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How to Answer
The 64 Toughest
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
Question 1 Tell me about yourself. 8
Question 2 What are your greatest strengths? 11
Question 3 What are your greatest weaknesses? 13
Question 4 Tell me about something you did or failed to do that you now feel a little ashamed of. 15
Question 5 Why are you leaving (or did you leave) this position? 18
Question 6 The Silent Treatment 20
Question 7 Why should I hire you? 22
Question 8 Arent you overqualified for this position? 25
Question 9 Where do you see yourself five years from now? 28
Question 10 Describe your ideal company, location and job. 30
Question 11 Why do you want to work at our company? 31
Question 12 What are your career options right now? 32
Question 13 Why have you been out of work so long? 33
Question 14 Tell me honestly about the strong points and weak points of your boss (company, management team, etc.) 34
Question 15 What good books have you read lately? 36
Question 16 Tell me about a situation when your work was criticized. 37
Question 17 What are your outside interests? 39
Question 18 The Fatal Flaw question 40
Question 19 How do you feel about reporting to a younger person (minority, woman, etc)? 42
Question 20 On confidential matters 44
Question 21 Would you lie for the company? 47
Question 22 Looking back, what would you do differently in your life? 48
Question 23 Could you have done better in your last job? 49
Question 24 Can you work under pressure? 50
Question 25 What makes you angry? 50
Question 26 Why arent you earning more money at this stage of your career? 52
Question 27 Who has inspired you in your life and why? 53
Question 28 What was the toughest decision you ever had to make? 54
Question 29 Tell me about the most boring job youve ever had. 54
Question 30 Have you been absent from work more than a few days in any previous position? 55
Question 31 What changes would you make if you came on board? 57
Question 32 Im concerned that you dont have as much experience as wed like in 59
Question 33 How do you feel about working nights and weekends? 61
Question 34 Are you willing to relocate or travel? 63
Question 35 Do you have the stomach to fire people? Have you had experience firing many people? 66
Question 36 Why have you had so many jobs? 67
Question 37 What do you see as the proper role/mission of
a good (job title youre seeking);
a good manager;
an executive in serving the community;
a leading company in our industry; etc. 70
Question 38 What would you say to your boss if hes crazy about an idea, but you think it stinks? 72
Question 39 How could you have improved your career progress? 73
Question 40 What would you do if a fellow executive on your own corporate level wasnt pulling his/her weightand this was hurting your department? 74
Question 41 Youve been with your firm a long time. Wont it be hard switching to a new company? 76
Question 42 May I contact your present employer for a reference? 77
Question 43 Give me an example of your creativity (analytical skillmanaging ability, etc.) 78
Question 44 Where could you use some improvement? 79
Question 45 What do you worry about? 80
Question 46 How many hours a week do you normally work? 80
Question 47 Whats the most difficult part of being a (job title)? 81
Question 48 The Hypothetical Problem 82
Question 49 What was the toughest challenge youve ever faced? 83
Question 50 Have you consider starting your own business? 84
Question 51 What are your goals? 87
Question 52 What do you for when you hire people? 88
Question 53 Sell me this stapler(this pencilthis clockor some other object on interviewers desk). 89
Question 54 The Salary Question How much money do you want? 93
Question 55 The Illegal Question 95
Question 56 The Secret Illegal Question 98
Question 57 What was the toughest part of your last job? 101
Question 58 How do you define successand how do you measure up to your own definition? 102
Question 59 The Opinion Question What do you think about AbortionThe PresidentThe Death Penalty(or any other controversial subject)? 103
Question 60 If you won $10 million lottery, would you still work? 105
Question 61 Looking back on your last position, have you done your best work? 107
Question 62 Why should I hire you from the outside when I could promote someone from within? 108
Question 63 Tell me something negative youve heard about our company 109
Question 64 On a scale of one to ten, rate me as an interviewer. 109

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.