22 of the Toughest Interview Questions and Answers

We live in a world full of cut-throat competition. Irrespective of which industry you belong to, landing your dream job has become extremely difficult and tricky. People today work determinedly at every stage, right from creating an impressive resume to building an awesome personal brand just to stay ahead of the curve. It is thus natural to get nervous when you are about to face your interview rounds.

While you can never exactly know what your recruiter might ask, there are certain questions that usually pop up. Over the years, recruiters around the world have refined their questionnaires to get some important answers from their candidates. How you answer these questions can decide your chances of getting your desired job.

In this article, we will explore some of these tough interview questions. We will understand why recruiters ask these questions and the answers they expect from candidates. In this manner, you will have a fair idea of the meaning behind some of these tough interview questions and answers and feel much more confident while facing your upcoming interview rounds. 

Here's what this article will cover:

  1. Why Are Tough Interview Questions Important?
  2. Why Do Employers Ask Tough Interview Questions?
  3. Most Common Difficult Interview Questions With Example Answers
  4. Difficult Personality Based Questions
  5. Tough Previous Work-Related Questions
  6. Other Common Difficult Questions
  7. Tips to answer some of the tough questions
  8. How to make the best impression?

Why Are Tough Interview Questions Important? 

Some of the hard to answer interview questions that we will explore in this article are designed to reveal a candidate’s core personality that is difficult to figure by just reading their resume. Personality traits like facing challenges, facing failures, and accepting criticism can only be revealed through these answers to difficult interview questions. How you answer them is instrumental in landing your dream job.

Furthermore, the ability to find an answer to tough interview questions on the spot is a measure of your quick thought-processing skills and creativity levels. When you prepare hard interview questions and answers, you are pushing yourself to bring out the best of your capabilities. 

Why Do Employers Ask Tough Interview Questions? 

Recruiters usually have to go through a pile of applications before they find the right candidate. It is not a simple task to separate the best candidates for the job.

Therefore, employers look at difficult interview questions and answers as a tool to filter the best candidates from their list of applicants. These questions act like markers for recruiters to identify people who would fit best for the role.

Most Common Difficult Interview Questions With Example Answers 

1) What critical feedback do you most often receive? 

What They Want to Know - Through this question, employers are looking to understand if you are actively listening to the criticism you receive. This attribute shows that you are constantly looking to work on yourself and positively accept the feedback given to you.

How to answer this question - Approach this question by accepting that you pay attention to what feedback you receive. Let them know that you reflect on it seriously and work on implementing it in your daily life. 

Example - “In the past, I have been told that I rely a lot on my own biases and assumptions about people instead of relying on data. My first reaction is usually to think based on my personal assumptions. I now try to give myself a moment before jumping to conclusions and study data to take actions.” 

Difficult Personality Based Questions

Here are some of the best answers to tough interview questions when it comes to your personality:

1) Are you willing to fail? 

What They Want to Know - Employers ask this question to understand how you digest failure and if you take it as a learning lesson. The last thing an employer wants is a candidate that cannot get back up when things go wrong.

How to answer this question - Through your answer, you must convey that, despite failures, you maintain a positive outlook towards the exciting possibilities future prospects might bring and hope to learn from your mistakes. Sharing a relevant experience here can speak volumes about how you tackle difficult situations. 

Example - “While failing can be frustrating, I have always tried to look at it as a route to success. I strongly believe in failing fast and early to gain clarity in moving ahead. While working on my startup, we failed at scaling quickly only to realize that we were targeting the wrong customer base. A slight shift in our target audience helped us achieve scale quickly to raise a round of funding.” 

2) How do you handle stress? 

What They Want to Know - Stress can often cause frustration and push you to react irrationally and impulsively with your team members. How you handle stress is key to maintaining great company culture.

How to answer this question - Acknowledge stress as a contagious phenomenon and chart out your plan on how you believe stress in the workplace can be handled. 

Example - “Stress can be a huge distraction from pursuing your goals. In a workplace, stress can greatly affect team spirit. Therefore, I personally believe the best way to tackle stress is through open communication. Being honest with each other and sharing your views regularly can be instrumental in breaking stress and bringing everyone on the same page.”

3) What is your biggest weakness?

What They Want to Know - Employers ask this question to check if you are aware of your flaws and actively working on them. Knowing your flaws is a sign of humility and focus. 

How to answer this question - State your weakness and proceed to explain how you work on countering it. 

Example - “One of my biggest weaknesses is speaking too soon. I am actively working to be a better listener and process my thoughts before voicing them.” 

4) Do you have any regrets?

What They Want to Know - Employers usually ask this question to check if you are stuck with some regret in your life. Regrets are a baggage in people's lives that keep them from realizing their potential

How to answer this question - A spirit to let go of the past and a positive attitude towards the future should be reflected in your answer.  

Example - “I do not have any regrets in my life. I have made mistakes in my past but I have always tried my best to learn from them. My efforts are in not repeating my mistakes and always learning something from them.” 

5) If you could relive the last 10 years of your life, what would you do?

What They Want to Know - This question is again closely connected with understanding if you have any regrets.

How to answer this question - The best way to answer this question is by highlighting some of the best times from the last 10 years. 

Example - “I would probably not change anything from the last 10 years. These were some of the most amazing years in which I built 2 products from scratch and met some of the best people who shaped my career in the right direction.”

6) Are you lucky? 

What They Want to Know - Employers ask this question to determine your approach to life. This question reveals if you are an optimistic or pessimistic person. 

How to answer this question - Approach this answer with a note of gratitude and by acknowledging your efforts and hard work in accomplishing everything that you have.

Example - “I consider myself fortunate to be in the position I am and for the opportunities that have come my way. While I am grateful, I am also proud of the effort I have put in to make the best of all the opportunities I have had.”

7) What have you learned from your mistakes? 

What They Want to Know - It is often easy to identify your mistakes but difficult to take a lesson from them. Through this question, employers try to understand your ability to learn and apply your lessons.

How to answer this question - Sharing an incident that highlights how you learn from your mistakes and evolve may be the best way to answer this question. 

Example - “One of my earliest mistakes was to hire employees that weren’t experienced enough just to cut costs. I have learned to invest properly in things that make or break your project. Hiring the best talent is extremely crucial and can only help you save money.” 

8) Why have you been out of work? 

What They Want to Know - Being out of work can signal a lack of ambition or effort. Employers ask this question to know what you have been doing since your last employment and if you have been utilizing your time well.

How to answer this question - A willingness to learn about yourself and your interests is always a good sign. Let them know that you've spent your time off work productively so as to chart a course for your future endeavours. 

Example - “I left my last job because I realized I needed a career shift since my work had become extremely monotonous. I took some time off in understanding what I truly wanted to do. I spent my time researching the latest in technology and business, reading case studies, and improving my communication skills to be better prepared for my next opportunity.”

Tough Previous Work-Related Questions 

1) What did you like or dislike about your previous job? 

Employers ask this question to understand if you enjoy your work and to get an idea of how your general attitude could be in your new organization. A healthy, positive and welcoming attitude counts! 

Example - “I loved working in my previous organization. I enjoyed the new technology I was introduced to. While I enjoyed most things, I disliked the lack of challenges towards the end of my term.”

2) Who was your best supervisor and who was the worst? 

Employers ask this question to know if you have the ability to pick up positive traits from your seniors and apply them in your professional life. 

Example - “I was fortunate to work with great mentors who have helped me be at the position I am today. I would specifically like to mention Mr. XYZ who showed me how to always lead by example.” 

3) What was the most and least rewarding about your last position? 

Ensure you focus on the positive while answering this question to not sound too complaining. Employers seek to find out if you tend to dwell in the negativity of a situation or move on to the positive aspects of a job. 

Example - “I have thoroughly enjoyed my last job where I got to learn a lot. The most rewarding was an opportunity to work with new technology and experiment with the product. The only small downside could be the long working hours which were a result of bad time management.”

Other Common Difficult Questions 

1) Tell me about a time you overcame an obstacle

Through this question, employers try to understand how you deal with challenges and find hacks to overcome them. Assert that you maintain a learning attitude in your stance. 

Example - “I firmly believe that obstacles are gateways to new opportunities. One of the obstacles while running my startup was funding. I overcame this by consistently researching and connecting with investors in my city and industry domain. This was followed by convincing them of my vision and getting them to invest in my startup.” 

2) What have been your most positive and negative management experiences? 

Through this question, employers want to understand your attitude towards handling teams, resources, and leadership qualities. 

Example - “While I have had to make tough management decisions, I haven’t seen them as negative experiences. I have had the opportunity to build and guide a team of extremely capable engineers and designers. I have learned a lot about technology and design through them as well.” 

3) Why are you leaving your current position? 

This question tells your employer about the things that mattered to you and what can possibly push you to leave your job. They can then check if their company can provide you with what you expect. 

Example - “While I enjoyed my last job thoroughly, I am trying to move towards new challenges that can expand the horizon of my work.” 

4) How many pennies if stacked on top of each other would equal the height of the Empire State building? 

Employers may ask such questions just to rattle you. Such questions do not have a wrong answer, but employers try to check if you can maintain your presence of mind and provide an answer with some logical backing. 

Example - “We can start by considering some of the known entities. The height of the building is roughly 1500 feet. Then we can assume that around 15 pennies stacked over one another can equal one inch. Multiplying the two can give us an approximate answer of 270,000 pennies.” 

5) Why do you want to work here? 

Employers ask this question to check if you have understood your role in their company and why you think it would be great for you. 

Example - “I think I love solving interesting problems. I think this company is solving a very important problem that affects people’s lives every day. It is also a challenging problem especially due to the current competition in the space. I want to work here to try and contribute to the solution.” 

6) Why should we hire you? 

Employers ask this question to understand how you look at yourself and your abilities. This question helps them understand how you can stand out amongst other applicants. This is an important question and you should be prepared with your answer.

Example - “I think I have the necessary experience in driving this solution forward. My startup experience also gives me a fresh perspective on problem-solving which could be instrumental in building this product with an innovative, out-of-the-box approach.” 

7) Tell me about yourself.

This question is usually asked as an introductory question. Make sure you highlight some of your achievements that would matter to the job you are applying for while answering this question. 

Example - “I have worked as a product manager in the last 4 years. Building roadmaps, user journeys, understanding customer needs, market analysis, and making decisions based on metrics were some of the most important things I was responsible 

8) What’s your greatest achievement? 

Employers answer this question to understand what you consider as something that added the most value to your professional satisfaction. 

Example - “When my product turned one last year, more than 200 users volunteered to celebrate this occasion. I knew at this moment that I had added value to people’s lives and it was the greatest feeling.” 

9) What do you expect from your supervisor? 

Through this question, your employer wants to understand if you are someone who has the capability to consistently learn from your superiors. Having reasonable expectations from your supervisor is a sign of ambition and curiosity. 

Example - “I look forward to work under someone who can push me towards my full potential and provide me with constructive feedback that can help me identify my flaws and correct them.”

10) Tell me something you would have done differently at work.

This is very close to the question asked about your past mistakes. Make sure you carefully tone your answer to help your employer understand that you always hope to learn from your mistakes. 

Example - “I have committed mistakes in the past but I have always tried to experiment with my work and learn from the things that go wrong. In my early days, I could have probably learned a lot faster if I would have asked for feedback openly instead of trying to figure out everything on my own.” 

11) How much do you expect to get paid? 

Employers ask this question to understand how much you expect to earn. It is important to ask for a realistic figure based on your expertise and experience. 

Example - “I am looking for something around $50,000 per month, considering my experience and abilities. However, I am more interested in this opportunity and excited about the idea. I am open for negotiations for the same.” 

Tips to answer some of the tough questions

Finally, now that we have explored some of the answers to hard interview questions and their possible answers, here are a few tips that can help you crack them and make a great impression. 

- You can't dodge those tricky questions so be prepared

Questions that have no wrong answers are usually tricky and can take you by surprise. Make sure you research and prepare yourself for such questions. 

- Be ready for the “Why are you leaving” question

The reason why you are leaving your current organization can tell your recruiter what excites you and what could be a deal-breaker. The answer you give here also talks about your loyalty and commitment. Thus, it is important to prepare yourself for such questions. 

- Prepare for some tough questions if you were fired from your last job 

If you were fired from your last job, it can be tricky to get hired again. Make sure you tell about your perspective and how it has been a learning for you. Make the employer feel like you have taken it in your stride and are ready to face your next challenge.

- Know what to do if you don’t have an answer

Don't panic. Not knowing an answer can also be handled elegantly. Accept you don’t know the answer and try to openly contemplate why this might be the case. 

How to make the best impression? 

Finally, here are a few tips to create a great impression at your interview:

  • Dress for the job
  • Arrive on time
  • Address every person in the room
  • Be confident in your abilities
  • Answer diplomatically when it comes to tricky questions
  • Be honest about your flaws
  • Show consistent curiosity
  • Display a willingness to learn

An interview is just an opportunity to exhibit your best professional self. Know that the only person standing in your way is you. Don’t panic, be transparent, and confident in your approach. Plus, preparation is key!

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