41 difficult interview questions to assess candidates and review their skills

A challenging part of hiring the right applicant for a specific role involves finding a reliable, trustworthy means of assessing your candidates’ work-related behavior, skills, and traits. While using a skills assessment with Role specific tests is a useful first step in the hiring process, you may also need to ask difficult interview questions and check your candidates’ answers to create a shortlist.

At TestGorilla, we know that making a suitable list of interview questions and preparing for an interview with candidates may be time-consuming — and it can be tricky.

Knowing if the questions are challenging enough isn’t easy. If you’re unsure which difficult interview questions are ideal for your hiring process, this article will help — we have put together a list of top interview questions to ask your candidates. 

Read on for the ultimate list of difficult interview questions.

19 common difficult interview questions to ask candidates in an interview

These frequently-asked difficult interview questions will help you discover more about your interviewee’s experience. Add the most suitable ones to your list.

1. Name three reasons we should hire you.

2. Why did you choose to apply for this vacancy?

3. Tell me what you know about our business.

4. Explain why you left your previous role.

5. Explain why there are gaps in your employment history.

6. Are there any management styles that hinder your productivity?

7. What would you alter if you could change one thing about your current role?

8. What are your goals and ambitions if hired for this role?

9. Are you interested in management roles? Why or why not?

10. Do you perform well in fast-paced work environments?

11. Are you most productive when self-managing projects or receiving support?

12. What would your ideal job be?

13. Do you have a qualification or degree? Which transferable skills did you hone?

14. Name three important duties you expect to handle if hired for this role.

15. Name three main accomplishments you achieved in your current role.

16. Name the least rewarding part of your current role.

17. Tell me about your goals for the next ten years.

18. Describe a role model who you aspire to emulate.

19. How have you inspired new employees at your current organization?

5 common difficult interview questions and answers

Here are five difficult interview questions you could ask applicants in an interview. Consider the sample answers provided to evaluate your interviewee’s responses.

1. Name the least rewarding part of your current role.

Although your applicants may not enjoy every aspect of their current role, they may have methods to make the unrewarding aspects more interesting. For example, teachers who think meeting with their students’ parents is less rewarding than planning lessons may offset this by preparing positive and negative feedback for their students. 

The key is to ensure that your candidate has a coping strategy for when things get tough, and that they can recognize any potentially tricky aspects of the role.

2. Do you have a qualification or degree? Which transferable skills did you hone?

Not every applicant will have a qualification or degree, but if they do, they should mention some examples of transferable skills they learned during the course. For example, an English literature graduate may explain that they honed critical thinking skills when evaluating literary classics. 

Seventy-five percent of new jobs require a degree, but only 40% of candidates have one. To increase their chances of working for your organization, applicants without degrees or qualifications may focus on their work experience in the interview and explain what they have learned. If they can show that they possess the required skills with solid examples, they may be the candidate for you.

3. Tell me what you know about our business.

By asking this difficult interview question, you can learn if your applicants researched several aspects of your business, which gives some indication of their motivations, passions, and genuine interest in the job. The best answers will explain the candidates’ findings related to your company’s:

• Goals

• Values

• History

• Services

• Management style

• Reputation and feedback

It’s important to remember that even after completing research, candidates won’t necessarily know everything about your organization. This is not a major issue — as long as they are able to show that they want to learn more, and that they are willing to put the effort in.

4. Do you perform well when completing fast-paced work duties?

While some applicants may have experience with fast-paced work, others may not possess these skills. However, even if applicants have never worked in this type of environment, they should plan to enhance their productivity and have tangible actions in place to achieve this.

Applicants may also refer to some hard and soft skills that help them manage fast-paced work duties. For instance, their time-management skills or ability to show great attention to detail may help them complete their duties quickly and without errors. 

If part of your candidate review process involves assessing problem-solving and attention-to-detail abilities, consider using our Time Management test and Attention to Detail test (available on our free plan) before the interview.

5. Why did you choose to apply for this vacancy?

If you want to check your candidates’ enthusiasm about your vacancy, ask them this difficult interview question. To answer it well, candidates may refer to the company research they did before the interview. 

The top answers to this question will mention three factors — listen for the following components:

• Your applicant’s desire to complete new and challenging duties

• Your organization’s brand reputation and professionalism

• Your applicant’s transferable skills that align with your open role

10 difficult interview questions for assessing applicants’ actions and behavior

These behavioral interview questions are ideal for assessing your applicants’ actions in challenging work-related situations. Select suitable options from the list to assess your candidates.

1. Describe a time your supervisor disagreed with a decision you made.

2. How do you create innovative solutions for challenging situations?

3. What do you do if you receive the same negative feedback twice?

4. Have you ever disagreed with a coworker? How did you resolve the situation?

5. Have you ever noticed an undetected problem in your current role?

6. Describe a time you failed at work.

7. Tell us about a situation in which you received negative feedback. 

8. Which methods do you use to learn about new trends in this industry?

9. Name two factors that motivate you.

10. Is it more important to complete tasks well or quickly so you can achieve a deadline?

5 difficult interview questions and answers about work-related actions and behavior

We’ve selected five difficult interview questions about work-related actions and behavior. Check out the sample answers to assess your interviewees’ responses.

1. Tell us about a situation in which you received negative feedback.

Completing perfect work won’t always be possible for every applicant, especially if they are new to a role. In situations like this, they may receive negative feedback from team members or leaders.

The ideal way to receive negative feedback is to understand how the advice relates to the project and clarify any confusion before completing new projects.

Consider whether your applicant’s work has improved after they implemented the negative feedback by asking follow-up questions such as, “How did your output improve after receiving the negative feedback?” 

Remember to ask for specific examples to really test your candidates.

2. How do you create innovative solutions for challenging situations?

Eighty-six percent of executives suggest that innovation is one of their top three priorities, yet less than 10% are satisfied with their business’s innovative strategies. Since innovation can help applicants solve challenging tasks and is a key priority for executives, consider how your candidates think of innovative methods.

A few methods applicants may use to handle challenging situations include: 

• Working with different departments to discuss new ideas 

• Combining two ideas to achieve the best results

• Using problem-solving skills to understand the cause of the issue

After applicants describe their strategies, ask them how their innovative solutions helped resolve or improve the situation. You may also compare their responses with their Problem solving test results, which you could ask them to complete before the interview.

3. Is it more important to complete tasks well or quickly so you can achieve a deadline?

To respond to this difficult interview question, applicants must consider whether they would ignore a deadline to achieve an excellent output. They may explain that neglecting attention to detail to submit work on time can affect a company’s brand and that submitting work late can ruin a business’s reputation.

Top answers will mention that efficient project management and task prioritization are crucial for completing projects, helping teams achieve deadlines, and producing excellent work. They may also suggest strategies they’d implement to avoid this situation, and mention what they would do to keep clients happy and satisfied.

4. Name two factors that motivate you.

Knowing what drives an applicant to perform well in the workplace can directly impact employee productivity — every professional needs motivation to enhance their output, and understanding this motivation is important for hiring the right candidate. Many factors may motivate a candidate to perform well in an organization, from learning and development opportunities to company culture. 

For example, your applicant may be driven to complete unfamiliar tasks when they can learn new skills, or feel more inspired to handle difficult projects after they receive learning and development opportunities. 

Assessing your applicants’ motivation and drive is easy with our Motivation skill test — simply include this test in your skills assessment and check your candidates’ results. 

5. Describe a time you failed at work.

Even if a candidate has failed to complete a task adequately, they should be willing to improve. The key to assessing your applicants’ responses to this difficult interview question is to consider their strategies to avoid similar mistakes in the future.

For example, a content writer may attempt to include high-quality external links in their articles after initially failing to understand the importance of a website’s domain authority. They may check the domain authority using SEO tools to avoid repeating SEO-related mistakes. 

The best way to assess your candidates is to assess whether they can recognize their mistakes, and learn from them moving forward. 

12 difficult interview questions related to skills, traits, and abilities

Ask these difficult interview questions related to skills, traits, and abilities to evaluate applicants, and determine if their abilities are an ideal match for your role.

1. How would you rate your attention to detail for tasks that require accuracy?

2. How would you rate your problem-solving skills in complex situations?

3. How would your boss rate your team collaboration and communication skills?

4. Are there any methods you prefer for upskilling?

5. Name one skill that makes you a unique candidate.

6. Describe a skill you need to improve.

7. Name three recent books you’ve read.

8. Name a personality trait that hinders the quality of your work.

9. Do you consider yourself good at time management? Why or why not?

10. How would your current employer describe you?

11. How would your current coworkers describe you?

12. How would you rate your people management skills when coaching team members?

5 difficult interview questions and answers related to skills, traits, and abilities

We’ve listed five difficult interview questions about key traits and abilities along with sample answers here. Use the answers to evaluate your candidates’ responses.

1. How would you rate your attention to detail for tasks that require accuracy?

Many jobs and tasks require a strong attention to detail, and this is important in roles such as quality assurance work and editorial duties. If you are hiring to fill a vacancy that requires detail-oriented team members, ask your applicants this difficult interview question.

Applicants may describe successful duties or projects they have completed by focusing on every detail. They might also mention that attention to detail helped them make less mistakes. 

Using our Attention to Detail test, you can determine if your applicant’s attention to detail matches their response. 

2. Name a personality trait that hinders the quality of your work.

We all have our weaknesses, but even if your applicants have traits that hinder their work processes, they must try to implement strategies that enhance the quality of their output. For example, candidates who aren’t conscientious may create lists to ensure they meet targets or complete projects more efficiently.

We offer several personality tests — including our Big 5 OCEAN and Enneagram tests — to facilitate your personality assessment processes. You can also use them to learn more about your applicants and how they would affect the team dynamic if hired.

3. How would you rate your problem-solving skills in complex situations?

More than 60% of employers seek evidence of their candidates’ problem-solving abilities — and for good reason. Problem-solving skills are vital for handling complex situations and help candidates think of unique methods to handle them.

Applicants may mention examples of complex situations to support their answer, and provide evidence of their problem-solving skills. For example, a software developer applicant may discuss in the context of debugging applications or software testing.

Using our Problem solving test and asking problem-solving interview questions are the fastest, most reliable ways to assess your applicants’ skills. 

4. How would you rate your people management skills when coaching team members?

If your applicants hope to become your next team leader or coach, they must have excellent people management skills. To determine whether they have the ideal skillset, consider whether candidates can provide specific examples of times they’ve successfully coached team members.

Ask them the role they played, the difference they made, and the outcome of the project or situation. You may also use our Leadership and People Management test to assess them.

5. How would your boss rate your team collaboration and communication skills?

Forty-five percent of employers want to hire applicants with good spoken communication skills, as this can play a key role in enhancing team collaboration. If you’re one of the employers looking for a candidate who can share ideas with team members, ask them if their current manager thinks they communicate well, and ask for examples.

When responding to this difficult interview question, applicants may talk about situations in which their communication yielded good results. For instance, an SEO expert may share about a time they reminded content writers to include internal links in an article and explain the positive results of this communication.

Using our Communication skills test is the simplest way to assess applicants’ spoken and written communication skills and active listening abilities.

5 tips for using difficult interview questions in an interview

Along with this list of difficult interview questions, we have also provided five helpful tips for using them in an interview. Check out the dos and don’ts of using difficult interview questions.

1. DO use a skills assessment before asking candidates difficult interview questions

Hiring top candidates can be challenging and time-consuming, but this first tip helps you save time and hire easily — ask applicants to complete a skills assessment and then use difficult interview questions.

The main advantage of using skills tests first is easy candidate comparison. You can instantly see which applicants have the best role-specific or soft skills, and choose which candidates to invite to an interview.

2. DO take notes when applicants respond to your questions

When you ask candidates difficult interview questions, they may respond with long, detailed answers that include examples of their experiences. To ensure you don’t forget any information they provide, jot down notes of their responses.

Don’t forget that an interview scorecard or a structured document will help you easily organize your notes and compare your applicants’ responses — this method can help you make your final decision. 

3. DON’T hire applicants based entirely on personality-related interview question responses

Responses to personality-related interview questions will help you predict potential changes in your team dynamic upon hiring an applicant. They will also inform you about your applicants’ values, and help you to determine whether they match your expectations. Despite this, you should avoid hiring applicants based entirely on their personalities or traits — you need a good combination. 

Instead, review your applicants’ hard skills, soft skills, and experience to fully understand whether they are a good match for your organization.

4. DON’T forget to allow applicants to ask questions

While you should lead the interview and ask most of the questions, your applicants may need more information about your business and want to ask their own questions. Remember to give them a chance to inquire whether your company matches their expectations.

When your applicants ask questions, providing up-to-date information about your company will ensure they have the correct facts to make an informed decision if you offer them a job. Try to prepare in-depth responses before you allow applicants to ask questions.

5. DO compare skills assessment results with your applicants’ responses

After the interview, you will have a lot of candidate data to review, including qualitative interview question responses and quantitative information generated from skills tests. 

We recommend comparing your applicants’ information with their responses to difficult interview questions. This hiring method is objective and thorough — it will help you avoid hiring unsuitable candidates.

Assess your interviewees with difficult interview questions and skills tests

Although discovering more about your applicants’ talents may be challenging, asking them difficult interview and follow-up questions will ensure you get the right in-depth information about their skills. Pair this with our skills assessment and Role specific tests to easily create a shortlist of applicants whose skills match your expectations.

Try TestGorilla at no cost to determine if skills assessments are ideal for your hiring process, and use difficult interview questions to thoroughly assess your interviewees.