10 Unexpected Interview Questions Designed to Get Insightful Answers

“What is your greatest strength?”

“Name a time you faced a challenge at work.”

You’ve probably asked these generic questions more times than you’d like to admit. The problem isn’t just that they’re passé — it’s that candidates can see them coming a mile away and they’ve prepped predictable answers to your predictable questions. Instead, you want to generate thought-provoking answers.

You don’t want to ambush candidates, of course, but derailing them from rehearsed responses can reveal new insights into their personality, instincts, and soft skills — like the ability to think on their feet and manage unexpected challenges.

Here are 10 intriguing and unexpected interview questions that candidates probably haven’t prepared for. They might just make for some insightful conversation too.

1. Describe yourself in one word

As it turns out, it’s actually pretty hard to summarize your entire person in one single adjective. Especially when you’re put on the spot.

This question is particularly ideal for those Gen Z candidates with limited work experience, says Craig Myers, director of talent acquisition at Cadence Design Systems. “There is no right answer to this question,” Craig explains. “We just want to see how new grads think on their feet and outside their comfort zone."

For a challenging follow-up question, consider asking them to name one negative adjective that describes them. It’s easy to boast of positive traits, but if your candidate can admit a flaw, it shows that they’re self-aware and always looking to improve.

2. Tell me about an interesting experience or encounter you’ve had recently

The best recruits come equipped with insatiable curiosity and a creative edge — two key traits that make an employee ready to contribute to a company looking to stand out in an ever-changing, competitive consumer landscape. As Nancy Brown, CEO of The American Heart Association, wrote for Fortune, “Creative thinking serves as a catalyst; it inspires us to engage in conversation and analysis, and to assess all that might be possible.”

You’ll also get a sense of their perspective and person: what they like, dislike, and value.

3. What is your biggest pet peeve?

While no one wants to stump candidates just for the fun of it, you do want to get to know the real them — and that means both the good and the bad. No one’s perfect: we all have things that push our buttons.

Workplace expert and author Lynn Taylor breaks the value of this question down perfectly in one of her publications: “[We] want to learn about what irritates you firsthand and are hoping you'll offer at least some insight: How do you handle minor frustrations? Are you easily rattled? Do your pet peeves arise routinely in the position?”

Ultimately, you’re getting towards a solid understanding of what it will be like to work with the candidate on a daily basis. This question may also help you learn something unique about them.

4. How do you define success?

This one can be tough for candidates. A response can easily snowball into an excessively long and sentimental story. It probes into their personal vision, while also assessing questions of what candidates can add to your company's culture.

The best candidates might already have a well-defined sense of purpose — and can point out how it resonates with your company's values. While there is no real “correct” answer to a question like this, it does tell you a few things, like whether they’re more motivated by personal gain or collective causes, and whether their perspective aligns with the team they’d be working with.

5. Do you consider yourself lucky?

Nothing makes or breaks a candidate more than their attitude. This seemingly awkward question is actually quite telling when it comes to determining a candidate’s outlook.

Look for candidates who combine a sense of optimism and gratitude for those people and opportunities that have helped them, while still hitting on those skills that have ultimately allowed them to achieve their successes. Those that have trouble attributing their accomplishments to anyone besides themselves or focus more on missed chances might raise a red flag.

6. Tell me about a time you disagreed with a manager’s instructions or point of view in the workplace. What did you do?

Hopefully, your candidate won’t tell you about a time when they screamed at a former boss, or on the other hand, pretend they’ve never disagreed with anything asked of them.

Their answer will uncover the candidate’s sense of professionalism and humility, along with their judgment and instincts. How a candidate goes about handling a disagreement with a fellow employee or manager speaks volumes about their character, and whether they’re actually ready to be a positive team player or not.

The best candidates will also have a natural understanding of when to take direction and when to ask questions, and will be able to tell you a story of a time when they felt the need to go against the grain and take a risk. After all, according to Pandora vice president of talent Sarah Wagener, following our instincts pays dividends. “There are lost opportunities for all of us when we’re not following our instincts," she says. "There have been moments in my career where I have needed to make a decision driven by instincts and my gut feeling. When I reflect back, these were career-defining moments.”

7. How will you tackle this specific project expected of the role?

Instead of having your interviewee tell their whole life story, this prompt forces them to focus on one key selling point of their resume — which will likely require them to think a bit more before answering.

To really get them thinking, ask the candidate how they would go about tackling a project expected of them in the position they’re applying for. “Have them highlight key components, including goals, who they’ll consult with (by title), what data they’ll analyze, how they’ll communicate with their team, the metrics for assessing their plan’s success, etc.,” suggests HR thought leader Dr. John Sullivan in an article for Harvard Business Review.

Take note of the aspects of their response that are innovative — as well as any critical steps they may have missed. Their response will shed light on their ambition and perseverance in executing an undertaking from start to finish, as well as their organization and project management skills. 

8. When have you failed? What did you learn from this experience?

New York Times best-selling author and Leadership IQ founder Mark Murphy puts it simply: “Experiencing failure is inevitable. But, some people handle those times a lot better than others. And, those are the people you want to hire.”

Getting back up, brushing the dirt off our shoulders, and pushing forward is critical in both our personal lives and careers, especially when we’re faced with an unforeseen obstacle. Even if they pause at first, see if your candidate can share a harrowing tale and how they’ve ultimately used the experience as a teachable moment. If they can’t talk about failure, you may have a case of an inflated ego on your hands, which is anything but a productive addition to your team.

9. What two or three trends in our industry might disrupt our work, and how should we go about meeting these changes?

Change can be intimidating. But your best candidates won’t think so.

Instead, they’ll be revved up in the face of a challenge, utilizing their comprehensive knowledge of their industry, foresight, and creativity to brainstorm ways to approach shifts in the industry landscape that will benefit the company and put you at the leading edge.

“No one can predict the future, but you want someone who is thinking about it every day,” says Dr. John Sullivan. Adaptability makes the difference between a hire that is good for the moment, and a hire that will prove to be an asset for your team long-term.

10. Why are you memorable?

Loaded questions do have their place in a good interview, and there’s nothing like an existential question to get them to dig deep.

This unexpected interview question forces candidates to not only think about what sets them apart from the other resumes in your stack, but also how others view them and the impact they’ll make at the company if hired. You’ll get a perspective into their honesty, humility, self-awareness, and confidence. Bonus points for candidates that can deliver an answer that’s clear and right to the point, just like a good elevator pitch.

Incorporate these 10 tough questions for more insightful interviews. Overall, you’ll narrow in on the best talent for your business and streamline your interview process, saving both you and your top candidates time and energy so they can get to work, stat.