How to Answer The 16 Toughest Interview Questions

Question 49: What was the toughest challenge you’ve ever faced?

TRAPS:  Being unprepared or citing an example from so early in your life that it doesn’t score many points for you at this stage of your career.

Question 50: Have you consider starting your own business?

TRAPS:  If you say “yes” and elaborate enthusiastically, you could be perceived as a loose cannon in a larger company, too entrepreneurial to make a good team player…or someone who had to settle for the corporate life because you couldn’t make a go of your own business.

Also too much enthusiasm in answering “yes” could rouse the paranoia of a small company indicating that you may plan to go out on your own soon, perhaps taking some key accounts or trade secrets with you.

On the other hand, if you answer “no, never” you could be perceived as a security-minded drone who never dreamed a big dream.

Question 51: What are your goals?

TRAPS:  Not having any…or having only vague generalities, not highly specific goals.

Question 52: What do you for when you hire people?

TRAPS:  Being unprepared for the question.

Question 53: Sell me this stapler…(this pencil…this clock…or some other object on interviewer’s desk).

TRAPS:  Some interviewers, especially business owners and hard-changing executives in marketing-driven companies, feel that good salesmanship is essential for any key position and ask for an instant demonstration of your skill.  Be ready.

Question 54: “The Salary Question” – How much money do you want?

TRAPS:  May also be phrases as, “What salary are you worth?”…or, “How much are you making now?”  This is your most important negotiation. Handle it wrong and you can blow the job offer or go to work at far less than you might have gotten.

Question 55: The Illegal Question

TRAPS:  Illegal questions include any regarding your age…number and ages of your children or other dependents…marital status…maiden name…religion…political affiliation…ancestry…national origin…birthplace…naturalization of your parents, spouse or children…diseases…disabilities…clubs…or spouse’s occupation…unless any of the above are directly related to your performance of the job.  You can’t even be asked about arrests, though you can be asked about convictions.

Question 56: The “Secret” Illegal Question

TRAPS:  Much more frequent than the Illegal question (see Question 55) is the secret illegal question.  It’s secret because it’s asked only in the interviewer’s mind.  Since it’s not even expressed to you, you have no way to respond to it, and it can there be most damaging.

Example:  You’re physically challenged, or a single mother returning to your professional career, or over 50, or a member of an ethnic minority, or fit any of a dozen other categories that do not strictly conform to the majority in a given company.

Your interviewer wonders, “Is this person really able to handle the job?”…”Is he or she a ‘good fit’ at a place like ours?”…”Will the chemistry ever be right with someone like this?”  But the interviewer never raises such questions because they’re illegal.  So what can you do?

Question 57: What was the toughest part of your last job?

TRAPS: This is slightly different from the question raised earlier, “What’s the most difficult part of being a (job title…)” because this asks what you personally have found most difficult in your last position.  This question is more difficult to redefine into something positive.  Your interviewer will assume that whatever you found toughest may give you a problem in your new position.

Question 58: How do you define success…and how do you measure up to your own definition?

TRAPS:  Seems like an obvious enough question.  Yet many executives, unprepared for it, fumble the ball.

Question 59: “The Opinion Question” – What do you think about …Abortion…The President…The Death Penalty…(or any other controversial subject)?

TRAPS:  Obviously, these and other “opinion” questions should never be asked.  Sometimes they come up over a combination dinner/interview when the interviewer has had a drink or two, is feeling relaxed, and is spouting off about something that bugged him in today’s news.  If you give your opinion and it’s the opposite of his, you won’t change his opinions, but you could easily lose the job offer.

Question 60: If you won $10 million lottery, would you still work?

TRAPS:  Your totally honest response might be, “Hell, no, are you serious?”  That might be so, but any answer which shows you as fleeing work if given the chance could make you seem lazy.  On the other hand, if you answer, “Oh, I’d want to keep doing exactly what I am doing, only doing it for your firm,” you could easily inspire your interviewer to silently mutter to himself, “Yeah, sure.  Gimme a break.”

Question 61: Looking back on your last position, have you done your best work?

TRAPS:  Tricky question.  Answer “absolutely” and it can seem like your best work is behind you.  Answer, “no, my best work is ahead of me,” and it can seem as if you didn’t give it your all.

Question 62: Why should I hire you from the outside when I could promote someone from within?

TRAPS:  This question isn’t as aggressive as it sounds.  It represents the interviewer’s own dilemma over this common problem.  He’s probably leaning toward you already and for reassurance, wants to hear what you have to say on the matter.

Question 63: Tell me something negative you’ve heard about our company…

TRAPS:  This is a common fishing expedition to see what the industry grapevine may be saying about the company.  But it’s also a trap because as an outsider, you never want to be the bearer of unflattering news or gossip about the firm.  It can only hurt your chances and sidetrack the interviewer from getting sold on you.

Question 64: On a scale of one to ten, rate me as an interviewer.

TRAPS:  Give a perfect “10,” and you’ll seem too easy to please.  Give anything less than a perfect 10, and he could press you as to where you’re being critical, and that road leads downhill for you.

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