3 Tough Interview Questions

John Krautzel
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Preparing for the interview can be a stressful process; you try and rehearse your answers to some of the most common interview questions, but what about the uncommon ones? Hiring managers who ask tough or complex questions during the interview don't always expect a perfect, pageant-ready response. A few questions, like the ones listed below, don't come with a perfect answer, but they give employers valuable insight into what kind of employee you might be.

1. Tell Me About Something You Wish You Had Done Differently

This is a difficult question to answer, because no matter how you spin it, you'll end up rehashing details about something you didn't do very well. One thing the interviewer doesn't want to hear is a canned, rehearsed response, as this just tells him that you're either trying to hide something or simply don't want to answer the question. Neither scenario paints you in the best light, so keep it real. The hiring manager understands you're human, too, and wants to know that you're willing to be open and honest about your mistakes. Try to think of realistic examples of professional situations where you could have gone in a different direction or handled yourself better.

2. Can You Tell Me About a Challenge You Recently Overcame?

This question is often asked in the interview as a way to gauge your problem-solving abilities. But while you prepare a stellar response ahead of time, be ready to go deeper during the interview. Once you explain how you overcame a challenge, the interviewer may then ask about the actual process you went through to do so. What he's looking for is not necessarily an amazing tale about how you solved the impossible, but simply a willingness to get in there and try. Explaining the steps involved demonstrates your critical-thinking skills.

3. What Hobbies or Interests do You Have Outside of Work?

If you get this question during the interview, you might be tempted to loosen up and get into details about your antique Barbie collection or your penchant for off-track betting. While sharing details about the things you're most passionate about is fine here, it's not really what the interviewer wants to know. By asking this question, he is hoping to elicit a response from you that tells him you're a normal, well-rounded individual with healthy interests outside of the office. Don't be afraid to open up about things you like to do, as long as they aren't illegal, morally ambiguous or too provocative.

As nerve-wracking as it may be to prepare for tricky interview questions, understand the reasons why many companies like to ask them. Throwing you a curve ball during the interview is a clever way to not only gauge your personality but also determine how well you handle yourself under pressure, so don't stress over giving a perfectly delivered response.

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  • Nancy Anderson
    Nancy Anderson

    @Lori Wolff thanks for your question. There is no concrete answer here because every situation is different. Have you experienced a time when you and a coworker disagreed? How did you handle it? What about in your personal life? Challenges there? Honestly they just want to see how you will handle a situation where there is conflict. They may even give you a scenario and ask what you would do. I have been in interviews like that. So, unfortunately there is no one pat answer to this question. I typed in Tell Me About a Challenge You Recently Overcame in an Internet search and I got over 25 million responses. Take a look at some of those as they may help you to formulate your response. All the best.

  • Lori Wolff
    Lori Wolff

    I always get a version of question #2 in every interview. My problem is, I never know how to answer it. I would like concrete examples others have used so I might find a way to address this question. Silence in an interview is always awkward.

  • Valerie  W.
    Valerie W.

    Very informative as I have been out of work for awhile now, it reminded me how some interviewers will ask something and you just sit there with nothing to say except ahhh

  • Carol H.
    Carol H.

    I had an interviewer ask me about a tense situation and how I handled it. I was honest, to which I was regaled with everything I did wrong and what I should have done. And this was from a totally different business.

  • Jan Ketrow
    Jan Ketrow

    Don't forget the question, "If you could be any one, past or present, who would it be, and why?" It's also a zinger.


    Really makes me think clearly and on track to answer interview questions effectively.

  • lucy s.
    lucy s.

    Excellent advice

  • Natasha J.
    Natasha J.

    This was great information and feed back to share. I was asked all three questions and I felt they were really probing if I were a good fit within the organization and outside.

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