The 10 most revealing interview questions

Revealing interview questions

When was the last time that throwing a “what is your greatest weakness?” at a candidate got you an informative, unique response? Chances are, it’s been a while.

A job interview is only as informative as the questions you ask. And when you stick to the same clichés (the “why should I hire you?” type queries) then you probably won’t learn too much about your candidate.

Yes, some of the basics are standard for a reason – meaning, the responses to these questions tell you important things you need to know. But sticking exclusively to a standard list of questions can put you on autopilot, and keep your candidates relegated to their rehearsed responses. After all, the goal of an interview is to get at who a candidate really is – and, in turn, decide if they’re the right fit for the position.

To help, we asked a few hirers to share their go-to revealing interview questions – the questions that divulge the most about a candidate and give them real insight into whether they should hire them (and why).

With that, here are ten revealing interview questions (from real hiring managers) to take your next interview to the next level.

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

Ian Yates, co-founder of Fitzii, uses this question to reveal an applicant’s approach 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,” he says.

2. “What is a quarter of a half?”

“You’d be surprised how many people don’t know the answer,” says Bob Bentz, president of ATS Mobile, adding that a lot of the candidates that do answer will raise their voice at the end, like they’re unsure. “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,” he says. (The worst response he gets? “I’m not very good at math.”)

3. “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,” says Erik Bowitz, a senior resume consultant at Resume Genius. “Improvisation in business is crucial, even if it’s sometimes awkward.”

4. “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,” says HR consultant Arlene Vernon.

5. “Where would you like to spend Thanksgiving Day?”

A response to this question will tell you a lot about a candidate, says Jeffrey A. Oster, founder and CEO of “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? Are you enthusiastically planning for the upcoming dinner or are you dreading it?” says Oster. “There are a lot of subtleties to the question that help you understand the applicant.”

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

According to Killian Branding founder Bob Killian, this question 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.”

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

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

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

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

9. “A co-worker keeps offering you advice that is contrary to what your boss has told you – but he or 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,” says Stephanie Ciccarelli, CMO and co-founder of “It helps us to evaluate a candidate’s writing skills, and, more importantly, their character and ethical decision-making process.”

10. “Is there a story about yourself and your career that you’d like me to know?”

According to Sarah Walton, founder and CEO of Better Way Moms, a candidate that really knows him or herself will smile and relax, and then start musing on a personal triumph or something they’ve learned. “When someone chooses to answer the question, I always find out something really fun about them, and learn more about them as a person,” she says. “When interviewing someone, 80 per cent of what we’re looking for is cultural fit – this question really helps me see what a candidate is made of.”

For more interview tips and tricks, download our free eGuide, Interviewing for success. Here’s a sneak peek:

See also:
7 best interview questions to hire temporary employees
7 telling questions that reveal a candidate’s true potential


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