Tricky Job Interview Questions

According to employment expert Joyce Kennedy, the right answers to tricky job interview questions can make the difference between a job offer and a rejection letter.


Image Credit: Bob Smith

Today’s job seekers come from a diverse range of backgrounds and career fields. Displaced career veterans, recent college graduates, employed workers seeking a career change – every job seeker has a unique set of career objectives and job search goals.

But despite the diversity of job seekers and the constantly shifting landscape of the job marketplace, the hiring process remains the same. It all boils down to learning how to nail the job interview.

“Job interviews are still those crucial meetings that seal the deal on who gets hired and who gets left on the outside looking in,” says Joyce Lain Kennedy, author of the award-winning book Job Interviews For Dummies®, 4th Edition (Wiley, 2011) “And with any good job interview come questions that always seem to trip us up.”

Why have you been out of work so long? How many others were laid off? Why you? 

The interviewer is fishing to determine whether there was a layoff of one (you), or whether your former manager used the theme of recession and budget cuts to dump groups of second-string employees. “Any direct answer to why you were included in a reduction in force is risky because anger toward your former managers could pop up, raising doubt about your self-control,” says Kennedy. “A better idea: Punt. Shake your head and say you don’t know the reason, because you were an excellent employee who gave more than a day’s work for a day’s pay.”

How did you prepare for this interview? 

The employer is really asking if you think the job is important enough to research it or whether are you going through the motions without preparation, making it up as you go? “The best answer?” says Kennedy. “You very much want this job, and of course you researched it starting with the company website.”

Do you know anyone who works for us?

“Nothing beats having a friend deliver your résumé to a hiring manager, but that transaction presumes the friend is well thought of in the company,” notes Kennedy. “Remember the birds-of-a-feather rule: Mention a friend inside the company only if you’re certain of your friend’s positive standing.”

Where would you really like to work? Doing what? 

“Caveat: Never, ever mention another company’s name or another job,” says Kennedy. “A short ‘Hire me!’ answer is a version of: ‘This is the place where I want to work, and this job is what I want to do. I have what you need, and you have what I want. I can’t wait to get to work here.’”

What bugs you about coworkers or bosses? 

“Mention that you’ve been lucky to have good bosses who are knowledgeable and fair, with a sense of humor and high standards,” advises Kennedy. “Past coworkers were able, supportive, and friendly. Smile your most sincere smile. Don’t be lured into elaborating further.”

Can you describe how you solved a work/school problem? 

“The answer is obvious,” says Kennedy. “Anticipate a question about how your mind works and have a canned answer ready. A new graduate might speak of time management to budget more time for study; an experienced worker might speak of time management to clear an opportunity for special task force assignments.”

Can you describe a work/school instance in which you messed up? 

“Speaking of mistakes, here’s a chance to avoid making one during your job interview,” notes Kennedy. “Never deliver a litany of your personal bad points. Instead, briefly mention a single small, well-intentioned goof and follow up with an important lesson learned from the experience.”

A Little Extra Help: What to Say When You’re Uncertain. 

Don’t panic if you are asked a question that you have no idea how to answer. Take a deep breath, look the interviewer in the eyes, and say that while it’s a great question, you would like to mull it over and come back to it. If you’re lucky, the interviewer may forget to ask it again. “But if the question does resurface and your brain goes on holiday, say that you don’t know the answer and that, being a careful worker, you prefer not to guess,” recommends Kennedy. “If you’ve otherwise done a good job of answering questions and confidently explained why you’re a great match for the position, the interviewer probably won’t consider your lack of specifics on a single topic to be a deal breaker.”


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