Tough Job Interview Questions and the Best Answers

At a job interview
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Preparing for a job interview means being ready to answer the basic interview questions that almost every hiring manager asks – but it also means anticipating more challenging questions. Job interviews always seem to have at least a few tough questions.

Some are trick questions, and others are designed to put you on the spot to see how you react. Then, there are those that don't have a right or wrong answer; these questions are intended to show how you think. With those, how you respond is as important as what you say when you answer.

Why Are Tough Interview Questions Important?

These tougher questions have a purpose: they give the interviewer a deeper sense of who you are and whether you're a good fit for the company.

Try to provide anecdotes and specific examples from your previous work experiences in your answers, especially focusing upon how these experiences have shaped you as an employee.

The Balance/Catherine Song 

12 Common Tough Interview Questions and Best Answers

Here are some of the toughest interview questions that employers ask, along with advice on how to respond and sample answers.

Personality Questions

Preparing for an interview is a good chance to reexamine yourself. The interviewer wants to see what type of personality you have. These questions get to that core and dig into who you are on a personal level. Your response will help the interviewer determine whether you are a good match for what the organization is seeking in the employees they hire.

1. Are you willing to fail?

What They Want to Know:  Employers are interested in how you respond to failure. Do you learn from it and build upon the experience to do better in the future?

While I don’t enjoy failure, sometimes it happens – particularly when you’re not sure which approach would be best for a project and you choose the wrong one. Not everything you try is going to work, and you just have to accept this and know when to change course. I learned this for the first time when, as a new project manager at Building Designers, I was tasked with coordinating the installation of a green HVAC system in a historic hotel. It became clear, after construction started, that the materials we were using would lead to a substantial cost overrun – so I had to resort to my “Plan B” in order to provide the deliverables we’d promised. One should always have a “Plan B!”

More Answers: How do you handle stress?

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

What They Want to Know: This is a “trick question” that employers will sometimes use to see if they can trip you up and make you reveal character flaws. So, be careful not to provide too much information. It’s also fine to say that there’s nothing about the last 10 years that you regret.

The last 10 years have been the most exciting of my life, and I wouldn’t change a thing. I’ve been blessed in that I’ve had so many opportunities to learn and to grow both as a professional and as a person, first in college and then in my first job at ABC Corporation.

3. Are you lucky?

What They Want to Know: This open-ended question is asked to determine whether you are an optimistic or a pessimistic individual. Is your glass half-full or half-empty? Tailor your response in such a way that you can highlight the unique strengths you offer.

I consider myself to be extremely fortunate in that I’ve been offered some great opportunities by some wonderful people and have been able to take full advantage of them. My manager at Hughes Hotel saw my potential back when I was a front desk agent, and she encouraged me to develop my skillset and to become an event planner. Since I love to cook, I also earned my chef certification so that I could offer private catering to clients to complement my event planning services.

More Answers: What motivates you?

 The “Weakness” Questions

Ah, the "What is your greatest weakness?" questions! They are painful, but interviewers love to ask them, and you need to be ready with a good answer.

They want you to be honest, but you don't have to dig into your dark past or reveal everything.

There is a good way and a bad way to answer these questions. One thing is for sure: you should never say, "I don't have any."

It’s also a bad idea to offer canned answers such as, “I’m a perfectionist.” (The interviewer will rightfully suspect that you don’t consider that to be a weakness, and will chalk the question up as a loss -- or worse, judge you for being cagey.)

The best way to answer questions about weaknesses is to be honest, positive, and focused on solutions. Choose a weakness that wouldn’t be a deal-breaker, and then describe how you overcame it. For example, describe a time when you realized your skills needed brushing up and then talk about what you’ve done to improve yourself.

4. What have you learned from your mistakes?

What They Want to Know: No employee is perfect 100% of the time – everyone makes mistakes occasionally. Employers ask this question to gauge your flexibility and your willingness to own your errors and to learn from them.

Mistakes are great learning experiences. While I try very hard not to make them, I’ve come to recognize that sometimes you just make a bad call. Years ago, our department was sorely understaffed, and the pressure was on to hire a new paralegal. So our selection team basically hired the first candidate who walked in the door, without really vetting him or extending our job search. He lasted all of two weeks. We learned that it pays to take the time to find good talent, even if you yourself have to work overtime until the position is filled.  

5. What do people most often criticize about you?

What They Want to Know: This question assesses your self-awareness and your ability to accept criticism. A good strategy is to talk about a “weakness” that has actually proven to be a strength.

People often tell me that I’m too hard on myself – I invest a fair amount of my ego into my work, and always worry that the copy I produce might not be “good enough.” I think that’s a fairly common mindset among writers, though, and I’d rather try to raise the bar than to complacently dash off a lot of ill-conceived text.

6. Why have you been out of work?

What They Want to Know: When they review their job candidates, a major red flag for employers is when someone has been unemployed for more than a few months. It’s in their best interest to learn whether this was a result of the candidate’s personal weaknesses (lack of ambition, laziness, or a poor work ethic) or whether there were extenuating circumstances beyond the individual’s control. 

After the company I worked for was sold and I was laid off, I decided to take the time to really assess my career trajectory. Although working at the call center paid the bills and it allowed me to capitalize upon my “people skills,” the work itself had become monotonous for me. So I decided to go back to school to finally become a physical therapist – a dream I had put on hold.

More Answers: Why were you fired?

 Previous Work Questions

Employers want to get a feel for how you handle workplace situations and what you think of your colleagues. These questions look back at your jobs, and it's a good idea to be prepared to answer them.

Try not to say many negative things—but if you do put a positive spin on them. You don't want to look like a whiner or that guy in the office who can't get along with anyone!

7. What did you like and dislike about your previous job?

What They Want to Know: The tone with which you answer this question is more important than the response you provide; the interviewer is trying to learn whether you are a complainer. Focus on the positive, and make sure that you don’t whine about a work task that will be essential in your new role.

I’m an introvert, and so I really appreciated the fact that my lab supervisor allowed me to work independently, without much supervision. I’m a very organized, analytical person who can focus like a laser beam on the small details of a scientific experiment. The only thing I disliked about the position was that the project funding was always in jeopardy – a common problem, and one I helped to remediate by writing a few grant proposals that were funded by the NIH.  

8. Who was your best supervisor and who was your worst?

What They Want to Know: This is another question where a hiring manager is primarily seeking to gain insight into your personality. Can you appreciate the positive traits of your supervisors, or are you eager to throw shade on them? Avoid doing the latter and focus on what you’ve learned from your previous bosses, without casting judgement on them as being “good” or “bad.”

Sample Answer: I’ve learned a lot about how to be a good manager from the supervisors I’ve had in the past. My favorite boss, Ted Jones, taught me to lead by example, and that there is no task too small for a manager to perform if it helps his team. That’s a quality that some of the managers I had early in my career lacked, and so I’m glad that Ted took me under his wing.

9. What was most and least rewarding about your last position? 

What They Want to Know: As with all tricky questions, you’ll want to emphasize the positive when answering this interview question. Focus on praising the elements of the job that will be most important in your new position. The “least rewarding” answer should mention something minor and innocuous, that won’t be important to your work for your new employer.

I was born to be a pediatric charge nurse, and I loved the opportunities I had at Houston General to proctor new nurses. The only thing I disliked was the commute, which is why I’m eager to find a nursing job closer to home.

 Tough “On the Job” Questions

This round of questions is trying to probe for how you would work in the company's environment. Each workplace is different in the expectations they have of their employees, but honest answers can help bridge any gaps.

10. What do you expect from a supervisor?

What They Want to Know: Your interviewer is interested in knowing whether you, as an employee, are coachable and have reasonable expectations of your supervisor; answering this question negatively (by listing what you dislike in supervisors) won’t earn you much credit. Provide an honest example of the management style that is most likely to motivate you to do your best work.

Sample Answer: I find I thrive in situations where my supervisors take the time to provide me with constructive feedback about my performance. This allows me to know that I’m on the right track. I also appreciate it when they have an “open door” policy where their staff feel encouraged to approach them about issues.

11. Tell me about something you would have done differently at work.

What They Want to Know: This is another version of a “weakness” question, so think carefully about which example you would like to share. Emphasize how you learned from the situation and / or were able to turn it to your advantage.

I made the mistake, back when I was just starting out, of thinking that I shouldn’t ask other people for help (even if they offered it). I was afraid that this would make me look incompetent or needy. What happened, as a result, was that I made a few mistakes that could have been avoided had I simply asked a peer about what approach I should take. It didn’t take long for me to realize that it was more productive to ask for help (as well as to offer it back in return).

12. How much do you expect to get paid? 

What They Want to Know: Employers want to know that your salary demands are reasonable. The safest strategy is to provide a believable ballpark figure, accompanied by a statement of your willingness to negotiate your pay scale.

Sample Answer: The major online salary calculators indicate that retail managers at my level of experience here in Miami can expect to earn between $48K and $52K. I’m more than open to negotiating this, depending upon your benefits package.

 Tips to Answer Tough Interview Questions

Are you still a bit worried about how you’ll handle the toughest interview questions? These tips should help as you prepare for your conversation with a hiring manager.

Get ready for a few questions without right or wrong answers (e.g., “Describe yourself,” or “How would you calculate the amount of toilet paper needed to span the state of New York?”) can be particularly tricky. Here are a few examples:

Prepare yourself to answer “Why are you leaving?” questions. Questions about why you are looking for work are among the toughest you will face, particularly if the circumstances are less than positive. An honest, well-thought-out answer can get you through this round of questioning.

Decide how to explain if you were fired from your last job. Especially if you’ve been fired, it’s important to have a strategy in place to deal with questions about why you’ve left your previous job. Best practice is to keep it simple, stay positive, and end on an upbeat note. Showing your readiness for a new direction in your life can turn a negative experience around. Be confident in this answer.

Know what to do if you don’t have an answer. Sometimes, despite doing all the preparation you can for an interview, you just don't have an answer or can't think of something to say right away. It happens more frequently than you might think.

Don't panic! When you can’t answer an interview question immediately, the goal is to buy yourself some time. Don’t rush. Take a deep breath. Ask for clarification if you need it. And if worse comes to worst, use your follow-up letter as a way to answer once you’ve had some time to research and formulate a response.

How to Make the Best Impression

You will need to put a little thought into answering these tough curveballs, and they're just a few examples of tricky questions. Many times, the interviewer wants to see how well you respond to changing environments and how fast you can think on your feet.

Be prepared with a few answers to the most common questions, but also be ready for something totally off-the-wall. If you need to, repeat the question as you come up with your answer. It's a great trick because it gives you time to think.