8 Interview Questions Business Owners and Managers Should Be Asking

interview-questionsInterviews can be stressful no matter which side of the desk you’re on. Business owners and managers face a difficult task in selecting what they hope to be the right candidate based on just a piece of paper and a few interactions. Often, the difference between choosing the best possible candidate or a flop, depends as much on the questions that interviewers ask, as how prospective employees answer.

In this post we’ll go over some interview questions that are sure to help you choose the right people for the job.

1. Why are you looking for a new position? Why are you looking for this position?

This question seems like an easy one, but it can be more revealing than it first seems.

Maybe your candidate was fired from their last position, or they’re unhappy in their current job. These things are good to know. Why were they fired? What makes them unhappy in their current job? What would make them happier? Was it the employer or do they have unrealistic expectations?

Asking these sorts of questions allows your interviewee to really explain why they’re there. It allows you to get a good sense of what their goals are, and how they view their work and what’s important to them in a company and career path. Don’t be afraid to ask follow up questions and really dig in on this one, it can be very enlightening and also help build some solid rapport early on in the process.

2. Tell me about a time you worked independently. What was the outcome? How did it make you feel?

This is a good question to ask because it allows your interviewee to show off their skills and explain what responsibilities they have had in the past. Passion scores points on this one. If they really know their stuff and take pride in their work, you’ll see their eyes light up at the opportunity to walk you through every step of the process and share a time they are likely proud of.

Additionally, asking what the outcome was, rather than just “a time” they worked independently will help you to understand if a potential employee is goal oriented or not. Do they see the big picture when they’re working, or get bogged down in the details? Did their company land the big sale or was the project accomplished before deadline? Even little outcomes can help showcase that they understand how their work contributes to the bigger picture.

3. Tell me about a time you had to _____________.

Fill in the blank with something specific to the position they’re interviewing for. What you want to look for in their answer is specificity. It’s one thing for an interviewee to tell you they’re good at something, this question gives them the opportunity to show you.

There is one caveat on your end, however: You need to ask about something you expect them to be skilled at, that isn’t part of their routine. Asking a skilled auto mechanic, for example, to describe a specific time they changed a tire would be like asking them to describe a specific time they turned a doorknob; it’s so second nature they don’t even think about it. Instead, you might ask an auto mechanic to tell you about a time they had to deal with an impatient or disgruntled customer.

4. What professional accomplishment are you most proud of?

Just like the one above this question demands an answer in specifics. It will also help you get a feel for an interviewees values, and help you understand whether they would be a good fit with your company’s culture.

What they are most proud of will also give you insights into the areas of their skillset that they are most passionate about. Someone might work in sales but instead of their most proud moment being when they closed a huge deal, it might be when one of their clients was so happy with the customer service experience that they wrote a letter to the president of the company.

5. What’s the most difficult problem you’ve solved at a previous job?

This question will help you understand how well an interviewee can solve problems and think creatively. It will also show you how well they can work under pressure. How dire was their problem? Were they under a deadline? Were people at risk? What steps did they take and how did they eventually figure it out?

6. If you are hired, what is one thing that concerns you most about the position or responsibilities?

A potential employee who can answer this question well will be telling you two things about them: 1.) They’ve thought about this position past the interview, and they’re proactive enough to start preparing for the challenges they’ll need to face. 2.) They know enough about their field to be able to anticipate what these challenges might be.

If someone says “absolutely nothing,” then you might be a little worried as to whether they are doing the above two things, and if they are realistic about the challenges of this job. Everyone should have some concerns about the unknown, and being comfortable enough to share them is a great trait to look for.

7. If I ask a previous boss of yours what your biggest strength and biggest opportunity for growth are, what do you think they would say?

Whether the interviewee actually tells you what their boss would think, or what they think, it doesn’t really matter. You want to hear their take on both of these…and especially why they think this is.

Understanding that we all have areas for improvement, and how valuable it is to recognize this within ourselves, is a great asset to have in an employee. They will be more likely to take constructive criticism, and they’ll strive to improve instead of having a false confidence that they know it all.

Another important aspect of this question to pay attention to is how they talk about their relationship with their previous boss. If this person is going to work for you, it’s important that you have respect for each other. Does the way they talk about a previous employer describe the sort of dynamic you strive for with your employees?

8. Who is the person you look up to most, and why?

Despite being highly qualified, some people just don’t interview well. It can be nerve wracking, even for people who normally do well under stress. Asking who your interviewer looks up to can be a fun icebreaker and help an interview run more smoothly, while having the added benefit of helping your interviewee focus. If they’re thinking about a person they really look up to, whose philosophies they admire, and goals they strive for, it can help clear away the jitters and remind them of the person they want to be.

It’s human nature not to completely understand ourselves. Asking questions where an interviewee tells stories from their lives can allow an astute manager to glean things about their skills and abilities they wouldn’t have even thought to say directly.

A final pro tip: There aren’t necessarily right or wrong answers to any of these questions (though some could certainly send up red flags). What’s important is to just allow these types of questions to give you a better understanding of this person’s personality, skills, and whether they are good match for this position.


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