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22 Hard Interview Questions To Challenge Your Candidates & Find a Great Hire

Morgan Lichtenstein
7 min read

"Tell me about yourself."

"What is your biggest weakness?"

"What are your greatest strengths?"

Candidates have come to expect these same interview questions — and likely have perfected answers for them. If you want to go beyond canned responses, you'll need to ask some unique and tough interview questions. This way, you'll get genuine answers that will better inform your next hiring process.

Here are 22 of the most challenging interview questions to consider for your next round of hiring.

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

This kind of "value-based interview question" allows you to assess a candidate's work ethic and the values they might bring into the work environment. In turn, this can help you determine whether a candidate may be a good cultural fit for your team. Consider, for example, whether your candidate's answer aligns with the values you've decided are most important to your growing company.

Be sure to also balance out this type of value-based question with some competency-based questions that focus on skills. This will allow you to create a more comprehensive candidate profile.


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

This question makes it easier to gauge how well a candidate handles conflict, especially with a supervisor. Preferably, your candidate will be able to respond that they have been able to respectfully disagree with a supervisor in the past and have productive conversations about the conflict while still following the supervisor's directives. 

On the other hand, an employee who simply stayed silent or disrespectfully disobeyed their supervisor is probably not a good fit for your company.


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

Candidates should be self-aware enough to acknowledge their personal deficits while learning from their mistakes. An individual who can't admit to having faced any type of failure may have an ego and is probably not the kind of person you want on your team.

But some individuals handle failure a lot more gracefully. The people who can deal with failure make better employees because they transform mistakes into learning opportunities instead of wallowing in them.


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

This is a great way to see just how committed a person is to overcoming the inherent difficulties of a position. Ideally, a candidate will answer that they're confident in persevering with the job for as long as it takes them to succeed.


5. What type of manager would you never want to work for?

Different management styles work for different employees depending on their work ethic, character, and values. Asking this type of question can help you determine whether a candidate's personality fits your managerial style. 

Hopefully, your candidate will also be able to speak a bit about past managers they've had and how their management style brought out the best in them.


6. 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 the criticism they received. In that case, this might indicate 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 is also 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.


7. How would your boss, coworkers, or direct reports describe you?

This question allows your candidate to talk about their positive traits and will help you gauge their ability to prioritize teamwork. A great answer demonstrates that the candidate can forge strong relationships with fellow employees and may also reveal whether they'll fit your company culture well. However, be on the lookout for candidates who use this question as an opportunity to bad-mouth previous team members.


8. Tell me about a time you experienced conflict with another team member. How did you handle it?

Here's another question that will help you gauge a candidate's conflict-management skills with direct supervisors and coworkers. A promising candidate should be able to provide a concrete example of a time when they respectfully disagreed with a team member and details on how they worked through the problem.


9. How would you motivate an uninspired team?

This is an especially important question to ask if you're looking to hire for a supervisory or leadership position. Hopefully, your candidate will have past work experience with inspiring teams to meet project deadlines, increase productivity, or improve the quality of their work output. 

Look specifically for answers that allude to setting clear goals, rewarding team members, and providing them with the resources they need to succeed.


10. How would you define success?

This is one of those difficult interview questions you can use to determine what your candidate views as most important in their professional lives. One candidate may focus more on meeting team goals as a measure of success, whereas another may focus on personal growth. 

Consider whether your candidate's answer aligns with what you're looking for in new talent, then use that to inform your hiring decision.


11. Tell me about a time when you had to give difficult feedback to a colleague. How did you approach the situation?

Here's another one of those tough questions you should ask when you're hiring for a supervisory or leadership role. 

Giving less-than-stellar feedback to an employee is never easy or enjoyable, but a promising candidate should be able to provide specific examples from their work at a previous job. Preferably, the candidate approached the situation tactfully and offered the support the colleague needed to improve.


12. Give me an example of a time when you had to work with limited resources on a budget. How did you manage the situation?

This is not just a question for those in finance.

Resourcefulness and creative problem-solving are some of the best traits you can find in any employee — and this question allows you to measure both of those qualities directly. 

If an interviewee can provide an example of a time when they made a project succeed with limitations at their last job, this may indicate that they're excellent critical thinkers and can think on their feet.


13. How do you stay current with developments and changes in your industry?

Your industry is constantly changing and evolving — so of course, you want to hire employees eager to keep up with the latest innovations. 

A candidate's answer to this question helps you gauge how invested they are in their work and their motivation to achieve their career goals. It’s even better if they can list specific industry publications or other resources they follow to keep up with the latest news.


14. How do you handle stress in the workplace, and what techniques do you use to manage it?

Here's another one of those hard interview questions that force an interviewee to talk about something that's probably a little uncomfortable for them. Still, it's an important question because it can help you assess a candidate's self-awareness and ability to self-regulate under stressful situations. 

Ideally, your candidate can discuss positive stress management techniques, such as identifying stressors, speaking with supervisors, and getting support.


15. What motivates you to do your best work, and how do you maintain motivation over time?

This is a great job interview question to ask regardless of what type of position you're hiring for. It gauges the values and motivators that drive a candidate to succeed. 

If a candidate is just there to collect a paycheck, they're probably not the right fit for your company culture. If they're motivated to grow, build relationships with others, and work as a team, then you might be looking at your next new hire.


16. How do you approach communication with stakeholders who have differing levels of technical knowledge or expertise?

Communication skills are vital in any position, but this is especially true for positions that require employees to essentially "translate" technical jargon to other team members who may not speak the industry language. 

A candidate's response here can tell you a lot about their communication style and level of experience acting as a liaison between different departments or teams.


17. Give me an example of a time when you had to work with a team that had conflicting priorities or goals. How did you handle it?

Conflict is inevitable when a team is working on a project — but team members and leaders with excellent conflict-resolution and project management skills can keep everybody on the same page and keep things moving forward. 

Your interviewee should be able to provide a specific example that demonstrates their ability to refocus a conflicted team and get things back on track through tried-and-true conflict-management techniques.


18. What are you currently reading?

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

In a world of rapid technological changes, a person needs to read a lot to keep up with trends. It's an added benefit if they mention a book by an industry influencer or if they’re reading blogs about your type of business.

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


19. Explain how you overcame a significant challenge.

This question is a great way to weed out members who shy away from difficult situations while also gauging an applicant's problem-solving and critical-thinking skills. 

Your candidate should be able to explain what they accomplished, how they did it, and what they learned from the experience. Their answers can also help you determine whether they're a creative thinker or how resilient they are under changing circumstances.


20. 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, allowing your company to flourish.

An applicant’s answer might show their passion for coaching others and their approach to staff development.


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

This uncommon 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. This is a highly desirable quality 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 know this and will own up to their shortcomings. Look for responses indicating the individual is willing to make amends after losing emotional control and focuses on conflict resolution instead of perpetuating disputes.


22. Why should we hire you over our other candidates?

This may seem like a real kicker of a question, but it's actually a great way to gauge a candidate's confidence and ability to advocate for themselves when it matters most. Look here for answers that refer back to a candidate's specific skill set and experience and how those relate to the qualifications needed for the job.


Ready To Take Your Recruitment Process to the Next Level?

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That’s why at Hunt Club, we do the heavy lifting for you. When you partner with us as your hiring specialist, you'll get end-to-end recruitment support and a team dedicated to your success.

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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