400 Interview Questions to Ask Business Owners

Want to get inside the mind of a business owner? The right questions can unlock a world of wisdom, tips, and real-life stories.

Whether it’s about daily routines, long-term goals, or the struggles they face, asking thoughtful questions can give you a front-row seat to their world. Get your notepad ready because we’ve got the ultimate list of questions that’ll help you uncover the secrets to their success! 

About Their Marketing Strategies

  1. Can you describe your business in a few sentences?
  2. Who are your main customers?
  3. What makes your product or service special?
  4. How do you currently advertise your business?
  5. How much do you spend on marketing each month?
  6. What social media platforms do you use? Why?
  7. Do you have a website? What’s its main goal?
  8. Do you use email marketing? How often do you send emails?
  9. What’s been your most successful marketing campaign?
  10. Have you ever had a marketing campaign that didn’t work out? Why?
  11. Do you work with influencers or bloggers?
  12. How important is word-of-mouth for your business?
  13. Do you offer any special deals or discounts?
  14. Do you have a loyalty program for repeat customers?
  15. How do you keep track of your marketing results?
  16. Do you use online ads like Google Ads or Facebook Ads?
  17. How do you decide where to place ads?
  18. How do you get new ideas for your marketing?
  19. Do you have a marketing team or do you do it yourself?
  20. Do you have a marketing budget? How did you decide on the amount?
  21. How do you make sure your marketing message is clear?
  22. What’s the main thing you want people to know about your business?
  23. Do you attend trade shows or networking events?
  24. How do you handle negative reviews or feedback?
  25. Do you ever work with other businesses to cross-promote?
  26. What marketing tools or software do you use?
  27. How do you find the right keywords for your business?
  28. Do you ever use print materials like flyers or brochures?
  29. How do you choose images or videos for your marketing?
  30. How often do you update your marketing strategy?
  31. Do you have an app? What does it do?
  32. How do you keep your customers coming back?
  33. Do you use SMS (text) marketing?
  34. How do you make your marketing more personal?
  35. What are your future marketing plans?
  36. How did you get your first customers?
  37. How do you handle competition in your market?
  38. Do you have any marketing tips for new business owners?
  39. What’s one marketing trend you’re excited about?
  40. Is there anything you wish you knew about marketing when you first started?

About the Challenges They Face

  1. What was the biggest obstacle you faced when starting your business?
  2. How do you handle cash flow issues?
  3. What’s your biggest day-to-day challenge?
  4. How do you find and keep good employees?
  5. Have you ever had to let someone go? How did you handle it?
  6. How do you balance work and personal life?
  7. What do you do when a product or service isn’t selling well?
  8. How do you deal with difficult customers?
  9. Have you ever faced any legal challenges?
  10. How do you make tough business decisions?
  11. What’s the hardest part about managing a team?
  12. Do you face any challenges with suppliers or vendors?
  13. How do you keep up with changes in your industry?
  14. How do you handle stress or burnout?
  15. What keeps you up at night?
  16. Have you ever had to pivot your business model?
  17. Have you faced any challenges with technology or software?
  18. How do you handle seasonal fluctuations in business?
  19. How do you stay motivated when things get tough?
  20. What’s your plan if your business faces a crisis?
  21. Do you have trouble getting loans or funding?
  22. How do you make sure your business stays relevant?
  23. What kind of insurance challenges do you face?
  24. How do you manage your time effectively?
  25. Do you face any challenges in customer retention?
  26. How do you tackle quality control issues?
  27. Have you ever had issues with business partners?
  28. Do you face any challenges in expanding your business?
  29. How do you compete with bigger companies?
  30. What are some challenges you face in your local market?
  31. How do you deal with unexpected costs or expenses?
  32. How do you maintain a positive work environment?
  33. Have you faced any challenges in keeping up with regulations?
  34. How do you approach training and development for your staff?
  35. Do you have challenges with inventory management?
  36. How do you ensure data security and privacy?
  37. What’s the hardest thing about being a business owner?
  38. How do you handle changes in consumer behavior?
  39. Do you face challenges in international markets?
  40. What would you do differently if you could start your business again?

About Starting Their Business

  1. What inspired you to start your business?
  2. Did you start alone or with a team?
  3. How did you come up with the name for your business?
  4. What was the first step you took to start your business?
  5. How long did it take to go from an idea to actually opening?
  6. Did you need a lot of money to start? How did you get it?
  7. Did you write a business plan?
  8. What kind of research did you do before starting?
  9. Did you have any mentors or advisors?
  10. What was the first product or service you offered?
  11. How did you decide on the location for your business?
  12. What was the biggest surprise you encountered when starting?
  13. Did you quit a job to start your business?
  14. How did you make your first sale?
  15. What was the most helpful piece of advice you received?
  16. Did you face any setbacks or failures early on?
  17. What legal steps did you have to take to start?
  18. How did you decide on pricing for your products or services?
  19. What’s the main thing you wish you knew before starting?
  20. How did you get your first customers?
  21. Did you build a website yourself or hire someone?
  22. How did you decide what to focus on first?
  23. What tools or software were crucial in starting your business?
  24. Did you have any initial partnerships that helped?
  25. Did you have experience in your industry before starting?
  26. How important was networking when you started?
  27. Did you face any family or personal challenges when starting?
  28. How did you choose your business structure (like LLC, corporation)?
  29. Did you get any grants or awards?
  30. How did you build your initial team?
  31. How did you know it was the right time to start your business?
  32. What scared you the most about starting?
  33. Did you start with a storefront or go online first?
  34. How did you handle early criticism or doubt?
  35. Did you have to learn any new skills?
  36. How did you come up with your logo and branding?
  37. Did you take any courses or read any books that helped?
  38. What role did social media play in starting your business?
  39. Did you use any crowdfunding or get any investors?
  40. What are the top 3 lessons you’ve learned since starting?

About Their Company Culture

  1. How would you describe your company culture in three words?
  2. What values are most important to your business?
  3. How do you make new employees feel welcome?
  4. Do you have any team-building activities or events?
  5. Is there room for employees to grow and move up in the company?
  6. How do you handle conflicts between team members?
  7. What role does diversity play in your company?
  8. How does your company give back to the community?
  9. What’s the most popular perk or benefit you offer to employees?
  10. How often do you have team meetings?
  11. How do you encourage creativity among your team?
  12. Is your company more like a family or like a sports team?
  13. How do you handle work-life balance for your employees?
  14. How do you celebrate wins or achievements?
  15. How do you help employees who are struggling?
  16. What skills do you value the most in your team members?
  17. Do employees have flexibility in choosing work hours or locations?
  18. How does your company handle stress and burnout?
  19. What’s one thing you’re doing to improve employee well-being?
  20. How open are you to feedback from your team?
  21. Do you have any office traditions?
  22. How do you ensure effective communication among team members?
  23. What qualities do you look for when hiring new people?
  24. How do you keep remote employees engaged?
  25. Do you have a dress code? Why or why not?
  26. How do you handle employee training and development?
  27. What role does leadership play in your company culture?
  28. How does your company handle mistakes or failures?
  29. What’s the most unique thing about your company culture?
  30. Do you have regular performance reviews?
  31. How do you keep morale high?
  32. How involved are employees in decision-making?
  33. Do you have a mission statement?
  34. How does your company stay up-to-date with industry trends?
  35. How do you measure employee satisfaction?
  36. How important is transparency in your company?
  37. How do you recognize and reward hard work?
  38. Do employees have the opportunity to work on personal projects?
  39. What’s the average length of employment for your team?
  40. If your company were a person, how would you describe its personality?

About Their Daily Routine

  1. How do you start your day?
  2. What’s the first thing you do when you get to work?
  3. Do you have a set schedule or is every day different?
  4. What time do you usually start work?
  5. How do you prioritize your tasks for the day?
  6. Do you use any tools or apps to manage your time?
  7. What’s the most important part of your day?
  8. Do you have a morning routine?
  9. How much time do you spend on emails?
  10. What’s a task you do every single day?
  11. How do you handle interruptions?
  12. Do you take regular breaks? What do you do during them?
  13. How do you keep your energy up throughout the day?
  14. What time do you usually finish work?
  15. Do you have an evening routine to wind down?
  16. What’s the last thing you do before leaving work?
  17. Do you work on weekends?
  18. How do you manage work-related stress daily?
  19. Do you have any daily rituals that help you focus?
  20. How do you balance daily tasks with long-term projects?
  21. How much time do you spend in meetings each day?
  22. Do you eat lunch at your desk or take a break?
  23. How do you handle urgent issues that come up?
  24. What’s one task you wish you could eliminate from your day?
  25. How much time do you spend with your team each day?
  26. How do you stay updated with industry news?
  27. Do you exercise or do any physical activity during the day?
  28. How often do you check social media?
  29. Do you have a daily goal or target?
  30. How do you stay in touch with customers or clients daily?
  31. Do you have any daily habits that have contributed to your success?
  32. How do you manage distractions?
  33. Do you have a set time for brainstorming or creative thinking?
  34. How often do you check in on your business finances?
  35. Do you have a daily checklist?
  36. What’s your go-to productivity hack?
  37. Do you listen to music or podcasts while working?
  38. How do you make time for family and personal life?
  39. What’s one thing you never skip in your daily routine?
  40. Do you have a “shutdown” ritual to end your workday?

About Customer Service

  1. How do you make sure customers are happy?
  2. What’s your strategy for handling customer complaints?
  3. Do you have a customer service team? How big is it?
  4. How do you train your staff in customer service?
  5. Do you use any special software to manage customer service?
  6. How quickly do you aim to answer customer questions?
  7. What’s the most common question customers ask?
  8. Do you ask for customer feedback? How?
  9. How do you deal with an unhappy customer?
  10. What do you think sets your customer service apart?
  11. Do you have a return or refund policy?
  12. How do you measure customer satisfaction?
  13. Do you have any loyalty programs for customers?
  14. How do you make online customer service personal?
  15. What’s the toughest customer service situation you’ve faced?
  16. Do you have different strategies for online and in-store customer service?
  17. How do you stay updated with customer service trends?
  18. Do you offer customer service on social media?
  19. How do you handle a customer who’s wrong?
  20. What’s the biggest challenge in providing excellent customer service?
  21. Do you follow up with customers after they make a purchase?
  22. How do you handle long wait times or queues?
  23. Do you have a script for customer service calls?
  24. How do you maintain good service during busy times?
  25. Do you offer self-service options for customers?
  26. How do you make sure customer data is safe?
  27. Do you offer any guarantees or warranties?
  28. How do you decide to update or change customer service policies?
  29. How important are customer reviews to your business?
  30. Do you have any rewards for employees who excel in customer service?
  31. How do you keep your customer service team motivated?
  32. Do you outsource any customer service tasks?
  33. How do you adapt customer service for different cultures or languages?
  34. Do you have a system for tracking customer interactions?
  35. How do you deal with difficult or aggressive customers?
  36. Do you have any partnerships that help with customer service?
  37. How do you manage customer expectations?
  38. What’s your approach to after-sales service?
  39. Do you ever exceed customer expectations on purpose?
  40. Can you share a story of turning a dissatisfied customer into a loyal one?

About Their Long-Term Goals

  1. What’s your big dream for your business?
  2. Where do you see your company in 5 years?
  3. Do you plan to expand to new locations?
  4. Are you thinking of diversifying your products or services?
  5. How do you plan to stay ahead of the competition?
  6. Do you have a roadmap for your business?
  7. What milestones do you want to hit in the next few years?
  8. Are you considering going public or getting acquired?
  9. Do you have a succession plan in place?
  10. How do you plan to increase revenue?
  11. Are you looking to enter new markets or industries?
  12. Do you aim to be a leader in your industry? How?
  13. What kind of partnerships are you looking to build?
  14. How do you plan to improve your customer experience long-term?
  15. Are there any big changes coming up that customers should know about?
  16. What’s the biggest goal you’re working toward right now?
  17. Do you have any plans for social responsibility or giving back?
  18. Are you planning to hire a lot more people?
  19. How are you investing in technology for the future?
  20. Do you plan to change your business model?
  21. How do you plan to grow your brand?
  22. What’s your plan for staying relevant as trends change?
  23. Do you have goals for company culture?
  24. Are you looking to get more funding or investors?
  25. How will you adapt to future changes in your industry?
  26. What’s the most important thing you need to achieve long-term success?
  27. Are you considering any mergers or acquisitions?
  28. How are you planning for economic uncertainties?
  29. Do you plan to launch any major marketing campaigns?
  30. What’s your long-term strategy for employee training and development?
  31. Are you planning any big collaborations?
  32. Do you aim for international growth?
  33. What kind of legacy do you want to leave?
  34. Are you planning to update your infrastructure?
  35. What are your environmental sustainability goals?
  36. Do you have a contingency plan for crises?
  37. How do you plan to manage growth responsibly?
  38. What’s your exit strategy, if you have one?
  39. How often do you revisit and update your long-term goals?
  40. What would achieving your long-term goals mean for you personally?

About How They Handle Employees

  1. How do you find the right people to hire?
  2. What do you look for in a job interview?
  3. How do you onboard new employees?
  4. How do you handle employee conflicts?
  5. Do you have any programs for employee development?
  6. How do you handle poor performance?
  7. How often do you check in with your team?
  8. Do you have an open-door policy?
  9. How do you motivate your employees?
  10. What’s your approach to remote work?
  11. How do you manage a diverse team?
  12. How do you handle time-off requests?
  13. What do you do to make sure everyone feels included?
  14. How do you delegate tasks?
  15. How do you keep your team updated on company news?
  16. Do you do performance reviews? How often?
  17. How do you handle resignations?
  18. Do you have any team outings or events?
  19. How do you approach work-life balance for your team?
  20. Do you encourage employees to speak up?
  21. How do you manage a team during busy periods?
  22. How do you handle employee benefits?
  23. Do you have a policy for side gigs or freelancing?
  24. How do you support employee mental health?
  25. What’s your strategy for team communication?
  26. Do you offer opportunities for skill development?
  27. How do you make tough decisions that affect your team?
  28. What’s your policy on remote work?
  29. How do you make sure your team is aligned with company goals?
  30. Do you offer any incentives like bonuses or profit sharing?
  31. How do you approach internal promotions?
  32. Do you have any employee recognition programs?
  33. How do you create a sense of team unity?
  34. What’s your policy on using personal devices at work?
  35. How do you ensure workplace safety?
  36. Do you have guidelines for professional conduct?
  37. How do you handle disputes between employees?
  38. Do you do team-building exercises? What kind?
  39. What steps do you take to retain good employees?
  40. How do you ensure that your team is happy at work?

About How They Adapt to Change

  1. How do you handle unexpected changes in your industry?
  2. What’s the biggest change your business has gone through?
  3. How do you keep up with new trends?
  4. Have you ever had to pivot your business model? How did it go?
  5. How do you prepare your team for changes?
  6. What’s your approach to adopting new technology?
  7. How do you deal with changes in customer behavior?
  8. How flexible is your business strategy?
  9. How do you manage risk when things change?
  10. How do you decide it’s time for a change in direction?
  11. Have you had to deal with big changes in your team? How did you handle it?
  12. How do you communicate changes to your customers?
  13. How do you keep your business agile?
  14. What was a change that turned out to be a blessing in disguise?
  15. How do you evaluate the success of a change?
  16. Do you consult your team when making big changes?
  17. How do you stay ahead of competitors when things change?
  18. How important is it for your company to be adaptable?
  19. How do you balance sticking to a plan versus adapting?
  20. What’s a change you resisted but had to accept? What did you learn?
  21. How do you adapt your marketing strategies?
  22. How do you manage financial shifts or challenges?
  23. Have you ever had to change suppliers or vendors? How did you adapt?
  24. What’s your approach to changing regulations or laws?
  25. How do you handle changes in leadership roles?
  26. Have you ever had to adapt to cultural changes in your team or customer base?
  27. How do you deal with seasonal changes in your business?
  28. How quickly can you implement changes if needed?
  29. How do you make sure changes are effective?
  30. How do you involve customers in changes to your products or services?
  31. How do you adapt to negative feedback?
  32. Have you had to change your pricing strategy? How did you do it?
  33. How do you update your skills to adapt to changes?
  34. Have you ever had to change your target audience?
  35. How do you handle it when a project isn’t going as planned?
  36. What’s your approach to economic fluctuations?
  37. Have you ever had to scrap a project or idea completely?
  38. How do you stay calm during periods of change?
  39. Do you have a contingency plan for emergencies?
  40. What advice do you have for other businesses about adapting to change?

About Their Personal Work-Life Balance

  1. How do you manage your time between work and personal life?
  2. What’s a typical day like for you?
  3. Do you have set work hours?
  4. How often do you take breaks or vacations?
  5. How do you handle stress?
  6. Do you work on weekends? Why or why not?
  7. How do you make time for family and friends?
  8. Do you have any hobbies you like to do to unwind?
  9. How do you keep yourself healthy?
  10. How do you separate work time from personal time?
  11. Do you have a morning routine? What is it?
  12. What time do you usually stop working for the day?
  13. Do you work from home? How do you manage distractions?
  14. How do you handle work-related calls or emails during off-hours?
  15. What do you do to relax after a tough day at work?
  16. How much sleep do you aim to get each night?
  17. Do you have any tips for maintaining a work-life balance?
  18. How do you keep work from affecting your mood at home?
  19. Do you have a specific place where you like to work?
  20. How do you prioritize tasks between work and home?
  21. Do you use any tools or apps to manage your time?
  22. How do you recharge your energy?
  23. Have you ever felt burnt out? How did you handle it?
  24. Do you schedule personal time just like work tasks?
  25. How do you make sure you’re not always thinking about work?
  26. What’s the hardest part about balancing work and life?
  27. Do you have a mentor or coach for work-life balance?
  28. How do you handle urgent work issues during personal time?
  29. How important is time off for you?
  30. Do you like to travel? Does it help you balance work and life?
  31. Do you have any work-life balance goals?
  32. How has your approach to work-life balance changed over time?
  33. Do you ever take mental health days?
  34. How do you handle work when you’re not feeling your best?
  35. Do you ever work on vacations?
  36. How do you balance your role in the business with other roles in your life?
  37. What sacrifices have you had to make for your business?
  38. Do you feel like you have a good work-life balance right now?
  39. What would you change about your current work-life balance if you could?
  40. Any advice for others struggling with work-life balance?

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Bea is an editor and writer with a passion for literature and self-improvement. Her ability to combine these two interests enables her to write informative and thought-provoking articles that positively impact society. She enjoys reading stories and listening to music in her spare time.