Top 20 Tough Interview Questions (Example Answers Included)

By Mike Simpson

Have you ever faced off against an interview question that stopped you dead in your tracks? You know you heard the hiring manager ask it. But after that, your mind starts reeling, and you can’t figure out how to begin. That’s usually what it feels like to get hit with genuinely tough interview questions.

Now, while you might assume that brainteasers are the tricky questions you have to worry about most, that isn’t necessarily the case. Some of the hardest interview questions around don’t involve a hiring manager actively trying to throw you off your game or asking you something unfathomable.

Instead, tough interview questions can be anything that leaves you feeling like there’s a million-degree spotlight positioned over you. Sure, it may be a tricky brainteaser, but it could also be something that makes you feel vulnerable, self-conscious, or otherwise put on the spot.

Luckily, it is possible to navigate even the hardest interview questions with ease. If you want to make sure you’re up for the challenge, here’s what you need to know…

How to Answer Tough Interview Questions

Before we get into tough interview questions and answers examples, let’s take a step back. There’s a good chance you’re wondering, why would a hiring manager ask tough interview questions anyway? Well, there are a few reasons.

One is that making the process challenging boosts later job satisfaction. That’s right; when an interview process is 10 percent harder, employee job satisfaction down the road is 2.6 percent better. Crazy sounding, but it’s true.

Second, replacing an employee usually costs 33 percent of that worker’s salary. That’s why finding a great candidate the first time is such a priority. It saves money. So, hiring managers may use hard questions to help them find the best.

Now that you have an idea of why a hiring manager may throw you a curveball during the interview, let’s move onto another important topic. It’s also critical to know how you should approach answering any question. That way, if you get hit with one you (or we) didn’t see coming, you’ll be able to tackle it.

Let’s face it, run of the mill job interview questions aren’t that tricky. Usually, the hiring manager has to spend at least part of the meeting gauging your abilities in a typical manner, so they go with a straightforward approach to touch on those topics.

For example, “Do you have skill X?” is a breeze to answer. All you have to do is confirm whether or not you have it, provide a relevant example, or showcase your willingness to learn, and you’re done.

So, what kind of question usually ends up on the tougher side of the equation. Well, behavioral interview questions, of course. Even the simpler ones require finesse. But, if the hiring manager decides to strike with a doozy of a question, you might not have a clue where to begin.

What makes an interview feel tough can vary. Sometimes, simply being caught off-guard is enough to qualify a question as tricky. At times, it’s because the question is complex, multi-part, or requires a ton of calculations. It’s even possible for one to feel like a difficult interview question because answering makes you feel vulnerable or exposed.

Regardless of why you find it tough, having a strong strategy can help. It gives you a touchstone for creating exceptional answers, making it easier to think on your feet and craft a great reply.

And what strategy would that be? Well, this one.

First, get to know the STAR Method. It’s a great way to build a foundation for answering any behavioral interview question, including tricky ones.

Next, spend time with the Tailoring Method. It’ll help you generate highly relevant and engaging answers, ensuring you provide the hiring manager with clear insights regarding how you’d excel in that specific role.

Finally, mix the STAR and Tailoring Methods together, and that’s it. With those two approaches in hand, you’re in good shape.

We also wanted to let you know that we created an amazing free cheat sheet that will give you word-for-word answers for some of the common interview questions you will almost always face in an interview!

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Top 3 Tough Interview Questions

Now that you understand why hiring managers ask hard questions, as well as how to deal with them, it’s time for the big stuff. Here’s a look at 3 of our top tough interview questions and answers.

1. What are the pros and cons of failing on the job?

Many hiring managers ask you to discuss an on-the-job failure and how you handled it. This question is a bit trickier. Instead of focusing on a misstep, you actually have to cover not just its value as a learning experience – a classic way for tackling the more common version of the question – but also the less pleasant aspects.


“Failing on the job can create an opportunity. In my last position, we had a project get overrun with scoop creep. I failed to speak up about the challenges the extra features were causing to the timeline, and we missed a key deadline.

However, that experience taught me the value of being open about the impact of such changes in the future. That made me a better project manager down the line, as I wasn’t just more aware, but also more willing to discuss my concerns earlier in the process.

It is true that failing on the job has drawbacks. As I mentioned before, we missed a deadline on that project. Speaking with the customer about the timeline issue was difficult, and it harmed the company’s and my reputation. Luckily, by being transparent, diligent, and working quickly, we were able to deliver an excellent product in the end, and that allowed me and the company to recover.”

2. Do you consider yourself to be lucky?

This question actually accomplishes a few things. First, it can help the hiring manager gauge your attitude, as your reply could reveal whether you are an optimist, pessimist, or realist.

Second, it also gives them insights into how you view luck. After all, what one person considers lucky may be seen as the result of hard work, dedication, or something else by another candidate.


“I don’t consider myself lucky in a traditional sense. I have been fortunate enough to have a chance to seize certain opportunities and to engage with some amazing people. However, I also took action, seizing opportunities when they arose to better my life and further my career.

For example, in my last position, I had a chance to take on a critical project. I took it on enthusiastically, using it as an opportunity to broaden my skillset, collaborate with knowledgeable professionals, and step up as a leader. While I was fortunate to get a chance to have oversight of the project, its success was based on my diligence. In a way, I created my own luck, ensuring I excelled by fully dedicating myself to the task-at-hand.”

3. Can you tell me something that you dislike about your current or most recent job?

Here’s another difficult interview question that some hiring managers like to use. With this, they get to assess your level of honesty, to find out what you may be looking for in your next employer, and to see if you may be a good fit for the role or company’s culture. Plus, they are opening the door (wide) for you to make a mistake and really badmouth your current or last employer – something that’s generally a no-no.

Now, this question isn’t an invitation to dish without any repercussions. As with any of the hardest interview questions around, you have to answer tactfully and strategically. You want to be open, but not to the point that it bites you in the behind.


“The main reason I’m looking for a new employer is to have opportunities to advance. While I enjoyed my time with my last company and value what I learned while working with them, growth opportunities are somewhat limited at this time. As a result, I believe that it’s time for a new challenge if I am going to keep my career on target.

My goal is to be able to broaden my skills and experience, and a new position is the best approach for doing that. Plus, it will give me a chance to bring value to a new employer, and that’s something I’m genuinely excited about doing.”

17 More Tough Interview Questions

Here are 17 more tough interview questions you might encounter when trying to land a job:

      1. If you had a chance to go back to any point in the last ten years and change something, what would you change and why?
      2. What is your greatest weakness?
      3. When you receive negative feedback, what is it usually about?
      4. Are there any duties you won’t take on?
      5. What kind of manager would you never want to work for?
      6. Why do you think you’re better than the other candidates trying to land this job?
      7. Tell me about a time you weren’t able to overcome an obstacle.
      8. How do you handle work-related stress?
      9. Describe your worst experience with management.
      10. Do you have any career-related regrets?
      11. Why is there a gap in your resume?
      12. Why were you fired from your last position?
      13. If you could only use one word to describe yourself, what would it be?
      14. Your resume shows that you worked in one position for company X for five years. Why weren’t you promoted during that time?
      15. If you had a chance to land any job right now, would it be this position?
      16. What would you do if you worked for a manager that continuously took credit for your work?
      17. Have you ever taken an unpopular stance on a work-related issue? How did it turn out?

5 Good “Tough” Questions to Ask at the End of an Interview

When your interview gets ready to come to an end, you’ll have to handle one of the hardest interview questions around; do you have any questions for me?

While the start of your answer is easy – it should always be “yes” – the next part isn’t so simple. You have to have great questions to ask, ensuring you come across as engaged and enthusiastic, while also allowing you to gather some valuable insights.

Typically, it’s hard to throw the hiring manager off their game here. However, that are some questions that they may not hear often, if at all. If you want to stand out from the crowd, here are five good tough questions to send the hiring manager’s way:

    1. What happened to the last person who worked in this role?
    2. How important is this position in your (the direct manager’s) eyes? What about upper management?
    3. Based on my resume and what we’ve discussed so far, is there any part of this job that you feel I couldn’t handle?
    4. When it comes to feedback, is it given freely, or will I need to seek it out?
    5. What is the hardest part of managing this position for you?

Putting It All Together

In the end, you’ll probably face at least a few of these hard questions to answer during your career. But unlike many other candidates, you came here, giving you a leg up on handling some of these tricky questions. Take advantage of what you’ve learned, including the tough interview questions you can ask the hiring manager listed above. That way, you can stand out from the crowd, answering these doozies with ease and navigating the whole process like a boss.

As always, good luck!

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Download our "Job Interview Questions & Answers PDF Cheat Sheet" that gives you word-for-word sample answers to some of the most common interview questions including:

  • What Is Your Greatest Weakness?
  • What Is Your Greatest Strength?
  • Tell Me About Yourself
  • Why Should We Hire You?
  • And more!

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About The Author

Mike Simpson

Co-Founder and CEO of Mike is a job interview and career expert and the head writer at His advice and insights have been shared and featured by publications such as Forbes, Entrepreneur, CNBC and more as well as educational institutions such as the University of Michigan, Penn State, Northeastern and others. Learn more about The Interview Guys on our About Us page.