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October 22, 2021

16 Favorite Interview Questions from Some of the Sharpest Business Leaders

When you're interviewing a candidate for an open position, it's important to know how they will fit into your company.

Many interview questions are boring and repetitive. You have probably heard or been asked many of these questions before in previous interviews.

Here is a list of 16 great interview questions that really dig deep and allow you to get to know the person in front of you - as well as their motivation.

Question to Help Understand A Candidate's Transitioning into a Role

These questions help you understand if the candidate has prepared for how they will make the transition into the role, especially in terms of work style and personality.

  • Consider yourself three years from now. What do you hope will have changed about you by then?

Questions to understand employee motivation

Understanding employee motivation is so key to creating a healthy, vibrant company culture.

  • What's the greatest achievement in your professional life over the last five years?

Questions to understand if they're fit for the role you're offering

A candidate that fits the role you are offering will be able to provide examples that show they understand what the role needs.

  • What are you excellent at that you've outgrown?
  • What's the difference between someone who excels in your position versus someone incredible?
  • What do you think you'll get from us personally or professionally that you can't find anywhere else in the world?
  • What are the three most essential functions of your job? How would you rank yourself from best to weakest among these characteristics?
  • What kind of impact has your presence had on your previous company during the years you were a part of it?

Questions about teamwork

Teamwork is just as important as individual work. It's key that a candidate can demonstrate how they have contributed to a team in the past and what their philosophy is about working with teams.

  • Tell me about a time when you disagreed with your supervisor. What steps did you take to demonstrate that you were correct? What was the conclusion?
  • What was the one thing from your previous firm's culture that you want to bring to your new one? What aspect do you want to be sure doesn't show up in the next company?

Questions about learning from past mistakes and getting better

Learning from past mistakes (while not doing the same mistakes again) is the absolute key to success.

  • What is the lowest point in your professional life? Did you notice how you were feeling at the time? What did you do next?

Questions to test self-awareness

Self-awareness might be tough to understand when you're interviewing a candidate, so it's key to test for this right from the start.

  • What is the most common misconception your coworkers have about you?
  • What would others say if I went and spoke with individuals who don't think much of you?

Questions to understand how open candidates are to feedback

Being open to feedback is incredibly important in the workplace. You have to be able to work with your team, listen to their suggestions and critique, and respond appropriately.

  • What is one negative remark that, even though it was true, you had a hard time hearing? Why was it difficult and what did you do with the information? What did this experience teach you about yourself?

Question to understand candidate passions

Passions drive people and help connect them to their work. It helps if a candidate is passionate about the industry they are in as it will make them more likely to succeed.

  • What was the most recent thing that made you geek out and dive deep into?

Questions to understand how they perceive the world around them

How people see the world around them affects how they make their work decisions.

  • What characteristics would you seek out if you were in my shoes when hiring for this position?
  • What other questions have I not asked that I should have?


The above questions will help you as a leader to understand how your candidate thinks and feels about their previous work experiences as well as the position they’re applying for.

The more insight you gain from the interview questions, the better decision you will be able to make when making a hiring decision.

Asking the right questions during an interview can mean the difference between hiring an amazing employee, or hiring someone who will not be a good fit.


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