questions to ask business owners

50+ Questions To Ask Business Owners? + Tips To Nail The Interview

There are many different types of questions you can ask business owners, such as those designed to break the ice, questions about the company’s operations, questions about the owner’s background and experiences, questions intended to evoke anecdotes, and questions intended to gauge the owner’s ability to take charge.

Let’s delve even further into the specifics of each of these categories!

Ice Breaker Questions

These are the questions that bridge the gap of unfamiliarity between the questioner and the business owner. These questions act as a medium to connect with the individual and spark a conversation that can build long-term relationships.

Often, people are unable to crack deals or simply get what they need due to the lack of confidence to interact with a stranger. The knowledge of topics that are of interest to both parties is a confidence booster.

Initiating a conversation with a business owner through these questions not only leads to prolonged discussions but also presents a sincere and wise image of the questioner to the business owner.

A few good ideas of such questions are:

  1. What inspired you to start your own business, and what was the biggest challenge you faced in getting started?
  2. What motivated you to choose this exact industry that you’re in?
  3. What has been the most rewarding experience you’ve had as a business owner, and why?
  4. What are the core values that guide your business, and how do you ensure they are reflected in everything you do?
  5. What are some of the most important skills you’ve developed as a business owner, and how have you honed them?
  6. What are your thoughts on the current state of the industry in which your business operates?
  7. What are some of the biggest mistakes you’ve made in your career, and what did you learn from them?
  8. Can you share a funny or interesting story related to your business or industry?
  9. I am interested in the industry you are working in. Would you like to share some details about your business?
  10. What’s your perspective about the real estate industry (or any other relevant business) these days?
  11. What do you think about digitalization and how has it affected your business?
  12. How do you motivate your team and maintain a positive company culture, and what do you look for when hiring new employees?
  13. What would you advise a person who wants to start a business in this domain?
  14. How do you balance your work and personal life, and what strategies do you use to manage your time effectively?
  15. What’s the topic that has interested you the most recently?

Asking out-of-context ice-breaking questions can result in a feeling of discomfort and indignation for the business owner. So you should remember that the questions you put up should be general and relevant to the person you’re dealing with.

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Personal Questions

Personal questions help in understanding people’s attributes and their situations better. Personal questions are mostly directed toward the person’s daily life and family.

While talking to an individual, most folks get so enraptured and intrigued that they forget the boundaries of their short-lived relationship. Hence, this can be termed as the phase of communication where most people falter reluctantly — make sure you don’t fall into this phase!

After engaging in some healthy ice-breaking activities, try tapping around in the person’s past, present, and future with casual questions; just keep in mind that people’s tolerance has decreased over time, so be careful not to offend them.

Keeping these aspects in consideration, you can ask such personal questions to a business owner:

  1. What is your favorite way to relax and unwind after a long day at work?
  2. How do you stay motivated and focused on your goals, especially during difficult times?
  3. What is the most important lesson you’ve learned in your personal life that has helped you succeed in business?
  4. How much did your family members and peers support starting your business?
  5. What do you prioritize more family or business?
  6. How do you manage stress and maintain a healthy work-life balance, and what advice would you give to others struggling with these issues?
  7. What do you consider to be your greatest personal achievement, and why?
  8. What are your hobbies and interests outside of work, and how do they contribute to your overall well-being?
  9. What are your future personal goals, and how do they relate to your business goals?
  10. What was your childhood like, and how has it shaped who you are today?
  11. How do you maintain your mental and emotional health, and what practices do you follow to stay centered and focused?
  12. What is the best advice you’ve ever received, and how has it influenced your personal and professional life?
  13. What motivates you to keep pushing forward and pursuing your goals, even when faced with setbacks or obstacles?
  14. How do you balance your personal values with the demands of running a business, and what steps do you take to ensure that your decisions align with your principles?
  15. What is something you’ve always wanted to learn or experience, but haven’t had the chance to yet?
  16. What is your biggest fear or challenge, and how do you cope with it?
  17. What is something about you that most people would be surprised to learn?

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Business Related Questions

Business-related questions are the most important and impactful tools for obtaining information from the answerer. They are usually raised on topics of mutual interest and have the least chance of getting skipped by the business owner.

As far as the scope of business-related interrogation is concerned, it depends on the closeness of the relationship built between the questioner and the answerer.

These questions should be inclined toward seeking insights from the individual’s experience. The focus of the conversation should be on knowing the benefits and losses incurred so that newcomers can be helped.

Some suggested business-related questions can be:

  1. What motivated you to start this business?
  2. What is your company’s main mission and values, and how they guide your workings and decision-making?
  3. What do you think is than stand out point of your business that sets you apart from your competitors?
  4. What are some of the biggest challenges you’ve faced in the past and how have you overcome them?
  5. How do you stay on top of industry trends and changes, and what strategies do you implement ensure that your business stays relevant and competitive?
  6. What role does tech play in your business, and how have you adapted to changes in the digital landscape?
  7. What are the digital marketing strategies you implement to proliferate your growth?
  8. How do you measure success in your business?
  9. Can you walk me through your decision-making process, and how do you ensure they align with your business goals?
  10. There’s risk and uncertainty in every business, how do you manage them in your business?
  11. Can you tell about a time when you had to make a difficult business decision, and how you tackle the situation?
  12. How do you foster a culture of innovation and creativity within your company?
  13. How do you plan to strengthen your customer service?
  14. What is your approach to team management, and how do you ensure that your employees are motivated and engaged in their work?
  15. How do you stay connected with your customers, and maintain strong relationships with them?
  16. Can you talk about a time when you had to pivot your business strategy, and what led to that decision?
  17. How do you plan to improve your pricing strategy in future?
  18. How do you ensure that your company remains financially sustainable?
  19. What are your growth plans for the future, and how do you plan to achieve it?
  20. How do you stay up-to-date on changes in laws and regulations that impact your business?
  21. Can you talk about a successful marketing campaign or initiative that your business has launched, and what made it successful?
  22. What advice would you give to someone who is starting a business in your industry/domain?
  23. How do you exactly balance short-term goals with long-term vision?

Business-related questions should be crisp and clear for the business owner to respond to conveniently. The interviewee should have a knack for obtaining valuable details from the entrepreneur they are talking to.

However, it is suggested to avoid questions pointing to critical subjects like information about clients, partnerships, income generated, scandals, etc.

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Leadership Based Questions

Leadership is the most valuable skill that is responsible for an organization’s success or failure. A business owner who has led a company through several ups and downs is the fittest person to guide people about ownership and risk-taking abilities.

Hence, such questions target particular instances that portray the strong will and grit of the individual.

Depending upon the business type, a few common questions that are based on the leadership qualities of business owners are:

  1. How do you define your leadership style?
  2. How did you manage the survival of your company during the COVID lockdown?
  3. Did you ever had a situation when you had to make a tough decision, and how did communicate that decision to your team?
  4. How do you build trust and rapport with your teammates, and how do you make sure that your team feels supported and valued?
  5. How do you approach a conflict and resolve it? And how do you manage disagreements or disputes within your team members?
  6. How do you motivate and inspire your employees?
  7. How do you foster a culture of accountability, responsibility, and ownership within your organization?
  8. How do you maintain a culture of innovation and experimentation within your organization?
  9. Can you discuss a time when you had to deal with a challenging team member, and how you addressed the situation?
  10. How do you handle feedback, both positive and negative?
  11. Can you tell us about a successful project or initiative that your team has undertaken, and what role you played in its success?
  12. How do you ensure that your team is aligned with your business goals?
  13. How do you deal with key employee exits and thereafter recruitments?
  14. What is your approach to professional development, and how do you encourage your teammates to learn and grow within their roles?
  15. How do you build relationships with key stakeholders, such as investors, clients, or partners?
  16. Can you talk about a time when you had to lead your team through a crisis or challenging situation?
  17. How do you prioritize your time and responsibilities as a leader?
  18. What factors do you consider when assigning tasks or responsibilities to your team?
  19. Can you discuss a time when you had to change or adapt your leadership style to better suit the needs of your team?
  20. What is that one piece of advice that you would give to someone who is stepping into a leadership role for the first time?
  21. Who is your mentor or role model who has influenced your leadership style, and what lessons you have learned from them?
  22. What strategies do you use to promote diversity and inclusion within your organization?
  23. How do you ensure the stability of the company during the downfall of growth and sales?

Leadership questions extract the best insights from an established entrepreneur’s journey for beginners who plan to make a living out of their business. These questions should be highly focused and followed by a series of relevant follow-ups.

This is necessary because often priceless information unavailable in books or on the internet gets revealed through the experience of the successful entrepreneur being interviewed.

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Anecdotal Questions

Anecdotal questions refer to news about the individual or their business in the market. They often point to rumors heard about the person or some trivial matters that sparked a fire among the people.

They offer mixed emotions of excitement, fun, hesitation, and discomfort when answered. At times, anecdotal questions become instrumental in fact-checks about the individual.

As every individual has their own story, questions belonging to this category are weird and depend upon the person being interviewed. They often act as triggers to make the individual give off hidden facts.

Some random examples of such questions are:

  1. Can you tell me about a moment when you first realized you wanted to start your own business?
  2. What’s been your biggest challenge in starting and growing your business?
  3. Can you share your funniest/ most memorable moment that happened while running your business?
  4. Have you ever had to make a tough decision that went against the grain, and how did you deal with it?
  5. What’s been your most significant accomplishment as a business owner?
  6. Can you talk about a mistake you made early on in your business and what you did you learn from it?
  7. How do you balance your work life and personal life?
  8. Can you tell me about a time when you had to pivot your business strategy, and what led to that decision?
  9. What has been your most significant investment in your business, and what returns have you seen from that investment?
  10. Have you ever faced significant competition in your industry, and how did you you make sure your business stood out?
  11. What’s been your biggest challenge in leading and managing your team?
  12. Can you share a story of a customer or client who had a significant impact on your business? (can be a negative/positive impact)
  13. What’s been your biggest risk as a business owner, and how did you decide whether or not that risk was worth it?
  14. Can you talk about a time when you had to rebrand or refresh your business/brand?
  15. How do you stay up-to-date on the latest trends and tech in your industry?
  16. Do you have any plans of acquiring another company?
  17. Can you share a story of a failure or setback that you experienced in your business, and how you bounced back from it?
  18. What’s been your most significant investment in marketing and advertising?
  19. What metrics do you use to evaluate the progress and success in your business?
  20. Can you talk about a moment when you felt especially proud of your business and your team?

These are case-specific questions that can cause both rage and pleasure but definitely surprise the answerer. Hence, the questioner must ensure that the timing of such questions is perfect.

There should have been enough conversation before raising such topics. The business owner should be ready to face these bullets as they might cause agitation and heat up the conversation.

6 Tips To Nail The Interview

Once done with the important frontline questions, it becomes unavoidable to include a few backup ones. This set of queries helps in maintaining the flow of the interview.

Not only do they intrigue the guest but also provide detailed information on the related topic to the audience.

Ask Follow-Up Questions

Asking follow-up questions is a compulsory ritual followed by all meticulous interviewers. Not only does this activity show interest and eagerness to learn from the individual’s work but also unfolds the hidden segments of the business’s journey to date.

These questions are related to the previously discussed topics and aim at getting more details about a given subject. Guests answer these questions with great attention in order to leave no room for further explanation.

An example could be, initiating a conversation with a fundamental question like — “Why did you not expand your business overseas?”

Post the interviewee’s answer, if required more details can be dug out by asking follow-up questions like — ”Do you have business plans to move overseas if the situation improves in the future?” & “Why have you not been able to eradicate the obstacles that have not let you expand?”

Such precise and proper follow-ups during interviews reveal information at times that are not available in the press releases of the companies or in case studies. Hence, they help in obtaining exclusive information on unexplored topics.

Don’t Ask ‘Yes/No’ Questions

When the motive is to fetch details, objective questions cannot be a part of the questionnaire. Questions requiring single words or one-liners as responses not just provide insufficient information but also result in the breakage of the conversation.

For instance, questions related to figures like:

  1. How many employees work in your organization?
  2. How long have you been in the industry?
  3. How much profit has the company made in the current year?

Also, questions related to the agreement on a subject:

  1. Do you have plans for expansion?
  2. Do you provide regular hikes to the employees?
  3. Do you incorporate CSR activities in your annual calendar?

One should abstain from asking such questions or if needed include them in the closing phase of the conversation.

Don’t Be Vague, Be Direct and Polite

Vagueness in any conversation results in confusion and complexity. It is the cause of numerous issues like unintelligibility, ignorance, unsuitability, and mistrust. Incomprehensible questions are usually skipped or answered casually.

While interviewing an individual, if the questions are not clearly understood by the answerer there are very few chances of the interview being successful. Unclear questions will lead to mistaken interpretations and finally result in wrong answers.

On the other hand, clarity in questions boosts the answerer’s confidence and increases the chances of getting exactly what is needed.

During business interviews, the interviewee looks for publicity for his/her brand and defends it on all fronts. Hence, it is mandatory to ensure that all questions are to the point so that the best answers can be received.

Always Warm Up A Guest By Asking Icebreakers

Guests appearing for an interview resemble tender coconuts that have to be conditioned properly before we reap their benefits. Like exercises, warm-up is also necessary before appearing for interviews.

Warm-ups before interviews help in getting familiar with the agenda and preparing accordingly. It is like a rehearsal before a grand performance.

Icebreakers initiate a conversation and set up the foundation for high-end needs like formal get-togethers, business dealings, and even impromptu discussions. They are a medium for winning the guests’ confidence and making them comfortable for a healthy conversation to be followed.

Don’t Get Too Personal

Interviews often go haywire when the conversation crosses the boundaries of professionalism and hurts the integrity of the person or his/her organization.

In the heed to achieve colorful and piquant information from the business owner, questions violating the privacy of the individual or the organization are asked. This should not be the case with sincere interviewers who abide by the norms of disciplined operations.

People refrain from answering tough questions related to their families or dark past even if they are directly connected with the subject matter.

Hence, proper cognizance of the topics to be discussed should be maintained and thorough revisions of the questionnaire should be performed to ensure foolproof operations.

Be Confident

Confidence is the key to performing with the highest capabilities. Any task performed with low confidence is probable to fail due to a lack of firm belief in the work done.

Conversations with dignitaries who have boundless experience in their fields are often solicitous and tricky to handle. Being confident while putting up questions to these veterans, supports an overall comfortable conversation.

Once the individual sees the determination in the eyes of the questioner, they feel liable to answer responsibly and to the best of their ability. The questions are taken seriously and answers are given thoughtfully.


Q1. What is the best question to ask a CEO?

A CEO is the topmost official in a company’s management structure. Hence, interviewing a person of that designation opens the doors to unlimited and unmatchable insights about the company.

Interviewers should make the most of that opportunity and ask important questions that intrigue them the most about that person or the company.

An example could be: “What are the principles you follow at work that have led you in executing successful business operations?”

Q2. How do you interview a business owner?

Indeed recommends carrying out the interview of a business owner in the most professional and convenient manner.

Beginning with a proper warm-up through ice-breaking questions, followed by multi-channel interrogation via categories of questions like personal, business-related, anecdotal, future prospects, etc.

The right questions will create a smooth flow in the conversation that reassures the business owner and eases your task too!

Maintaining professionalism while digging deep into the event timeline of a business is a compulsory requirement. Emphasis should be on learning from the experiences of the individual and showcasing them to the public in an elaborate fashion.

Q3. What are the 4 basic business questions?

According to American Express, business owners need to be asked the most elementary questions for gaining complete knowledge and tips about running a successful business.
1. Here are some of the best questions to ask:
2. Which market does the business serve?
3. What do you look for in job candidates for being potential employees?
4. What is the revenue or turnover of the business?
5. What is the success story of your venture?

There can be a pile of questions to serve this purpose viz-a-viz, questions about the launch of the venture, the biggest challenges faced, the business expenses, the target customer base, the revenue generated, and the future business plans.

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