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15 Interview Questions To Ask Your Next Hire



Question: What’s one must-ask interview question for your first few startup hires?


1. Will You Make Copies?

“At startups, everyone needs to pitch in, including doing the occasional administrative task. By asking prospective hires if they will make copies, you can identify those who have the “do whatever it takes” attitude that will help your startup succeed.”

Bhavin Parikh | CEO, Magoosh Test Prep



2. Past Experience Takes Precedence

“I would want to know, first and foremost, that the hire has had success in the startup environment before. It’s a unique culture that requires a certain mindset and approach.”

Alexandra Levit | President and Founder, Inspiration at Work




3. Where’s Your Initiative?

“”Can you give me an example of when you demonstrated high initiative?” As a startup, you need people that will go above and beyond their role and produce amazing value for the company.”

Jun Loayza | President, Ecommerce Rules



4. Completion Is Key

“How have you worked around resourcing and staffing limitations to accomplish a project? Startups are always trying to juggle multiple priorities and there’s never enough manpower to get stuff done. Asking about times where someone was able to come up with a project, idea, or initiative, and then oversee it to completion – despite obstacles – allows you to discover a lot.”

Matt Mickiewicz | Co-Founder, Flippa and 99designs



5. Find Out About the Formative Years

“I always ask candidates to tell me about a difficult or challenging event from their childhood that they feel has shaped them into who they are today. It gives me insight into who they think they are as a person, what motivates them, and how they deal with unexpected issues that may arise.”

Vanessa Nornberg | President, Metal Mafia



6. One Word: Why?

“Why do you want to join a startup? Understanding one’s motivation for pursuing a job, particularly an entrepreneurial one, is critical. Make sure your first few hires are risk-tolerant entrepreneurs like yourself, and that your objectives are aligned. You want people who aren’t going to bail at the first bump in the road.”

Michael Tolkin | CEO, Merchant Exchange



7. Stump Them With the Obvious

“Ask them if this a job or is it a career. The two are very different from each other, and can sum up the persons work mentality.”

Jerry Piscitelli | Owner / Inventor, Portopong LLC




8. Do You Get Seasick?

“I would ask the following: “If we had news that the company may go belly up in two weeks, what would you do?” This question will test the person’s stomach for the swaying seas of a startup. If they respond by indicating an “increased” level commitment, then you have a winner. If they allude to retreating and “playing it safe” they may not have the necessary fervor.”

Kent Healy | Founder and CEO, The Uncommon Life



9. What’s Your Favorite Movie?

“Startup hires need to be almost as passionate as you are about your vision. By asking, “What is your favorite movie?” you can see how they can passionately express themselves. Don’t hire those who are as dead a a door knob when they answer this question.”

Nancy T. Nguyen | President & CEO, Sweet T Salon



10. Identify Their Personality

“Ask simple questions to determine the character of the potential hire. Some startup hires cannot handle the startup mode, not because of education and past experience, but simply because their character does not fit the type of environment one would find in startups. One question to ask is, “Do you want to be in a startup, or do you want to appear to be a in a startup?” It’s an honest question.”

George Mavromaras | Founder and President, Mavro Inc. | Praetor Global LLC.



11. Make It an RPG

“Ask plenty of role-playing questions – the interviewee will project their motivation for applying to the startup. You’ll also get a deeper understanding of them as an individual and what they can bring to the table.”

Justin Beck | Co-Founder and CEO, PerBlue



12. What Happens When You’re Wrong?

“Ask for an instance of when they were dead wrong about something. How they respond is telling –  do they have the ability to admit it, ask for help and move on, or do they try to fix it themselves? Are they willing to admit it happens often? That’s a sign of not being afraid to fail.”

Susan Strayer LaMotte | Founder, exaqueo



13. All Roads Lead to Success

“The first few hires in a startup are crucial, so make sure they’re on-board with your company’s vision, first and foremost. Ask where they see themselves in relation to the company five years down the road. Make sure they envision the company’s destination the same way you do, even if they see the path a little differently.”

Nick Friedman | President, College Hunks Hauling Junk and College Hunks Moving



14. Let’s Talk Numbers

“Ask them how much they want to earn. First, this question usually catches people off-guard, which helps you evaluate how quickly they can adapt. Second, it allows you to see how flexible they are, as well as how committed they are to the company’s growth.”

Nicolas Gremion | CEO,



15. Change Is Constant

“How comfortable are you with change, and how do you handle it? If you run a startup, you need people who are flexible enough to grow with you. If someone doesn’t handle transitions and change well, you need to know that before you invest in them.”

Brent Beshore | Owner/CEO, AdVentures



Photo Credits

The YEC | Ambro |

Author : Young Entrepreneur Council

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

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