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The Toughest Questions These Entrepreneurs Were Asked By Potential Hires (And How They Responded)

When it comes to job interviews, many employers are focused on the questions they’ll be asking each candidate and the best way to phrase those questions in order to get the information they need to make a quality decision. However, what many employers may not prepare for are the difficult questions they’ll be asked by the candidates and how they should go about answering them while still shining a positive light on their company.

Throughout their careers, the members of Young Entrepreneur Council have been asked their fair share of tough questions by interviewees. Below, they share some of the most challenging questions, how they responded and why they believe other employers should respond the same way.

1. ‘Why is this position available?’

One really tough question is, “What happened to the last person in this position?” or “Why is the position available?” It can be an easy question to answer if we just created the job to prevent duties from overwhelming another worker or if the former employee found another job at a bigger company and moved. However, the question can be awkward if the former employee quit without notice, was unhappy or decided to work for the competition. Any answer tends to reflect more on us than the employee, even if the details bear out that we weren’t at fault for the discontent. Plus, you don’t want to be overly critical of a former employee because that shows a lack of loyalty. I answered it by stating that our employee decided to move on in a different direction and that created the open position. – Baruch Labunski, Rank Secure

2. ‘How much debt do you have on your books?’

This question stemmed from the candidate feeling unstable in prior consulting roles where their employers took on investors or, in some cases, sold the company, thus changing the dynamic and culture. The employee was asking in a very intelligent way to gauge the stability of our business. At first, I was surprised, but we believe in financial transparency, and I had no issue sharing the state of our liabilities, which are all short term. – Marjorie Adams, Fourlane

3. ‘Can I continue working on my startup while working here?’

One of the tough questions I was asked by a potential hire was, “Can I continue working on my startup while working with the company?” To that, I responded, “If it doesn’t affect your deliverables, then sure.” There’s nothing wrong with them pursuing a dream project as long as their performance isn’t affected at work. If they can keep up with the deadlines without having to compromise on work quality, then they’re doing justice to the role they’re hired for. – Stephanie Wells, Formidable Forms

4. ‘How will this role improve my industry knowledge and experience?’

One of the most challenging and honest questions I have faced on the hiring table is, “How will this role improve my knowledge and industry experience?” This is a pragmatic question as this is directly connected with the future aspirations of the candidate. The candidate is asking about the growth opportunities that they will get from us as a company. I simply answered that they would get enough learning opportunities to polish their skills and knowledge as most modern brands are value-based setups. I also asked them, “Before you get in and help us grow, how will you evaluate yourself or your skills? What you need is a fresh challenge, and through the learning experience, you can grow yourself and get ready for the industry.” – Vikas Agrawal, Infobrandz

5. ‘What is your corporate culture surrounding women with children?’

Many people, especially women looking to start families during their careers, are concerned with flexibility. Many potential hires for larger corporations are asking about the FMLA leave policies and corporate culture surrounding women with children. The best thing any owner or manager can do is point to other women with children in their corporation and offer to connect the potential hire with them if they wish to discuss further, and offer to send them a copy of the company’s leave policy. If you don’t have any mothers in your business and haven’t thought about FMLA or maternity and paternity leave for new parents, then these candidates can see that they won’t thrive within your current structure. – Lauren Marsicano, Marsicano + Leyva PLLC

6. ‘What can I do to make my job better?’

I was once asked a tough question by a potential hire. They wanted to know what they should expect from their job and what they could do to make it better. I answered by telling them that there is no such thing as a perfect company. It’s up to the individual to make it better, and if they are willing to work hard and put in the time, then they will have success with this company. The tough questions that come up during interviews are ones that you’re not prepared for or don’t know how to answer. You need to be ready for anything, but it’s important not to give generic answers like, “I’m looking for someone who is passionate about their job.” – Kristin Kimberly Marquet, Marquet Media, LLC

7. ‘Is there anything that would make you not want to hire me?’

It’s always impressive to hear, “Is there anything on my application that would make you not want to hire me?” This is a tough question, but one that’s so important for hiring a high-quality candidate. In many cases, the applicants asking this type of question are genuinely interested in the role and want to clear up any doubts. Use this opportunity to answer your interviewee honestly. Let them know if you see any red flags and allow them to explain themselves. – Chris Christoff, MonsterInsights

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