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15 Unconventional Questions to Help You Conduct an Interview

Conducting a productive interview is not an easy task for a recruiter. If a candidate is well-prepared and gives great answers to standard questions, it can be challenging to determine if they are truly the right fit for the position. To save time and make better hiring decisions, we suggest looking at candidate interviews from the perspective of global companies with experience. They are not afraid to experiment. Are you?


1. “Why do you want to work with us?”

At Philz Coffee, interviews start with this question even before the in-person meeting. Jacob Jaber, the CEO of the company, notes that it helps avoid wasting valuable time on candidates who aren’t potential Philz Coffee employees.

2. “So, what’s your story?”

Richard Funess, Managing Partner at Finn Partners, immediately confuses candidates with this question. Its ambiguity and lack of a right or wrong answer force people to think on their feet and come up with a story. If an applicant hesitates or takes a long pause, it suggests that their thinking may not be broad enough. It’s not so much about what the candidate says but how they handle themselves.

3. “Why have you changed jobs N times in N years?”

Shama Kabani, the founder and CEO of The Marketing Zen Group, asks this question to understand how professionally a candidate has evolved. Based on the answer, you can immediately gauge what motivates them, under what circumstances they are willing to switch jobs, and how they speak about former bosses. The key is not the number of job changes but the reasons behind them.

4. “Describe yourself in one word.”

Craig Myers, Talent Acquisition Director at Cadence Design Systems, likes to ask this question to Generation Z and individuals with limited work experience. It’s essential to see how a candidate thinks outside their comfort zone. If they answer positively, follow up by asking what word they would use to describe themselves negatively. This response will reveal if the candidate acknowledges their shortcomings.

5. “Is there something you passionately believe in, but almost no one supports you in it?”

Peter Thiel, co-founder of PayPal, asks this question casually during a conversation. It aims to assess the originality of a person’s thinking and whether they can openly share their judgments in an unusual setting. Thiel believes that thinking outside the box is quite challenging and more complex than commonly thought.

6. “Do you consider yourself smarter than everyone you know?”

According to Larry Ellison, the co-founder and former CEO of Oracle, this question is well-suited for young professionals. It might seem that this question is intended to filter out the arrogant, but Larry is actually looking for those who will answer, “Yes!” If a candidate hesitates to assert themselves and names someone else, they’ll invite that person for an interview. Larry Ellison aims to hire true intellectuals.

7. “On a scale from 1 to 10, how lucky do you feel in life?”

Tony Hsieh, the CEO of Zappos, often asks candidates to rate their life’s luck on a scale from 1 to 10. As with other similar questions, there is no right answer, but there are concerning ones. For instance, if a candidate rates themselves at the extreme ends, either 1 or 10, it raises alarms. If they give themselves the lowest rating (1), it suggests that everything in their life has been a series of unfortunate events beyond their control. A rating of 10 indicates a lack of self-trust and belief in their own capabilities.

8. “Tell us about a time when things didn’t go as planned: your expectations were not met, or a project failed.”

Tony Knopp, the co-founder and CEO of Spotlight Ticket Management, uses this question to identify candidates with the right approach and work ethic. Candidates’ responses often involve blaming others, downplaying their contributions, or reflecting on how they leveraged their experiences for personal growth. Tony Knopp avoids hiring those who speak negatively about others and shift blame. If a candidate takes responsibility for their actions and can apply past experiences positively, they are more likely to become part of Spotlight Ticket Management.

9. “What annoys you the most?”

This unexpected yet intriguing question initially stumps candidates but helps provide a broader understanding of their personalities. After all, everyone gets annoyed by something. Lynn Taylor, an expert in workplace issues and author of bestsellers, believes that this question primarily aims to give the recruiter insight into whether the person can be a daily team member. What irritates them? Is there something in the company that annoys the candidate? It’s essential to understand this before starting a collaboration.

10. “What animal would you consider your spirit animal?”

Ryan Holmes, the CEO of Hootsuite, used this question to select an excellent team member. During the interview, the candidate mentioned that she liked ducks, which exhibit external calm but are actively busy and working underwater. This became a fitting description for her future role.

11. “When was the last time you wore a costume?”

This question can be customized for any candidate because it’s not about the costume but the reason behind wearing it. David Gilboa, the co-founder of the eyewear manufacturer Warby Parker, believes that the candidate’s response to this question effectively demonstrates whether they can fit into your company culture and contribute to its success.

12. “Could you arrange this deck of cards?”

Christopher Penn, Vice President of Marketing Technologies at SHIFT Communications, hands a shuffled deck of cards to candidates during their meetings and asks them to organize the cards correctly. Candidates can seek clarification on what the correct order is, but the point of the exercise is to assess their questions and their ability to adapt to a new and unfamiliar task. Penn does not hire candidates who become lost or stay silent.

13. “How would you test an elevator?”

Microsoft used to ask this question during interviews years ago, but it can still be a useful question for your candidate interviews. No knowledge of elevators is required; it’s about how the candidate analyzes an unfamiliar situation and evaluates ways to solve it.

14. “You’ve seen our office. What would you change about it?”

The first thing this answer reveals is how well the candidate aligns with the company’s culture. Additionally, it allows them to offer their opinion on the spot. According to Nancy Divine, Vice President of HR at Axceler, this helps the company not only hire the right employees but also brings new interior design ideas to the table.

15. “I’m not entirely convinced that you’re the right fit for us…”

This statement can turn a regular interview into a stress interview. But Mitchell Harper, one of the CEOs of BigCommerce, uses it when hiring someone for a sales role. How the candidate behaves, what questions they ask, and how they react are all indicators of their suitability. Candidates may ignore the statement, agree with it, or challenge it. Those who challenge it are often the ones Harper hires.

To Ask or Not to Ask?

Of course, not all companies require creativity and the ability to adapt quickly. You can stick with standard interview questions if that’s sufficient for your needs. However, if you’re looking for a true A-player, a sales manager, or a position that involves making unconventional decisions, you can select suitable questions from our list and use them in your interviews. The experience of global companies shows that such an unconventional approach helps find the candidates who are a perfect fit for your organization.

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