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Simple Truths About Tough Interview Questions

The 10 Tough Questions You Need To Be Ready To Answer

“What is your greatest weakness?”

The natural response is to admit to a genuine personality flaw or negative tendency, period—for example, “I have a really hard time getting out of bed in the morning, and am frequently late.” This level of candor can quickly torpedo your candidacy. However, it is possible to respond honestly without hurting yourself.

Just a few short years ago, the sage advice on how to respond to this question was to confess that you are impatient with lazy people—that is, coworkers who don't give 100 percent all the time (as you do). The other highly recommended approach was to respond by admitting that you are a perfectionist—which, of course, actually turns out to be a tremendous benefit to the organization. You're a martyr, consistently doing whatever it takes to get the tasks done correctly, under budget, and on time, no matter the personal cost. The trouble is, these responses became a little too common. Even if they were true, they strained credibility a bit, depending on the person and the circumstances. If you are, in fact, a perfectionist, you may choose to respond in this manner. In general, however, it's best to avoid personality traits here. After all, personality traits are extremely difficult to change, and your goal is to demonstrate that you are working on improving your “weakness.”

Consider the question from the prospective employer's point of view. The underlying concern is that you have some type of serious character flaw. The interviewer's hope is that you will simply blurt it out in the heat of the moment, under the pressure of the interview situation. Don't do it!

The strategy of identifying a weakness rather than a character flaw, and then pointing out its positive aspects, is a sound one. It's also important to place the weakness in your past; you have conquered it! Here's an example:

“Although I tend not to dwell on weaknesses, I'm human, and I have limitations just like everyone, so I constantly strive to improve myself to become an even more effective worker. I used to become frustrated when the work of others negatively impacted progress on my own projects. Now, I've come to understand that everyone has unique contributions to make, and I offer to assist coworkers with challenges they encounter in order to expedite or improve overall progress, whenever appropriate. I've learned that working cooperatively in the spirit of teamwork ultimately creates a better, more profitable result for the company.”

“How would you describe your personality?”

Here is another instance where your research on the organization and target position is key to responding with a strong answer. Choose a few characteristics that genuinely describe you and also mesh with what you have learned about the prospective employer's expectations for the position. Think about traits of the ideal candidate, either based on what is listed in the job description or what the interviewer has shared. Your goal is to portray yourself as someone who can hit the ground running and be a solution to the organization's challenges, all while sharing some honest information about your personality.

Following are some examples of areas to consider as you develop your personality self-portrait:

  • • Is working well in a fast-paced, high-pressure environment one of your strengths? Do you thrive on this energy? Most importantly, does this reflect the prospective employer's work environment?
  • • Do you prefer to work as an independent contributor, or as a team member? Which of these work situations do you thrive in? Most importantly, which reflects the prospective employer's work environment?
  • • Are you a natural leader? Do you thrive in leadership roles? Most importantly, does this position require leadership skills?
  • • Do you genuinely enjoy multitasking in an atmosphere of constantly shifting priorities? Do you thrive in this environment? Most importantly, does this reflect the prospective employer's work environment?
  • • Are you a highly effective communicator who is skilled in finding ways to express ideas to particular audiences? Most importantly, does this position require excellent speaking or writing capabilities?

These are just a few areas to consider in developing your personality self-portrait. This is really an elevator speech that is focused on your key personality traits, which also happen to be vital to succeeding in the new position. Adapt your elevator speech from Chapter 2 so that it highlights the personal characteristics that relate most strongly to your target position. Here's an example of a personality self-portrait:

“I'm an upbeat problem solver who finds joy in learning new things. A quick study, I adapt well to changes and maintain my high-energy positive attitude that supervisors will tell you lifts morale and supports team spirit. In fact, I've found that I thrive in a dynamic work environment. I take pride in meeting deadlines and doing what it takes to get the project done correctly the first time, on budget. I'm known for my ability to quickly establish rapport and trusting relationships with people at all levels, both inside and outside the company. The truth is, I enjoy working with people, and this has enhanced my ability to achieve results throughout my career.”

“Have you ever been fired?”

Clearly, this doesn't rate as a tough question if you have never been fired. If you have been fired, however, it's important to distinguish among the categories of firing. Take special care in choosing your words here. To many, being fired means that you were dismissed “for cause"—that is, for wrongdoing of some kind. If this is what happened and you are asked this question, prepare your answer with these points in mind:

  • • Accept responsibility for your action(s). Don't blame coworkers or management.
  • • Avoid degrading yourself, and refrain from sharing excessive details of the situation.
  • • Be sure to place the event in the past, and demonstrate that you have moved on.
  • • Find a way to share that you have learned important lessons from the experience that, in fact, make you even wiser and hence more valuable to future employers.

Here's an example:

“I trusted a colleague to follow up on a major project while I reluctantly left on a family vacation that had been planned literally years in advance. There was a breakdown in communication, the project was botched, and the account was lost. It was a tough call, but I understand the decision. I'm still on good terms with many of the managers there—please feel free to contact them if you wish. I learned valuable lessons about accountability and following through, and believe I'm a stronger candidate and more valuable asset to a future employer as a result of this experience.”

Downsized or rightsized

In the previous example, the dismissal was based upon your actions (or lack of action). By contrast, if your position was eliminated because of some force of nature beyond your control, such as a merger, acquisition, closure, or workforce reduction initiative, simply explain the situation. Remember that it's completely inappropriate to express bitterness or assign blame to the former employer; it's equally important to refrain from acting as though it was your fault. Your delivery is all-important here: Simply and calmly relate the facts, and then bring the conversation back to your being the right person for the position, following the thread of what you have stated.

Leadership change

If you were let go because of a leadership change, this was likewise out of your hands, so calmly and briefly relate the facts: “There was a total changeover in top management that resulted in my being let go, along with a number of my colleagues.” If you know how many employees were fired as a result of the management change, then state that figure. If it's more compelling stated as a percentage, then express it in those terms: “In fact, more than 30 percent of the company's workforce was let go during this period.”

“Why have you been out of work for such an extended period of time?”

Usually the underlying concern here is that there you may have some serious problem or flaw that has prevented you from securing employment more quickly. It's not uncommon for people to be “between jobs” for extended periods of time in the current economic climate. (By the way, the definition of “extended” is whatever the interviewer believes it to be. It's not worth arguing the point or trying to convince the interviewer that 10 months really isn't so very long if he or she believes otherwise.) Be honest, and, as always, refrain from blaming others or the economy. Accept accountability for your choices and respond in an upbeat, optimistic tone. Honestly and briefly relate the facts, which can then be connected to the expectations of the position. Try to identify at least one thing you did during the gap that makes you a stronger candidate for your target position. Following are some examples:

“I decided to take the time to find something fulfilling, which would be truly rewarding and a good fit. In the meantime, I've been sharpening some of my skills through some courses in Web-based marketing at Upstate Community College. I pursued a few job opportunities during this period and, ultimately, turned down offers, as I determined they simply weren't a close enough fit. It sounds like this position would be an excellent fit, and I'm sure that I could make a meaningful contribution to your success. You mentioned that you're looking for someone who has experience in new product launches.”

“For years, I have wanted to travel through China. This interlude provided the opportunity to fulfill this lifelong dream. Because my partner was fortunate enough to be eligible for a sabbatical at the same time, we decided to take advantage of the opportunity. I find exposure to different cultures and people of different backgrounds to be simply fascinating and invigorating. My work schedule never permitted an extended trip such as this. I returned with a new appreciation of this great country of ours, as well as a connection to people on the other side of the world. You mentioned that you deal with suppliers in Asia. Although I'm not an expert, I now have an understanding of that culture that could prove helpful.”

“I used this time to manage our move and get us settled into our new home. We had our eyes on a wonderful 19th-century farmhouse that had been on the market but out of our reach. I was able to focus on negotiating a much better deal than we anticipated. Because it needed some major work, I was able to do many of the renovations myself during this period. I learned that my project management skills were definitely transferable to selecting and coordinating the contractors for the work I didn't do, such as the plumbing and electrical. It didn't hurt to be on-site while the contractors were working, either. I recall the job description listed project management as a key skill….”

“Would you give me an example of an obstacle you've had to overcome to get the job done?”

Here's an opportunity to review the success stories you developed in Chapter 2 and select one that is most relevant to the target position. The interviewer is really asking about your problem-solving capabilities. Keep the following points in mind:

  • • Be sure to describe the obstacle without sounding like you are bad-mouthing the former employer in any way.
  • • Illustrate the obstacle clearly enough for the interviewer to understand what was so challenging about them, but without spending too much time on details that don't strengthen your story, and which may prove distracting.
  • • Identify the personal characteristics and skills that allowed you to conquer the obstacle and accomplish the objective. Be sure that these characteristics and skills are relevant to your target position and directly connected to elements of the job description.

“Have you ever had a disagreement with coworkers or your boss, and if so, how did you handle it?”

The primary underlying concern here is whether or not, and to what extent, you are a troublemaker. The interviewer wants to know how you get along with your colleagues and bosses. Good communication skills are essential anytime there's more than one person involved in any endeavor, and things only become more complex as larger groups of people interact together. You need to demonstrate that you are level-headed, rational, and an effective communicator. Here are two examples:

“I've been very fortunate to have worked in places where my input and contributions were sought in order to finish projects on time and under budget. I am comfortable offering my opinions but I'm always sensitive to others, and I never criticize a coworker—or anyone—in an open meeting.”

“When something comes up that I feel strongly about, I ask for time to sit down and discuss the issue one-on-one, either with a coworker or manager. I'm actually looking for an environment where people work together to solve problems and strive to exceed the customers’ expectations. Am I in the right place?”

“Why should we hire you?”

This is actually a cousin of the “greatest strengths” question; however, it calls for a direct connection between your value and the organization's needs. Do you see how the interviewer is, consciously or unconsciously, asking you to make the hiring decision easier? By all means, connect the dots for the interviewer! Your elevator speech is already prepared, and hopefully you've updated it based upon your research on this prospective employer and target job. Now, take a moment or two to breathe, and then link what you have learned in the interview about the target position's deliverables to what you have discovered or sensed the interviewer values.

Quoting coworkers or supervisors is a very effective way of offering additional relevant, positive information about yourself without sounding as though it's your own high opinion of yourself. Phrases such as “Supervisors have complimented me on my…” or “I'm told that I have…” can function as lead-ins to help you discuss the accolades you've received with your interviewer. Speak enthusiastically and with energy.

“What did you dislike the most about your last job?”

One universal simple truth that has appeared throughout this book is that it's never helpful to speak ill of former employers. However justified you may feel in criticizing them, these kinds of remarks ultimately do not strengthen your candidacy, nor do they reflect well on your level of professionalism from the interviewer's perspective. Whining about former employers suggests that you do not take accountability for your decisions. Save your complaints for close, trusted friends, and maintain an upbeat, positive demeanor in job interviews.

The interviewer's underlying motive here is to determine how good a match you are for the target position. How compatible are you with the organization? For example, if the new position calls for a great deal of travel, and you state that the aspect you disliked the most about your last job was that you had to travel often, what do you suppose the interviewer will conclude? You get the idea. Following are some examples:

“There really isn't anything that I can point to that I dislike about being a customer service representative. I feel so fortunate to have found a field that suits my talents and that I genuinely enjoy. You mentioned that this position requires a lot of time on the phone. Well, in my last position, I demonstrated that dealing with customers on the phone is one of my strengths.”

“I liked pretty much everything about my job. Because you've pressed, though, I guess I would say that I'm seeking an opportunity where I can contribute even more to the success of projects. I'm especially interested in a planning and scheduling role, and from what I understand, this position requires someone with those skills.”

“I've discovered that if you approach everything with an open mind and a positive attitude, and keep the overall mission of the company as the guiding principle, there really isn't anything that a strong, motivated team can't accomplish. I really feel fulfilled when I can contribute to a successful operation.”

“What was your biggest failure?”

The interviewer wants to give you another opportunity to reveal a serious weakness, and also perhaps to learn more about if and how you overcome adversity. Briefly describe the failure, and focus on what the failure has taught you or reminded you, and how this realization has led you to improve your decision-making or problem-solving. Then, redirect the discussion to one of your subsequent accomplishments, demonstrating that you have learned lessons from your failures. A number of highly successful businessmen have been quoted as saying that they learned much more from their business failures than from their successes.

Absolutely refrain from choosing an example that enters the realm of personal issues such as marriage, bankruptcy, or the misdeeds of a relative. Choose an example from the past, and be sure to make clear that the episode truly is in the past and that you have learned from it. Here's an example:

“To make extra money while I was in school, I accepted a job selling personal products through networking and home parties. I really was only looking for some extra money, a friend of mine said she was doing quite well at it, and thought I would enjoy the work, too. My research on the company indicated that it was reputable, with a solid line of quality products. Ultimately, I did make a little money, but had difficulty finding adequate time to really make a success of it. In fact, I vowed that I would never, ever take on another sales role. This is ironic, in light of my successful track record in financial and insurance product sales. I discovered that I excel at what I'm most passionate about, and I believe very strongly that everyone needs and deserves sound advice in these areas from experts with the utmost integrity.”

“What is the last book you've read?” or “What is the best book you've read recently?”

The interviewer may be opening a window into your areas of interest away from work without asking the more direct, slightly-less-tough question, “What are your hobbies?” There may also be an element of trying to catch you off guard with an out-of-the-blue question.

Depending on your specific career field, the best impression may be made by choosing a current book on business, management, or self-improvement. Feel free to choose other areas, but you would be best served to be able to relate what you learned from the book directly to your work life. For example, if you strongly prefer not to choose a volume on customer service or team building, but rather insist on a New Age topic, be prepared to explain how the book's message has helped you learn to cope with stress.

It's not recommended to pull a title out of the air simply because you've heard of it, but haven't read it. Take care! The interviewer may well have read it. He or she may be eager to ask you follow-up questions, happy for the opportunity to discuss details of the author's message with someone else who has read the book. Also, choosing the hottest best-seller may sound disingenuous, especially if you truly haven't read the work and aren't prepared to discuss highlights or your impressions.

The book you choose will make a statement about you and your potential as an employee with the target organization. Choose carefully; avoid controversial authors and subjects (such as religion, politics, gender issues, and sexuality). The very best choices will be books that have somehow inspired or helped you to improve your skills or abilities, thus making you an even stronger candidate.

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Job Descriptions and Careers, Career and Job Opportunities, Career Search, and Career Choices and ProfilesJob Search, Job Interview Questions, & Job Interview TipsSimple Truths About Tough Interview Questions - The 10 Tough Questions You Need To Be Ready To Answer, Tips From The Pros