10 Tough Sample Interview Questions for Employers to Ask

Image of a sign that says, "Ask more questions." Sign is on a wall in-between two clocks

Interviews are tough anyways, so why ask tough questions? Because it helps you get to the root of someone’s personality. It will help you see how they react when they are tested and challenged.

Ask anyone a tough question and you’ll probably learn something about them, their habits, or hear a story from their perspective. These are 10 tough sample interview questions you can pick from for your next interview.

Sample Interview Questions for Employers

  1. How did you manage a work-related problem that you created?
  2. What projects are you currently working on in your free time? What was the most recent milestone you reached with that project?
  3. If you had to choose, which is most important to you: the approval of your mom or your dad and why?
  4. What do you think a company owes its employees?
  5. What current trends do you think affect our business?
  6. If you were to be hired, what do you think would be a reason you might not stay in this position or with the company?
  7. What was the most useful criticism you’ve ever received?
  8. [Describe a scenario of a difficult situation they might experience in this position.] How would you handle this?
  9. What risks did you take in your last position?
  10. What flaws do you see in our industry of in your particular position? What would you do to fix that?

Bonus fun question: Which would you rather be able to do, run at 100mph or fly at 10mph?

Think about these questions yourself. They’re tough, right? Good! You should be asking some tough questions in your interviews. Every interview is different, you’re hiring for different positions and looking for unique personalities to fill them. Create your own tough questions that will help you identify whether your candidates have the personality and skills you are looking for.

Ask questions that make people stop and think. They might not give the perfect answer, but seeing how they process this and react to difficult or unexpected situations can give you great insight to their character.

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