12 Tough Interview Questions and Answers (With Helpful Tips)

During a job interview, your interviewer may ask you questions that require more thoughtful answers. Tough interview questions can vary widely between industries, but there are several tough questions employers commonly ask to learn more about you as a candidate and assess your skills. Reviewing some tough interview questions and their sample answers can help you become better prepared for your own interview. In this article, we list some examples of tough interview questions and sample answers.

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Key takeaways:

Employers ask tough questions to learn how you process information and solve problems.
Before creating an answer to a tough interview question, take a few seconds to process your thoughts and ask clarifying questions if needed.
Prepare to discuss your approach and explain your reasoning when answering these questions.

Tough interview questions with sample answers

Interviewers ask more difficult interview questions to learn important information about you that you may not have on your resume. These questions also help them assess your thought processes and your ability to think creatively and apply logic to different problems. Tough questions can make it easier for them to gauge your experience level and comfort with difficult tasks. When preparing for your interview, consider the following tough questions and answers:

1. Tell me about yourself

Employers likely ask this question early on in the interview process, and recruiters often ask it during early-stage phone interviews or recruiter screens. To answer the question effectively, provide a short synopsis of your educational background and professional career. Highlight some of your proudest achievements and discuss the aspects of your professional experience that are the most relevant to the role. Example: "After graduating with an associate degree in fashion merchandising, I began my career working as a retail merchandising specialist in a local department store. There, I organized the weekly merchandising calendar and helped improve the online shopping experience. In my current role as a fashion merchandiser at Serial Rock Outfitters, I manage the development of five fashion lines. Last month, I developed relationships with 15 new merchants, which has helped increase revenue by over 20% so far." Read more: Interview Question: "Tell Me About Yourself" (With Answers)

2. What critical feedback do you most often receive?

This question is similar to “What are your greatest weaknesses?”, and employers ask it to assess your sense of self-awareness and determine whether you're actively working on improving yourself. To answer this question, think of a genuine piece of criticism you've been given or a weakness you're aware that you have along with ways in which you work to overcome the weakness. Provide a brief explanation of the critique and how you're working on improving it. Example: “In the past, I've been told that I tend to talk over others in meetings. While I do get excited about the projects I'm working on and I enjoy collaborating with others, I understand the value of active listening and the importance of having diverse ideas. I've made it a point to listen actively by taking notes and make myself the last one to contribute while others are sharing.” Related: Qualities of a Good Listener and How To Be One in 6 Steps

3. Tell me about a time you overcame an obstacle.

Employers ask this question to understand how you deal with difficulties. You can use the STAR method when answering behavioral interview questions like this. Provide a brief summary of the situation, your role in the situation, the action you put into place to resolve the issue and how the issue was resolved as a result. Briefly mention what you learned during the process. Example: “I worked as a retail manager at a department store during prom season. A customer purchased a dress online and had it delivered to the store where it was accidentally purchased by another customer. Before calling the original buyer, I located the same dress at another location nearby. I ordered it to be pressed and delivered to her home the morning of prom with a gift card to thank her for her understanding, and she immediately wrote us a five-star review on several review sites.” Related: 18 Tough Open-Ended Questions (And How To Answer Them)

4. How do you handle stress?

Stress is a component in many jobs, employers want to know that you can handle it constructively and manage more difficult duties while still maintaining a positive attitude. You can answer this question by explaining how you typically respond to stress with a supporting example. This shows employers that you're able to manage stressful situations well. Example: “Communication is key for me in stressful situations, even if over-communicating is necessary to ensure everyone understands the requirements of a project. For example, I was working on a project with another team and we learned there was duplicate work being done. By scheduling a weekly standup and establishing open lines of honest communication with our teams and managers, we completed the project on time and ended up achieving an important company goal sooner than expected.” Read more: Interview Q&A: How To Answer "How Do You Handle Stress?"

5. What have been your most positive and negative management experiences?

Employers might ask you this question to understand what you like and dislike in certain management styles. This might help them decide whether or not you would be a good match for a certain manager. Try to answer this question honestly and as tactfully as possible and emphasize the positive characteristics first. Example: “I prefer collaborative managers who give their teams the resources and tools to accomplish tasks together. My last manager emphasized process improvement and used whiteboards to support our brainstorming sessions. I also felt like she listened to my needs and helped me obtain the resources I needed to achieve my goals. One of my past managers, while talented and knowledgeable, tended to manage our team's work closely with little flexibility, which left little opportunity for professional improvement."

6. What's your biggest weakness?

Employers may ask about your weaknesses to determine if you have a sense of self-awareness. They also ask it to determine how you're working to improve your skills. In your answer, be honest about your greatest weakness and share examples of how you're overcoming it. This can also enable you to further discuss your growth mindset. Example: “One weakness I've been working on is my ability to provide constructive criticism. In the past, I've struggled with how to offer criticism without affecting my team's feelings, but I understand how providing feedback on work or projects is extremely valuable to my team. To improve on this, I've been writing down my feedback before I approach my colleagues. This helps me to plan out my answer and offer more realistic criticism.” Related: 7 Tricky Interview Questions With Example Answers

7. Why are you leaving your current position?

Why you're leaving your current position can be important information for employers to understand. It helps them ensure the opening is a better fit for your skill set and background, They might also ask it to make sure your reason for leaving wasn't because of your performance or conduct. Answer this question honestly, but refrain from providing too many overly personal or negative details. Example: “While I highly valued my time at the previous company I worked for, there are no longer many opportunities for growth that align with my career goals. This position aligns perfectly with my skill set, and it offers plenty of opportunities to advance my career over the next few years.” Related: How To Explain Your Reasons for Leaving a Job

8. How many pennies, if stacked on top of each other, would equal the height of the Empire State Building?

Employers may ask questions with no right or wrong answer to better understand your thought processes. They often want to gauge whether you can think analytically, handle ambiguity and communicate clearly. Before answering this question, spend a few minutes thinking about how to prepare a logical answer. It's also appropriate to ask follow-up questions for more information or context, though they may not provide the answer. Example: "I'm aware that the Empire State Building is about 1,500 feet and about 15 stacked pennies equal an inch. Considering there are 12 inches in a foot and the building height is 1,500 feet, I'd multiply 15 by 12 to achieve 180. I'd then multiply 180 by 1,500 to achieve a total of 270,000 pennies."

9. Why do you want to work here?

Employers often ask this question to make sure you've thought about your decision to apply for employment at their company. This question might be particularly important if you're transitioning into a new industry or job. Be honest about why you want to work at the company and emphasize the intrinsic value the job can offer you over extrinsic values such as higher pay and better benefits. Example: “When I began searching for a new position, I purposefully sought out companies that are committed to integrity, philanthropy and innovation, and your company ranks at the top of the list. Edison Enterprises International has always been future-oriented, and it's made an effort to use technology to help improve the customer experience. I'm excited about an opportunity where I can use my passion for user experience to support innovation, and this role would allow me to do just that." Read more: How Best To Answer: “Why Do You Want To Work Here?”

10. Why might we hire you?

Employers ask this question to better understand what differentiates you from other candidates they might be interviewing. To answer, explain how your experience, skills and attributes make you the best fit for the job. Make sure to review the job description carefully before preparing your answer to understand what qualities they prefer in a candidate. Example: “I believe my passion for problem-solving and proven experience in office management make me an excellent fit for the role. In my previous role as an office manager, I created a plan to reorganize the office supply closet by category. Since items were easier to find, we placed fewer orders and saved 30% on office supplies that year. I'm excited to apply the skills I've gained over the past four years as a manager to a new role.” Related: Interview Q&A: “Why Should We Hire You?” (4 Sample Answers)

11. Do you have any regrets so far in your professional career?

Employers might ask this question to learn more about your career path and potential shortcomings. To answer this question, you might discuss some of the mistakes you've made or share some professional shortcomings that are unlikely to affect your ability to perform the job. Explain what you've learned from your experiences and try to keep your answer positive. Example: “I do sometimes wish I had known what I wanted to do early on in my career instead of spending years in an industry that didn't challenge me like I wanted. Having more years to develop myself professionally and advance would help me be even better at my job. Even so, I learned skills in my previous career that I wouldn't have otherwise learned that help me in my job today, including time management and communication."

12. What's your greatest achievement?

Employers might ask this question to better understand what you consider to be your most valuable accomplishments. It helps them learn what you prioritize in your career, especially if you have several notable achievements. To answer, think about a recent example that's related to the job in some way. Briefly explain the achievement, your role in it and why it's particularly valuable to you. Example: “Last year, my team won an award for the most innovative process improvement. My role was to organize the team to brainstorm the different ways we might improve the production process. We tested three proven ways and implemented the one that worked best for us. Our updates decreased time to production by 20%, allowing us to double our output."

Tips for answering tough interview questions

While some interview questions are expected, others may surprise you. It's important to prepare as much as possible for unexpected scenarios. You can do this by preparing a few examples and asking others in your industry for unexpected questions they've encountered in interviews. Here are some additional helpful tips:

Take your time

Employers tend to prefer that you craft detailed, thoughtful answers to their questions. Rather than answer immediately, take a minute to develop an appropriate response. This ensures that you're able to answer the question to the best of your knowledge.

Answer honestly and confidently

Before your interview, practice your answers several times to increase your confidence and become more prepared to respond naturally. Employers recognize that candidates have weaknesses, so be honest about your own. Discuss your unique abilities and skill set and try to keep the tone of the interview positive and productive.

Be prepared to discuss salary

Some difficult questions may also ask you about your pay expectations. If you're unsure what salary is appropriate for the position you're interviewing for, use a salary calculator to evaluate the pay range for your location, industry and experience. You can also counter the employer's salary question by asking them about their own range.

Prepare your own questions

Preparing your own questions and asking them during or after the interview shows employers that you're well-prepared and curious. Recognize that employers often have time restrictions, so try to limit your questions to ones that aren't already in the job posting or company website. For example, you might ask the employer about company culture or inquire about the metrics they use to measure success in the role.