How to Answer The Toughest Interview Questions

How to Answer The Toughest Interview Questions

How to Answer The Toughest Interview Questions.

During a job interview, you may be asked tough questions that necessitate more thought.
Tough interview questions vary greatly across industries, but there are a few tough questions that employers frequently ask to learn more about you as a candidate.

In this article, we will highlight why employers ask tough questions and what they are looking for in your answer. Then, we look at some tough interview questions and sample answers.

Why employers ask tough interview questions

  • Employers ask tough questions to find out how you process information and solve problems.
  • Prepare to explain your reasoning and discuss your approach.
  • Remain composed, take a minute to gather your thoughts, and if necessary, seek clarification.

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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.

BEST ANSWER: Start with the present and tell why you are well qualified for the position.  Remember that the key to all successful interviewing is to match your qualifications to what  the interviewer is looking for. In other words you must sell what the buyer is buying. This  is the single most important strategy in job hunting.  

So, before you answer this or any question it’s imperative that you try to uncover your  interviewer’s greatest need, want, problem or goal.

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To do so, make you take these two steps:

  1. Do all the homework you can before the interview to uncover this person’s wants  and needs (not the generalized needs of the industry or company)
  2. As early as you can in the interview, ask for a more complete description of what the  position entails. You might say: “I have a number of accomplishments I’d like to tell  you about, but I want to make the best use of our time together and talk directly to  your needs. To help me do, that, could you tell me more about the most important  priorities of this position? All I know is what I (heard from the recruiter, read in the  classified ad, etc.)”

Then, ALWAYS follow-up with a second and possibly, third question, to draw out his  needs even more. Surprisingly, it’s usually this second or third question that unearths what  the interviewer is most looking for.

You might ask simply, “And in addition to that?…” or, “Is there anything else you see as  essential to success in this position?:

This process will not feel easy or natural at first, because it is easier simply to answer  questions, but only if you uncover the employer’s wants and needs will your answers make the  most sense. Practice asking these key questions before giving your answers, the process will  feel more natural and you will be light years ahead of the other job candidates you’re  competing with.

After uncovering what the employer is looking for, describe why the needs of this job bear striking  parallels to tasks you’ve succeeded at before. Be sure to illustrate with specific examples of your  responsibilities and especially your achievements, all of which are geared to present yourself as a  perfect match for the needs he has just described.

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.

BEST ANSWER: You know that your key strategy is to first uncover your interviewer’s  greatest wants and needs before you answer questions. And from Question 1, you know how  to do this.

Prior to any interview, you should have a list mentally prepared of your greatest strengths. You  should also have, a specific example or two, which illustrates each strength, an example  chosen from your most recent and most impressive achievements.

You should, have this list of your greatest strengths and corresponding examples from your  achievements so well committed to memory that you can recite them cold after being shaken  awake at 2:30AM.

Then, once you uncover your interviewer’s greatest wants and needs, you can choose those  achievements from your list that best match up.

As a general guideline, the 10 most desirable traits that all employers love to see in their  employees are:

  1. A proven track record as an achiever…especially if your achievements match  up with the employer’s greatest wants and needs. 
  2. Intelligence…management “savvy”.
  3. Honesty…integrity…a decent human being.
  4. Good fit with corporate culture…someone to feel comfortable with…a team player  who meshes well with interviewer’s team.
  5. Likeability…positive attitude…sense of humor.
  6. Good communication skills.
  7. Dedication…willingness to walk the extra mile to achieve excellence.  8. Definiteness of purpose…clear goals.
  8. Enthusiasm…high level of motivation. Confident…healthy…a leader.

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.

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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 you 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.”

Alternate strategy (if you don’t yet know enough about the position to talk about such a  perfect fit):

Instead of confessing a weakness, describe what you like most and like least, making sure  that what you like most matches up with the most important qualification for success in the  position, and what you like least is not essential.

Example: Let’s say you’re applying for a teaching position. “If given a choice, I like to spend as  much time as possible in front of my prospects selling, as opposed to shuffling paperwork back  at the office. Of course, I long ago learned the importance of filing paperwork properly, and I  do it conscientiously. But what I really love to do is sell (if your interviewer were a sales  manager, this should be music to his ears.)

How to Answer The Toughest Interview Questions

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.

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.

Example: Pause for reflection, as if the question never occurred to you. Then say, “You  know, I really can’t think of anything.” (Pause again, then add): “I would add that as a general  management principle, I’ve found that the best way to avoid regrets is to avoid causing them  in the first place. I practice one habit that helps me a great deal in this regard. At the end of  each day, I mentally review the day’s events and conversations to take a second look at the  people and developments I’m involved with and do a doublecheck of what they’re likely to be  feeling. Sometimes I’ll see things that do need more follow-up, whether a pat on the back, or  maybe a five minute chat in someone’s office to make sure we’re clear on things…whatever.”

“I also like to make each person feel like a member of an elite team, like the Boston Celtics or LA  Lakers in their prime. I’ve found that if you let each team member know you expect excellence in  their performance…if you work hard to set an example yourself…and if you let people know you  appreciate and respect their feelings, you wind up with a highly motivated group, a team that’s  having fun at work because they’re striving for excellence rather than brooding over slights or  regrets.”

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.

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(If you have a job presently)  

If you’re not yet 100% committed to leaving your present post, don’t be afraid to say so. Since  you have a job, you are in a stronger position than someone who does not. But don’t be coy  either. State honestly what you’d be hoping to find in a new spot. Of course, as stated often  before, you answer will all the stronger if you have already uncovered what this position is all  about and you match your desires to it.

(If you do not presently have a job.)  

Never lie about having been fired. It’s unethical – and too easily checked. But do try to deflect  the reason from you personally. If your firing was the result of a takeover, merger, division  wide layoff, etc., so much the better.

But you should also do something totally unnatural that will demonstrate consummate  professionalism. Even if it hurts , describe your own firing – candidly, succinctly and without a  trace of bitterness – from the company’s point-of-view, indicating that you could understand  why it happened and you might have made the same decision yourself.

Your stature will rise immensely and, most important of all, you will show you are healed from  the wounds inflicted by the firing. You will enhance your image as first-class management  material and stand head and shoulders above the legions of firing victims who, at the slightest  provocation, zip open their shirts to expose their battle scars and decry the unfairness of it all.

For all prior positions:  

Make sure you’ve prepared a brief reason for leaving. Best reasons: more money,  opportunity, responsibility or growth.

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.

BEST ANSWER: Like a primitive tribal mask, 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.

Whatever you do, don’t let the Silent Treatment intimidate you into talking a blue streak, because  you could easily talk yourself out of the position.

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.

BEST ANSWER: By now you can see how critical it is to apply the overall strategy of  uncovering the employer’s needs before you answer questions. If you know the employer’s  greatest needs and desires, this question will give you a big leg up over other candidates  because you will give him better reasons for hiring you than anyone else is likely to…reasons  tied directly to his needs.

Whether your interviewer asks you this question explicitly or not, this is the most important  question of your interview because he must answer this question favorably in is own mind  before you will be hired. So help him out! Walk through each of the position’s requirements  as you understand them, and follow each with a reason why you meet that requirement so  well.

Example: “As I understand your needs, you are first and foremost looking for someone who  can manage the sales and marketing of your book publishing division. As you’ve said you need  someone with a strong background in trade book sales. This is where I’ve spent almost all of  my career, so I’ve chalked up 18 years of experience exactly in this area. I believe that I know  the right contacts, methods, principles, and successful management techniques as well as any  person can in our industry.”

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“You also need someone who can expand your book distribution channels. In my prior post,  my innovative promotional ideas doubled, then tripled, the number of outlets selling our  books. I’m confident I can do the same for you.”

“You need someone to give a new shot in the arm to your mail order sales, someone who  knows how to sell in space and direct mail media. Here, too, I believe I have exactly the  experience you need. In the last five years, I’ve increased our mail order book sales from  $600,000 to $2,800,000, and now we’re the country’s second leading marketer of scientific  and medical books by mail.” Etc., etc., etc.,  

Every one of these selling “couplets” (his need matched by your qualifications) is a touchdown that  runs up your score. IT is your best opportunity to outsell your competition.

Question 8 – 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.

BEST ANSWER: This question is your opportunity to hit the ball out of the park, thanks to  the in-depth research you should do before any interview.

Best sources for researching your target company: annual reports, the corporate newsletter,  contacts you know at the company or its suppliers, advertisements, articles about the  company in the trade press.

Question 9Where 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.

BEST ANSWER: Reassure your interviewer that you’re looking to make a long-term  commitment…that this position entails exactly what you’re looking to do and what you do  extremely well. As for your future, you believe that if you perform each job at hand with  excellence, future opportunities will take care of themselves.

Example: “I am definitely interested in making a long-term commitment to my next position.  Judging by what you’ve told me about this position, it’s exactly what I’m looking for and what I  am very well qualified to do. In terms of my future career path, I’m confident that if I do my  work with excellence, opportunities will inevitable open up for me. It’s always been that way  in my career, and I’m confident I’ll have similar opportunities here.”

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.

BEST ANSWER: The only right answer is to describe what this company is offering, being  sure to make your answer believable with specific reasons, stated with sincerity, why each  quality represented by this opportunity is attractive to you.

Remember that if you’re coming from a company that’s the leader in its field or from a  glamorous or much admired company, industry, city or position, your interviewer and his  company may well have an “Avis” complex. That is, they may feel a bit defensive about being  “second best” to the place you’re coming from, worried that you may consider them bush  league.

This anxiety could well be there even though you’ve done nothing to inspire it. You must go  out of your way to assuage such anxiety, even if it’s not expressed, by putting their virtues high  on the list of exactly what you’re looking for, providing credible reason for wanting these  qualities.

If you do not express genuine enthusiasm for the firm, its culture, location, industry, etc., you  may fail to answer this “Avis” complex objection and, as a result, leave the interviewer  suspecting that a hot shot like you, coming from a Fortune 500 company in New York, just  wouldn’t be happy at an unknown manufacturer based in Topeka, Kansas.

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