11 Questions All CEOs Should Ask Early-Stage Hires

In the early stages of your business, it's more important than ever to hire for passion in your mission.  By the Young Entrepreneur Council (YEC)

You always want to do your best to hire the right people, but when you're an early-stage startup with only a handful of employees, it's more important than ever. Hiring someone who isn't a good fit or doesn't share your company's values could have serious implications on your future success. So we asked our community of founders and CEOs: What's one critical question founders should ask all early-stage hires regardless of job role and why?

1. How Well Do You Multitask?

Marcela De VivoEarly-stage hires will have to wear a million hats, their roles will change, and they need the flexibility to adapt to the needs of the business. When you are interviewing, ask them for examples of how they multitask, and give them a test on the spot. They need to prove their flexibility on the spot. If they cannot multitask, you'll have to compensate by hiring more people.

 

 

– Marcela DeVivo, Gryffin Media

2. What Is Your Definition of a Stressful Day?

Kim KaupeEarly-stage hires must be able to handle the pace and atmosphere in which you, the founder, have. It is important to find out if there version of "very busy" and "stressed" match yours. If someone is easily stressed by an average or regular obstacle you face they probably aren't the best fit for your company.

 

 

– Kim KaupeZinePak

3. Why Do You Want to Work Here?

Heather SchwarzWhen you have a small team and limited amount of funding, every new hire needs to understand on day one what your business is about and what unique challenges you face. Is a candidate just interested in working for a startup? Or is he or she truly interested in your company and larger industry? See what applicants know about you up front and make sure they're aware of what they're getting into.

 

 

– Heather Schwarz-LopesEarlyShares

4. What Are You Like?

Heather McGoughIf I like you, you're likely going to find a place in my company. I want to learn what you believe you will bring to the company, what you want to learn, and what you do not want to do. Maybe you work fast, can do more with less, or consider yourself a problem-solver. I want to hear them describe their accomplishments, as well as know what they hope to learn and what they hate working on.

 

 

– Heather McGoughLean Startup Co.

5. What Is Your Passion?

mina changYou need to figure out each person’s real passion. Identifying this passion is the best way to ensure that you engage the new hire in a way that will maximize his or her potential.

 

 

 

– Mina ChangLinking the World

6. Do You Own Your Work?

Elizabeth SaundersIn the early stages of your business, it's essential that the people working for you have an ownership mindset. That means taking full responsibility for getting their work done, following up, asking for help and problem solving. When this ownership mindset is present, you can delegate with confidence and trust that activities will get done well and on time.

 

– Elizabeth SaundersReal Life E®

 

7. What Type of Personalities Do You NOT Work Well With?

kelsey MeyerThis question will tell you a lot about a person. We want to see if they immediately start bashing old coworkers/bosses, which might be a sign of drama to come. We also want to know if they can be adaptable, and it leads to the question of -- if you don't work well with that personality -- what do you do to overcome it? It is a good conversation starter and can lead to a lot of questions about working on a team.

 

 

– Kelsey MeyerInfluence & Co.

8. What Are Your Restrictions?

Zoe Barry, ZappRxYou need to understand restrictions team members may have. For example, is there a base salary they cannot dip below? Early hires may also have restraints around working hours, as is the case with new moms and dads. It is essential for the founding team to design the culture for new hires to include benefits that address these restrictions but don’t directly impact the company’s burn rate.

 

 

– Zoe BarryZappRx

 

9. How Do You Spend Your Time Outside of Work?

Shalyn DeverIdeally, I am looking for the new hire to say, "I’m taking a class online," "earning a certification" or "reading a new book about the industry." This helps me understand if this person is passionate about learning and furthering their career.

 

 

– Shalyn DeverChatter Buzz Media

10. How Well Do You Understand Possible Early-Stage Instability?

G. Krista MorganI always ask people what their financial situation is (are they the main breadwinner in the family)? I ask if they understand that funding is not stable in the early stage of a company like ours. I make it clear that we will do our best to meet our obligations, but that this isn't a job that is guaranteed by any means. Setting an expectation up front about that is important.

 

 

– G. Krista MorganP2Binvestor

11. How Did You Feel the Last Few Weeks at Your Previous Company?

Mona PatelAsking this question helps me figure out if candidates are bored, burnt out, feeling cornered, pushed out or ideally, ready to move on. I want candidates to focus on how they can help me and what it will be like to align our efforts for the good of the company AND the candidate. The red flag is when they talk too much about themselves and what they want, rather than what we can do together.

 

 

– Mona PatelMotivate Design


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.