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How to Answer Inherently Negative Interview Questions

interview tips interviewing job interview tips Apr 12, 2024
woman struggling with answering online interview questions

Nasty, mean, awful, EVIL interview questions! How in the world are you supposed to answer them? What are employers really looking for? Is it to make you suffer, or are they hoping to see how well you handle challenging questions?


While some employers are probably a little bit sadistic, most are hoping to learn something about your character.


What are inherently negative interviewing questions? Basically, anything that has a negative outcome or “makes you look bad” is an inherently negative question. For example, “What is your greatest weakness?” is probably the most famous negative question.


However, over the years, negative questions have become more sophisticated and painful, especially for the job seeker. Do these look familiar?

  • Tell me about a time that you had to deal with a conflict at work.
  • Tell me about a time that you failed.
  • Describe your worst boss.
  • What is a company policy that you disagreed with? How did you handle it?


If you are like most job seekers, you may just be praying that these questions will never be asked. Unfortunately, you do need to prepare for the inevitable time when you will grilled like a cheap hamburger.


Handling Inherently Negative Questions

While past advice might have encouraged people to “turn a negative into a strength,” that just doesn’t work in modern interviews. Instead, we need to take an honest approach – but not too honest! Then we need to immediately follow up with how you deal with the issue or what you learned from it.


Here’s your steps for any inherently negative question:

  1. Honestly and concisely state the issue.
  2. Talk about how you deal with it OR what you learned.


The second part—how you manage those weaknesses or what you learned from a situation—matters the most. In fact, two-thirds of your answer should be devoted to it.


Sample: What is your greatest weakness?

  1. I would say that my greatest weakness is that I can take on too much.
  2. To deal with this, I keep a running calendar of all my deadlines and milestones. That way, I am sure to complete my projects in a timely manner without sacrificing quality.


Warning: Don’t Use Fatal Flaws

A fatal flaw is anything that would immediately disqualify you from a job. For example, if an executive assistant stated that their weakness was that they aren’t detail-oriented, they would not be hired for the role. After all, being detail-oriented is a critical attribute for any high-performing executive assistant.


About Situational or Behavioral Questions…

Sometimes, an inherently negative question demands a story to accompany it. Yes, that’s right. Companies are creating more negative behavioral interview questions. In these cases, the outcome is most important.


But what about the super-negative outcomes, like “Tell us about a time when you failed?’ Again, 2/3 of the answer needs to address what you learned. The reason why employers ask these questions is to see how you have grown professionally, as well as to test your honesty in an interview.


Remember, for any question that requires you to think of a real-world scenario or example, be sure to follow the STAR story format:

Need more practical strategies for answering negative questions?

Check out our "Ace the Interview Without Going Crazy" online course:


Wondering how effective your job search is? Schedule a complimentary 30-minute consultation with one of our career coaches, Donna Shannon or Dia Kline

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