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11 Hard Interview Questions to Challenge Your Candidates

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October 22, 2021

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While the interview is an essential part of the recruiting process, you only have a limited amount of time to ask questions.

That's why you need to make the most of it. If you want to level up your recruiting game, consider asking decidedly unconventional interview questions. Candidates have come to expect the same old interview queries, which they’ve prepped for ad infinitum.

By asking clichéd questions, you’ll only get canned responses. This won’t help you make hiring decisions. Minimizing the possibility of candidates serving up their well-rehearsed answers will provide you with more valuable insights you can use to make better decisions.

Here are 25 hard interview questions to challenge your applicants:

  • Can you share a story that reveals what values are important to you?

This question is known as a “value-based interview question.” While you need to hire candidates who have excellent professional abilities, you also should find people who share your company values. This makes them a better cultural fit.

It’s probably best to combine value-based interview questions with competency-based ones that focus on skills. Doing that will help you create a more comprehensive candidate profile, allowing you to make more objective hiring decisions.

To help you assess candidates’ answers, decide which values are most important to your enterprise. These are the core values all team members should share.

Candidates might talk about their work ethic or other values they'd bring to the work environment. Look for responses that provide insight into the individual's principles and passions.

  • Tell me about a time you disagreed with a supervisor’s directives. How did you handle it?

The response to this query can tell you a lot about a candidate’s willingness to overcome the unspoken taboo in our society about challenging a supervisor. It’s unavoidable—disagreement is an inevitable part of every workplace.

Bosses can make mistakes, and employees should be allowed the freedom to diplomatically point this out. Having team members who blindly follow your orders no matter what isn’t good for your company.

On the other hand, you won't want to hire someone who does this disrespectfully because criticism should be shared constructively. If a candidate's answer reveals they can't do this, they lack the ability to be a team player.

Another not-so-good answer to this question is the applicant saying they disagreed but kept their mouth shut. Employees should always share any concerns they have with their boss.

However, after sharing their opinions, they should follow a supervisor's orders even if they disagree. Of course, this shouldn’t apply if the boss asked the candidate to do something unethical.

  • Tell me about a time in your life when you failed. What did you learn from this experience?

A candidate should be self-aware enough to acknowledge their personal deficits while learning from their mistakes. An individual who can't admit failure may have a massive ego—not exactly the kind of person you want on your team.

Nobody’s perfect, and failure is an inescapable part of life. Being able to get back on our feet after a bruising defeat is essential, whether we’re dealing with a work debacle or a personal setback.

Some individuals handle failure a lot better than others.  The people who are good at dealing with it make better employees. That’s because they’ll transform the inevitable disasters that happen on the job into learning opportunities instead of wallowing in them.  

  • How much time are you willing to invest in failing at this job before you eventually succeed?

If you really want to throw a candidate for a loop, ask them this question. Not many applicants will expect a question like this.

By posing this question, you’ll see how committed they are to the inherent difficulties of the position. It will help you determine how much they're willing to persevere—a desirable quality in a job applicant.

A good answer might be a candidate saying they’re willing to stick with the job for as long as it takes to succeed. A not-so-good way to handle the query is by changing the subject or sidestepping it.

  • Is there a type of manager you would never want to work for?

This question will help you determine if a candidate’s personality fits your managerial style. Different management styles work for different employees depending on their work ethic, character, and values.

They should mention a few previous managers they admired and what it was about their style that brought out the best in them.

See if a candidate not only talks about the type of manager they would never want to work for but also identifies a management style that works for them. If they name a couple of different styles, this might indicate that they have some flexibility.

  • What's the most common criticism people have about you?

This question assesses the candidate's self-awareness and ability to accept criticism. Let's say an applicant gets defensive about criticism they received. In that case, this might be a red flag indicating they won't take criticism well when they start working for you. If they answer the question by saying they’re never criticized because they have no weaknesses, this also might be a red flag.

The candidate should be upfront about any criticism they faced in their professional life and its effect. Bonus points if they give an example of how they used it to facilitate personal and professional growth.

Sometimes, they’ll try to get out of answering the question by talking about a weakness that’s actually a strength. Try not to let applicants do this.

  • How would your boss, coworkers, and people you supervise describe you?

This is an opportunity for your applicant to talk about their positive traits. It will help you to gauge the applicant's ability to work as a team and how well they interact with others.

An answer you believe is genuine could show that the candidate can forge positive relationships with fellow employees. The question might also reveal whether the candidate fits into the company culture in their last job and if they’ll fit into your culture.

If the candidate uses the question as an opportunity to bad-mouth previous team members, consider this a red flag.

  • What are you currently reading?

Job seekers who are avid readers tend to be good communicators.

In a world of rapid technological changes, a person needs to read a lot to keep up with trends. Bonus points if they mention a book by an industry mover or shaker who’s influential in your industry or if they’re reading blogs having to do with your type of business.

 This question could also reveal their eagerness to learn new things—an invaluable quality in any employee.

  • Explain how you overcame a significant challenge.

This is an excellent question because it weeds out team members who shy away from difficult situations.

It gives you a chance to learn about the candidate’s problem-solving and critical thinking skills. The applicant should explain what they accomplished, how they did it, and what they learned from the experience.

You’ll be able to find out how they handle adversity and their ability to think on their feet. Their answer could help you figure out if they're a creative thinker or how resilient they are under challenging circumstances.

  • Give me an example of someone you were able to promote because of the coaching you provided. How did you make this happen?

This is an excellent question to ask if you're hiring for a managerial role. That's because you want to bring people into your enterprise who help others grow and succeed, which will allow your company to flourish.

An applicant’s answer might show how passionate they are about coaching others and their approach to staff development.

  • Provide me with an example of a time you lost your temper. What happened, and what was the outcome?

Asking this question will give you insights into a candidate’s emotional intelligence.

Emotional intelligence means a person can competently handle their own and other people’s emotions. Emotional intelligence is a highly desirable quality to have in business because it helps improve communication, problem-solving, and the ability to manage others.

It’s natural for people to lose their tempers from time to time. Emotionally intelligent people are aware of this and will own up to their personal shortcomings. Look for responses that indicate the individual is willing to make amends after losing emotional control and focuses on conflict resolution instead of perpetuating disputes.

Ready to take your recruitment process to the next level?

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Whether you need to hire a single individual or fill an entire department, we'll find you the top-tier talent you need.

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