The 62 hardest interview questions for in-depth candidate assessment

If you need a handy way to appraise your candidates’ skills and keep time-to-hire low, the combination of skill assessments and interviews is the best way to do this. 

Check out our role-specific skill tests to create a skill assessment. But what’s the best way to perform an in-depth candidate interview?

Asking applicants the hardest interview questions will prompt them to think before they respond and help you create an engaging dialogue with them. This type of question is perfect for an in-depth candidate assessment process and ensures you have all the information needed to make the right hiring decision. 

Find some of the hardest interview questions in this article to assess your candidates in an interview.

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47 of the hardest interview questions to ask at the start of the interview

Find out if your candidates are a good match for your vacancy by asking them a few of these interview questions at the start of the interview.

1. Which people inspire you to achieve challenging goals?

2. Describe the key responsibilities of this role.

3. Explain how your experience makes you a good match for the role.

4. Tell me which factors motivate you in the workplace.

5. Name one reason we shouldn’t hire you.

6. What are your salary expectations?

7. How much time do you need to start actively contributing to our business and achieve results?

8. What was your worst job and why?

9. What was your best job and why?

10. Name your weakest skill.

11. What made you choose our company when applying for a job?

12. How will you contribute to our business and team?

13. Have you ever missed a project deadline?

14. What makes you a unique candidate?

15. Explain why a company hasn’t hired you so far.

16. Why are you applying for this role?

17. What do you want to achieve within ten years?

18. Which five adjectives would your colleagues use to describe you?

19. Name something you don’t enjoy about this field of work.

20. Name something you don’t enjoy about your current role.

21. Describe a time you made a serious mistake at work.

22. Which work environment is ideal for you?

23. Tell me about a time you were involved in a team conflict.

24. Tell me about a time you had to take a break at work to handle stress.

25. When are you the most productive?

26. When are you the least productive?

27. Describe a digital skill you need to improve.

28. Do you have any strategies for improving your communication skills?

29. Do you have any methods for improving your time-management skills?

30. Do you have any strategies for improving your attention to detail for this role?

31. Do you have any methods for improving your problem-solving skills?

32. Do you have any strategies for improving your negotiation skills? 

33. Describe a situation when you received negative feedback you didn’t understand.

34. Name a time you noticed your boss was wrong. How did you handle the situation?

35. If you could change anything about your career, what would you change?

36. Have you read any career-related blogs recently?

37. Describe your role’s most boring tasks and explain how you handle them.

38. Explain why you’ve had so many jobs.

39. Would you make any changes to our company?

40. Name three choices that will enhance your career progress.

41. How would you respond if a team member is slacking off?

42. Don’t you consider yourself overqualified for this role?

43. What is your ideal company?

44. Describe what you know about our organization.

45. Have you ever overcome a challenging obstacle?

46. Do you regret any career choices you have made? Why?

47. How would you respond if your boss asked you for your honest opinion about a bad idea?

10 of the hardest interview questions and answers for reviewing candidate answers

Below, you’ll find our sample answers to ten of the interview questions from the previous section to help you review your applicants’ responses.

1. Describe a situation when you received negative feedback you didn’t understand.

If applicants have received negative feedback they didn’t understand, they should first avoid getting defensive. The feedback could enhance their output or the quality of their work, so they should know why it’s important to make sure they understand it.

One of the best ways to handle this situation is to restate what you heard and ask questions about the aspects you didn’t understand. Look for answers that describe a similar process.

2. Do you have any strategies for improving your communication skills?

All interactions in the workplace involve communication, and tone of voice and body language are important components to it: the tone of voice is the vehicle of 38% of the transmitted information, while body language is responsible for another 55%. 

If applicants could have different strategies to improve their skills and overall communication with coworkers, such as to:

• Recap essential details of the conversation

• Ensure the messages match the company’s mission

• Are timely with responses and share information frequently

Our Communication skill test is the best way to review your applicants’ active listening and verbal communication skills.

3. Do you have any methods for improving your time-management skills?

Strong time-management skills have many advantages in the workplace. They can enhance your company’s reputation, increase employee productivity, and help staff complete work on time. 

Several strategies can help applicants improve their time-management skills, such as to:

• Make plans or a list of priorities

• Set goals and allocate time to achieve them

• Be mindful of distractions

• Use time blocks

If you want to assess their time management skills, the best method is to use our Time Management skill test.

4. Describe a time you made a serious mistake at work.

Being able to admit mistakes when answering this interview question shows applicants’ integrity and honesty. Are they able to explain what they learned from it? The best answers will describe how your applicant took accountability for their errors and used them as learning opportunities.

For example, if a software engineer admits their application had security vulnerabilities, consider whether they took responsibility for any security issues and learned from the mistake.

5. Describe a digital skill you need to improve.

Improving technical skills can help candidates be more productive and focused. While only 40% of workers improved their digital skills during the pandemic, this is still an essential goal for many candidates.

The key to assessing responses to this interview question is to consider whether applicants have a plan to enhance their digital skills. Ask them if they are willing to take courses or read books to improve.

6. Do you have any strategies for improving your attention to detail for this role?

Attention to detail is essential for many duties, such as editorial, teaching, and receptionist work. By asking this interview question, you can check whether your candidates understand why attention to detail is important for the role they have applied for. You can also find out how your applicants plan on improving this skill.

Some methods that can help applicants improve their attention to detail include to:

• Create lists

• Limit distractions

• Use organizational tools

• Complete work more slowly and focus on details

Our Attention to Detail test is one convenient option for assessing applicants’ abilities. Learn how they handle intricate processes and details with this test. 

7. Do you have any methods for improving your problem-solving skills?

Problem-solving skills are important in the workplace. Candidates with this skill are cognitively prepared to handle challenging assignments by prioritizing tasks, planning and executing strategies, and anticipating additional problems.

There are many ways in which applicants can improve their problem-solving skills. For example, they can: 

• Share ideas with coworkers to learn new problem-solving strategies

• Improve analytical skills to assess root causes of problems

• Practice creative and critical thinking

Assessing your applicants’ problem-solving skills is quick and simple with our Problem Solving and Critical Thinking tests. Use these tests for a data-driven hiring process.

8. Tell me about a time you were involved in a team conflict.

Asking applicants this interview question will test their conflict-management abilities. Candidates should have a strategy for handling disputes with team members; for example, they could:

• Talk with the other team member and use active listening

• Recognize the points they disagree on

• Understand the points they agree on

• Create a plan to handle the points of disagreement

• Complete the actions required to resolve the conflict

9. Name something you don’t enjoy about this job.

To understand your applicants’ perspective on their field of work, ask them this interview question. Your candidates’ should mention one thing they dislike about their job, which may be a lack of career opportunities or limited flexibility in their schedule. 

Although this question requires candidates to discuss things they dislike, be wary of candidates criticizing coworkers, managers, or teams. They should provide a balanced answer that shows their passion for the role. This way, you will know if they’re motivated to take on similar responsibilities at your organization.

10. Describe your role’s most boring tasks and explain how you handle them.

It’s normal that applicants have preferred tasks and assignments that they dislike. A good answer will explain how candidates manage to stay motivated when completing monotonous work. It will show how candidates handle these responsibilities and view them as intriguing challenges to maximize productivity.

Watch out for applicants who do not feel satisfied  with their roles or complain about boring tasks – they may lack the motivation required to join your team. 

5 of the hardest interview questions and answers for specific roles

Decide if your interviewees have the right role-specific knowledge and experience by asking them some of these role-specific interview questions. Review and score their responses with the help of our sample answers.

1. How would you fix coding errors?

This interview question is ideal if you’re hiring software developers or programmers. Candidates should know how to make code work by debugging it. 

When they respond, they should mention a few steps to help them fix coding errors. For example, they can:

• Use Visual Studio to find code problems

• Review lists of errors

• Look at the errors one by one

• Use code analyzers

2. Sell me this product.

If you need to test your candidates’ sales skills, you can ask them to show their abilities directly by selling you a product. Candidates may use a few techniques to demonstrate their pitching skills. 

For instance, they may:

• Ask you about your role or responsibilities

• Establish a connection between your responsibilities and the product

• Explain how the product can help you address specific pain points

• Offer you the opportunity to try the product for free (for a limited time)

• Look for opportunities to close the sale after the “trial period”

3. How would you make your lessons more engaging?

Teachers have a huge impact on their students: 98% of people think good teachers can change a student’s life. But to achieve this goal, teachers must deliver engaging lessons to motivate students. 

A few steps candidates may mention to keep pupils more focused include to:

• Use engaging educational games 

• Use multimedia such as videos, sound recordings, and photos

• Ask students to present their work to others

• Get students to work in groups

4. Name one customer service subskill that enhances the customer experience dramatically.

Your candidates can prove they have the right customer-service expertise with an insightful response to this interview question. 

Some customer-service subskills they might mention are:

• Communication skills

• Problem-solving abilities

• Empathy

• Adaptability

• Active listening

You can learn more about your candidates’ customer-service experience by asking follow-up questions related to these skills, such as, “How has empathy helped you enhance the customer experience in the past?”. 

If you need precise data on your candidates’ customer-service skills but don’t want to increase your time-to-hire metrics, use our Customer Service skill test. 

5. Are there any Microsoft Office Suite skills you need to work on?

IT professionals should have strong Microsoft Office Suite skills but might need to hone their abilities if they don’t use all Office applications very often. In that case, they can name one skill they need to work on and explain how they would improve. 

Some applicants might explain they’d like to complete an online Microsoft Office Suite course. Others might use video tutorials. Use our Microsoft Office test to see who already has the skills you need.

10 of the hardest interview questions for managerial roles

If hiring a manager, you can ask them some of these 10 hardest interview questions to appraise their managerial experience.

1. Describe your most difficult management experience.

2. How would you coach an employee who’s failing to meet targets?

3. Describe a time your most experienced employee lost motivation. What did you do?

4. How do you support your team during challenging projects?

5. Name a time you had to demote an employee.

6. How do you incorporate your company’s goals into your strategy?

7. How do you ensure your team trusts your choices?

8. Describe your most successful problem-solving strategy.

9. Have you ever received negative feedback from senior management?

10. How do you ensure your team collaborates efficiently with other departments?

5 of the hardest interview questions and answers for managerial roles

Evaluate your candidates’ suitability for managerial roles by assessing their answers using our sample answers below. 

1. Have you ever received negative feedback from senior management?

Negative feedback is important for managers, and especially those who have transitioned to the role recently. 

Your applicants should explain how they accept negative comments from senior leadership and what they do to implement the necessary changes to their work and use it as a learning opportunity.

Check if your candidates can provide specific examples of times they received negative feedback and ask extra questions to see how the feedback improved their work. For instance, if an applicant received feedback on motivating a team, you may ask, “How did your motivational strategies change after that?”

2. How do you ensure your team collaborates efficiently with other departments?

Since interdepartmental collaboration can increase productivity and morale, finding a candidate to facilitate communication between teams is essential.

Candidates should name some methods to encourage cross-functional communication and explain their effectiveness. For example, they might:

• Use different communication tools and strategies

• Schedule regular meetings

• Create summaries of each discussion

• Resolve interdepartmental conflicts

3. How would you coach an employee who’s failing to meet targets?

Coaching can enable underperforming team members to change their approach efficiently and achieve goals. Consider whether your applicants have coaching experience and can provide examples of how their coaching strategies helped an employee who was failing to meet targets.

For example, applicants may schedule one-on-one meetings to discuss company targets and use efficient communication to share their expectations with the employee. They might also evaluate the reasons why the team member is struggling and look for ways to help them address challenges. 

4. How do you support your team during challenging projects?

Setting realistic goals, conducting frequent reviews, and providing encouragement and recognition are a few strategies your candidate could use to support a team that’s working on a challenging project. Other methods include to:

• Hold brainstorming sessions

• Create plans for the project together

• Keep team members involved when making decisions

Project-management skills can also help managers make project-related decisions with their team to achieve business goals. If you need to assess these, use our Project Management test.

5. How do you ensure your team trusts your choices?

From being transparent in their decision-making process to admitting mistakes and communicating effectively, many methods help managers build trust with a team. Additionally, some applicants may use team-building activities, and others may hold regular team meetings. 

Whichever method they use, applicants should describe the outcomes of their processes to help you appraise their managerial expertise.

At what stage of the hiring process should you use the hardest interview questions?

The hardest interview questions you plan to ask applicants should always be used near the bottom of your recruitment funnel, after you assess applicants’ skills with skills tests and ask some easier questions. 

Data-driven, bias-free, and effective skill testing combines well with different interview methods and ensures you can easily identify the most talented applicants and create a shortlist of those of them you’d like to invite for an interview. 

Here’s how to combine skill testing with interviews:

• Step 1: Build a skill assessment of up to five tests 

• Step 2: Send invitations to candidates with just one click 

• Step 3: Wait for candidates to complete the assessment

• Step 4: Check results to see how well your candidates performed

• Step 5: Choose the candidates you want to interview

• Step 6: Start with easier interview questions and increase the intensity; keep the hardest interview questions for the middle or the end of the interview

• Step 7: Hire and onboard an employee

As you can see, it’s not necessary to screen resumes if you use skill assessments. If you want to compare applicants and ensure you’re hiring a suitable employee, skill tests give you the accurate data you need.

Put your applicants’ skills to the test using some of the hardest interview questions out there

All there is to a successful hiring process is using the right tools, such as skill assessments and interview questions of varying difficulty. And to make sure you’re hiring the most qualified candidate, include some of the hardest interview questions from this article to put your candidates’ skills to the test.

By combining skills tests and interviews, you’ll quickly find the right employee for your team.

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