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GET HIRED! How To Handle Some Difficult Questions At A Job Interview

Updated on June 2, 2012

GET HIRED! How To Handle Some Difficult Questions At A Job Interview

One caution that I offer you: Please don’t try to memorize/regurgitate the sample answers below. Any hiring manager worth his value will ask follow up questions and probe for more information, so be prepared to expand on anything that you say. Throwing out buzzwords and catch phrases sounds impressive on the surface, but if you can’t develop them into rational thoughts and real world examples, the hiring manager will be able to see right through you.

1. Tell me about yourself.

Why I Ask It.

This is the first question that I ask, and it’s my favorite. OK, technically it’s not a question, it’s an invitation: an invitation for you to make my job easy and eliminate yourself from consideration. This is usually accomplished in one of two ways (and I apologize for the unpleasant imagery): diarrhea of the mouth, or constipation of the mouth.

If they exhibit diarrhea of the mouth, they answer the simple question with fifteen minutes of stream of consciousness rambling. Normally contained within this rambling, are useful nuggets of information that may immediately tell me this is not a good candidate to consider for a job offer: “I barely made it here today, since I live ninety minutes away and my car is going to die any day” “I’m the sole caregiver for my elderly great aunt and that requires almost a 24/7 commitment.” “I am very involved in my church and I spend most weekends outside the grocery store seeking converts for Pastor Skip.”

By contrast, constipation of the mouth is when the applicant can’t put together any coherent thought about what should be the easiest topic in the world to talk about. Everyone can talk about themselves, usually for hours on end – it’s the main reason why first dates don’t turn into second dates – the person can’t stop talking about themselves. But when a job applicant answers the question with “well, um, yeah, I dunno, this is hard, I don’t know what to say,” I can pretty much decide that they may be lacking the social skills need to work for me.

What Response I Want To Hear

When I offer this invitation, I want you to tell me about you – don’t recite what’s on your resume, I already have that printed in front of me. Tell me what isn’t there, particularly if it shows that you have goals and that you have stability –

Sample Answers

“I’ve been training to run my first marathon next year”

“I recently achieved my goal of quitting smoking after ten years.”

“My wife and I are saving money for a dream vacation to Hawai’i for our twenty-fifth anniversary.”

2. What is your greatest weakness?

Why I Ask It

I usually begin with “what is your greatest strength”, which is easy for everyone to answer. But when you turn the table and ask about their greatest weakness, it becomes a much more difficult question to answer. Everyone has areas of imperfection, so don’t be afraid to admit them, but definitely try to show that you are not only aware of the defect, but that you are actively trying to fix it. Asking the question at an interview presents a great opportunity for the applicant to show that they can take a negative and turn it into a positive.

What Response I Want To Hear

The one response that I do not recommend is “I don’t have any weaknesses.” (yes, I have actually received this answer before.) This answer tells me that you not have the very obvious weaknesses of being arrogant and conceited. As a hiring manager, I’ll pass.

Be selective in what you share as your greatest weakness. It’s not wise to tell a potential employer that your greatest weakness is a dependency on prescription painkillers, an interest in online porn sites or an explosive temper that has landed you in jail on several occasions.

Be honest and tell me an area that you feel you can improve on, but take it a step farther and tell me what you are doing to improve it.

Sample Answers

“I can be too much of a perfectionist, but I am learning to focus on what is truly important and not worry about the trivial things that may not matter.”

“I tend to put my job before my social life but I am looking to strike a better work/life balance by limiting my extra hours to important projects and tight deadlines”

“I get impatient when other people don’t do their jobs correctly, so I try to build good relationships with my co-workers so that if I offer them constructive feedback it will be well received.”

3. Why did you leave your last job? (or Why are you looking to leave your current job?)

Why I Ask It

There is an old axiom that the best indicator of future performance is to look at past behavior. This is especially true in the world of employment. How an employee behaves at the job is typically consistent from one work place to another. If you’ve left your past three jobs because of conflicts with your manager, guess why you’re likely to leave your next job? If every job has had no opportunity for advancement, maybe the problem isn’t the job, maybe you’re not an attractive candidate to move to the next level.

What Response I Want To Hear

Anything that you say about a former job or a former boss should be spun in the most positive way possible. It’s a simple truth that if you are going to sit there and bad mouth your current boss to me, then five years from now, you’ll be sitting in front of another hiring manager bad mouthing me.

It is important to keep two things in mind anything you are talking about a former job or a former boss. 1- As part of the hiring process, I’m likely to be contacting your former boss for a professional reference. If I come away with a different impression that you the version you are selling, you may lose the sale altogether and get passed over. 2. Even scarier, in our world of online networking and social media, there is a reasonable chance that I may know (or know of) your former boss.

Back when I was doing retail management, I received an application from an employee at a branch in a neighboring state who wanted to transfer to my store. I interviewed her and noted her comments about her current store, and then I called her former manager, who happened to be someone I had met at a company seminar the year before. We had a nice conversation, caught up on old times, and I gathered some information from him on the notes I had taken. In the end, the employee’s version of events didn’t jive very well with the manager’s version. Since I already had a existing relationship with the manager, I chose his version of events, and therefore didn’t accept the transfer request.

Sample Answers

“The company culture focused on individual results, and I feel that I am more of a team player.”

“After spending six years in the same job, I decided that I was ready for a change but the opportunities at that company didn’t offer me enough new challenges.”

“My boss had a different vision for the company than I did, so I am looking for a company that will be better aligned with my vision.”

4. Tell me about a time when…

Why I Ask It

I have several variations of these situational questions and tend to ask five or six during most interviews. (Tell me about a time when your work was criticized, Tell me about a time when you had a disagreement with a co-worker, Tell me about a time when you completed a project and you were told it wasn’t done right, etc.) When answered correctly, the interviewee shares important details with me about how they react to different situations and how their personal work ethic mixes with the rough and tumble reality of today’s corporate world. When answered poorly, however, the applicant tends to gloss over the answer with vague responses that tell me nothing about them as an employee. And telling me nothing, tells me everything. Next please.

What Response I Want To Hear

When I ask one of these behavioral questions, I want to hear details about a specific event and how you responded. Don’t spend too long giving me more details than I need about the situation, just give me enough to understand the situation. “What happened” is important, but its not as important as knowing how you reacted, what you learned from the experience, and how you would handle the situation differently the next time.

Sample Answers

Sorry, no sample answers on this one. The questions are intended to solicit very personal examples that are unique to you and your work experience. Everyone’s answers will be different, but the key is to be prepared to answer these types of questions. Prior to your interview, give some thought to some of the most significant achievements (and failures) of your career, and how you can use them as talking points in your interview.

5. Do You Have Any Questions For Me About the Position, the Company or the Industry?

Why I Ask It

Usually, by the time I’ve gotten to this final item on my list of interview questions, I’ve already grilled the applicant for forty-five to sixty minutes. Its time to wrap up, but I always like to offer the applicant an opportunity to ask questions for themselves.

What Response I Want To Hear

Whenever I solicit questions from an applicant, I inevitably receive the same one “What does this position pay?” or “What benefits are offered?” I understand that salary and benefits are important, I would never state otherwise. But when you’ve advanced this far in the hiring process, and you are afforded a final opportunity to sell yourself to a potential new boss, you can do better than leaving the impression that you’re only in it for the money (even if you are). I want to know that you have a real interest in the position for which you are applying and the company for which you are wanting to work.

Sample Answers

“As a manager, you’ve been with the company for a long time. What are the reasons why you enjoy working for this company?”

“I read in the news about an upcoming merger between company X and Y. What affect for you foresee on the industry, and specifically this company, if that happens?”

“I’ve seen that the stock price of the company has been stagnant for the past several months. Do you think it will be affected when this quarter’s financials are reported?”


Do you have any additional tips or experiences to share on difficult interview questions and strategies for answering them? Do you have any questions have that I can answer, or related topics that I may want to address in a future hub?


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