The most awkward interview questions can actually be the most powerful

The job interview. Easily one of the most important interactions you’ll ever have with a team member. It’s in this major meeting where you’ll learn how this human-shaped piece fits into your company’s jigsaw puzzle.

To make the most of this critical conversation, here are some my favorite awkward interview questions to ask on the big day. At MaxCDN, I’ve used these questions in interviews with almost everybody I have interviewed. I find these questions can help break past the standard “what will you do for me” questions that often surface in an interview.

Instead, use these questions to go deeper and learn more about what makes your new employees tick. We’ll begin with a classic:

Tell me about yourself.

There’s a reason this is one of the most commonly asked interview questions you’ll ever come across— it’s really useful! Not only does this question quickly get the ball rolling, it allows you to ease in to the interview while still (hopefully) receiving an answer with some substance.

Obviously, you aren’t looking to hear about this individual’s life story. Instead, look for a confident, coherent answer that highlights experience and qualities you need in your organization.

The ideal answer: A quick summary of motivations, experience, and leading strengths; the ‘elevator pitch’ for potential employees.

What was a really difficult problem that you resolved at your previous job?

This is a question that quickly shows whether an interviewee has some depth to their qualifications. Unlike a resume or a LinkedIn profile, this is a question that is hard to talk around. It’s a question that requires a detailed answer.

Use this question to learn how this individual handles pressure, changing circumstances, or the responsibility of working within a team. You can even encourage a deeper response by using leading statements such as “That must have been stressful,” or “How did you cope with this”.

The ideal answer: A brief description of the problem with a more detailed explanation of how the candidate took action and responsibility for the outcome.

What are the last 3 books that you have read, and which 3 books have influenced you the most.

This is a great one to ask closer to the end of the interview. With this question, you’ll quickly discover whether someone spends time on their own passions and personal development outside of work. It also helps you connect with your potential new team member on a more personal level and learn a little about their growth mentality.

I like to use this question to discover whether a potential employee will take their personal growth into their own hands. Ideally, I want to hire a team member who won’t rely on me to provide all their development opportunities.

The ideal answer: You’re looking for a combination of speed and substance. If your candidate has to think at length about the last the three books the read, they may not be an individual who invests in their own development.

On a Scale From 1 to 10, How Lucky Are You?

There’s a famous quote by Henry Ford that goes, “Whether you think you can, or you think you can’t— you’re right.” When you’re looking for that perfect fit with your next team member, I suggest you find individuals who lean heavily towards “can”.

Ask this question to discover who has the confidence, optimism, and self-esteem to make their own luck. The kind of person who believes they “can”, even in the face of what might seem like overwhelming odds to someone else. Seek these people out, they’re going to be your go-to team members when the going really gets tough.

The ideal answer: You’re looking for individuals who firmly believe that life has a way of working itself out in their favor. These folks are the kind who tend to their heads during chaotic times.

A Quick Disclaimer

Finally, before I leave you, let me just dispel the notion that these questions lose their power when they’re posted online. To anyone coming to a MaxCDN with a prepared list of answers to these questions, I salute you.

At least now I know you’re someone who does your research.

I’m a serial entrepreneur and I write about things I have learned along the way. I’m passionate about helping entrepreneurs and executives to find success and harmony in business and at home.

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