Interview Questions to Ask a Business Owner

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:

Origination of the business
Processes and challenges during the startup stage
Operations questions
Financial questions
Marketing questions
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)

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:

“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)

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.

  1. 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.

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

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.

  1. 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.