You can learn a lot from entrepreneurs. They can teach you how to overcome business failures, how to manage employees, how to implement your business idea, and so on. But what are the questions to ask an entrepreneur?
Engaging in conversations with entrepreneurs can be a valuable learning experience. They have the ability to guide you through handling failure, provide insights on employee management, and even share tips on revolutionizing industries, securing substantial funding, and developing innovative products.
However, it’s crucial to be well-prepared with thoughtful questions before meeting with an entrepreneur. To help you get started, consider using the following questions, which span topics like mentorship, finances, business strategies, and more.
33 Questions To Ask an Entrepreneur
Starting your own business and becoming an entrepreneur is a dream of many individuals. Asking questions to entrepreneurs will help you understand the downfalls of running and managing a business.
Having insights to all the insights of an entrepreneurship journey, makes it easier for you to start your business in no time. It helps you understand the personality traits of entrepreneurship, characteristics of being an entrepreneur, and what it takes to be an entrepreneur.
When you have the entrepreneurship mindset, and when you meet an entrepreneur, make sure that you ask the following questions. Here are 33 questions to ask an entrepreneur in order to understand the in and out of running a successful business.
33 questions to ask an entrepreneur:
1. How will I know if I need to move on from my business?
2. What’s the right structure for my business?
3. When should I make my first hire?
4. How do you find the right suppliers?
5. What numbers should I look at to measure my success?
6. When will I know if I need to raise funding?
7. How should I define success as an entrepreneur?
8. What’s the best piece of advice you’ve received?
9. How can I best support you?
10. What mistakes should I avoid?
11. How can I reach my goals?
12. What can I do to better my business?
13. Where do you get your information (such as news) from?
14. How do you reward yourself when you succeed?
15. How did you decide between becoming an entrepreneur and working for someone else?
16. What inspired you to become an entrepreneur?
17. Where do you see yourself in five years?
18. What would you tell other young aspiring entrepreneurs?
19. What’s the biggest challenge you face as a young entrepreneur?
20. How do you choose ideas to invest in?
21. What should I look for when finding someone to help with my finances?
22. What should I prioritize to set my business up for financial success?
23. How do I raise money?
24. How much money should I save for myself?
25. Where should I invest money earned through my business?
26. How much capital did you raise to start your business?
27. Tell me about a time you said “I’m done with this” and wanted to walk away.
28. Do you ever feel dumb or stupid?
29. What does your morning routine look like?
30. How do you balance your personal life with your career?
31. What’s your biggest achievement in life?
32. Would you change anything about your career?
33. What makes a bad entrepreneur?
1. How will I know if I need to move on from my business?
Entrepreneurs develop the skill of recognizing when it’s time to let go of an idea or business, especially considering the high failure rate of 90% for startups. You can learn valuable insights about identifying signs of a failing idea and understanding what steps to take when failure appears inevitable.
Asking entrepreneurs, “How will I know if I need to move on from my business?” is crucial because it taps into their experience and insights.
They’ve often faced the challenging decision of recognizing when to let go of an idea or venture. By posing this question, you open the door to valuable advice on identifying signs of a struggling business and understanding the indicators that suggest it might be time for a change.
Entrepreneurs can share their wisdom on navigating such pivotal moments, helping you make informed decisions about the future of your own business.
2. What’s the right structure for my business?
Businesses can adopt various structures based on factors such as ownership and industry. To gain valuable insights, conduct thorough research and seek out entrepreneurs within your specific industry who can provide their perspective.
Asking entrepreneurs, “What’s the right structure for my business?” is essential because it taps into their wealth of experience and expertise. Entrepreneurs have navigated the complexities of different business structures, considering factors like ownership, industry dynamics, and more.
By posing this question, you open the door to personalized advice, gaining insights on the most suitable business structure for your specific circumstances.
Entrepreneurs can share practical wisdom that goes beyond theoretical knowledge, helping you make informed decisions about the structure that aligns best with your business goals.
3. When should I make my first hire?
Entrusting significant tasks to an employee marks a significant milestone. An experienced entrepreneur can share insights into the decision-making process behind hiring their first employee, shedding light on aspects such as their financial situation and the specific responsibilities associated with the new role.
Asking entrepreneurs, “When should I make my first hire?” is crucial because it taps into their practical experience and decision-making insights. Entrepreneurs have faced the pivotal moment of bringing in their initial team members and can provide valuable guidance.
By posing this question, you open the door to receiving personalized advice on factors such as business growth, workload, and financial considerations that influence the timing of making that first crucial hire.
Entrepreneurs can share real-world experiences, helping you navigate the decision-making process and determine the right moment for expanding your team.
4. How do you find the right suppliers?
For those selling a physical product, the choice of a supplier holds immense importance and can significantly impact the success of your business.
Using inexpensive materials, for instance, might compromise the integrity of your product. Seek advice to distinguish between reliable and subpar suppliers, ensuring that your business is built on quality and trust.
5. What numbers should I look at to measure my success?
Determining success varies for each business; it could involve factors such as total revenue, net profit, or even market share. If you find yourself unsure about which metrics to prioritize as an entrepreneur, seek guidance from an experienced professional.
Asking a veteran entrepreneur what key indicators they focus on can provide valuable insights and help you navigate the path to success.
6. When will I know if I need to raise funding?
Nearly seven out of ten entrepreneurs use their personal funds to kickstart their ventures. However, as your business expands, the demand for capital increases.
Seeking advice from an entrepreneur well-versed in fundraising can guide you in the right direction to secure funds when the need arises.
7. How should I define success as an entrepreneur?
Entrepreneurs embark on business ventures for various reasons. Some seek to be their own boss, while others aspire to achieve financial success by making millions of dollars.
A reliable mentor can offer valuable guidance on how to define success according to your own aspirations and goals.
8. What’s the best piece of advice you’ve received?
Engaging your mentor with questions can provide invaluable insights into entrepreneurship. Discover the guidance that has shaped successful founders. What tips do they still hold dear to this day?
9. How can I best support you?
Approach your mentorship as a mutually beneficial relationship. Your mentor generously shares their experience and advice with you, but they might also anticipate learning something from you. Therefore, don’t hesitate to inquire about what you can offer in return.
10. What mistakes should I avoid?
No matter how hard you try, it’s challenging to anticipate every situation and risk. Consult your mentors to learn about common business pitfalls you should steer clear of.
11. How can I reach my goals?
At times, it’s easy to become overwhelmed by the big picture. Seeking advice from your mentor on what steps to take in the short term and long term to achieve your goals can provide tangible guidance towards realizing your dreams.
12. What can I do to better my business?
Share an overview of your venture with your mentor and inquire about areas for improvement. They might suggest refining your messaging, cutting down expenses in specific areas, and offering an objective opinion on your business plan.
13. Where do you get your information (such as news) from?
Entrepreneurs must stay informed about the world, encompassing business trends, news, and more. When talking to one, inquire about their sources of information. They might suggest new websites, blogs, podcasts, shows, newsletters, and more.
14. How do you reward yourself when you succeed?
Embarking on entrepreneurship is akin to running a marathon, so inquire with founders about how they sustain their motivation. They might choose to take a day off after reaching a significant milestone or indulge in a night out with friends.
15. How did you decide between becoming an entrepreneur and working for someone else?
Making the leap into entrepreneurship requires dedication. Inquire with entrepreneurs about how they arrived at that decision and the factors they took into consideration.
16. What inspired you to become an entrepreneur?
Some individuals may have established their business during the pandemic, while others might have launched a venture in their college dorms. Inquiring with young entrepreneurs about what inspired them can provide valuable insights into whether entrepreneurship is the right path for you.
17. Where do you see yourself in five years?
Inquiring with a young entrepreneur about where they see themselves can offer insights into their motivations and future goals. This, in turn, has the potential to inspire you to dream big.
18. What would you tell other young aspiring entrepreneurs?
Young founders can provide valuable insights into their recent challenges, lessons, and triumphs. Inquire about what advice they would offer to others in a similar situation. This can enhance your understanding of the current landscape of entrepreneurship.
Related: 39 best entrepreneur lessons
19. What’s the biggest challenge you face as a young entrepreneur?
The age of entrepreneurs can be a double-edged sword. On the positive side, it gives them time to learn from mistakes.
Conversely, it presents them with challenges specific to their age, such as investors perceiving them as naive or facing encouragement from family to pursue a regular job. Discover their significant challenges and the strategies they employ to overcome them.
20. How do you choose ideas to invest in?
Founders often encounter a barrage of ideas. Inquire about how they decide which ones to invest in. What criteria do they consider, and what does their decision-making process look like?
21. What should I look for when finding someone to help with my finances?
Many business owners choose to hire someone to oversee their finances and operations, but this decision demands meticulous planning and research.
Chase Spenst, a finance entrepreneur, provides the following advice: “Seek out someone who can handle bookkeeping and generate reports to keep you informed. Ideally, this individual should have prior experience running businesses. Look for someone with a natural curiosity.”
22. What should I prioritize to set my business up for financial success?
Businesses frequently face tight budgets with a multitude of needs. Learn how to prioritize; this could involve prioritizing the development of your product or hiring an accountant, for example.
23. How do I raise money?
Securing funds may involve seeking investors, utilizing crowdfunding, and exploring other avenues. Reflect on the level of ownership you wish to maintain, the amount of money required, and the urgency in raising it. Consulting with an experienced entrepreneur can guide you through the intricacies of this process.
24. How much money should I save for myself?
Numerous entrepreneurs reinvest all their profits back into their business. However, at some point, it becomes essential to allocate yourself a salary and relish the rewards of your hard work. Seek guidance from an entrepreneur to help find the right balance.
25. Where should I invest money earned through my business?
After accumulating some funds, deciding how to allocate them among different departments can be challenging. Seek advice on optimizing your cash, whether it’s by expanding operations or enhancing marketing efforts.
26. How much capital did you raise to start your business?
Posing this question provides insights into the initial expenditure you can anticipate. Armed with this information, you can then create a budget and plan accordingly, especially if they have details specific to your intended industry.
27. Tell me about a time you said “I’m done with this” and wanted to walk away.
Entrepreneurs experience burnout rapidly, be it due to a co-founder departing before launch or a marketing campaign stumbling. Founders frequently grapple with the desire to throw in the towel.
Discover the strategies that help them persevere, so you can combat feelings of defeat you might encounter in the future.
28. Do you ever feel dumb or stupid?
Even the most self-assured individuals make evident mistakes. This question encourages the interviewee to share less-than-stellar moments, which can serve as valuable learning experiences for you.
29. What does your morning routine look like?
Individuals who are highly productive are more inclined to stick to a consistent morning routine, and this holds true for entrepreneurs as well. While you may already have a routine in place, posing this question can spark inspiration for trying out new activities.
30. How do you balance your personal life with your career?
Business owners don’t adhere to the typical 9-to-5 schedule. It can be beneficial to understand how entrepreneurship influences your social life. Gain insights into how founders manage to strike a work-life balance, especially during hectic periods.
31. What’s your biggest achievement in life?
Thriving entrepreneurs, who have achieved milestones such as launching successful products or transforming an industry, likely boast a myriad of accomplishments.
However, what holds the utmost significance to them can differ. Posing this question can provide you with various perspectives on defining success in business.
32. Would you change anything about your career?
As an entrepreneur, you are bound to make numerous mistakes. By asking a more experienced professional what they would change in their careers, you can learn about potential pitfalls to avoid.
33. What makes a bad entrepreneur?
Let’s be honest: Success in entrepreneurship isn’t for everyone. This question helps you understand traits to steer clear of as you aspire to become a founder. You can heed their advice, recognize any negative characteristics in yourself, and then work on mitigating them with better habits.
Hey, I am Sachin Ramdurg. I run and manage futuredecider.com website that helps students, graduates, and professionals, to find and decide on their future career with ultimate future career advices and future career guides. I have an overall 12+ years of career guidance experience in multiple domains which has helped multiple students, graduates, and professionals to find the best career path for their future.