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How to Answer

The 64 Toughest
Interview
Questions
THIS BOOK IS DESIGNED TO PROVIDE ACCURATE INFORMATION ON THE
SUBJECTS COVERED. HOWEVER, IT IS DONE WITH THE UNDERSTANDING THAT
THE PUBLISHER IS NOT ENGAGED IN RENDERING LEGAL, ACCOUNTING OR
PROFESSIONAL SERVICES. IF LEGAL ADVICE OR OTHER PROFESSIONAL
ASSSTANCE IS REQUIRED, THE SERVICES OF A COMPETENT, PROFESSIONAL
PERSON SHOUID BE SOUGHT. ANY NAMES USED IN THE TEXT ARE FICTITIOUS AND
FOR ILLUSTRATIVE PURPOSES ONLY. ANY RESEMBLANCE TO ACTUAL PERSONS
OR COMPANIES IS PURELY COINCIDENTAL AND UNINTENTIONAL.
Dedication:
This report is dedicated to courage and knowledge,
the two qualities most needed
to succeed in any human challenge,
especially a job search.
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

64 Toughest Questions Page 1


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

64 Toughest Questions Page 2


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.

64 Toughest Questions Page 3


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!

64 Toughest Questions Page 4


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.

64 Toughest Questions Page 5


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.

64 Toughest Questions Page 6


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.

64 Toughest Questions Page 7


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.

64 Toughest Questions Page 8


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.

64 Toughest Questions Page 9


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û‹/¾Y a constructive way. So my goal in this case would be to see if my boss and I
could make his idea even stronger and more appealing, so that it effectively overcomes
any initial reservation I or others may have about it.”

“Of course, if he overrules me and says, ‘no, let’s do it my way,’ then I owe him my full
and enthusiastic support to make it work as best it can.”

Question 39 How could you have improved your career progress?


TRAPS: This is another variation on the question, “If you could, how would you live your
life over?” Remember, you’re not going to fall for any such invitations to rewrite person
history. You can’t win if you do.

BEST ANSWER: You’re generally quite happy with your career progress. Maybe, if you
had known something earlier in life (impossible to know at the time, such as the booming
growth in a branch in your industry…or the corporate downsizing that would phase out
your last job), you might have moved in a certain direction sooner.

But all things considered, you take responsibility for where you are, how you’ve gotten
there, where you are going…and you harbor no regrets.

Question 40 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?
TRAPS: This question and other hypothetical ones test your sense of human relations
and how you might handle office politics.

BEST ANSWER: Try to gauge the political style of the firm and be guided accordingly.
In general, fall back on universal principles of effective human relations – which in the
end, embody the way you would like to be treated in a similar circumstance.

Example: “Good human relations would call for me to go directly to the person and
explain the situation, to try to enlist his help in a constructive, positive solution. If I
sensed resistance, I would be as persuasive as I know how to explain the benefits we
can all gain from working together, and the problems we, the company and our
customers will experience if we don’t.”

POSSIBLE FOLLOW-UP QUESTION: And what would you do if he still did not change
his ways?

ANSWER: “One thing I wouldn’t do is let the problem slide, because it would only get
worse and overlooking it would set a bad precedent. I would try again and again and
again, in whatever way I could, to solve the problem, involving wider and wider circles of
people, both above and below the offending executive and including my own boss if
necessary, so that everyone involved can see the rewards for teamwork and the
drawbacks of non-cooperation.”

64 Toughest Questions Page 332


“I might add that I’ve never yet come across a situation that couldn’t be resolved by
harnessing others in a determined, constructive effort.”

Question 41 You’ve been with your firm a long time. Won’t it be


hard switching to a new company?
TRAPS: Your interviewer is worried that this old dog will find it hard to learn new tricks.

BEST ANSWER: To overcome this objection, you must point to the many ways you
have grown and adapted to changing conditions at your present firm. It has not been a
static situation. Highlight the different responsibilities you’ve held, the wide array of new
situations you’ve faced and conquered.

As a result, you’ve learned to adapt quickly to whatever is thrown at you, and you thrive
on the stimulation of new challenges.

To further assure the interviewer, describe the similarities between the new position and
your prior one. Explain that you should be quite comfortable working there, since their
needs and your skills make a perfect match.

Question 42 May I contact your present employer for a reference?


TRAPS: If you’re trying to keep your job search private, this is the last thing you want.
But if you don’t cooperate, won’t you seem as if you’re trying to hide something?

BEST ANSWER: Express your concern that you’d like to keep your job search private,
but that in time, it will be perfectly okay.

Example: “My present employer is not aware of my job search and, for obvious reasons;
I’d prefer to keep it that way. I’d be most appreciative if we kept our discussion
confidential right now. Of course, when we both agree the time is right, then by all
means you should contact them. I’m very proud of my record there.

Question 43 Give me an example of your creativity (analytical


skill…managing ability, etc.)
TRAPS: The worst offense here is simply being unprepared. Your hesitation may seem
as if you’re having a hard time remembering the last time you were creative, analytical,
etc.

BEST ANSWER: Remember from Question 2 that you should commit to memory a list
of your greatest and most recent achievements, ever ready on the tip of your tongue.

If you have such a list, it’s easy to present any of your achievements in light of the
quality the interviewer is asking about. For example, the smashing success you
orchestrated at last year’s trade show could be used as an example of creativity, or
analytical ability, or your ability to manage.

64 Toughest Questions Page 333


Question 44 Where could you use some improvement?
TRAPS: Another tricky way to get you to admit weaknesses. Don’t fall for it.

BEST ANSWER: Keep this answer, like all your answers, positive. A good way to
answer this question is to identify a cutting-edge branch of your profession (one that’s
not essential to your employer’s needs) as an area you’re very excited about and want to
explore more fully over the next six months.

Question 45 What do you worry about?


TRAPS: Admit to worrying and you could sound like a loser. Saying you never worry
doesn’t sound credible.

BEST ANSWER: Redefine the word ‘worry’ so that it does not reflect negatively on you.

Example: “I wouldn’t call it worry, but I am a strongly goal-oriented person. So I keep


turning over in my mind anything that seems to be keeping me from achieving those
goals, until I find a solution. That’s part of my tenacity, I suppose.”

Question 46 How many hours a week do you normally work?


TRAPS: You don’t want to give a specific number. Make it to low, and you may not
measure up. Too high, and you’ll forever feel guilty about sneaking out the door at 5:15.

BEST ANSWER: If you are in fact a workaholic and you sense this company would like
that: Say you are a confirmed workaholic, that you often work nights and weekends.
Your family accepts this because it makes you fulfilled.

If you are not a workaholic: Say you have always worked hard and put in long hours. It
goes with the territory. It one sense, it’s hard to keep track of the hours because your
work is a labor of love, you enjoy nothing more than solving problems. So you’re almost
always thinking about your work, including times when you’re home, while shaving in the
morning, while commuting, etc.

Question 47 What’s the most difficult part of being a (job title)?


TRAPS: Unless you phrase your answer properly, your interviewer may conclude that
whatever you identify as “difficult” is where you are weak.

BEST ANSWER: First, redefine “difficult” to be “challenging” which is more positive.


Then, identify an area everyone in your profession considers challenging and in which
you excel. Describe the process you follow that enables you to get splendid results…
and be specific about those results.

Example: “I think every sales manager finds it challenging to motivate the troops in a
recession. But that’s probably the strongest test of a top sales manager. I feel this is one
area where I excel.”

64 Toughest Questions Page 334


“When I see the first sign that sales may slip or that sales force motivation is flagging
because of a downturn in the economy, here’s the plan I put into action immediately…”
(followed by a description of each step in the process…and most importantly, the
exceptional results you’ve achieved.).

Question 48 The “Hypothetical Problem”


TRAPS: Sometimes an interviewer will describe a difficult situation and ask, “How
would you handle this?” Since it is virtually impossible to have all the facts in front of you
from such a short presentation, don’t fall into the trap of trying to solve this problem and
giving your verdict on the spot. It will make your decision-making process seem woefully
inadequate.

BEST ANSWER: Instead, describe the rational, methodical process you would follow in
analyzing this problem, who you would consult with, generating possible solutions,
choosing the best course of action, and monitoring the results.

Remember, in all such, “What would you do?” questions, always describe your process
or working methods, and you’ll never go wrong.

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.

BEST ANSWER: This is an easy question if you’re prepared. Have a recent example
ready that demonstrates either:

1. A quality most important to the job at hand; or


2. A quality that is always in demand, such as leadership, initiative, managerial skill,
persuasiveness, courage, persistence, intelligence, etc.

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.

BEST ANSWER: Again it’s best to:

64 Toughest Questions Page 335


1. Gauge this company’s corporate culture before answering and…

2. Be honest (which doesn’t mean you have to vividly share your fantasy of the
franchise or bed-and-breakfast you someday plan to open).

In general, if the corporate culture is that of a large, formal, military-style structure,


minimize any indication that you’d love to have your own business. You might say, “Oh, I
may have given it a thought once or twice, but my whole career has been in larger
organizations. That’s where I have excelled and where I want to be.”

If the corporate culture is closer to the free-wheeling, everybody’s-a-deal-maker variety,


then emphasize that in a firm like this, you can virtually get the best of all worlds, the
excitement of seeing your own ideas and plans take shape…combined with the
resources and stability of a well-established organization. Sounds like the perfect
environment to you.

In any case, no matter what the corporate culture, be sure to indicate that any desires
about running your own show are part of your past, not your present or future.

The last thing you want to project is an image of either a dreamer who failed and is now
settling for the corporate cocoon…or the restless maverick who will fly out the door with
key accounts, contacts and trade secrets under his arms just as soon as his bankroll has
gotten rebuilt.

Always remember: Match what you want with what the position offers. The more
information you’ve uncovered about the position, the more believable you can make your
case.

Question 51 What are your goals?


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

BEST ANSWER: Many executives in a position to hire you are strong believers in goal-
setting. (It’s one of the reason they’ve achieved so much). They like to hire in kind.

If you’re vague about your career and personal goals, it could be a big turnoff to may
people you will encounter in your job search.

Be ready to discuss your goals for each major area of your life: career, personal
development and learning, family, physical (health), community service and (if your
interviewer is clearly a religious person) you could briefly and generally allude to your
spiritual goals (showing you are a well-rounded individual with your values in the right
order).

Be prepared to describe each goal in terms of specific milestones you wish to


accomplish along the way, time periods you’re allotting for accomplishment, why the goal
is important to you, and the specific steps you’re taking to bring it about. But do this
concisely, as you never want to talk more than two minutes straight before letting your
interviewer back into the conversation.

64 Toughest Questions Page 336


Question 52 What do you for when you hire people?
TRAPS: Being unprepared for the question.

BEST ANSWER: Speak your own thoughts here, but for the best answer weave them
around the three most important qualifications for any position.

1. Can the person do the work (qualifications)?


2. Will the person do the work (motivation)?

3. Will the person fit in (“our kind of team player”)?

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.

BEST ANSWER: Of course, you already know the most important secret of all great
salesmanship – “find out what people want, then show them how to get it.”

If your interviewer picks up his stapler and asks, “sell this to me,” you are going to
demonstrate this proven master principle. Here’s how:

“Well, a good salesman must know both his product and his prospect before he sells
anything. If I were selling this, I’d first get to know everything I could about it, all its
features and benefits.”

“Then, if my goal were to sell it you, I would do some research on how you might use a
fine stapler like this. The best way to do that is by asking some questions. May I ask
you a few questions?”

Then ask a few questions such as, “Just out of curiosity, if you didn’t already have a
stapler like this, why would you want one? And in addition to that? Any other reason?
Anything else?”

“And would you want such a stapler to be reliable?...Hold a good supply of staples?”
(Ask more questions that point to the features this stapler has.)

Once you’ve asked these questions, make your presentation citing all the features and
benefits of this stapler and why it’s exactly what the interviewer just told you he’s looking
for.

Then close with, “Just out of curiosity, what would you consider a reasonable price for a
quality stapler like this…a stapler you could have right now and would (then repeat all
the problems the stapler would solve for him)? Whatever he says, (unless it’s zero), say,
“Okay, we’ve got a deal.”

64 Toughest Questions Page 337


NOTE: If your interviewer tests you by fighting every step of the way, denying that he
even wants such an item, don’t fight him. Take the product away from him by saying,
“Mr. Prospect, I’m delighted you’ve told me right upfront that there’s no way you’d ever
want this stapler. As you well know, the first rule of the most productive salespeople in
any field is to meet the needs of people who really need and want our products, and it
just wastes everyone’s time if we try to force it on those who don’t. And I certainly
wouldn’t want to waste your time. But we sell many items. Is there any product on this
desk you would very much like to own…just one item?” When he points something out,
repeat the process above. If he knows anything about selling, he may give you a
standing ovation.

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.

BEST ANSWER: For maximum salary negotiating power, remember these five
guidelines:

1. Never bring up salary. Let the interviewer do it first. Good salespeople sell their
products thoroughly before talking price. So should you. Make the interviewer
want you first, and your bargaining position will be much stronger.
2. If your interviewer raises the salary question too early, before you’ve had a
chance to create desire for your qualifications, postpone the question, saying
something like, “Money is important to me, but is not my main concern.
Opportunity and growth are far more important. What I’d rather do, if you don’t
mind, is explore if I’m right for the position, and then talk about money. Would
that be okay?”

3. The #1 rule of any negotiation is: the side with more information wins. After
you’ve done a thorough job of selling the interviewer and it’s time to talk salary,
the secret is to get the employer talking about what he’s willing to pay before you
reveal what you’re willing to accept. So, when asked about salary, respond by
asking, “I’m sure the company has already established a salary range for this
position. Could you tell me what that is?” Or, “I want an income commensurate
with my ability and qualifications. I trust you’ll be fair with me. What does the
position pay?” Or, more simply, “What does this position pay?”

4. Know beforehand what you’d accept. To know what’s reasonable, research the
job market and this position for any relevant salary information. Remember that
most executives look for a 20-25%$ pay boost when they switch jobs. If you’re
grossly underpaid, you may want more.

5. Never lie about what you currently make, but feel free to include the estimated
cost of all your fringes, which could well tack on 25-50% more to your present
“cash-only” salary.

64 Toughest Questions Page 338


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.

BEST ANSWER: Under the ever-present threat of lawsuits, most interviewers are well
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. For example, your interviewer, a devout
Baptist, recognizes you from church and mentions it. Here, you could gain by talking
about your church.

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…

Another example: If asked, “Do you plan to have children?” you could answer, “I am
wholeheartedly dedicated to my career“, perhaps adding, “I have no plans regarding
children.” (You needn’t fear you’ve pledged eternal childlessness. You have every right
to change your plans later. Get the job first and then enjoy all your options.)

Most importantly, 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 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.

64 Toughest Questions Page 339


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 obviously can’t respond to an illegal question if he hasn’t even asked.
This may well offend him. 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.

So 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.

So, too, if you’re in any different from what passes for “normal”. Make sure, without in
any way seeming defensive about yourself that you mention strengths,
accomplishments, preferences and affiliations that strongly counterbalance any
unspoken concern your interviewer may have.

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.

BEST ANSWER: State that there was nothing in your prior position that you found
overly difficult, and let your answer go at that. If pressed to expand your answer, you
could describe the aspects of the position you enjoyed more than others, making sure
that you express maximum enjoyment for those tasks most important to the open
position, and you enjoyed least those tasks that are unimportant to the position at hand.

64 Toughest Questions Page 340


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.

BEST ANSWER: Give a well-accepted definition of success that leads right into your
own stellar collection of achievements.

Example: “The best definition I’ve come across is that success is the progressive
realization of a worthy goal.”

“As to how I would measure up to that definition, I would consider myself both successful
and fortunate…”(Then summarize your career goals and how your achievements have
indeed represented a progressive path toward realization of your goals.)

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.

BEST ANSWER: In all of these instances, just remember the tale about student and the
wise old rabbi. The scene is a seminary, where an overly serious student is pressing the
rabbi to answer the ultimate questions of suffering, life and death. But no matter how
hard he presses, the wise old rabbi will only answer each difficult question with a
question of his own.

In exasperation, the seminary student demands, “Why, rabbi, do you always answer a
question with another question?” To which the rabbi responds, “And why not?”

If you are ever uncomfortable with any question, asking a question in return is the
greatest escape hatch ever invented. It throws the onus back on the other person,
sidetracks the discussion from going into an area of risk to you, and gives you time to
think of your answer or, even better, your next question!

In response to any of the “opinion” questions cited above, merely responding, “Why do
you ask?” will usually be enough to dissipate any pressure to give your opinion. But if
your interviewer again presses you for an opinion, you can ask another question.

Or you could assert a generality that almost everyone would agree with. For example, if
your interviewer is complaining about politicians then suddenly turns to you and asks if
you’re a Republican or Democrat, you could respond by saying, “Actually, I’m finding it
hard to find any politicians I like these days.”

64 Toughest Questions Page 341


(Of course, your best question of all may be whether you want to work for someone
opinionated.)

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.”

BEST ANSWER: This type of question is aimed at getting at your bedrock attitude
about work and how you feel about what you do. Your best answer will focus on your
positive feelings.

Example: “After I floated down from cloud nine, I think I would still hold my basic belief
that achievement and purposeful work are essential to a happy, productive life. After all,
if money alone bought happiness, then all rich people would be all happy, and that’s not
true.

“I love the work I do, and I think I’d always want to be involved in my career in some
fashion. Winning the lottery would make it more fun because it would mean having more
flexibility, more options...who knows?”

“Of course, since I can’t count on winning, I’d just as soon create my own destiny by
sticking with what’s worked for me, meaning good old reliable hard work and a desire to
achieve. I think those qualities have built many more fortunes that all the lotteries put
together.”

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.

BEST ANSWER: To cover both possible paths this question can take, your answer
should state that you always try to do your best, and the best of your career is right now.
Like an athlete at the top of his game, you are just hitting your career stride thanks to
several factors. Then, recap those factors, highlighting your strongest qualifications.

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.

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BEST ANSWER: Help him see the qualifications that only you can offer.

Example: “In general, I think it’s a good policy to hire from within – to look outside
probably means you’re not completely comfortable choosing someone from inside.

“Naturally, you want this department to be as strong as it possibly can be, so you want
the strongest candidate. I feel that I can fill that bill because…(then recap your strongest
qualifications that match up with his greatest needs).”

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.

BEST ANSWER: Just remember the rule – never be negative – and you’ll handle this
one just fine.

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.

BEST ANSWER: Once again, never be negative. The interviewer will only resent
criticism coming from you. This is the time to show your positivism.

However, don’t give a numerical rating. Simply praise whatever interview style he’s been
using.

If he’s been tough, say “You have been thorough and tough-minded, the very qualities
needed to conduct a good interview.”

If he’s been methodical, say, “You have been very methodical and analytical, and I’m
sure that approach results in excellent hires for your firm.”

In other words, pay him a sincere compliment that he can believe because it’s anchored
in the behavior you’ve just seen.

Good luck in your job search!

The Editors

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