How to Answer The 16 Toughest Interview Questions

Question 1: Tell me about yourself?

TRAPS:  Beware, about 80% of all interviews begin with this “innocent” question. Many candidates, unprepared for the question, skewer themselves by rambling, recapping their life story, delving into ancient work history or personal matters

Question 2: What are your greatest strengths?

TRAPS: This question seems like a softball lob, but be prepared. You don’t want to come across as egotistical or arrogant. Neither is this a time to be humble. 

Question 3: What are your greatest weaknesses?

TRAPS: Beware – this is an eliminator question, designed to shorten the candidate list. Any admission of a weakness or fault will earn you an “A” for honesty, but an “F” for the interview.

Question 4: Tell me about something you did – or failed to do – that you now feel a little ashamed of.

TRAPS: There are some questions your interviewer has no business asking, and this is one.  But while you may feel like answering, “none of your business,” naturally you can’t.  Some interviewers ask this question on the chance you admit to something, but if not, at least they’ll see how you think on your feet.

Some unprepared candidates, flustered by this question, unburden themselves of guilt from their personal life or career, perhaps expressing regrets regarding a parent, spouse, child, etc.  All such answers can be disastrous.

Question 5: Why are you leaving (or did you leave) this position?

TRAPS: Never badmouth your previous industry, company, board, boss, staff, employees or customers.  This rule is inviolable:  never be negative.  Any mud you hurl will only soil your suit.

Especially avoid words like “personality clash”, “didn’t get along”, or others which cast a shadow on your competence, integrity, or temperament.

Question 6: The “Silent Treatment”

TRAPS: Beware – if you are unprepared for this question, you will probably not handle it right and possibly blow the interview.  Thank goodness most interviewers don’t employ it.  It’s normally used by those determined to see how you respond under stress.  Here’s how it works:

You answer an interviewer’s question and then, instead of asking another, he just stares at you in a deafening silence.

You wait, growing a bit uneasy, and there he sits, silent as Mt. Rushmore, as if he doesn’t believe what you’ve just said, or perhaps making you feel that you’ve unwittingly violated some cardinal rule of interview etiquette.

When you get this silent treatment after answering a particularly difficult question , such as “tell me about your weaknesses”, its intimidating effect can be most disquieting, even to polished job hunters.

Most unprepared candidates rush in to fill the void of silence, viewing prolonged, uncomfortable silences as an invitation to clear up the previous answer which has obviously caused some problem.  And that’s what they do – ramble on, sputtering more and more information, sometimes irrelevant and often damaging, because they are suddenly playing the role of someone who’s goofed and is now trying to recoup.  But since the candidate doesn’t know where or how he goofed, he just keeps talking, showing how flustered and confused he is by the interviewer’s unmovable silence.

Question 7: Why should I hire you?

TRAPS: Believe it or not, this is a killer question because so many candidates are unprepared for it.  If you stammer or adlib you’ve blown it.

Question 8: Aren’t you overqualified for this position?

TRAPS: The employer may be concerned that you’ll grow dissatisfied and leave.

Question 9: Where do you see yourself five years from now?

TRAPS: One reason interviewers ask this question is to see if you’re settling for this position, using it merely as a stopover until something better comes along.  Or they could be trying to gauge your level of ambition.

If you’re too specific, i.e., naming the promotions you someday hope to win, you’ll sound presumptuous.  If you’re too vague, you’ll seem rudderless.

Question 10: Describe your ideal company, location and job.

TRAPS: This is often asked by an experienced interviewer who thinks you may be overqualified, but knows better than to show his hand by posing his objection directly.  So he’ll use this question instead, which often gets a candidate to reveal that, indeed, he or she is looking for something other than the position at hand.

Question 11: Why do you want to work at our company?

TRAPS: This question tests whether you’ve done any homework about the firm.  If you haven’t, you lose.  If you have, you win big.

Question 12: What are your career options right now?

TRAPS: The interviewer is trying to find out, “How desperate are you?”

Question 13: Why have you been out of work so long?

TRAPS: A tough question if you’ve been on the beach a long time.  You don’t want to seem like damaged goods.

Question 14: Tell me honestly about the strong points and weak points of your boss (company, management team, etc.)…

TRAPS: Skillfull interviewers sometimes make it almost irresistible to open up and air a little dirty laundry from your previous position.  DON’T

Question 15: What good books have you read lately?

TRAPS:  As in all matters of your interview, never fake familiarity you don’t have.  Yet you don’t want to seem like a dullard who hasn’t read a book since Tom Sawyer.

Question 16: Tell me about a situation when your work was criticized.

TRAPS:  This is a tough question because it’s a more clever and subtle way to get you to admit to a weakness.  You can’t dodge it by pretending you’ve never been criticized.  Everybody has been.  Yet it can be quite damaging to start admitting potential faults and failures that you’d just as soon leave buried.

This question is also intended to probe how well you accept criticism and direction.

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