34 Interview Questions to Ask a Business Owner

  • Brandon Boushy by Brandon Boushy
  • 1 year ago
  • Blog
  • 0
A black tablet and a cup of coffee on a desk

On occasion, you’ll have opportunities to answer interview questions as a small business owner.

The interview questions will vary depending on what you are being interviewed about. Regardless of the type of interview, we’ll provide a list of questions to help you prepare your answers.

The list of questions typically falls into 6 categories including:

  1. Origination of the business
  2. Processes  and challenges during the startup stage
  3. Operations questions
  4. Financial questions
  5. Marketing questions
  6. Fun questions

We’ll start by discussing some of the different types of interviews you might have as a small business owner, then get into the questions. Keep reading to learn what questions you might have to answer as a business owner.

Types of interviews you might have with small business owners

Many business owners are happy to answer questions on a variety of subjects. Each business owner is different, so you should probably do a little research before contacting them.

The typical types of interviews that a small business owner might conduct include:

  • Hiring Interviews (H)
  • Subject Matter Expert Interviews (SME)
  • Business Investment Interviews (BI)
  • Company Profile Interviews (CP)

Once I get to the list of questions, I will use the letters (H, SME, BI, CP) to indicate which types of interviews the question is appropriate to include in the interview. Let’s discuss each of the 4 interviews.

Hiring Interviews (H)

An interview with a business owner

Hiring interview questions should primarily focus on the operations of the business. These would include questions about essential skills, responsibilities, company culture, and terms of employment.

As a job applicant, having a good list of questions to ask shows that you aren’t just looking for a job, you are interested in how the company’s goals align with your own.

As the business owner or hiring manager, you should be prepared to answer these questions honestly. One of the most challenging discussions will be about covid discussions when they come up.

Questions to ask business owners during covid

No one wants to talk about covid, but it’s important. Everyone wants to be somewhere they are valued, and there is a broad spectrum of mentalities on covid.

We don’t need to be political here, but is an employee going to like working at a place where they are the only one who takes Covid seriously?

During an interview there may be questions like:

  1. “What are your policies on PPE involving Covid?”


    2.  “If someone in the workplace is diagnosed with Covid, what should we expect to happen?”

I’ll warn you that businesses are adopting 3 positions on this:

  • Super cautious. (I have a friend that has been quarantined 8 times since Covid started due to potential exposure.)
  • Follow local recommendations (Most prevalent)
  • Blatantly disregarding the local recommendations ( I have another friend who has had 6 people out with “pneumonia” in the last month, and all continued working while sick.)

As a business owner, be honest. Tell them how you handle them and move on.

If you are the one potentially being hired and agree with the answer, show genuine agreement with the business owner. If you aren’t in agreement, it’s pretty easy to tell that you disagree. If you are complacent. Don’t ask about Covid. It’s a touchy subject.

Subject Matter Expert Interviews (SME)

When small business owners are interviewed as subject matter experts, the interview questions tend to focus on a specific subject matter.

For instance, when we interviewed Paul Akers we tended to focus on subjects involving lean manufacturing and business growth because he is a recognized subject matter expert.

Watch some of Paul’s interviews if you want some great info on lean practices and business growth.

 The questions in these interviews may span all 6 types of questions to ask a business owner, but make sure the questions are relevant to the subject.

For instance, a question about how much the company makes wouldn’t be necessary for an interview on improving employee quality of life.

Often you’ll see business owners or CEOs on TV answering interview questions about their industry or market share.

These types of interviews can be extremely beneficial by exposing your company to new customers who didn’t even know the business exists.

Business Investment Interviews (BI)

A lady interviewing a business owner

Good questions to ask small business owners when considering investing in them will be heavily focused on the business operations, financials, marketing, and strategy.

These are the aspects that drive success. As a business owner, make sure you are prepared for them.

Whether the interview is with a bank, a potential partnership, or family members who are considering investing in a small business, you should expect the questions to be heavily focused on whether the money will be invested in a profitable venture.

Before entering one of these interviews, you’d better already have a written business plan. You’ll need to make sure it is updated and you are comfortable discussing the plan in great detail.

If you don’t already have a business plan, check out our blog How to Write a Business Plan and follow the steps to create your own.

Company Profile Interviews (CP)

Company profile interviews are mostly focused on highlighting what the company is doing.

These interviews will be more focused on their services, products, operations, and what makes the company different from its competitors.

These types of interviews tend to be easy to answer questions to put the small business in the best light possible.

At UpFlip, we tend to include questions from all categories because it helps small business owners get a better understanding of how each industry works. Keep reading to find out more.

Many Business Owners Answer Questions About Their Inspiration

As a business owner, you can expect most interviews to ask questions about how you started your business.

You should expect these interview questions to come at the beginning of the interview because they are easy questions to help people get to know you.

Let’s look at some of the good interview questions to ask small business owners.

    3. What were you doing before you started (insert company name)? (SME, BI, CP)

This question is to get some background history. It is an opportunity to tell the story of your journey before starting your business.

Maybe you were in a related field, and maybe you weren’t. The most important part is to be honest and relatable.

I’m excited to hear about all the new businesses that started because people were laid off during the pandemic and used the time and generous unemployment to start their businesses.

If you are one of these people, reach out to us. We’d love to tell your story.

    4. How did you come up with the idea for (insert business name)? (H, SME, BI, CP)

Employees creating great ideas for business

This is normally going to be one of the first interview questions about the business.

The interviewer is looking for a moment where you can give some background about your history and connect with your potential customers, employees, or investors. Make the store interesting, but quick.

Here’s how I would answer it:

I had a lot of jobs before getting my engineering degree and MBA. I knew I loved learning and telling stories, so I decided to try my hand at business research and have been blogging ever since. I’ve been working for myself for 3x longer than I ever worked for an employer, and I love every minute of it.

It’s a quick answer but explains a ton about who I am and what I am about. Make sure to practice your responses so your interview is a success. Nothing is more embarrassing than getting stage fright because you weren’t prepared.

Business Formation  and Process Questions to Ask a Business Owner 

The business formation stage is the period when the business owner is in the process of turning an idea into a company.

Questions in this section should be around the business plan, selecting a business location, startup costs, funding resources, creating the product, selecting vendors, and computer systems.

Let’s look at good questions to ask entrepreneurs during the startup stage.

    5. Do you have a business plan? (BI, CP)

At Upflip, we ask every business owner this question to find out what guides their decision-making process. Some have a detailed business plan, while others track their achievements with a checklist.

Have your business plan ready if talking to investors.  Whether it’s a bank, family members, or a potential partnership, you need documentation.

Unless you are well known for your expertise in the market, small businesses need to prove they understand the industry before someone agrees to spend hard-earned money investing in you.

     6. Did you start the business as a sole proprietorship, corporation, or LLC? (BI, CP)

Most of the time, we won’t include this in our video interviews because the most common answer is an LLC. An LLC creates a separate entity that protects your assets. 

Knowing the answer can provide insight into approaches that people take to offering their services.

For instance, a corporation has much more stringent requirements than LLCs and sole proprietorships. Be prepared to explain why you went with the option you did if the answer is a different answer than an LLC.

    7. What were your startup costs? (SME, BI, CP)

Questions about startup costs should be included in most lists of interview questions for business owners.

It helps investors understand how much you have put into the business and helps others understand the cost of starting a business.

Be prepared to document where the money was spent when the interview questions are coming from a potential investor. 

Company profiles will typically include this question in a list of questions to ask.

   8. Follow-up Questions to ask entrepreneurs- Can you break down the costs for us?

An orange sticky note on a cork board

Upflip will normally ask for a breakdown of the startup costs when talking to business owners to provide our clients with reasonable expectations.

9. Another followup: How do government regulations and startup costs create a barrier to entry in your field?

A subject matter expert might have to answer questions like this when talking on TV or to government officials about the costs of government regulations. 

For instance, in Las Vegas, getting licensed across all 4 licensing districts in the area can be substantially more expensive than getting licensed in other places with only one licensing agency.

10. How did you fund your small business? (H, SME, BI, CP)

A business owner should be prepared to talk about funding a business in all types of interviews. How a business owner got the resources for a company can tell people a lot about their experience and the future of the company.

A business owner who started a company with an inheritance might not necessarily understand how much time it takes to accomplish their goals as the business owners who spend working hours at their other job performing the same work.

Investors are specifically interested in funding. Follow up questions to ask entrepreneurs include:

   11. Do you have other outstanding business debts? What are they?

   12. What will the funding you are requesting be used for?

During a hiring interview, I would not expect potential employees to ask this question unless there are sincere concerns about the viability of the company.

For instance, if you are asking employees to work for equity only, this question would be reasonable to ask a business owner.

If you are discussing this question as a subject matter expert, this is a great opportunity to discuss creative ways of funding a business.

13. What were some challenges you faced when creating your product? (SME, BI, CP)

For those who create a new product, you should be prepared to answer this question. It’s one of the questions that most people can’t answer.

Most people have never created a new product and don’t have an idea how to start.

If you faced a scenario where you had no idea where to start, make sure to honor that in your answers.

The readers or viewers will appreciate having an example of someone who went from clueless about how to accomplish their goal to a success story.

I found Jason Hernandez’s interview to be a great story about creating a product. Check it out below.

14. How do you select vendors for your companies? (H, SME, BI, CP)

While it is getting easier to find resources on vendors and services to simplify the hard work of starting a business, many people who have only worked for other companies aren’t familiar with the resources necessary to start a business.

Many products are purchased through distributors as opposed to the manufacturer.

If you have ever tried to provide services to a corporation or government, you’ll know that they have specific requirements for their service providers.

   15. Follow-up question: Once you’ve selected a vendor how do you verify they are performing up to those standards?

You can stand out as a small business by having similar standards for judging subcontractors.

If you have standards, make sure to show them to your interviewers, potential investors, and even clients if they ask about them.

Questions to ask entrepreneurs about equipment computer systems (SME, CP)

When considering interview questions for business owners, ask about the computers, equipment, and software they use to support their business.

Some of the questions to ask a business include:

   17. What software do you use to track your inventory and sales?

   18. What is the most profitable piece of equipment for your business?

   19. Where are the best places to buy equipment?

   20. What software can’t you live without?

These are some of the best equipment-related questions to ask entrepreneurs about their business. Keep reading for questions to ask a business owner about operations.

Operations questions to ask a company about their business

Operations are focused on issues like how many employees a company needs, how to identify top customers, how to differentiate yourself from competitors in the market, and how to divide responsibilities amongst the team.

Here are some of the top interview questions to ask entrepreneurs regarding managing their business.

   21. What does a normal day at your company look like? (H, CP)

Employees, take note! This is one of the best questions to ask a business owner before starting working for them.

This needs to be answered during the interview to make sure the company is a good fit for your life. It’s hard to find success with a company if you can’t work during the times they actually need you.

This question also helps people considering buying a business in the industry decide if it’s the right type of company for them. Check out our blog How to Buy a Business for more information on buying a business.

    22. How do you manage customer relationships? (H, BI, CP)

An iPad and some coloured pens on a desk

Asking about managing customer relationships is a great way to understand the small business owner.

Interview questions and answers about customer relationships help people get an idea of how the business interacts with customers.

If the business owner has a customer relationship management tool, then that can be used to monitor sales, profit margins, and what deals tend to appeal most to each customer.

Without that, each relationship is legitimately owned by the person as opposed to the company

If you want to sell your business in the future, make sure to get a CRM set up ASAP.

Salesforce and HubSpot are popular CRMs. It will help create value that can be passed on to the next owner when you decide to cash out of your business.

   23. How do you delegate tasks? (H, SME, CP)

Success is often a benefit that comes when you trust others to handle parts of the business you know less about. For example, people in their 20s are way better at social media marketing than someone in their 60s. 

Know what you are good at and delegate the rest.

Make sure to have a strategy for how to support customers and business processes.

As the business owner, be prepared to determine what drives the most value and focus on those activities.

Everyone can follow your sales processes if you provide them a good example of how to provide service for customers. Be prepared to answer questions on how you delegate. It can help people immensely.

Financial Questions to Ask the Owner of a Company (BI)

There are so many financial questions to discuss with the owner of a company that we created an entire blog on financial matters.

Get better prepared for financial questions by reading our blog Net Working Capital.

You’ll need to answer these questions mostly for investors. The questions will be ones like:

   24. What was last year’s net profit?

   25. What was the change in your cash flow last quarter?

   26. What was year-over-year sales growth?

   27. Do you have enough cash to continue operations and service additional debt?

To learn more about answering financial questions, check out Investopedia. They are one of my favorite financial resources.

Marketing Questions You Might Be Asked as a Business Owner

Marketing questions should be focused on how to find customers.

In recent years, the majority of marketing is focused on digital marketing because it operates as a closed-loop.

This means you can monitor the success at reaching customers and determine exactly which channel and marketing campaign generates the most profit.

   28. What social media channels get the best results?

   29. What are your favorite marketing tools to use?

   30. What percent of revenue do you spend on marketing?

   31. What unique marketing strategies do you use to drive results?

Fun Questions to ask Business Owners

A white notepad on a brown desk

As an interviewer, all questions don’t have to be serious. If you are interviewing a business owner, be prepared to ask some fun questions. Here’s some fun and insightful questions that are typically in interviews: 

    32.What are your favorite books?

    33.Who are your favorite entrepreneurs to follow? 

    34. What are some business opportunities today that you wish someone would tackle?

Just make sure your focus is on ethical questions to ask a business owner. You don’t want to ask them questions that would ruin their career.

As a business owner, if someone asks you a question that could cause problems, don’t take offense. Laugh it off and politely decline to answer.

Whether you are an interviewer, business owner, or just a curious person, the world offers so many opportunities to learn from other people. When you see someone offer a service you appreciate, let them know and ask yourself, “How can I apply this to my market?

Subscribe to our mailing list for more great articles and videos about how entrepreneurs like you find ways to make a profit doing what they love.

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