7 Go-To Interview Questions for Savvy Entrepreneurs

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Welcome to Recruiter Q&A, where we pose employment-related questions to the experts and share their answers! Have a question you’d like to ask? Leave it in the comments, and you might just see it in the next installment of Recruiter Q&A!

Today’s Question: What is your favorite interview question to ask potential hires, and why?

The answers below are provided by members of FounderSociety, an invitation-only organization comprised of ambitious startup founders and business owners.


steve1. What Was the Worst Job You Ever Worked at?

I like asking new hires to describe the worst job they’ve ever worked at. Most interview questions focus on the positives – great bosses, strengths, and so on. However, you can tell a lot about a person by how they speak of negative experiences, and you can learn a lot about someone’s personality by how they frame their enemies.

Steven Buchwald, The E2 Visa Lawyer  

Vivek2. Here’s a Problem We’re Facing. What Would Be Your Approach to It?

I’m a big fan of the “five why” approach to understanding a problem and why someone thinks the way they think. If someone is looking for a function that requires autonomy (which most early hires tend to be as you expand operations), understanding why someone thinks the way they do and how they go about making the decisions they make is important.

Vivek Narayan, GorMonjee Inc.  

Arry3. What Are Three Things I’m Good at – and Three Things I’m Not?

After a candidate has spent about 20-30 minutes with me doing more standard interview questions and has had the chance to ask a question or two themselves, I ask them a very awkward question to find out if they have the chutzpah to speak up and take a chance, how well they can read people, and whether or not they have the ability to follow simple directions.

Arry Yu, GiftStarter.com  

Steve4. Are You Nervous?

Asking this simple question allows you to find out if the candidate is being honest by simply reading their body language. If you can tell they aren’t being honest about this question, what’s to say they are honest about “business-related” questions?

Steven Newlon, SYN3RGY Creative Group  

jessica5. What Would You Do If You Were CEO for a Day?

I ask what their day would look like if I were to put them in charge of my company for a day. By asking this question, I am able to get an idea as to whether this is something that excites them or intimidates them, which allows me to decipher the leaders from the followers. What I’m looking for is someone who wants to take initiative, has great ideas for implementation, and has suggestions for improvement.

Jessica Baker, Aligned Signs  

ajmal6. Can You Act Out This Scenario?

I interview candidates for a tutoring position, so I like to request that they act out a scenario of how they would teach. I ask them to teach me an academic topic (such as a math or reading problem) as if I were the student. This allows me to see in real time how well the tutor would perform actually working with students.

Ajmal Saleem, Suprex Learning  

nadia7. What Inspires You?

Asking this question allows me to get an idea of what motivates the candidate and how genuine they are.

Nadia Hansen, Result Logix  


By Recruiter Q&A