Making Your First Hire? 11 Questions to Ask to Ensure They’re the Right Fit

When making your first hire, no matter the position, what’s one question you should ask during the interview to determine if they’re the right person to take on this new business with you? Why?

Hiring first employee
photo credit: Kindel Media / Pexels

These answers are provided by Young Entrepreneur Council (YEC), an invite-only organization comprised of the world’s most successful young entrepreneurs. YEC members represent nearly every industry, generate billions of dollars in revenue each year, and have created tens of thousands of jobs. Learn more at

1. ‘What about this role excites you?’

This is a deceptively simple question. To answer it well, the candidate needs to demonstrate knowledge of what the role entails and what the responsibilities are, how their past experiences and skill set make them a great fit for the role and genuine passion and excitement. The best responses are well-structured, personable and somewhat relatable.

Greg Soh, RoadFlex

2. ‘What’s one thing you would have done differently in your last position and why?’

The candidate’s answer to this question shows you their character when it comes to accountability, humility and insight. If they can’t think of one thing, then that shows a lack of insight. If they deflect and are quick to blame, that shows lack of accountability. Humility is in how they deliver their answer.

Givelle Lamano, Lamano Law Office

3. ‘How adaptable are you?’

When you’re in the early stages of launching a business, a critical question for potential hires is “How adaptable are you?” Getting a new business off the ground requires constant pivoting, and it takes a certain personality to navigate that effectively. The right candidate will be able to change direction quickly and often. If they can’t, they’re not a fit, and it’s best to know that upfront.

Samuel Saxton,

4. ‘What are your long-term career aspirations?’

I think it’s important to ask this question because you want to make sure that the person you’re hiring is someone who is looking to stay with the company for the long haul. You don’t want to keep training new employees every few months, so it’s important to find someone who is committed to their career and will be there for the long run.

Pratik Chaskar, Spectra

business communication

5. ‘What are your toughest communication challenges?’

Communication is everything, especially in a small team. There are going to be ups and downs and growing pains, but understanding how someone communicates is absolutely essential to growth and partnership. Even if you are hiring someone with the intent to train them, you have to have clear communication lines to grow together.

Matthew Capala, Alphametic

6. ‘Why do you want this position?’

The first question to ask when interviewing a new hire is, “Why do you want this position?” This will help you find out if the person is truly interested in the position or just wants a job. This will help to weed out the candidates who are not a good fit and make it easier to focus on those who are.

Kristin Kimberly Marquet, Marquet Media, LLC

7. ‘What areas do you have expertise in?’

Your first new hire will need to wear multiple hats, so it’s critical that they bring multiple skill sets, experience and knowledge to the table. This question is also essential because it helps ensure you’re hiring someone with different expertise from your own. You don’t want to duplicate knowledge and skills at this point; you want to expand.

Jonathan Prichard,

8. ‘How do you deal with challenges at work?’

One question you should ask during the interview is, “How do you deal with challenges at work?” This is an interesting question because the answer can reveal a lot about a person. It also gives them an opportunity to talk about real events at their previous job. You’ll learn a lot about the candidate and whether they have the skills needed to work through difficulties. 

Blair Williams, MemberPress

Interviewing new employee candidate

9. ‘Why should I hire you?’

One very important question that you need to ask your first hire is, “Why should I hire you?” It’s a great question to identify the candidate’s potential and understand if they are the right fit for your business. In doing so, you need to look for answers that tell you what they can do for the company and not for answers that just talk about their personal traits that make them the best fit.

Thomas Griffin, OptinMonster

10. ‘What does a good work-life balance look like?’

Ask them what they think a good work-life balance looks like. Listen carefully for the interviewee to introduce their own limitations. If they don’t say anything meaningful about other commitments, probe deeper. Try to get past the part of the process where they are trying to impress you with their work ethic. No one can work all the time, even (or maybe especially) when starting up a new company.

John Hall, Calendar

11. ‘What made you leave your last job?’

You want to know if they are going to have the same issue with your company if you hire them. Their answer will reveal a lot about their work ethic, values and attitude. It’s a tricky question to answer, but their response will give you a good idea of whether or not they will be a good fit for your company.

Adam Preiser, WPCrafter