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5 Unusual (But Important) Job Interview Questions to Ask

Nicole Fallon
Nicole Fallon
Aug 09, 2015

Every employer knows how challenging it can be to evaluate and interview job candidates.

Although someone may look good on paper, hiring managers must figure out how to ask the right questions — and look for the right answers — to determine how well-suited that person is to the position and the organization.

But the old standards like, “Tell me about yourself” and “Why do you want to work for us?” don’t always reveal everything you want to know about a candidate. Job seekers already know to expect these questions, and have likely prepared answers based on what they believe you want to hear. It’s not that those responses aren’t truthful: They’re just not always useful for evaluating the “real” candidate, the person who will ultimately end up becoming a member of your staff.

If you want to dig a little deeper and really find out what kind of person your candidate is, here are five unusual but important questions you can ask during the interview. [8 Tips for Hiring the Right Person for the Job]

“Why shouldn’t I hire you?” In general, the entire job interview process revolves around the candidate proving to the employer why he or she should be hired for the position. So why is it good to ask the exact opposite question? Jay Gould, CEO of video advertising company Yashi, said the way interviewees choose to respond “tells you everything you need to know about them.”

“This question isn’t necessarily about divulging weaknesses,” Gould said. “It’s designed to identify their integrity, self-awareness and transparency, which I believe are the most important strengths a person you wish to work with can possess. I’ve learned more about people from this question than any other question I’ve ever asked because people aren’t prepared to answer it.”

Gould noted that the best answers to this question are ones that honestly represent the interviewee. When someone is self-aware and candid enough to share something with you, it shows you that they have the key quality of integrity and might be the right person for the job, he said. 

“How do you like to celebrate success?” With so many companies placing an emphasis on cultural fit, this type of question can help you see into a candidate’s personal work style and ideas about company culture.

“[It’s] somewhat softer in nature and helps get to the heart of matching the right people with the right company,” said Susan Vitale, chief marketing officer of applicant tracking system iCIMS. “We’ve [also] heard of companies asking candidates how they feel about having a best friend at work, to describe their perfect corporate culture, and to share something wacky or unique about themselves.”

Vitale said the best answers to “soft” questions like these really depend on what your company values. If, for example, a candidate says that his or her perfect work environment is one in which people are heads-down and focused on the tasks at hand, but your environment is far more collaborative and values teamwork to win, there may not be a match.

“How was your last company different from the competitors?” Many hiring managers will ask candidates about his or her previous employer, but it’s often only in a personal capacity — what did they like and dislike, how did they get along with their boss and colleagues, etc. Ian Siegel, co-founder and CEO of job platform ZipRecruiter, advised asking this question because it will show whether the interviewees truly understood their previous employer’s business objectives, or if they simply followed directions without being engaged in their work.

“The answer should be more indicative of a candidate’s way of thinking,” Siegel said. “It’s important to remember there’s a learning curve in any new company, or even a new role within the same organization. You can’t expect your candidates to immediately ascertain all the ins and outs of your business’ demands and obstacles, but you need to look for answers that demonstrate they have the capacity to think about the problems you’ve presented in a way that aligns with your company’s goals and expectations.”

“Why did you choose to join your last employer?” Almost every interview includes a question about why the candidate left (or wants to leave) a job, but most hiring managers don’t think to ask why he or she took the job in the first place. Eileen Adler, chief human resources officer at PeopleFluent, a human capital management (HCM) software company, said asking this provides a window into the person’s decision-making process, as well as what he or she wants and needs in a work environment.

“Listen carefully to how people talk about their work colleagues,” Adler said. “For example, do they wish their work colleagues would move faster, or slow down? Do they describe their past environment as chaotic or loose? How did they enjoy those work experiences? These are all clues to whether a person will fit in your organization. The key here is that you need to know what makes people successful in your own environment.”

“Tell me about a disagreement you had with someone in a senior role.” Situational questions that ask candidates to describe a challenge they’ve overcome, or what accomplishment they’re most proud of have become a popular way to assess a person’s problem-solving skills. But assessing someone’s people skills — particularly as they relate to dealing with his or her superiors — is just as important. Doug Upchurch, a founder and head of people development at Insights, said this question can weed out candidates who are “yes” men and women, because the last thing you want as a leader is to hire a carbon copy of yourself.

“[Companies need] diversity of thought,” Upchurch said. “Hiring in your image doesn’t create an innovative team that is looking for continuous improvement. [This question] shows how willing candidates are to lean into a difficult conversation — respectfully, of course. It’s critical to creating a team that’s diverse, vibrant and learning from one another.”

On the opposite end of the spectrum, a candidate’s response can also tell you if he or she is too conflict-focused.

“Some people like to stir the pot, and that’s not what you need [either],” Upchurch said.

When you’re evaluating a candidate’s responses to any of these questions, Adler reminded hiring managers that they and they alone can define the “right” answers based on the kind of environment and team they want to create.

“The right answer is the one the fits your work environment — that is, the one that will make [the candidate] successful within your organization,” Adler told Business News Daily. “Listen carefully to how people talk about their successes and their failures. That’s where you will answer your ‘fit’ question.”

Nicole Fallon
Nicole Fallon
Nicole Fallon has written hundreds of B2B-focused articles on topics such as marketing, business technology, leadership, and HR/organizational management. In addition to covering small business trends and software reviews, Nicole runs a digital marketing agency, where she and her team create high-quality content for a wide range of B2B and B2C brands.