Difficult, confusing interview questions and answers

1. What critical feedback do you most often receive?

This question is similar to “What are your greatest weaknesses?” Employers ask this question to see if you have a sense of self-awareness and that you’re actively working on self-improvement. To answer this question, think of a genuine piece of criticism you’ve been given, or a weakness you’re aware of. Provide a brief explanation of the critique and how you’re working on improving it.

2. 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.

3. How do you handle stress?

Stress is a component in many jobs, employers want to know you’ll handle it constructively with a good attitude to maintain good company culture. You can answer this question by explaining how you typically respond with an example to support it.

4. 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 fit under a certain manager. You should answer this question honestly and as tactfully as possible.

5. What’s your biggest weakness?

Employers may ask about your weaknesses to see if you have a sense of self-awareness and how you’re working to improve.

6. Why are you leaving your current position?

This is valuable information for employers to understand. It helps them ensure the opening will be a better fit, make sure they can provide for what your previous employer did not or see if you might have contributed to a negative experience for both you and the employer. Answer this question honestly, but refrain from providing too much personal or negative detail.

7. How many pennies, if stacked on top of each other, would equal the height of the Empire State building? (Or other questions with no right or wrong answer)

Employers may ask questions like this to understand your thought processes. They want to gauge whether you can think analytically, deal with ambiguity and communicate clearly. It is completely appropriate and even encouraged to ask for a few minutes to gather your thoughts. Even if your answer seems silly or wrong, employers are simply looking for an answer with logical support. It is also appropriate to ask follow-up questions for more information or context, though they may or may not provide the answer.

8. Why do you want to work here?

Employers often ask this question to make sure you’ve put thought and research into your decision to seek employment at their company. This question might be particularly important if you’re changing industries or job roles.

9. Why should we hire you?

Employers might ask this question to 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 carefully review the job description beforehand to understand what qualities they’re looking for.

10. Do you have any regrets?

Employers might ask this question to get a self-assessment on possible shortcomings in your life. To answer this question, you might choose to say that you do not have any regrets in life for a certain reason. Be sure to let them know that you have made mistakes, you have learned from them to become better. If not, you might select a regret or shortcoming that is both professional and would not hinder your ability to perform the job in any way.

11. Tell me about yourself

Employers will likely ask this question early on in the interview process, or you might have to answer it in early-stage phone interviews or recruiter screens. To answer this question, you should provide a quick synopsis of your education, highlights of your professional experience and achievements and what brought you to the position you’re applying for.

12. What’s your greatest achievement?

Employers might ask this question to understand what you consider to be your most valuable accomplishments. To answer, think about a recent example that is ideally related to the job in some way. Briefly explain the achievement, your role in it and why it is valuable to you.


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