Tackling Tough Interview Questions

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Every IT professional preparing for a job interview dreams of questions that are predictable and relatively easy to answer. However, most employers are likely to throw a few curveballs—the challenging questions that send a job seeker’s pulse racing.

Interviewers take this approach to test your ability to think quickly and creatively, as well as to get a better sense of your personality and professional motivations. The key to making the right impression is careful preparation. By practicing your responses, you can keep nervousness in check and convey professionalism and confidence. Here are several sample questions and strategies for answering them:



  • Why should I hire you? Try to think of this question as a request for an overview of your strengths. Focus your response on the qualities you know the employer seeks in candidates. For example, “Your company’s ad mentioned you were looking for a network administrator with strong Windows XP and 2000 skills. I am a Microsoft Certified Systems Engineer and have extensive hands-on experience with these applications. I also share your firm’s commitment to quality service and recently received an award for my work during a major systems upgrade at my current employer.”
  • What is your greatest weakness? The best response is one that’s honest, but brief. You don’t want to knock yourself out of the running by detailing shortcomings that could affect your ability to perform the job. Try to focus on minor issues––such as the fact that public speaking is not your forte––and if you can, mention ways you’re working to overcome them.
  • Tell me about your worst boss. This isn’t an invitation to go on and on about your previous manager’s bad habits. Instead, address one negative point and try to highlight something you gained from the relationship to balance it out. For instance, you might mention that a supervisor wasn’t a great motivator because she seemed to have lost enthusiasm for the IT field and talked regularly about starting an unrelated business. However, you learned from the experience the value of maintaining your own professional drive by finding a mentor and staying active in technology associations.
  • What are your salary expectations? Before the interview, try to find out the salary range for the position. If the hiring manager won’t share the information, cite a range that is in line with your marketability and the value of your skills and experience in today’s market. Read association statistics, salary surveys and government reports to determine typical starting compensation in your specialty. That way you can respond confidently, knowing your answer is based on current research.
  • You are lacking skills/experience. Why should I still consider you? Since the interviewer is expressing reservations about your qualifications, you need to make a persuasive case for remaining a contender. Mention how you’ve overcome skill deficiencies in the past and reiterate your strongest assets. For example, “While I have only one year of experience with UNIX, I am confident I could enhance my expertise very quickly. When I first joined my last employer, I wasn’t familiar with a proprietary software program they used, but after some online training and additional time studying on my own, colleagues began turning to me for advice with the program! Given my ability to master new technology, my strong project management skills and my extensive knowledge of systems security, I believe I could make a positive impact at your firm.”
  • What did you like least about your previous job? Employers will be paying particular attention to your response to this question, taking note of whether you have issues with certain management policies, business practices, responsibilities or work styles. The wisest move is to address aspects of your previous job that are different from the position for which you’re interviewing. Maybe you disliked being the sole technical support professional at a small firm because there were no advancement opportunities, and you now want to be part of larger organization that will allow you to continue learning and assume greater responsibilities.


While you can’t predict what will come up, preparing for challenging subject matter will build your confidence and enable you to provide more compelling responses. Practice your answers to tough questions while remembering that the hiring manager’s goal is simply to make sure you can do the job––not to give you a hard time. Also, keep in mind that you may not be able to anticipate every query. Our company recently surveyed executives, asking them to describe the strangest questions they had been asked during job interviews. The responses ranged from, “What would I find in your refrigerator?” to “If you could be any animal, what would you be?” In situations like these, where queries are too quirky, a better question to consider might be: Do I really want this job?

Katherine Spencer Lee is executive director of Robert Half Technology, a leading provider of IT professionals on a project and full-time basis, which offers online job search services at www.rht.com. She can be reached at klee@certmag.com.


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