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Some Creative Questions to Ask in a Job Interview

Avoid timeworn, clichéd questions, such as “What are your strengths and weaknesses?” when you are interviewing a candidate for a new job. Instead, develop a list of questions designed to elicit responses that will be most helpful in evaluating a candidate’s suitability for your position and organization.

Here are some questions to get you started:

  • “Who was your best boss ever and why? Who was the worst, and, looking back, what could you have done to make that relationship better?” Among other things, the answers give you insight into how the candidate views and responds to supervision. In today’s team-oriented workplace, you want employees who try to minimize these clashes and not use them as excuses.

  • “Are you more comfortable and successful working alone with information or working with other people?” The ideal answer here is “both.” People who say they like working with information are obviously a good choice for technical positions, but it may be a red flag if they don’t also enjoy communicating and collaborating with other individuals.

  • “What sorts of things do you think your current/past company could do to be more successful?” You’re probing to find out whether the candidate has a clear understanding of his current or past employer’s missions and goals and whether he has worked with those goals in mind. Candidates who can’t answer this question well are demonstrating a lack of depth and interest.

    Make clear to the candidate that you’re not looking for proprietary or confidential information.

  • “Can you describe a typical day at work in your last job?” Strong candidates can give you specific details that you can verify later, but the main point of this question is to see how the applicant’s current (or most recent) routine compares with the requirements of the job in question.

    How interviewees describe their duties can prove highly revealing. Do you sense any real enthusiasm or interest? Do the details match the information you already have? You’re looking for enthusiasm and some indication that the applicant connects his current duties with company goals.

  • “What sort of work environment do you prefer? What brings out your best performance?” Probe for specifics. You want to find out whether this person is going to fit into your company. You also may uncover unrealistic expectations or potential future clashes. People rarely, if ever, work at their best in all situations. Candidates who say otherwise aren’t being honest with themselves or with you.

  • “How do you handle conflict? Can you give me an example of how you handled a workplace disagreement in the past?” You want candidates who try to be reasonable but nonetheless stand up for what’s right. Unfortunately, most candidates say the right things, which is why you want some specifics. Be suspicious if the answer is too predictable.

  • “How would you respond if you were placed in a situation that you felt presented a conflict of interest or was unethical? Have you ever had this experience in previous positions?” How individuals approach this question and any anecdotes they share can offer valuable insights as to how they may respond if faced with such a situation.

  • “What are your compensation expectations?” There’s no “trick” to this question. You simply want to get a sense early on if the candidate’s desired pay is in line with what you’ve budgeted for the open position. This can prevent you from continuing to move through the hiring process a promising candidate whose salary expectations far exceed your own.

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