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25 Tricky Interview Questions and How to Answer Them

By Peter K. Studner
Master Career Counselor
Author, Super Job Search IV: The Complete Manual for Job Seekers & Career Changers

The interview is the most important part of your job search. Yes, it’s important to craft a strong, accurate résumé — but like it or not, most jobs are secured or lost in the interview stage.

That’s why you should put more effort into preparing for interviews than you do into any other part of your job search campaign.

While there are no perfect answers to any one question, some thought and discussion about potentially tricky interview subjects can help you avoid disaster and get a job offer.

Since 1989, our company has been devoted to helping people transition into new jobs, careers, retirement activities, and business ownership.

Over the years of helping thousands of people move into the jobs they dream of, we’ve seen again and again that the most qualified candidates do not always get the best jobs. However, outstanding candidates always get the best offers.

That’s why our mission is to make outstanding candidates.

And that’s why my book, “Super Job Search IV,” gives job seekers the tools they need to succeed in any job search, and it dymystifies the process into a systematic, seven-step program that includes online resources and an app.

Scroll down for 25 of the possible interview questions — and answers — discussed in “Super Job Search IV”.


  1. What Salary Are You Looking For?
    Whenever possible, don’t provide a specific answer to this question until the negotiations phase, after a position has already been offered. To defer the discussion, try returning the focus back to the interviewer: “It’s hard to discuss salary without knowing more about the job or responsibilities.” Or, if you are discussing a specific job: “What is your range?” Then relate your experience to the salary range without being precise: “I think my experience would put me near the high end of your range, don’t you?”
  2. What Were You Making in Your Last Job?
    If at all possible, do not volunteer information about your past salary. A diplomatic way to put the salary question aside is to reply, “I was well compensated in my previous company but really do not wish to prejudice myself here by being too high or low. Can we delay this until after we’ve looked at all the aspects of your current need? What is your range for this job?”
  3. Have You Ever Been Fired?
    If the answer is yes, have a good explanation worked out and tested with friends. For instance: “We had a change in general managers, and although I had been doing a great job as you can see from my accomplishments, I was let go for one of his former associates.” Or: “The company decided to close down its California operation and offered me a job in Chicago. We would like to stay in this area so that’s why I’m looking around.”
  4. Can You Work Under Pressure?
    Indicate that you can and ask the interviewer how much pressure is involved in the position. Learn what the interviewer means by pressure. The definition can vary significantly from person to person and company to company. If you are a pro at pressure jobs, describe a few accomplishments.
  5. What Did You Think of Your Last Supervisor?
    Whatever your true feelings might be, stay positive. This is not the time or place to list your boss’s shortcomings or frustrating behaviors. Try a responses such as: “She was the kind of person I could learn from.” Or: “We were able to communicate well and things got done quickly.”
  6. What Is Your Greatest Strength?
    Before interviewing, reflect on your personal strengths and make a list of them (e.g., “natural number sense,” “able to multitask,” “good with people,” “able to teach others,” etc.). Then tie each of them to a professional accomplishment. When asked this question in an interview, answer with the strength you feel best fits the position being discussed, and be sure to offer the anecdote that goes with it. Conclude your response by asking the interviewer if this is the kind of quality that would help his or her company.
  7. What Is Your Greatest Weakness?
    As with your strengths, prepare a list of weaknesses beforehand. This time, tie each weakness back to what could also be considered a strength. For example, “I like to get things done. Sometimes I get impatient, but I’m getting a handle on it.” Or maybe you have actually come up with a way to mitigate your weakness: “I’m a stickler for details, but I do not want to be a micromanager. So at my last job, I asked each staff member to devise their own checklist of weekly tasks. It gave them some autonomy and satisfied my desire for quality control.”
  8. You’ve Moved Around a Lot. How Long Would You Stay with Us?
    Make sure that your answer doesn’t make you seem indecisive, fickle, or uncommitted. A good answer might be, “I’m seeking a long-term opportunity where I can learn and grow. Does this come with the position we are discussing?”
  9. What Motivates You?
    Resist the temptation to joke, “A steady paycheck!” Try to tie your motivation to the work being done at this specific company. In addition you could mention things like the opportunity to learn and grow, to work with smart people who are passionate about their jobs, to innovate, and to contribute to the success of an organization.
  10. What Do You Not Like to Do?
    This is a loaded question. A positive reply might be, “I’m the kind of person who does whatever is necessary to get the job done. When I do run into something disagreeable, I try to do it first and get it behind me. I have no particular dislikes.”
  11. How Would Your Boss, Coworkers, and Subordinates Describe You?
    Be ready to give some examples of the kind of team player you are. If you are not into office politics and have harbored good relationships at work, mention it. And remember that the interviewer may ask your references the same question. I strongly suggest meeting with your references before the interview stage in order to talk through your career goals and how the reference can best support them.
  12. What Is the Toughest Part of Being a Manager?
    A good reply is: “To surround myself with people who are better than I am in their individual specialties.”
  13. Why Do You Want to Work for Our Company?
    Your reply could be based on their reputation for products, management, international scope, technology, or as a nice place to work and grow. The most important thing is to avoid generic answers. Know their products, policies, and potential for you.
  14. Why Should We Hire You?
    If you know the job requirements and can match them with some accomplishments, briefly share those anecdotes. Then say, “If there are opportunities to do that and more here, then this is a great fit. What do you think?”
  15. What Has Been Your Biggest Failure?
    Discuss this question with friends, mentors, and possibly your references before the interview. If at all possible, think of something you were later able to correct. Then the story isn’t just about a failure, but also about a learning experience.
  16. What Kind of Day-to-Day Schedule Did You Have in Your Last Job?
    The interviewer isn’t looking for a minute-by-minute breakdown of a typical day. Stress action, performance, and results rather than administrative work.
  17. How Do You Feel About the Progress You Made in Your Last Position?
    Rather than discuss your feelings, per se, stress your accomplishments. For instance: “When I started with the Blake Company, I was given responsibility for their operations in Mexico and Costa Rica. After I turned them around, they made me general manager for Mexico and Central America. How are your international operations performing?” An answer like this communicates great information about your value as an employee while still conveying positive feelings about your progress.
  18. Did You Have Any Frustrations in Your Past Job?
    Frustrations are a normal part of any job, and interviewers know this—so don’t claim you didn’t have any. Relate some of the bottlenecks you experienced, but more important, indicate what you did to overcome them.
  19. Do You Like to Compete?
    Competition is great as long as it does not sacrifice the rest of the team. If you are competitive, relate that quality to the total company effort and not to your personal ambitions.
  20. How Long Do You Think It Would Be Before You Could Make a Contribution to Our Company?
    Don’t be in a hurry when providing an answer to this question. There normally is a period of transition before a new hire learns the ropes. You might say, “If the transition goes according to plan, I would guess relatively soon. What would you expect?”
  21. What Was the Last Book You Read?
    You do read. Saying that you don’t in this setting is a misstep. But be careful not to fib. Your interviewer may have read the same book!
  22. Don’t You Feel That You’re Overqualified for the Position?
    Ouch! If you have a lot of experience and the company is thinking of hiring a younger person, you may get this kind of query. A good answer is: “I imagine my experience would make me more valuable sooner!”
  23. Do You Mind Working for Someone of the Opposite Sex or Someone Younger Than You?
    It’s the job that counts. Stick to the job specification and don’t get sidetracked on implications.
  24. How Do You Take Criticism?
    Most people have problems taking criticism. If the criticism is part of a formal evaluation program where you can learn and improve, that is fine. “I would welcome the opportunity to learn how to do my job better. Do you have a formal program for employee evaluation?”
  25. How Do You Spend Your Free Time?
    Be reasonable. This is not the time to mention that you like jumping out of planes, even if it is true.

You may not be asked these specific questions in your interview, but knowing how you want to answer them will ensure that you’re prepared to discuss a wide variety of topics that might come up. You don’t want to have to formulate a complicated answer in the midst of an already nerve-wracking situation!


About Peter K. Studner

Peter K. Studner is the author of “Super Job Search IV: The Complete Manual for Job Seekers & Career Changers” (Jamenair Ltd., 2015, $26.95). A master career counselor and former chief executive and board member of companies in the United States, France, and Great Britain, he has helped thousands of people with their career transitions, and he trains other career professionals to deliver his easy-to-follow program. Super Job Search IV: The Complete Manual for Job Seekers & Career Changers is available on Amazon and at bookstores nationwide.

Learn more at www.SuperJobSearch.com.