Executives Reveal 6 Toughest Interview Questions to Find Top Candidates

Most candidates have the common job interview questions down pat. You know the drill: What’s your greatest strength? Your weakness?

However, some unique questions can be very telling of how well the candidate will fit into the team and succeed. We asked a handful of C-level executives about their favorite, toughest interview questions that have proven to reveal the most successful candidates.

Here are six of the toughest, most revealing interview questions. Drum roll please:

1.  ‘Have you ever failed?’

“Most smart people who interview will find a way of finessing this question,” says Mark Settle, CIO of BMC Software.

Those who say they’ve never failed are usually weeded out—everyone has failed at some point. “So, this question really forces the interviewee to ‘come clean’ about their people and problem management skills,” Settle says.

2. ‘What’s your favorite TV show?’

Joshua Weiss, CEO of TeliApp, a mobile app development firm, likes to ask questions that dig deep into the personality of his candidates.

Oddly enough, it’s not the technical questions that stump his candidates—it’s questions like their favorite TV shows, movies, pranks, etc. These are the questions that often weed out their highly qualified pool of applicants—of which they hire only 1 percent.

“We value opinions, especially when they differ, because it invites multiple streams and thought processes to solve complicated challenges,” Weiss says. “However, the method of communication of those differing opinions for us is paramount, and we find that our list of questions is so surprising to candidates that they often don't have time to think up a prepared response, which gives us a unique insight in to their personalities.”

3. ‘Tell me about your current boss or manager.’

Steve Schaffer, CEO of Offers.com, says this is one of his toughest questions. More specifically, he asks: “From your point of view, what is he or she good at? What are their weaknesses?”

It’s crucial to tread lightly here. The boss is paying close attention to not only your answer but also how you answer. Prepare a tactful answer.

It’s a good idea to—overall—talk positively about your past manager, even if you really disliked the guy. Be positive and talk about what you learned from his strengths and weaknesses.

4. ‘What processes have you instituted since assuming your current position?’

This is another gem of a question that Settle shared with us.

This question is great if you want to figure out  “whether a manager knows how to build organizational capability through process definition/discipline or whether they lurch from one problem/project to the next,” Settle says.

A great, solid answer includes a full explanation of how that process was worked and its results.

5. ‘How long are you willing to fail at this job before you succeed?’

That’s a trap if I’ve ever seen one! The question likely induces many “wait, can you repeat the question?” as a response.

Jon Sterling, CEO at Interview Circuit says this is his favorite question because candidates can’t immediately figure out what he wants to hear. Therefore, the answer can be very telling.

A good answer, he says, would be, “I'm willing to stick with this job for as long as it takes to succeed,” told CareerBliss. “That answer would indicate they have endurance and they're looking at this as a long-term opportunity.”

One poor way to answer is to dodge the question and talk about something else, which happens from time to time. More bad answers: “A few months,’ or, ‘I don't know, what do you think?”

6. 'Why are you here?'

The tech team here at CyberCoders finds this question to be not only a great ice-breaker but also a deep look into a candidate’s unique motivations. "Sometimes I will get thoughtful gems and insight into a candidate's personality from their response to this question," says CyberCoders CTO Matt Miller.

However, "if the candidate avoids or evades the question, then it shows me a nervousness and insecurity that would give a glimpse as to how they handle stressful situations (e.g. interviews)," Miller says.

Bonus Tip: Brainteasers are Out, Behavioral is In!

Did you hear about Google’s notoriously tough standards of GPA, test scores and crazy brainteasers are not a great predictor of success? Employers can reveal a lot more about the quality of the candidate by asking behavioral questions like the ones above!

Read more about it: Want to Succeed at Google? Nail the Behavioral Questions