Fielding the Best Interview Questions from Entrepreneurs and Business Owners

All entrepreneurs and business owners know the feeling of sitting in the seat on the other side of the desk. You sit and you wait as each question comes, coming up with the correct response seems like trying to drive through a minefield at times. Aside from the fear some interviews are able to produce, the act of setting through an interview is universal. Most people sit in front of the desk while some sit behind it. And sitting behind the desk gives room for creativity – picking out the perfect interview questions. They might be some you’ve heard before or thought of all on your own, but each is designed to weed out the best worker available.

Rescue a CEO and CEO Blog Nation asked entrepreneurs what their best interview questions are.

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Photo Credit: Vanessa ÓBriain
Photo Credit: Vanessa ÓBriain

What animal are you most like and why?

What animal do you think you're most like and why ? I ask that question as I'm trying to see if people will choose an animal other than being a dog. The most common answer by far is “I'm a dog” and it is always refreshing when you hear someone reply a different animal. IMO it also shows how they are willing to think outside the box and be more than just a “dog” person as such. I need animal people not just “dog” or “cat” people in my line of work.

Thanks to Vanessa ÓBriain, Gold Coast Pet Sitting


Photo Credit: Richard O'Malley
Photo Credit: Richard O'Malley

Give me three other uses for this object, other than what it was designed for

I have a favorite interview question that has served me well over the years. It works if I am either the main interviewer or just popping in for a quick meet and greet and this one question: While picking up an unsharpened pencil from the desk, I ask the prospect to “Give me 3 other uses for this object, other than what it was designed for.” The 3 other uses are not THAT, important. What I am looking for, however, is how they react to the unexpected, the unusual and frankly, the rather bizarre. That reaction is what I look for. How does the candidate handle the stress of such a unique question? Are they flustered? Genuinely amused? Completely frozen? This single question usually gives me more information about the candidate than several meetings and interviews of the standard variety.

Thanks to Richard O'Malley, The O'Malley Project

Related Post: Entrepreneur as Artist


Photo Credit: Mike Robinson
Photo Credit: Mike Robinson

Describe to me a familiar, multi-step process

We advise our clients on complicated building code or land use issues and need to be very clear with our clients about what they need to get their real estate project approved. Therefore, we need to hire excellent communicators that can simplify complex or technical requirements into clear answers that tell our clients what they need in non-technical terms. I ask our candidates to describe to me a familiar, multi-step process. For example, how make a cup of coffee. I evaluate them by how well they describe the steps involved, how well I follow them and how complete their answer may be. They get extra points if they also tell me what is required, what’s the time involved, what are the costs and not just the steps involved. It’s a simple way to figure out if they have the ability to think on their feet and communicate clearly.

Thanks to Mike Robinson, Permit Place


Photo Credit: Caroline Callaway
Photo Credit: Caroline Callaway

Tell me something you've really wanted in your life and how you went about obtaining it

My favorite interview question for candidates: “Tell me something you’ve really wanted in life and how you went about obtaining it.” This tells me so much about a candidate – from their ability to set goals, to their drive, to actually achieving them. In the PR industry, we need total bulldogs – people who are aggressive, who know what they want, and who find ways to make it happen. My best hires have been able to respond to this challenge with no hesitation.

Thanks to Caroline Callaway, Bolt Public Relations


Photo Credit: Tony Sorensen
Photo Credit: Tony Sorensen

What do your parents do?

I grew up in a single-parent family. My parents divorced when I was young, which was embarrassing as a kid. At the time, I felt like I was the only one who was growing up without two parents. Feeling like an outsider, my childhood experience gave me the drive to excel at sports. I was the captain of two teams, and one of the best athletes in school. After college, I worked at Enterprise Rent-A-Car and quickly became the #1 manager in Minnesota. I then transitioned my career and started my own search and consulting firm. Growing up as a young kid without a father in my day-to-day life impacted me significantly, and has been what's challenged me to be an overachiever.. Because of the impact of my own experience, some of the interview questions I ask individuals take them all the way back to their Jr. and Sr. High days, to identify why they made certain decisions. The hardest thing to interview for is drive, so when interviewing, I really dig deep to discover any life circumstances that may have made the individual an overachiever. Some of the questions I ask include: What activities were you involved in High School? What do your parents do? What was your first job? What is the one thing you are the most proud of?

Thanks to Tony Sorensen, Versique Search

Related Post: Who do you look up to?


Photo Credit: Anthony Butler
Photo Credit: Anthony Butler

What would you do if…

“You have been working on a prospect for the last couple of months and it is 2 days before the end of the quarter. If you can close the deal by COB tomorrow you will get a $20k bonus, and the company will make a large profit. If it pushes into the next quarter you will still receive your normal commission but not the bonus. The client has asked that you deliver something as part of the deal that is absolutely vital to them but you are not 100% certain you can deliver. You would need to get a clear answer from your engineering department but you happen to know they are really busy and unlikely to answer you in time for the deadline.” What do you do? This question often paralyzes a candidate. Some of them are trying to gauge me to guess what I want to hear: go for the close no matter what, or take care of the client? I had one candidate try to get me to tell him the right answer. Another interviewee flat out told me he would lie to the client and promise them everything to get the close and leave it up to engineering to figure out. The question is not about a right or wrong answer. It is to help me understand the character of the person I am going to trust the reputation of my company with for the next few years.

Thanks to Anthony Butler, Precision IT Group


Photo Credit: Donna Marie Thompson
Photo Credit: Donna Marie Thompson

What have you tried that's working/not working

Best interview questions are” What have you tried that is working” and “What have you tried that's not?”This gets at the essence of continuous innovation and profit tuning that is critical for small business owners to thrive in a competitive environment. It helps to demonstrate that we need to explore our options to make our businesses run better and that it's OK to make a mistake as long as you learn from it and move on.

Thanks to Donna Marie Thompson, Goals in Action, LLC

Related Post: Looking Back to Move Forward


Photo Credit: Sam Alibrando
Photo Credit: Sam Alibrando

If you were me, what question would you ask?

One of my favorite questions to ask a candidate is: “If you were me, what question would you ask yourself? Why would you ask it?… and then answer it.” This question gets at a few things that you might not get otherwise: 1- How the candidate thinks outside the box and more specifically, how they deal with complexity; 2- How well they understand the company’s needs; and, 3- It also can yield things that you never thought about asking. I almost always ask this question.

Thanks to Sam Alibrando, APC, Inc.


Photo Credit: Gail Tolstoi-Miller
Photo Credit: Gail Tolstoi-Miller

What are your accomplishments

I have interviewed thousands of candidates throughout my career. My favorite question is “What are your accomplishments?” Many candidates when they interview just review their skills. That is fine but what have you accomplished? If you cant explain your accomplishments – I do not want to hire you. It does not matter what level you are at – there must be something that you have accomplished that has improved or contributed to the success of the company. If you are not able to quantify or explain your accomplishments – what contributions are you bringing to the organization – it cant be much.

Thanks to Gail Tolstoi-Miller, Consultnetworx


Photo Credit: Adam Robinson
Photo Credit: Adam Robinson

What is the biggest misperception people have of you?

My favorite interview question is: “What is the biggest misperception people have of you?” because it shows the candidate's sense of their self-awareness. The question also gives the hiring manager a chance to get to know the candidate better.

Thanks to Adam Robinson, Hireology




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