The Interview Question that You Dread

Your Most Challenging Interview Questions and What to Say


interview questions that you dread imageWhat’s the one question that you dread hearing during the interview process? If dread is too strong a word, what’s the one question you are tired of hearing?

It might be a question that feels as though the interviewer is merely “checking the box” on a list of perfunctory questions. Maybe it feels as though he isn’t engaged in a conversation with you.

It could be the one question that exposes an area of concern, or a gap in your work history.


Wouldn’t you like to make the whole interview process easier by having ready ideas about what to say? You’re in luck.

This month, as part of our theme “How to Interview Like a Champion” I have been brainstorming with many of you to compile a list of challenging interview questions. Throughout the month, I will also brainstorm with you on the best ways to respond to these questions. At the end of the month, I will share the list of challenging questions and some of the responses I have gathered (and recommend.)


Avoid responses that “open a can of worms” in the interview.

A couple of ground rules for your interview answers:

  • Be authentic
  • Be brief
  • No “can of worms” responses
  • Remember W.I.F.T. (What’s in it For Them)


In other words, if someone asks why you left your last position, the following answers would likely open a can of worms, thus causing more questions and increasing levels of concern:


  • I thought my boss was less qualified than I am
  • I didn’t get along with my manager
  • The company was going in a new direction and I thought their strategy was unwise


Even if these answers are the truth (or your truth), remember, it’s all in how you choose to frame the situation. Don’t give an answer that paints you into a corner.


In the case of the first response, “my boss was less qualified than I am”, I hope that is not the true reason you left your last position. What other reasons motivated a move? Even if you parted ways amicably, and it was a mutual decision, those elements should not be included in your answer.


Think about how your response sounds to the interviewer and where their line of thinking might go next. Anticipate that line of thinking. Your goal is this: Never say negative things about your previous company or boss. Why? Right or wrong, your negative answer reflects more on you than on the company or that boss.


If you were with the company for a long time, say, over 10 years, it is reasonable to say that you had a very good run. You could point out the promotions or wins with that company and say that it was time for a new chapter and new challenges, before you became stale in your thinking. Include in your answer what you know about this company’s innovative strategies and explain how their product or service aligns with where your career is headed.


Choose the response that is authentic, in alignment with the opportunity, and with your next career move.


Again, make sure your answer is authentic. Maybe there was more than one reason to move on, and you are choosing to highlight the response that doesn’t cast a negative light on you or your previous company.


Do you have an interview question that you struggle to answer?


Add to our list and we will include it in our brainstorming and responses. Send your thoughts to Kathleen with the subject line:  Subject Line: Challenging Interview Questions


Happy interviewing!