13 Questions To Ask Your First Startup Hires


by The Young Entrepreneur Council (YEC)


Question: What one question should startup leaders ask early-stage startup hires to make sure there’s potential for growth?


1. Can You Adapt?

“Ask for examples in which potential hires completed tasks of projects that were outside their comfort area or not directly related to their role. At startups, employees will likely wear many hats, so it’s important for them to demonstrate adaptability to new tasks. For instance, our web developer recently built a mobile app by learning on the go.”


Bhavin Parikh | CEO, Magoosh Test Prep



2. Where Do You See Our Company in 5 Years?

“Their answer doesn’t have to be the same as yours (though if it’s drastically different, that might be a bad sign), but early-stage hires need to have a big-picture vision for the company and its growth and potential, rather than just thinking about the responsibilities of their specific role and what role they would play in the company right now.”


Stephanie Kaplan | Co-Founder, CEO and Editor-in-Chief, Her Campus Media



3. Where’s Your Autonomy?

“Can you provide me a couple of examples of times you worked independently to successfully get a project completed? This is a critical question for a startup because most entrepreneurs do not have the time to “babysit” in an early-stage company.”


Raoul Davis | CEO, Ascendant Group



4. What’s Your Availability?

“You need to know that your hires are in it for the long haul. While they may be excited about working in a new company, the fact is, if you hit a few rough spots and don’t show enough growth right away, they will fly away to another opportunity. But if you’ve established that they do not have high expectations for the short-term and can seriously run with it for the long haul, then it’s perfect!”


Danny Wong | Co-Founder, Blank Label Group, Inc.



5. What’s Your Dream Job?

“Too seldom do managers ask new hires about their life dreams and goals. This is especially important as Gen-Y employees seem to greatly value work satisfaction and work-life balance. Getting the answer to this question will help identify if the job candidate is a good fit for the position, or can help you gear part of the work toward the employee’s ideal career trajectory.”


Doreen Bloch | CEO / Founder, Poshly Inc.



6. What Do You Enjoy Learning?

“What do spend your free time learning about? This question cuts to the heart of whether a candidate is willing and eager to learn how to do new things. Early-stage hires who have no interest in expanding their skill set and who do not already invest free time doing so may find themselves woefully unprepared for managing later hires and projects.”


Victor Wong | CEO, PaperG



7. Have You Freelanced Before?

“I give my team plenty of ways to move forward, provided they help the company grow along the way. But to take advantage of these opportunities, I have to bring in self-starters. I’m reluctant to hire people who has never struck out on their own, if only because such people have already proven that they can keep growing.”


Thursday Bram | Consultant, Hyper Modern Consulting



8. How Comfortable Are You With Change?

“Outside of inquiring about their core skill set, most questions should revolve around flexibility and the willingness to tolerate change. Startups are about pivots, and most people can’t handle that much shift in direction. Startups are not for the faint of heart.”


Brent Beshore | Owner/CEO, AdVentures



9. Can You Commit?

“Regardless of if the person you hire is capable, talented, motivated, adaptive, autonomous or even magical – if they don’t want to build with you, it doesn’t matter. Make sure they can commit to building and growing with you and the company, and that this isn’t just a bridge for them to get where they really want to go.”


Yael Cohen | Founder, President, CEO, Fuck Cancer



10. How Much Do You Want to Earn?

“Ask the question that everyone avoids. 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, and how committed they are to the company’s growth.”


Nicolas Gremion | CEO, Foboko.com



11. Do You Want to Be an Entrepreneur Yourself?

“I’ve noticed that as an entrepreneur, I know a lot of other entrepreneurial people and thus it’s easy for me to want to hire other entrepreneurs. But the truth is that if someone is entrepreneurial, they’re going to want to strike off on their own eventually. Hire for the long-term, and ask if they want their own business or if they want to help you build yours.”


Nathalie Lussier | Creator, The Website Checkup Tool



12. Why Should I Hire You?

“This is a very direct and honest question that cuts to the core of the employee/employer relationship at an early stage. If someone can’t answer that in a way that makes you feel as if they’re right, they probably aren’t the person who’s going to delight you down the road. If someone nails it, you’ll know it.”


Derek Shanahan | Growth Marketing, Playerize



13. How High Is Your Initiative?

“Ask the candidate to give you an example of when they demonstrated high initiative. Startups need go-getters — people who won’t wait to be told what to do.”



– Jun Loayza | President, Reputation Hacks



Photo Credits

The YEC | Will Merydith