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 or you are asked to solve a problem. 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.
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? 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. More Answers: What has been the greatest disappointment in your life?
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. 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. 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.
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. More Answers: Why should I take a risk on you?
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. 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. More Answers: Interview questions about handling problems at your last job.
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. More Answers: What was it like working with your supervisor?
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. More Answers: What were your biggest successes and failures?
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. More Answers: How would you handle it if your boss was wrong?
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. More Answers: Do you have any pet peeves?
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. More Answers: Are you overqualified for this job?
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:
Tell me about your dream job. What makes you unique? Where else are you interviewing? Why should we hire you? Why shouldn’t we hire you?
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.
