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More Difficult Interview Questions

This post continues the series on how to answer difficult interview questions, this time with some less common but still possible zingers that may be thrown at you.

These particular ones are primarily designed test your character and bring out how you react to difficult and stressful questions.
As a Hiring Manager, I don’t normally use or like these types of questions, but with enough interviews you’re likely come across a version of them.

Question:  “What is a negative thing your last boss would say about you?”
How to Answer:  What you want to do here is state some minor mistake that you made and then add this: “But I think you’ll find my last boss would also tell you I admitted my mistake, learned from it and was a better employee as a result”.

Question:  “ Where do you see yourself five years from now?”
How to Answer:  While this question is intended to reveal if you have a reasonable amount of motivation and ambition, you certainly don’t want to come across as a threat.

Here’s the best way to field this question: “Well, in five years I hope I’ll have moved up one level and to be within shouting distance of moving up one more level.  This shows you have a healthy amount of ambition but avoids saying you want the Hiring Manager’s job.

Question: “Tell me what you think of your previous boss.”
How to Answer:   Uh oh!  You’re about to walk into a buzz saw unless you’re careful.  Under no circumstances – and I mean no circumstances – should you ever say a negative thing about either your previous boss or your previous company.  If you criticize a past employer, the Hiring Manager will very likely assume you’ll also bad mouth future employers. This is the kiss of death in an interview.

What you’ll want to do here is simply answer with something similar to this:  “My previous boss was very knowledgeable and someone from whom I learned quite a lot.”  This is generic enough to fit almost any situation without being untruthful.

Even if your previous boss was a jerk, you could still have learned a lot about what not to do as a boss…

Question:  “Tell me about a time where you were able to make order out of chaos.”
How to Answer:  I was actually asked this one while in an interview myself (many years ago!) and freely admit that I blew it.  This one is a particular favorite of some hiring managers so you should be ready for it.

What you need to do is prepare one or two examples of when you did things such as:  turn around a project that was in trouble, streamlined a procedure that was causing inefficiencies, stepped into a job where the predecessor left a complete mess, or any other experience that demonstrates you cleaned up a mess of some sort.

Question: “Give me five words that best describe your character.”
How to Answer: This is another favorite of hiring managers.  Its purpose is to show if you’re a good fit for that position, so the way to answer it is with adjectives taken right out of the job posting.

As an example, say that some of the qualifications from the job posting are: ability to get along with people, being a good team player, having good customer service attitude, the ability to learn new things quickly, and a good work ethic.  The five words from these that you could use to describe your character could be: friendly, supportive, helpful, intelligent and dedicated.   You can literally turn any qualification into an adjective in this manner.  Just be sure they truly describe you!

The bottom line is that you want to have your answers indicate that your character is a good fit for the job.  Just remember: when you study the job description carefully, you’ll be much better able to answer this question.

In my next post, we’ll look at some of the more unusual questions you may encounter and how best to answer them.

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