How to Answer the Most Difficult Interview Questions

Job interview
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You’re bound to be asked some difficult questions any time you interview for a new job. Although you can’t know for sure which challenging questions will come up, there are several common possibilities. It’s smart to practice answering tough questions during your interview prep.

Review sample questions and consider what appropriate responses might be, based on your background, skills, and the job opportunity. There aren't necessarily any right or wrong answers, but you will need to consider the requirements of the job you are applying for, your strengths, and the company culture before you respond.

Challenging Interview Questions and Answers

Questions About Co-Workers and Supervisors

Interviewers will ask about your experiences with your colleagues and managers to help determine how well you will fit in with a particular group. Try to keep a positive spin on all your answers, even when you may be tempted to criticize someone you worked with. Here are some examples:

  • Tell me about a time when you had to deal with a co-worker who wasn't doing his/her fair share of the work. What did you do and what was the outcome?
  • Give me an example of a time when you took the time to share a co-worker's or supervisor's achievements with others.
  • Tell me about a time that you didn't work well with a supervisor. What was the outcome and how would you like to have changed what happened?
  • Have you worked with someone you didn't like? If so, how did you handle it?
  • Tell me about a time that you helped someone.
  • Tell me about a time that you misjudged a person.
  • How do you get along with older (younger) co-workers?

How to Respond: Examples of the Best Answers

Questions About Your Abilities 

The hiring manager will be assessing your abilities during your interview so he or she can try to determine how successful you might be in the position you’re seeking. You should think about specific examples of positive outcomes from previous jobs. Here are some example questions:

  • Describe a decision you made that was a failure. What happened and why?
  • Tell me about a time that you needed to convey technical information to a non-technical audience.
  • Tell me about a time that you worked interpreting and presenting data.
  • Why do you think you will be successful in this job?
  • Tell me about a time that you participated in a team. What was your role and how well do you think you fulfilled it?
  • Tell me about a time when you were faced with conflicting priorities. How did you determine the top priority?
  • Tell me about a time when you failed.

How to Respond: Examples of the Best Answers

Questions About You

It’s appropriate for hiring managers to ask some personal questions during an interview, as long as they are professional and relate to your ability to do the job. Consider these questions:

  • What would you do differently if you could start your working life over?
  • How do you balance life and work?
  • What is your preferred way to communicate - instant message, phone, or email?
  • Do you check voicemail and email when on vacation?
  • What is your favorite book? How about your favorite movie?
  • What historical figure do you admire and why?
  • If you could choose anyone (alive or deceased) to have lunch with, who would it be?
  • What did you do during this six-month gap in employment?
  • What do you love to do for fun?
  • What led you to this point in your life?
  • Do you consider yourself successful?
  • What inspires you in a job?
  • What excites you most about the position and what do you think would be a stretch for you?
  • Who are the influencers in your life?

How to Respond:  Examples of the Best Answers

Questions About Your Career Goals 

When the interviewer asks you about your career goals, you’ll want to convey your ambition for the future and also stress your interest in learning and growing in the opportunity at hand. Your interviewer may want you to start with your graduation from college and explain the rationale behind each of your career moves. Also, she or she may ask you to explain the thinking process that went into making each of those decisions. In addition:

  • How many hours a day/week do you need to work to get the job done?
  • If you stayed with your current company, what would be your next move?
  • How do you measure success?
  • Describe your dream job.
  • Describe a job that would be your worst nightmare.
  • If you were the CEO of this company, what would be the top two things that you would do?

How to Respond: Examples of the Best Answers

Questions About Working With Other People 

In any position, interaction with your colleagues is essential, and how well you manage your relationships with others impacts the work environment for everyone. Interviewers will ask questions to determine how well you are able to work with others. For example:

  • How would you assess the skills, personality traits and work ethic of candidates by applying behavioral interviewing techniques?
  • What techniques have you used to motivate subordinates to improve performance?
  • Are you comfortable leading group discussions in a way that incorporates diverse views and draws consensus?
  • How do you develop a comfortable rapport with clients and determine their preferences for products and services?
  • Do you listen actively and emphatically to encourage clients to share their feelings and problems?
  • Have you created and delivered training sessions which engage the audience in active learning? Please describe.
  • How would you provide difficult news to an employee targeted for layoff?
  • Tell me about a time when you mediated conflicts between employees or with clients.
  • Are you able to resolve customer complaints with patience and creativity?

How to Respond: Examples of the Best Answers

More Challenging (and Some Strange) Questions

These questions don’t fall into any particular category and they may seem a bit unnerving. But they’re worth considering:

  • Are you a risk taker?
  • If you were an animal what would you be?
  • Convince me to hire you.
  • We unplugged that clock on the wall. Why did we do that?
  • Why shouldn't I hire you?
  • What does your current employer think you are doing today?

Interview Questions Employers Should Not Ask

Some of the most difficult interview questions to respond to shouldn’t be asked at all. These are known as illegal interview questions and employers should not ask them during a job interview. But, from time to time, hiring managers slip up and ask questions they shouldn’t. 

It pays to be prepared to handle illegal or inappropriate questions, so that you’ll know what to do. Depending on the situation, you might choose to end the interview, refuse to answer, or answer politely while avoiding the illegal part of the question.

The Bottom Line

Tough Questions Come in Several Different Types: You might be asked about your skills and abilities, how you get along with co-workers and supervisors, and about your long-term career goals.

Practice Answering Difficult Interview Questions: There are no right or wrong answers, but try to emphasize your skills and fitness for the job.

Got Some Extra Time? Prepare for the Really Out-There Questions: What kind of animal would you be, really, if you could be any animal?

Know Which Questions Are Illegal: Hiring managers shouldn’t ask you questions that could be used to illegally discriminate against you.