Job Search Series – Nailing the Interview – Part 6 – Those Sticky, Tricky Questions

Why should we hire you?

This question has stymied many candidates. And it’s not the only one. Recently, I had a conversation with career professional Lyn Leis, who enlightened me with her insight on the hot topic of interview questions. Today’s post combines Lyn’s insight with my experiences on both sides of the interview desk.

Before we take a look at some of the trickiest and stickiest interview questions, however, let’s examine the reasons behind the questions, which are usually a mix of standard, behavioral and — depending on the position — analytical.

Reason #1: Can you answer questions directly? Listen carefully to the interviewer’s questions and take care to answer them precisely. It can be easy when discussing yourself and your experiences to give more or different information than requested. Don’t let your mind wander should you hear a phrase that triggers something else. This is why it’s prudent to provide relatively short answers to interview questions; if the interviewer wants additional information about something you said, she will ask. Moreover, some interviewers ask questions qualified by numbers (for example, “describe yourself in three words”). Keep in mind that while she’s interested in the content of your answer, she also wants to know if you can follow directions and give the exact number of words requested. If you don’t answer questions directly an interviewer might conclude that either you cannot focus on the task at hand or you are ducking a question; either way, it raises a red flag.

Reason #2: What is your communication style? The ability to communicate is at the top of employers’ lists of qualities they seek in a job candidate. Can you speak, write and present coherently? Can you communicate effectively to any audience, regardless of size or composition? One of the reasons you are sitting in the interview at the moment is because your resume and cover letter were designed, formatted and written clearly and compellingly. Now it’s time to demonstrate that you can speak, present and converse as well as you write.

Reason #3: Will you say what your interviewer expects to hear? Your interviewer has already reviewed your resume, cover letter and other documents you submitted prior to the interview and has assessed your strengths as they relate to the position. As such, she expects to hear that you are aware of your qualifications in the same way and have given sufficient thought to the position. On the other hand, if your assessment is different from hers she will be impressed only if it demonstrates your thorough research and unique insight.

Reason #4: All questions are meant to assess your strengths and weaknesses for the position. When you’re asked a general question or a question that might not seem relevant, know that such questions are asked to evaluate your response as it relates to the position. Therefore, it’s especially important when you are asked open-ended questions such as, “tell me about yourself” or “what do you consider to be your greatest accomplishment,” to answer in the context of the position.

Reason #5: What is your personality? Do you have a sense of humor? Are you professional, relaxed and likeable? Do you possess business etiquette skills? Sometimes a question will seem to come out of left field or seem very personal. This type of question is often used to assess your personality or people skills. Just as important as your hard skills are your soft skills — that emotional intelligence that allows you to connect with people on a human level. If you’re asked such a question, take a moment to reflect on how you might be coming across to the interviewer; he might have asked the question because you have not yet displayed an aspect of your personality in which he is interested.

Knowing the reasons behind the interviewer’s questions will help you to prepare your answers to the following 10 of the trickiest and stickiest:

  1. Tell me about yourself. Remember your positioning statement? Here’s where it comes in handy. You may expand on it to answer this question, but keep your description concise. It should be short and snappy, upbeat and interesting. This is your opening statement, so keep it to no more than two minutes; don’t give your life’s story up front. You’re setting the stage for your interviewer to want to know more about you.
  2. Why are you interested in this position? Use a combination of your positioning statement and research of the company and the position to answer this question. Show the connection between your career history and/or goals and the company / industry / position. Here is where you will begin to connect the dots for your interviewer.
  3. Where do you see yourself in five years? Here, again, you will use your positioning statement as the basis to project how you see your career advancing. The interviewer wants to get a sense of your expectations, so keep them within reason for the industry, company and the current economic times. Painting too grandiose a picture could imply that you will become quickly dissatisfied and are not a good candidate after all.
  4. What is your greatest strength? Weakness? I like this approach: Based on your research of the position and your own self-assessment, answer this question in relationship to your match to the position. After all, that’s what’s relevant to your interviewer, who wants to know what she might have to deal with regarding your fit to the position and company culture. To prepare for this question, look at the job description. What is your greatest match? The answer to that will be your greatest strength for this position. Conversely, what are you lacking in requirements? The answer to that will be your greatest weakness. To compensate, you must include your plan to overcome this deficiency in order to demonstrate that you are aware of where you fall short and how you have already fixed it, are in the process of fixing it, or plan to fix it. For example, if you meet all the job prerequisites except for the three-year experience requirement you could point to (a) similar experience (b) a situation in which you were able to learn quickly or (c) explain how your other qualifications outweigh your lack of experience. Similarly, long experience might outweigh the lack of a degree.
  5. How would your boss / coworkers / direct reports / clients describe you? Select the best compliments and comments you can dig from memory or documentation; there have to be some!
  6. Tell me about a situation in which you had to persuade a group to follow your suggestion  or plan. How did you go about it, and what was the result? Prepare a SOAR story for this one, and for questions 7 & 8.
  7. Have you ever had a negative interaction with a superior or coworker? If so, how did you handle it?
  8. Describe a time that you were unsuccessful at something. How did you cope?
  9. How many hot dog stands are there in Manhattan? Okay, I threw this one in for fun. This type of question might be asked if you apply to a Wall Street or Silicon Valley firm. The interviewer is interested in your thought process in arriving at the answer, rather than the answer itself. For example, some smart candidates — as well as smart attendees to my workshops! — have said that they would go about estimating the total number by checking with City Hall to learn how many licenses had been issued, guesstimate the number of unlicensed stands and determine how many corners there are in Manhattan (which is designed as a grid), as well as any other relevant factors; then, they’d do the math.
  10. Why should we hire you? By now, you should be prepared to ace this question! Your answer will be a combination of your match to the position, positive attitude and deep and sincere interest in both the position and the company. And, don’t be afraid to throw in something personal. Example: “In addition to my qualifications for this position, it has long been my dream to work for this company because (complete the sentence). I don’t see this as just a job but a commitment to giving my all to making the team stronger, contributing to the positioning and growth of the company and learning as much as I can to become a more informed, experienced and valuable associate. I’m excited and eager for the opportunity.”

I hope these tips will help you to nail your next interview. And remember the most important tip: in answering interview questions you always want to accentuate the positive and eliminate the negative! And do it with a smile!

Until next time,


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