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I’ve interviewed a lot of people in my career for all kinds of positions and from many backgrounds. Most people have a few questions they always ask and some believe certain questions can quickly reveal what they need to know about a candidate’s cultural and positional fit.

The leaders with the greatest success in hiring the right talent often like to point to the exact questions that made it clear that a candidate would or wouldn’t work. I’ve made it a hobby to consider the questions that really made me think and to experiment with the ones that make it hard for interviewees to prep for, as those are the ones that reveal the most.

Go To Interview Questions

I often ask people from different walks of life about their “go to” interview questions and why are they so important. Here’s what I’ve collected:

  1. What are the failures that you most cherish? This question is the backbone of an effective interview where you want to learn a great deal about a candidate for a job or a partnership. All success is the result of turning failures into insights and even new mindsets. If someone sees failure as something to avoid instead of cherish, you can almost predict they won’t be successful.
  2. What are the qualities that you like least, and most, about your parents? This question is especially interesting. When I first saw it, it made me think and summarize thoughts that I had carried with me for a long time. Even as I read it now, I have very strong opinions on what I sought to embrace and what I long ago decided to do differently.
  3. Are you smart, or do you work hard? Good question. Don’t allow the answer to be both.
  4. If you could go back five years, what advice would you give your younger self? This is my second most favorite question for revealing a lot about oneself. It takes insight, vulnerability, and commitment to respond to this authentically. The fake answers stick out like a sore thumb.
  5. How do you develop yourself outside of the work environment? Development can take all shapes and sizes. It can be found in a hobby, a purposeful pursuit, or in an appetite to explore.
  6. Is it better to be extraordinary and late, or good and on time? Like all paradox questions, the simple answer is to be both on time and extraordinary. But don’t let your candidates get away with that. They must choose only one. The second part of the question, and equally important, is: why would you pick that one?
  7. What are you most curious about in life? Ask the candidate to express it in a question. I did this with high-potential sophomores in high school and their “curious questions” blew me away. Questions like, when you die of natural causes, what do you die from? Or, if you need oxygen for a fire, how can the sun burn so brightly up in the sky with no oxygen? I would have hired every one of them after our conversation.
  8. What is the most courageous thing you have done in your life? Everyone seems to have a different definition of courageous. It’s both revealing and informative to have people share theirs with you.

Have you ever been asked these questions? What questions do you ask your candidates? Which ones do you find to be the most revealing?