How To Answer The 64 Toughest Interview Questions

Table of Contents

General Guidelines in Answering Interview Questions....................................................... 3

Q1 Tell me about yourself.......................................................................................... 5

Q2 What are your greatest strengths?...................................................................... 6

Q3 What are your greatest weaknesses?................................................................. 6

Q4 Tell me about something you did – or failed to do – that you now feel a little ashamed of. 7

Q5 Why are you leaving (or did you leave) this position?.......................................... 8

Q6 The “Silent Treatment”......................................................................................... 9

Q7 Why should I hire you?......................................................................................... 9

Q8 Aren’t you overqualified for this position?........................................................... 10

Q9 Where do you see yourself five years from now?.............................................. 11

Q10 Describe your ideal company, location and job................................................. 12

Q11 Why do you want to work at our company?....................................................... 12

Q12 What are your career options right now?........................................................... 12

Q13 Why have you been out of work so long?.......................................................... 13

Q14 Tell me honestly about the strong points and weak points of your boss (company, management team, etc.)…................................................................................................................. 13

Q15 What good books have you read lately?............................................................ 14

Q16 Tell me about a situation when your work was criticized................................... 14

Q17 What are your outside interest?......................................................................... 15

Q18 The “Fatal Flaw” question................................................................................... 15

Q19 How do you feel about reporting to a younger person (minority, woman, etc)? 16

Q20 On confidential matters….................................................................................. 16

Q21 Would you lie for the company?......................................................................... 17

Q22 Looking back, what would you do differently in your life?................................... 17

Q23 Could you have done better in your last job?..................................................... 18

Q24 Can you work under pressure?.......................................................................... 18

Q25 What makes you angry?.................................................................................... 18

Q26 Why aren’t you earning more money at this stage of your career?................... 19

Q27 Who has inspired you in your life and why?....................................................... 19

Q28 What was the toughest decision you ever had to make?.................................. 20

Q29 Tell me about the most boring job you’ve ever had............................................ 20

Q30 Have you been absent from work more than a few days in any previous position? 20

Q31 What changes would you make if you came on board?.................................... 21

Q32 I’m concerned that you don’t have as much experience as we’d like in…........ 21

Q33 How do you feel about working nights and weekends?..................................... 22

Q34 Are you willing to relocate or travel?................................................................... 23

Q35 Do you have the stomach to fire people? Have you had experience firing many people? 23

Q36 Why have you had so many jobs?..................................................................... 24

Q37 What do you see as the proper role/mission of… …a good (job title you’re seeking); …a good manager; …an executive in serving the community; …a leading company in our industry; etc. 25

Q38 What would you say to your boss if he’s crazy about an idea, but you think it stinks? 25

Q39 How could you have improved your career progress?...................................... 26

Q40 What would you do if a fellow executive on your own corporate level wasn’t pulling his/her weight…and this was hurting your department?............................................................................ 26

Q41 You’ve been with your firm a long time. Won’t it be hard switching to a new company? 27

Q42 May I contact your present employer for a reference?....................................... 27

Q43 Give me an example of your creativity (analytical skill…managing ability, etc.) 28

Q44 Where could you use some improvement?....................................................... 28

Q45 What do you worry about?................................................................................. 28

Q46 How many hours a week do you normally work?............................................... 28

Q47 What’s the most difficult part of being a (job title)?............................................ 29

Q48 The “Hypothetical Problem”................................................................................ 29

Q49 What was the toughest challenge you’ve ever faced?....................................... 29

Q50 Have you consider starting your own business?............................................... 30

Q51 What are your goals?......................................................................................... 31

Q52 What do you for when you hire people?............................................................. 31

Q53 Sell me this stapler…(this pencil…this clock…or some other object on interviewer’s desk). 31

Q54 “The Salary Question” – How much money do you want?................................ 33

Q55 The Illegal Question............................................................................................ 33

Q56 The “Secret” Illegal Question.............................................................................. 34

Q57 What was the toughest part of your last job?..................................................... 35

Q58 How do you define success…and how do you measure up to your own definition?. 35

Q59 “The Opinion Question” – What do you think about …Abortion…The President…The Death Penalty…(or any other controversial subject)?....................................................................... 36

Q60 If you won $10 million lottery, would you still work?........................................... 36

Q61 Looking back on your last position, have you done your best work?................. 37

Q62 Why should I hire you from the outside when I could promote someone from within? 37

Q63 Tell me something negative you’ve heard about our company…...................... 38

Q64 On a scale of one to ten, rate me as an interviewer.......................................... 38

General Guidelines
in Answering Interview Questions

Everyone is nervous on interviews. If you simply allow yourself to feel nervous, you'll do much better. Remember also that it's difficult for the interviewer as well.

In general, be upbeat and positive. Never be negative.

Rehearse your answers and time them. Never talk for more than 2 minutes straight.

Don't try to memorize answers word for word. Use the answers shown here as a guide only, and don't be afraid to include your own thoughts and words. To help you remember key concepts, jot down and review a few key words for each answer. Rehearse your answers frequently, and they will come to you naturally in interviews.

As you will read in the accompanying report, the single most important strategy in interviewing, as in all phases of your job search, is what we call: "The Greatest Executive Job Finding Secret." And that is...

Find out what people want, than show them how you can help them get it.

Find out what an employer wants most in his or her ideal candidate, then show how you meet those qualifications.

In other words, you must match your abilities, with the needs of the employer. You must sell what the buyer is buying. To do that, before you know what to emphasize in your answers, you must find out what the buyer is buying... what he is looking for. And the best way to do that is to ask a few questions yourself.

You will see how to bring this off skillfully as you read the first two questions of this report. But regardless of how you accomplish it, 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 he wants, you can then present your qualifications as the perfect “key” that fits the “lock” of that position.

· Other important interview strategies:

· Turn weaknesses into strengths (You'll see how to do this in a few moments.)

· Think before you answer. A pause to collect your thoughts is a hallmark of a thoughtful person.

As a daily exercise, practice being more optimistic. For example, try putting a positive spin on events and situations you would normally regard as negative. This is not meant to turn you into a Pollyanna, but to sharpen your selling skills. The best salespeople, as well as the best liked interview candidates, come off as being naturally optimistic, "can do" people. You will dramatically raise your level of attractiveness by daily practicing to be more optimistic.

Be honest...never lie.

Keep an interview diary. Right after each interview note what you did right, what could have gone a little better, and what steps you should take next with this contact. Then take those steps. Don't be like the 95% of humanity who say they will follow up on something, but never do.

About the 64 questions...

You might feel that the answers to the following questions are “canned”, and that they will seldom match up with the exact way you are asked the questions in actual interviews. The questions and answers are designed to be as specific and realistic as possible. But no preparation can anticipate thousands of possible variations on these questions. What's important is that you thoroughly familiarize yourself with the main strategies behind each answer. And it will be invaluable to you if you commit to memory a few key words that let you instantly call to mind your best answer to the various questions. If you do this, and follow the principles of successful interviewing presented here, you're going to do very well.

Good luck...and good job-hunting!

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.

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.

9. Enthusiasm...high level of motivation.

10. 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.

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.)

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.

BEST ANSWER:

(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.”

“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 Aren’t you overqualified for this position?

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