As a small business owner, you can’t afford to make the wrong decision when growing your small-but-powerful team. Short of mind-reading, knowing the right questions to ask when hiring someone is the best way to find a strong candidate whose work ethic and career goals align with your small business’s growth plans.

There are also critical follow-up questions to ask your potential hire’s references to get a better perspective on the candidate’s skills and personality. Furthermore, as an employer, there are some potentially discriminatory interview questions you should never ask. Use this guide to navigate the interview process and identify the perfect employee.

10 important questions you should ask prospective hires

As you conduct a first formal meeting with a candidate, your line of questioning should help establish their background, working credentials and what makes them a good fit for your role. You’ve probably been asked the same questions yourself in job interviews. The goal is to find out if someone has what it takes to be a self-motivated, responsible and engaged worker — from day one.

1. What do you know about our company?

Any small business can tell a candidate all about their products, services and market position. By asking them what they already know about, you can uncover whether they’re interested in working for your company specifically or just tossing around resumes. If they’ve researched your small business or have direct experience as a customer or other stakeholder, learning their perspective on your specific business can help you understand why they want to work with you.

2. Why are you leaving your current position?

People leave positions for many reasons, and small businesses need to be aware of what motivates potential employees. If you’re not in a position to compete with more prominent companies on salaries, but you have a culture that’s appealing to the right type of candidate, understanding an employee’s motivations can help build a solid connection for future success.

3. What makes you qualified for this position?

The candidate’s resume or cover letter should provide this information, but hearing them say it in their own words can give you additional insights. Contemporary job seekers put hours of work into their resumes, and they often fill them with keywords and flashy action verbs to attract attention and pass online resume review software. Hearing their qualifications firsthand can tell you how they view themselves in relation to the position, and it can help you determine to what degree they understand the role and its requirements.

4. What excites you about this position?

This is one of many questions in an interview that can elicit a stock answer, but it can also show you a lot about who your candidate is and what they’re hoping to get out of the position. Sometimes the way someone answers this question can be as important as what they say. If your candidate becomes visibly excited while discussing the position and has firm examples of what motivates them, you may have a great candidate on your hands. After all, as a small business owner, you want your employees to be as passionate about your company as you are.

5. How do you work best: alone or with a team?

Small businesses run the gamut between tight-knit teams and independent, unsupervised work. So, it’s important to know how your prospective hire will fare under different work circumstances. Their answer can inform where they’ll fit into your small business structure and help you as you make plans to integrate them into your operations. You can also look for clues about how adaptable they are to different working environments. For instance, just because they prefer to work independently doesn’t mean they’re opposed to working as a team.

6. What is a professional challenge you’ve overcome?

Learning about your candidate’s tough experiences can show how they’ll handle the types of unexpected events that can affect small business operations. It’s also a good gauge of the situations they consider a challenge and an opportunity to see if they have the skills and aptitude for your role. You already know the issues you face daily in your business; you can use their answers to evaluate how well candidates would handle those challenges when they arise.

7. What professional achievement are you most proud of?

Asking about on-the-job accomplishments is good for several reasons. You can learn whether your candidate is a “doer” (someone who just gets their job done at the bare minimum level) or an “achiever” (someone who goes above and beyond to improve their company). You can also see how they measure achievement and whether they exhibit traits like humility and honesty. Suppose their best achievement is boosting sales by 500% or helping a colleague tackle a demanding project. In that case, either answer shows a lot about who they are as a worker and how they see themselves professionally.

8. What would you like to improve about yourself professionally, and what’s your plan to accomplish that improvement?

Good team members are always ready to better themselves. Asking if they have a plan for self-improvement can show you whether they’re willing to look honestly at their professional growth. Even if their goals aren’t entirely on track, knowing they’re open to improving themselves can be reassuring for small business owners who want someone with growth potential.

9. What are your long-term professional goals?

An open-ended question like this can help you understand where they want to go and whether your small business will fit into those plans. Candidates who say they want to work their way into management can be attractive to small business owners looking to scale their business and need dedicated managers to make it happen. Candidates who say they want to become business owners themselves can also present opportunities for mentorships.

10. What questions do you have for us?

This is one of the most crucial questions a small business owner or hiring manager can ask. Asking what questions a candidate has at the end of an interview can help illustrate their thought process, how thorough they are in their overall interview preparation and what they consider important. It can also give you some immediate feedback about how to improve your hiring process by immediately addressing candidate concerns.

If your star candidate answered the questions above with flying colors, it’s time to move on to their professional references you asked for in the job application.

5 questions you should ask references before hiring someone

In addition to asking questions of your candidates, you may also want to consult their references to learn more about candidates’ work experience and professional demeanor. Use these questions to ask references when hiring someone to develop a clear picture of how they see the candidate professionally.

1. How would you describe your working relationship with the candidate?

This question is important to ensure the reference knows the candidate professionally. While personal references can be helpful, they often come from a candidate’s friends or family, who invariably paint a rosy picture of your potential employee. Asking a reference to detail their day-to-day working relationship will give you valuable information about the candidate and how they interact with others in a business setting.

2. What are the candidate’s strengths and weaknesses?

You’ve heard the candidate explain their pros and cons, but getting the scoop from another party can provide context to those answers and offer a different perspective on the candidate’s abilities. Information from an outside source can show a broader and more candid view of your potential employee and give you more insight into their personality.

3. How has the candidate grown in the time you’ve known them?

Asking a reference how a candidate has improved professionally can reveal how much your candidate grew as an employee or undertook more responsibilities throughout their previous job. Those responses can indicate whether the candidate has the skills and initiative to help your small business scale and grow.

4. Tell me about a time the candidate made you proud.

Whether you’re interviewing former coworkers or supervisors, this inquiry can elicit a wide range of responses. It’s also specific enough to draw out an instance in which the candidate excelled at their job, made good choices or solved a problem. The answer can give you a glimpse into what you can expect from the candidate when they’re at their best.

5. Would you hire or rehire this candidate?

This question often produces a simple “yes” or “no,” but it’s important to help validate the reference and how they view the candidate. A reference may be willing to speak kindly of their experiences with your potential employee, but whether or not they’d re-extend a job offer speaks volumes. That can give you a more holistic view that will help determine whether they’re the right addition to your team.

As an employer, you represent your small business. Thus, the interview is your chance to make a good impression on potential employees. To avoid putting yourself and your candidate into an uncomfortable situation, make sure to steer clear of the following questions.

5 questions you should never ask when hiring

While there are many informative questions, there are also some you should absolutely avoid during a job interview, however innocent or conversational they may seem. Not only can these questions quickly make for an awkward interview, but also they can run afoul of discrimination laws and lead to bias in the hiring process. Avoid these queries.

1. What do you like to do in your free time?

Sure, it’s innocuous chitchat, but it can evoke answers that could lead to professional or personal bias. If a candidate says they like to go to church, hang out at the bar or visit the shooting range, they could be expressing personal views that could ultimately put you as the potential employer in a tricky position. If you choose not to hire someone based on these frank answers, it could cause a discrimination complaint. As such, avoid questions about personal lives.

2. Do you have kids/partners/pets?

Asking about a candidate’s personal relationships can lead to discussions of protected information. As an interviewer, you must be careful not to imply you’re more or less likely to hire someone based on whether they’re single, have children or prefer cats over dogs. Though they may seem polite, these types of questions have no bearing on a professional job interview.

3. How do you feel about this political/social issue?

This is a bit more obvious in its potential for discrimination, as candidates’ political and social views are irrelevant to their ability to do the job. Steer clear of this line of questioning unless you are a small nonprofit or community organization that directly advocates for a particular cause, which might explain why the candidate is applying for the job in the first place.

4. Where are you from?

It might be acceptable to ask on a first date, but it’s inappropriate for a job interview. Even if the answer is, “I was born and raised two blocks from here,” it can lead to bias or discrimination. More obviously, if the candidate explains they were born in another country, this question can lead to potential discrimination based on national origin, a protected category.1 You can, however, ask if a person is legally allowed to work in the United States.

5. How old are you?

Inquiring about a candidate’s age can quickly get a potential employer in hot water. Age is also a protected category, and employers are prohibited from discriminating against applicants over age 40. Even asking what year someone graduated from school could fall into this category, so it’s important to phrase age-related questions carefully, no matter the context.

It’s also important to research what questions are unlawful to ask during an interview.

Protect your business throughout the hiring process and beyond

Asking the right questions throughout the hiring process can protect you from hiring the wrong person. Knowing which questions not to ask can protect you from a potential complaint of discrimination or bias. At the same time, it’s also important to protect your professional venture.

Professional liability insurance, also known as errors and omissions insurance, protects your small business from the impact of claims that you failed to provide your services appropriately, causing monetary or reputational damage to a client.

So, as you’re preparing your list of questions to ask potential new team members, think about how else you’re protecting your small business. Download the Thimble mobile app or click “get a quote” to choose coverage by the job, month or year. To receive your quote, answer a quick set of questions — even simpler than those you’re now prepared to ask interviewees.


  1. U.S. Equal Opportunity Employment Commission. Who is protected from employment discrimination?