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The Hardest Interview Questions & How to Answer Them


Everyone is nervous on interviews.

If you simply allow yourself to feel nervous, you will do much better. Remember, it is difficult for the interviewer as well. In general, be upbeat and positive. Never be negative. Never talk for more than 2 minutes straight—no one wants to listen to rambling. Be sure to rehearse your answers, but don’t try to memorize answers word for word.

You must remember this strategy above all: before blurting out your qualifications, you must get some idea of what the employer wants most. Once you know what they want, you can then present your qualifications as the perfect “key” that fits the “lock” of that position. 

You should also remember to turn your weaknesses into strengths; never be negative. If you go negative, you are doing the interviewers job for them by pointing out why they shouldn’t hire you. You’re there to make yourself shine!

Most important of all: be honest...never lie.  If you go back and read our blog post about why you should NEVER “fake it ‘til you make it”, you’ll know why.

Here are some of the hardest interview questions we have ever encountered, and how to answer them.


Question: 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. 

PASSABLE ANSWER:  Disguise a strength as a weakness. 

Example: “I sometimes push my people too hard.  I like to work with a sense of urgency and everyone is not always on the same wavelength.”

Drawback:  This strategy is better than admitting a flaw, but it's so widely used, it is transparent to any experienced interviewer. 

BEST ANSWER: (and another reason it's so important to get a thorough description of your interviewer's needs before you answer questions): Assure the interviewer that you can think of nothing that would stand in the way of your performing in this position with excellence. Then, quickly review your strongest qualifications. 

Example: “Nobody's perfect, but based on what you've told me about this position, I believe I' d make an outstanding match. I know that when I hire people, I look for two things most of all. Do they have the qualifications to do the job well, and the motivation to do it well?  Everything in my background shows I have both the qualifications and a strong desire to achieve excellence in whatever I take on. So, I can say in all honesty that I see nothing that would cause you even a small concern about my ability or my strong desire to perform this job with excellence.”


Question: 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,” but 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.

BEST ANSWER:  As with faults and weaknesses, never confess a regret.  But don’t seem as if you’re stonewalling either.

Best strategy:  Say you harbor no regrets, then add a principle or habit you practice regularly for healthy human relations.


Question: 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, 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.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.

BEST ANSWER:  The Silent Treatment loses all it power to frighten you once you refuse to be intimidated.  If your interviewer pulls it, keep quiet yourself for a while and then ask, with sincere politeness and not a trace of sarcasm, “Is there anything else I can fill in on that point?”  That’s all there is to it.


 Question: 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.

BEST ANSWER:  You want to emphasize factors which have prolonged your job search by your own choice.

Example: “I had something that needed to be dealt with (medical condition, death of a love, etc.). I have handled it, and now I am 100% ready to re-enter the workforce”


Question: The “Fatal Flaw” Question

TRAPS:  If an interviewer has read your resume carefully, he may try to zero in on a “fatal flaw” of your candidacy, perhaps that you don’t have a college degree, you’ve been out of the job market for some time, etc. A fatal flaw question can be deadly, but usually only if you respond by being overly defensive.

BEST ANSWERS:  As every master salesperson knows, you will encounter objections (whether stated or merely thought) in every sale.  They’re part and parcel of the buyer’s anxiety.  The key is not to exacerbate the buyer’s anxiety but diminish it.  Here’s how…

Whenever you come up against a fatal flaw question: 

1. Be completely honest, open and straightforward about admitting the shortcoming.  (Showing you have nothing to hide diminishes the buyer’s anxiety.) 2. Do not apologize or try to explain it away.  You know that this supposed flaw is nothing to be concerned about, and this is the attitude you want your interviewer to adopt as well. 3. Add that as desirable as such a qualification might be, its lack has made you work all the harder throughout your career and has not prevented you from compiling an outstanding track record of achievements.  You might even give examples of how, through a relentless commitment to excellence, you have consistently outperformed those who do have this qualification. 

Once you’ve gotten the employer to start talking about his most urgently-felt wants and goals for the position, and then help him see in step-by-step fashion how perfectly your background and achievements match up with those needs, you’re going to have one very enthusiastic interviewer on your hands, one who is no longer looking for “fatal flaws”


Question: Could You Have Done Better in Your Last Job?

TRAPS:  This is no time for true confessions of major or even minor problems.

BEST ANSWER:  Again never be negative.

Example: “I suppose with the benefit of hindsight you can always find things to do better, of course, but off the top of my head, I can’t think of anything of major consequence.”


Question: 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, or spouse’s occupation…unless any of the above are directly related to your performance of the job.

BEST ANSWER:  Under the ever-present threat of lawsuits, most interviewers are aware of these taboos.  Yet you may encounter, usually on a second or third interview, a senior executive who doesn’t interview much and forgets he can’t ask such questions.

You can handle an illegal question in several ways. First, you can assert your legal right not to answer. But this will frighten or embarrass your interviewer and destroy any rapport you had. Second, you could swallow your concerns over privacy and answer the question straight forwardly if you feel the answer could help you. Third, if you don’t want your privacy invaded, you can diplomatically answer the concern behind the question without answering the question itself.

Example:  If you are over 50 and are asked, “How old are you?” you can answer with a friendly, smiling question of your own on whether there’s a concern that your age my affect your performance.  Follow this up by reassuring the interviewer that there’s nothing in this job you can’t do and, in fact, your age and experience are the most important advantages you offer the employer for the following reasons…

Remember that illegal questions arise from fear that you won’t perform well.  The best answer of all is to get the job and perform brilliantly. All concerns and fears will then varnish, replaced by respect and appreciation for your work.


Question: The “Secret” Illegal Question

TRAPS:  Much more frequent than the Illegal question 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?

BEST ANSWER:  Remember that just because the interviewer doesn’t ask an illegal question doesn’t mean he doesn’t have it.  More than likely, he is going to come up with his own answer.  So, you might as well help him out. How?  Well, you can’t respond to an illegal question if he hasn’t even asked.  And there’s always the chance he wasn’t even concerned about the issue until you brought it up, and only then begins to wonder.

You can’t address “secret” illegal questions head-on.  But what you can do is make sure there’s enough counterbalancing information to more than reassure him that there’s no problem in the area he may be doubtful about.

For example, let’s say you’re a sales rep who had polio as a child and you need a cane to walk.  You know your condition has never impeded your performance, yet you’re concerned that your interviewer may secretly be wondering about your stamina or ability to travel.  Well, make sure that you hit these abilities very hard, leaving no doubt about your capacity to handle them well.



Just remember that if you're called in for an interview, the hiring manager already saw something they liked about you. Just relax and stay positive.

Good luck and happy job hunting!

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