The Worst Things That Have Ever Happened to You

You’ve heard the phrase, “what doesn’t kill you makes you stronger,” right? Well, what doesn’t kill you also makes for good interview material.

Some of the trickiest interview questions are those that ask you to recall a negative experience or talk about your weaknesses. Questions like:

  • Tell me about a time when you failed.
  • What are your greatest weaknesses?
  • What is the greatest obstacle you’ve overcome?
  • What is the most difficult decision you have ever had to make?

These kind of questions can often catch candidates off guard. They might bring up painful, embarrassing and negative experiences. It is challenging to convey what happened without complaining or coming across as overly negative.

At the same time, negative experiences or challenges usually provide for lots of growth and learning. They will allow you to demonstrate to an employer how you tackle tough issues and show them you aren’t afraid of making mistakes. Nobody wants to hire someone who will run from problems.

Some tips for handling these types of interview questions:

  • Don’t dwell on the negative. State the situation and swiftly move on to how you dealt with the issue.
  • State the facts and avoid interjecting negative opinions about other people (For example,  “my boss was very demanding” is much better than, “my boss was rude and mean”)
  • Make sure to discuss the skills you used to overcome a challenge or deal with a problem.
  • Always end on a positive. What did you learn? How did the situation affect future decisions and actions?
  • Prepare in advance. These situations are tough to talk about and usually the questions we dread most. Practice your responses in advance.

Even if you’re not explicitly asked about a challenging situation, discussing those type of situations allows you to demonstrate how you’ve grown or used your skills in difficult circumstances.

What’s the most difficult interview question you have ever been asked?


Kelly is a career advisor at the University of Wisconsin-Madison, where she assists undergraduate business students with all aspects of their career development. Connect with Kelly on Twitter, her blog, LinkedIn or BrazenCareerist.

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