Delphi Group.

“There is no right answer to this question,” says Koulopoulos. “What I’m looking for is what motivates this person to work hard. I do not judge ambition; it comes in many forms. Notice, by the way, that I’m asking if fear of failure ‘drives’ him or her, not ‘paralyzes.'”

2. “Walk me through the first five things you would do if you got this job.”

Source: Kristi Hedges, executive coach, leadership development consultant, and author.

The point of asking this question, writes Hedges on her blog, is to get a gage on a candidate’s strategic thinking, prioritization skills, and execution style.

3. “What motivates you to get out of bed in the morning?”

Source: Brad Jefferson, CEO of Animoto, a cloud-based video service.

“What are they most inspired by?” explains Jefferson of what the question can reveal. “Is it because there’s a goal? Is it to beat the competition? Is it to work on a specific task? I really try to get in their head about what’s going to keep them going.”

The question also serves as a barometer for how the candidate’s motivation will translate in a work setting. “There will always be ups and downs in any business, and you want to make sure the person will be equally motivated during difficult times, if not more so.”

4. “Describe your proudest moment.” 

Source: Jay Gould, CEO and cofounder of Yashi.

“If they begin listing their professional accomplishments, they are missing an opportunity to illustrate their depth of character, or they might just be trying too hard to put their best foot forward,” explains Gould of why he likes the question. “There’s also a chance they just aren’t being honest.”

5. “Tell me something that’s true that almost nobody agrees with you on.”

Source: Pieter Thiel, co-founder of PayPal and president of hedge fund Clarium Capital, in a speech given to kick off his book “Zero to One” at Columbia University in 2014.

“It sort of tests for originality of thinking, and to some extent, it tests for your courage in speaking up in a difficult interview context,” Thiel later said of the question. “It’s always socially awkward to tell the interviewer something that the interviewer might not agree with…Most people think originality is easy, but I think it’s actually really hard, and when you find it, it’s really valuable.”

6. “What didn’t you get a chance to include on your resume?”

Source: Richard Branson, co-founder of Virgin Group, in his book, The Virgin Way: Everything I Know About Leadership.

“Obviously a good CV is important,” writes Branson, “but if you were going to hire by what they say about themselves on paper, you wouldn’t need to waste time on an interview.”

Tell Us What You Think

Do you have an insightful open-ended interview question to share? We want to hear from you! Leave a comment or join the discussion on Twitter.

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22 Comments on "7 Killer Interview Questions Managers Should Ask Prospective Hires ?"

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Let’s try this instead:

How would you describe the company in one word?
Why should I work here?
Is the company driven by determination to succeed or fear of failure?
What drives turning the lights on every morning?
What is the companies most shameful moment?
What does the company hold to be true that non of it’s employees agree with?
What else are you not telling me about the posted position?

Employers need to be scrutinized just as much as prospective employees and in some cased probably more so.


“Forty-six percent of new hires don’t last longer than 18 months”

That’s cute. Most jobs don’t last that long anyway before the layoff notices get handed out. Maybe we should be asking these questions of our elected officials who keep sending our industries overseas and to Mexico. Kick any who blink tot he curb.

Interesting… and more than likely they will be asked more often now that this article is out. They’re just questions. You are who you are. Don’t bother to hide that just to get hired – it’s going to come out eventually anyway. Less stress on you if you just stay yourself from the get go. The one problem I do have with this is I can see it being presented in interviews with folks struggling to find those minimum wage jobs to support their families. Where getting the job means more than you can imagine. I think this is just… Read more »
Bhagwan Iyyengar

It’s intresting, Ofcourse given nothing is just as straight forwad and there are complex situations, Age, Experience, Demonstrated and visible Behavior, Values, Culture other than claims of Skills, Competencies and achivements on the CV, Looking Inside the Org, Looking Outside, Looking from Competetion, The Time frame itself has a great impact but in reality how many( HR/Sales) personnel are Trained and validated to be qualified/certfied interviewers?


Fired 4 times in 4 years? I would not bother to bring Mr. Miller in for an interview.
Maybe the reason the other people quit doing the work was because of him.


I do love this article as it provides a good insight, but to an extent I have to agree with JP that some companies go through the interview process because it forms part of policies and procedures and they already know who they want in the position. If only more companies dealt with integrity and look at the person on a whole to discover the best fit for their organisation and having curve ball questions as listed above is a great way of discovering the person behind all the nerves and brilliant academics.

Eriq Mkwanazi

The best article,educational and insightful.


I find asking someone in an interview ” how would your best friend describe you and what does your best friend like /dislike about you?” Is a great way to find out if the candidate is self aware and open to criticism or other people’s opinions or suggestions. Most people won’t expect this question, so it will be a hard one to have practiced a response for, which will give you a good idea of Thier honesty.


I really like these questions. Seem more “real” than the usual ones that I’ve encountered. # 6 is especially a favorite of mine as I have been working for nearly 30 years & in order to make it through the ‘applicant tracking software’ I have to can my resume to resemble the posting. In answering this question I would be able to share details about how my years of experience have taught me to relate easily to the president of the company or the cleaning staff and to make all of them feel welcome & comfortable in working with me.


I absolutely love comment 12 by JP. It is so true. Half of these interviews are
total BS. I am a legal assistant with years of experience and now they want a degree in lieu of experience. It’s a joke and yes it’s true, you need to know someone.

People ought to just grow up and quit nit picking these things. You can either do the job or not. They will either train you or not. Most of these people are just fishing for candidates without even having a position open. 99 percent of the jobs out there are going to be for people that other people know. If you don’t know the people then you will get cut out. If an employer is hard up then they wont bother with asking this garbage. They need to stop teaching this garbage in college to the human resource people too.… Read more »
I don’t usually respond to these things but “John Miller”–I know you, I’ve worked with you before and I promise you the reason you have been fired 4 times in 4 years is not because you were doing the work of 2-3 people. It’s quite clearly because of your attitude. Then again, it made me laugh, so thank you. I think my own company could use some more open-ended questions that will get people out of their canned, rehearsed responses and better predict overall fit, flexibility and work style as we generally have an idea of qualifications before we schedule… Read more »

Re salary negotiations, I try to have three offers and then point out that Co A offers $15, 000 more than you and Co B offers $18, 000 more than you. Why?

I might then ask if that is their salary policy or do they just not have the money? If policy, why would I choose to work there? If ni money, theb that is all the more reason to offer me more, because of what I can do for their cimpany!


Some of the questions are insightful. I would be interested in questions that pertain to interviews on entry level jobs. We have a number of people applying for school or a free education and their motivations for applying are thwarted. It’s hard to weed these out. Any suggestions?

P Hughes

I have been asked 5 of these questions in interviews. The one about no one agreeing with you on one issue/point is a difficult one & is probably more about what you say about being the only one to think a certain way or how good you are at explaining your perspective. I think the 1st 5 things you would do can be a difficult one, because you have not yet been immersed in that company’s culture/policies and are unaware of so much.

Kathy Lynch
This is a great article. I loved #6, it made me think and it didn’t take long for me to have an answer. I answered these questions while reading the article, like a quiz on Facebook only harder. I really enjoyed it and the way it made me think. I didn’t go at this article looking for the answers to the questions…Well, maybe a little…but what I got was things that made me use my head. Yes, the questions were not what I expected, but that’s what I liked about them. Most interviewers I’ve seen ask, can you give me… Read more »

Well Mr. Miller, maybe an objective read of your own post will give you an indication of why you are having trouble holding on to a job. If you exhibit this toxic attitude at work, I wouldn’t care how hard you worked, I would let you go as well.


Trully a good article. From both perspectives and given some questions are for a academic result i can still use these in some of my interviewing


Good article


Number 6 is not makingy any sense.


Number 6 is not making any sense.

John Miller

I really don’t know who writes this tripe. It looks like some 20 something dim bulb given the lazy quoting of other people (bordering on an appeal to authority fallacy), the lack of originality and response area being twitter. Nobody gives a kitty about character in business any more. I’ve been fired 4 times in 4 years after doing the work of 2-3 people (with proof). People are lazy, dirty and will use another person instantly.

Your questions predict nothing.

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