The Most Revealing Interview Questions

by Ann Connor

So you just received a stack of resumes for a role you’re trying to fill in your company. Now what? While these resumes will detail the applicants college education, past employers, skills and possibly even interests, the piece of paper doesn’t truly tell you about the interviewees personality and if they will mesh well with your team and organization.


How many times have you heard the questions, “what are your strengths” and “what are your weaknesses”? At this point, every individual that has ever applied for a job has a well rehearsed and prepared answer. It’s the oddball and most revealing interview questions that will produce a conversation and allow you to really understand the applicant’s personality and thinking.

How do you spend your time away from work? Where did you spend your last three vacations? You want an employee that has interests outside the office, interests that are varied. It is critical for a good employee to welcome and support change in a work environment. Hiccups occur, deviations take place, rarely do things go as planned. If a candidate has a singular interest, and only vacation in one location, year after year, chances are this applicant will not do well with any form of variation and chaos in their daily schedule. Furthermore, if the interviewees interest outside the office includes building things, playing team sports, volunteering, then it’s an indicator the individual is willing to learn something new and can deal with a group environment.

What is something in your life that you deeply regret? This question may catch the applicant quite off guard as its quite thought provoking, forcing them to reveal the true and raw side of themselves. While its not overly personal, to the point of causing a possible Human Resource issue, the question does reveal your candidates integrity, honesty, and what truly matters to them.

During a team meeting, would you be willing to tell a joke or a sing a song? This question is actually two sided. First, if the candidate laughs and says “sure”, then you know your candidate an be easy going and wont take themselves too seriously. The work culture you set in your company is very important. Individuals usually spend more time in the office, than they do at home. As such, their job and their peers, become like a second family. If an individual cannot laugh at himself or herself, and does not know how to find humor in simply goofy office jokes, then it can throw off the dynamic of your group. There are plenty of times for you to be serious, during team powwows, during meetings, during presentations. But sometimes your team needs to laugh and relax and enjoy good old-fashioned fun. Second, motivation does not necessarily need to come from a manager, but can also be from associates on the team. Associates who can put themselves in the forefront with ideas, songs during meetings to break the ice, usually take risk to accomplish what he or she has set forth.

What are you reading right now? Always learning and being curious is an extremely treasured trait in an employee. Many ideas and innovations can come from employees who have innate interests. You want people who maintain the thirst for knowledge and always want to keep an upper hand on their competition.

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