How To Ace The Trickiest Interview Questions

If you are actively looking for work, you know the importance of adequately preparing for a job interview. These meetings, more than any other components of your search, are the events that will determine your success.

You can prepare yourself by gaining a thorough knowledge of the company, how the organization is positioned in the marketplace, their major competitors and both the long and short-term goals they hope to accomplish. You can, hopefully, also research the hiring manager and identify his or her immediate concerns. Moreover, you can practice your responses to frequently asked questions so that you feel well prepared to list your skills and accomplishments with confidence.

But how can you prepare for the tricky behavioral style questions that will likely be asked? Such questions seem impossible to anticipate, as they require event-specific answers. The good news is, preparing for behavioral style questions is easier than you think. For information and tips, please see my earlier article, 3 Key Tips to Help You Ace the Behavioral Style Interview.

Nevertheless, there is one additional wrinkle to be added to your interview preparation ... and it is a big one. Many times interviewers will ask you to provide examples of times when you were disappointed with your performance: you fell short of your goals, had a conflict with a boss or coworker or failed your team. Obviously, these types of negatively focused questions can be tricky!

It is helpful to realize that the goal of the interviewer is not to embarrass you. Rather, they want to determine your self-awareness, your attitude and your ability to take direction when needed. Therefore, you need to frame your responses to underscore what you have learned from the experience and how you grew from your earlier mistakes.

These types of questions will generally fall into three categories:

Your interpersonal skills (or lack thereof)
Typical question: Tell me about a time when you had a conflict with a boss/team member/customer or client.

How best to respond: This is when a "sandwich" response will come in handy. Begin with a positive, give an example of the difficult situation (briefly so as not to dwell on the unpleasant event) and end with a key learning experience.

Example: I pride myself on my personality and my ability to get along with most anyone. So it initially threw me when I had to work closely with a coworker who constantly criticized my work. After trying my best to get along with this person, I realized that he was feeling threatened by me as I had been assigned some projects that had formerly been under his control. Once I figured this out, I turned to him for advice and suggestions, and his criticism soon softened. He even became an advocate for my work in various managerial meetings. This experience taught me that, when these types of situations arise, you can generally resolve most any conflicts by taking the time to understand the other person's motives and needs.

Your personal weaknesses that have led to making professional mistakes
Typical question: Give me an example of a time when your actions caused your team to fall short of their goals.

How best to respond: The weaknesses questions are particularly challenging. They open the door to exposing not only mistakes you've made, but character flaws as well. This is the time to remember that brevity is best! You don't want to give a laundry list of your shortcomings: lack of personal responsibility, overlooking important details, failure to follow through, etc. Also, make sure the example you cite is not a weakness that would have a major impact on the position you want.

It is helpful to frame your response in the past tense, let the interviewer know you are aware of your weakness and the steps you are taking to overcome your flaw. Remember your interviewer is looking for attitude and awareness.

Example: When I was new to this field, I didn't anticipate the lead-time that was necessary to market our products effectively. I had assumed that, once the widgets hit the stores, they would garner ample word of mouth to fly off of the shelves. It didn't take me long, however, to realize that sufficient pre-production marketing was necessary to alert the public to the benefits of buying XYZ widgets. So I learned two valuable lessons: (1) thorough planning, research and adequate lead-time are important and (2) uneducated assumptions lead to mistakes.

How you bounce back from setbacks and failures
Typical question: Tell me about a time when you were disappointed in your performance.

How best to respond: Your response to these types of questions should be similar to how you would reply to a question about your weaknesses. You want to briefly state the situation but focus mainly on how you recovered and what you learned from the experience.

Example: When I first became team lead, I felt somewhat overwhelmed by competing obligations. In addition to my added responsibilities, the company was in the middle of launching a major new product. Unfortunately, my team missed one of the deadlines we were supposed to meet. Although this wasn't critical to the success of the product launch, I did recognize the importance of effective prioritizing in a leadership position. I'm proud to say that, since that experience, I've always given my projects the planning and time they need to be successful. In fact, although I've now been a team lead for years, I have never missed another deadline.

Like the examples above, with sufficient forethought and planning, you can handle even the trickiest of behavioral style interview questions. Use the job description as your guide, anticipate questions they might ask based on the required skills and experience in the posting and remember to focus on what you learned from any negative experiences you have encountered.

With thorough preparation and a confident attitude, you are well positioned to ace the interview ... no matter how difficult the questions. Better yet, you just might make a good enough impression to land that job you really want!

Mary Eileen Williams is a Nationally Board Certified Career Counselor with a Master's Degree in Career Development and twenty plus years of experience assisting midlife jobseekers to achieve satisfying careers. Her book, Land the Job You Love: 10 Surefire Strategies for Jobseekers Over 50, is a step-by-step guide that shows you how you can turn your age into an advantage and brand yourself for success. Updated in 2014, it's packed with critical information aimed at providing mature applicants with the tools they need to gain the edge over the competition and successfully navigate the modern job market. Visit her website at Feisty Side of and celebrate your sassy side!

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