64 Toughest Interview Questions

by Anita Spinelli, SPHR - Apr 10, 2010

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.

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 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.

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.

1. Tell me about yourself.

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.

2. What are your greatest strengths?

You know that your key strategy is to first uncover your interviewer's greatest wants and needs before you answer questions.

3. What are your greatest weaknesses?

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.

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

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

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

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.

6. The “Silent Treatment”

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.

7. Why should I hire you?

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.

8. Aren’t you overqualified for this position?

As with any objection, don’t view this as a sign of imminent defeat. It’s an invitation to teach the interviewer a new way to think about this situation, seeing advantages instead of drawbacks.

9. Where do you see yourself five years from now?

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

10. Describe your ideal company, location and job.

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

11. Why do you want to work at our company?

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

12. What are your career options right now?

Prepare for this question by thinking of how you can position yourself as a desired commodity. Also mention that you’re seriously exploring opportunities with one or two other firms.

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

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

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

Remember the rule: Never be negative. Stress only the good points, no matter how charmingly you’re invited to be critical.

15. What good books have you read lately?

Unless you’re up for a position in academia or as book critic for The New York Times, you’re not expected to be a literary lion. But it wouldn’t hurt to have read a handful of the most recent and influential books in your profession and on management.

16. Tell me about a situation when your work was criticized.

Begin by emphasizing the extremely positive feedback you’ve gotten throughout your career and (if it’s true) that your performance reviews have been uniformly excellent.

17. What are your outside interests?

Try to gauge how this company’s culture would look upon your favorite outside activities and be guided accordingly.

18. The “Fatal Flaw” question

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

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

You greatly admire a company that hires and promotes on merit alone and you couldn’t agree more with that philosophy. The age (gender, race, etc.) of the person you report to would certainly make no difference to you.

20. On confidential matters.

Never reveal anything truly confidential about a present or former employer. By all means, explain your reticence diplomatically.

For the rest of the article, go to the Archives section and download a copy. It contains much more information, such as traps to watch out for and examples to help you out.

Source unknown.