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

When you make your first hire, regardless of position, what is one question you should ask during the interview to determine if they are the right person to take on this new business with you? Because?

Hiring the first employee
Photo credit: Kindel Media / Pexels

These answers are provided by the Young Entrepreneur Council (YEC), an invitation-only organization made up 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. More information at

1. “What excites you about this role?”

This is a deceptively simple question. To answer this well, the candidate must 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 passion and excitement genuine The best answers are well-structured, enjoyable, and somewhat relatable.

– Greg Soh, RoadFlex

2. “What would you have done differently in your last position and why?”

The candidate’s answer to this question shows you their character when it comes to responsibility, humility and insight. If they can’t think of something, it shows a lack of understanding. If they deviate and are quick to blame, it shows a lack of responsibility. Humility is in how they give their answer.

– Givelle Lamano, Law Firm of Lamano

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?” Launching a new business requires constant pivoting and it takes a certain personality to navigate it effectively. The right candidate will be able to change direction quickly and often. If they can’t, they’re not suitable, and it’s best to know that in advance.

– 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 hire is someone who wants 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 haul.

– Pratik Chaskar, Spectra

business communication

5. ‘What are your most difficult communication challenges?’

Communication is everything, especially in a small team. There will be ups and downs and growing pains, but understanding how someone communicates is absolutely essential to growth and partnership. Even if you’re hiring someone with the intention of training them, you need to have clear lines of communication to grow together.

– Matthew Capala, Alphametica

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 figure out if the person is really interested in the position or just wants a job. This will help weed out candidates who aren’t a good fit and make it easier to focus on those who are.

– Kristin Kimberly Marquet, Marquet Media, LLC

7. ‘In which areas do you have experience?’

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 you make sure you’re hiring someone with different experience than your own. You don’t want to duplicate knowledge and skills at this point; you want to expand

– Jonathan Prichard,

8. ‘How do you face challenges at work?’

One question you should ask during the interview is, “How do you approach challenges at work?” This is an interesting question because the answer can reveal a lot about a person. It also gives them a chance to talk about real events in their previous job. You will learn a lot about the candidate and whether they have the necessary skills to overcome the difficulties.

– Blair Williams, MemberPress

Interview a new employee candidate

9. ‘Why should I hire you?’

A very important question 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 should look for answers that tell you what they can do for the company, not answers that only talk about their personal traits that make them a better fit.

– Thomas Griffin, OptinMonster

10. “What does a good work-life balance look like?”

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

– John Hall, Calendar

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

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

– Adam Preiser, WPCrafter

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