Five Unconventional Questions That All Hiring Managers Should Ask

joseph cole

Updated on May 3, 2023

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Apprehensive yet excited. That’s a job interview for you.

It is a jittery affair for parties on either side of the table. The candidate tries to sell their credentials and skills while the interviewer may want to put forward the best pitch about their company, their team, work, and benefits.

The job interviewer’s task in an interview is often the less discussed and under-analysed subject. With all the pitching, the interviewer has to make sure that she lands the correct candidate as the chances are, she might have to work with them for a considerable amount of time. She wants to build a great team that thrives on meritocracy backed by data. It’s imperative that the chaffing of applicants is accurate in order to make the most informed decision about them. Too much work, right?

Here are some unusual questions to ask that can help you know the candidate better, beyond their resumes in the few minutes you have been assigned together.

  1. Share an experience where you failed at your job? This question does a lot of good to you when you want to check if the candidate is risk averse or otherwise. The question also helps determine if the candidate possesses the ability to learn from experiences, a trait coveted by most hiring managers. The answer to this question will help you gauge if the candidate is introspective and confident in their ability to do better the next time.
  2. What is the toughest decision you had to make in the last few months? A good candidates will arrive on a decision based on logic and analysis. The decision making should reflect candidate’s ability to weigh both the business as well as the human aspect of the issue. A good mix of interpersonal considerations based on a data-driven process differentiates a great candidate from a good one.
  3. When was the last time you lost track of time? What was the task? The ability to commit passionately to a task is of utmost importance to any team leader for their high growth business. Only passion can lead to high creativity and productivity and that is where the brightest ideas stem from. This question will help you determine a candidate’s hunger and drive toward their work, irrespective of the number of years of experience they have. If they have even the slightest smolder of passion, lap it up and get ready to fire them up with the right kind of work and role.
  4. Ask them about their favorite sitcom. Sometimes a question as simple as the candidate’s favorite sitcom can answer heaps about their fitment into your organization’s culture code. They don’t need to have your cubicle aisle jokes at their fingertips, but if your quirky sense of humor is fun for the candidate and they get it and get it well, you can see a camaraderie sprouting right there. I see a highly collaborative team at work already.
  5. If you were to start a business, what would it be? Candidates with entrepreneurial leanings can bring a lot of drive, attitude and entrepreneurial spirit to your team. Entrepreneurial candidates also make a great fit for startups because they assimilate the differences between working for a corporation versus a startup. it doesn’t really matter what industry they choose, what matters is the fact that their enterprising nature rubs a lot of positivity in terms of ideas, hopes and dreams onto your organization.

Asking the right questions is only the second half of the task. The first half involves making the applicant comfortable enough so that the interviewer gets the right responses. A stressed candidate may not open up or deliver their best performance which can hinder the evaluation process. The interview is a collaborative conversation, where both parties on either side of the table contribute equally.

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