The ten most revealing interview questions

Hiring Advice Human Resources Industry News & Insights Uncategorised Woman doing math in her head

There are standard interview questions that almost everyone asks:

    Tell me about yourself
    Why do you think you are a good fit for this position?
    What is your greatest weakness?
    Why should I hire you?
    Where do you see yourself in five years?
    Why did you leave your last job?
    Do you have any questions for me?
    And more…

They are standard queries for a reason: the responses to these questions tell you important things you need to know.

But it can get boring for the interviewer, asking the same questions every time, and since candidates are expecting them, they often have their answers rehearsed. It can help to throw a curve ball, or at least spice things up by taking a new approach.

I’m not going to recommend you go the Google route – which even they have reportedly abandoned – and ask something obscure like “How many lighthouses are there in Canada?” or “If you were stranded on a desert island with nothing but a left shoe and a vinyl copy of Neil Young’s Harvest Moon, how would you use these items to make muffins?”

Rather, I asked some hiring managers to share their favourite interview question, “The question you feel reveals the most about the candidate and gives you real insight into whether you should hire them, and why.”

Here are the top 10 responses. I hope you find some inspiration.

“Tell me about the last time you attempted to do something but failed? What did you learn from this experience?”

“This question is great because it reveals the applicant’s attitude to setbacks. A strong answer will include accountability for the individual’s role in the setback, rather than just blaming the circumstances – or worse someone else – and actionable lessons that the applicant will apply in the future.” Ian Yates, co-founder and managing director, Fitzii

“What is a quarter of a half?”

“You’d be surprised how many people don’t know the answer. In addition, a lot of people will answer correctly, but with a raised voice at the end like they are not sure. This is a negative in my mind in that I want employees that are confident in their answers. If they get it wrong, but say the wrong answer with authority, I just may continue to consider them. The worst response: ‘I’m not very good at math.’” Bob Bentz, president, ATS Mobile

“Where would you like to spend Thanksgiving Day?”

“The response can tell you a lot about the person. Are they family oriented? Interested in caring for others? Willing, or not, to put up with weird uncle Harry and willing, or not, to multitask in the kitchen? If you prefer to go to your mom’s, there’s a strong likelihood that you’re also going to turf that project onto your co-workers. Are you enthusiastically planning for the upcoming dinner or are you dreading it? There are a lot of subtleties to the question that help you understand the applicant.” Jeffrey A. Oster, CEO/CMO,

“What was the last thing you cheated on or lied about?”

“The idea is to see how honest they might be, but mostly how they handle the question in a professional manner, because improvisation in business is crucial, even if it’s sometimes awkward.” Erik Bowitz, Senior Resume Expert, Resume Genius

“Provide me with 25 adjectives or descriptors of your work personality and skills.”

“The more confident and self-aware the candidate, the deeper they can go.” Arlene Vernon, HR consultant

“What did you learn about us from our website?”

“The answer reveals two things: whether they did their homework to prep for the interview, and how well they can articulate what they understand about our firm.” Bob Killian, Killian Branding

“What would you tip on a $335 bill? Can you talk out how you got your answer?”

“Those who can do math quickly and accurately in their heads tend to be some of the best people in development, support and sales.” David Daneshgar, co-founder,

“If I wrote you a check for $1,000,000, what would you do with it?”

“I’m still in a growth phase of my company, so I need to hire workaholics who are not adverse to a bit of risk. The right answer would be something along the lines of ‘start a business,’ ‘play the stock market,’ or ‘invest in a startup.’ Elizabeth Chabe, Partner and CEO, High Touch Group

“A co-worker keeps offering you advice that is contrary to what your boss has told you–but she has achieved the most sales and is constantly praised in team meetings. How do you handle the situation?”

“We ask this during interviews that are in person and via email, as it helps us to evaluate a candidate’s writing skills, and, more importantly, their character and ethical decision making process.” Stephanie Ciccarelli, CMO and co-founder,

“Was there a question you wanted me to ask, that I didn’t?” Or “Is there a story about yourself and your career that you’d like me to know?”

“Someone who truly knows themselves will smile and relax, then probably start in about a personal triumph or something they’ve learned about themselves throughout their career. Someone who is nervous, or unsure of themselves will hem and haw and say something like, ‘No, I don’t think so. You asked me everything.’

“When someone chooses to answer the question, I always find out something really fun about them, and learn more about them as a person. When interviewing someone, 80% of what we’re looking for is cultural fit – this question really helps me see what a candidate is made of and how well he or she will fit.” Sarah Walton, CEO, Better Way Moms