121 Questions You Must Ask Yourself As a Startup Entrepreneur

The startup level of any business is one of the most complex and, at the same time, most exciting levels in a business life cycle. What questions to ask startup entrepreneurs? Are there answers to questions for startups that will produce successful entrepreneurs? Will this startup succeed or fail?

Everything that you will build at this level will reflect the strengths and durability of the foundations of your startup.

Here, I want to share 121 questions that startup entrepreneurs must answer.

What Kind of Person Makes a Successful Entrepreneur?

A unique mix of personal qualities, skills, and experiences often characterizes a successful entrepreneur. Many different kinds of research try to find factors that will influence the success of entrepreneurs. One such research we conducted several years ago, and you can read more about that in the 15 critical entrepreneurial success factors to skyrocket your business.

Here are some other characteristics and factors that are commonly seen in successful entrepreneurs:

Passion

This is often the driving force behind successful entrepreneurs. They have an intense passion for their work or idea, which fuels their motivation and determination to overcome challenges. Without a passion for what you want to start or do, you can not expect to achieve success.

The excitement and enthusiasm from being passionate about your startup idea can keep you going even when things get tough. Startups often face numerous obstacles, including financial constraints, competition, and market uncertainties. In such situations, your passion keeps you motivated to push through.

For example, consider the story of Elon Musk, founder of SpaceX and Tesla, among other companies. His passion for sustainable energy and space exploration has driven him to overcome countless obstacles. Despite numerous setbacks, including multiple rocket failures at SpaceX, Musk’s passion has kept him going. Today, both companies are leaders in their respective industries, a testament to the power of passion.

Resilience

The road to entrepreneurial success often faces obstacles and setbacks. Entrepreneurs must have the resilience to keep going even when things get tough.

Resilience, often defined as the ability to recover quickly from difficulties or adapt well in the face of trouble, is a vital attribute for startup entrepreneurs. Given the dynamic and challenging nature of the startup ecosystem, resilience can be the difference between failure and success.

Remember that startups operate in an environment filled with uncertainties. Market trends can change rapidly, new competitors may emerge, and unforeseen challenges can occur anytime. Resilient entrepreneurs can maintain calm under such unpredictability, swiftly adapt to changes, and persistently follow their goals.

Also, failure is a common part of the entrepreneurial journey. Whether it’s a product or service that doesn’t resonate with customers, a failed funding round, or a fundamental employee departure, setbacks are unavoidable. Resilient entrepreneurs view these failures not as a dead end but as learning opportunities. They analyze what went wrong, learn from their mistakes, and use this knowledge to improve their strategies and operations.

Related: Everything You Need to Know About Financial Risk

Innovation

Entrepreneurship is all about innovation. As an entrepreneur, you constantly look for new ways to improve your products or services and are unafraid to take risks to make your ideas a reality.

Innovation provides you with a competitive advantage and differentiates you from your competitors. For instance, Uber disrupted the traditional taxi industry by innovating a new business model based on a ride-sharing app.

If you continuously innovate, startups can develop products or services that better solve customer problems, enhance user experience, and, thus, build stronger customer relationships.

Flexibility

The business world is constantly changing, and successful entrepreneurs know how to adapt. They’re able to pivot their business strategies as needed to stay competitive.

For startups, having the flexibility to adapt to changes is essential. It allows you to seize new opportunities or mitigate potential threats. For example, consider how many businesses quickly adapted to remote work during the COVID-19 pandemic.

Or, consider the case of Netflix. When they started, they were a DVD rental service. However, they saw the trend of increasing internet speeds and the potential of streaming technology, so they pivoted. Today, Netflix is one of the largest streaming services globally, demonstrating how flexibility can lead to extraordinary success.

Decision-Making and Problem-Solving Skills

Entrepreneurs have to make countless decisions daily to solve problems. Those who succeed can often make intelligent, informed decisions quickly.

Decisions made by entrepreneurs set the strategic direction of the startup. Whether choosing a suitable business model, identifying target markets, or setting goals, these decisions significantly impact the startup’s future.

For example, consider Jeff Bezos, the founder of Amazon. One of his critical decisions was to allow third-party sellers on Amazon’s platform. Despite concerns about competition with Amazon’s own products, Bezos saw the bigger picture: more variety would attract more customers and create a win-win situation for all parties. This decision played a significant role in Amazon’s growth into the e-commerce giant it is today.

Related: 16 Real-life Organizational Decision-Making Examples

Leadership

Successful entrepreneurs are strong leaders. They know how to inspire and motivate their small team and understand the importance of fostering a positive company culture.

Effective leadership is crucial for building a high-performing team of employees. A good leader attracts talent, fosters a positive work environment, motivates the team, and helps them reach their full potential. For example, Richard Branson, founder of Virgin Group, is renowned for his employee-centric leadership style, which is instrumental in building strong and motivated employees across his numerous ventures.

Another example is Steve Jobs and his leadership that transformed Apple from a struggling company into one of the most valuable companies in the world. His ability to inspire his employees, make bold decisions, solve complex problems, and influence stakeholders was central to this turnaround.

Networking Skills

Building and maintaining relationships is crucial for your success. Successful entrepreneurs are excellent networkers who can connect with others and build mutually beneficial relationships.

Networking allows you to connect with other professionals in your industry or related fields. These connections can be a rich source of valuable information and insights, helping entrepreneurs stay updated on trends, challenges, and opportunities. For example, attending webinars or industry conferences can provide practical knowledge that can be applied to your startup.

By attending networking events and being active on professional networking platforms like LinkedIn, you can also identify potential candidates who could bring valuable skills to your startup.

Related: How to Build Powerful Innovation Networks and Partnerships

Financial Literacy

Understanding finance is critical to running a successful business. You need to know how to manage finances, understand financial statements, and make sound financial decisions.

Understanding important financial concepts will help you create realistic budgets and financial plans. These are critical to ensure your startup has sufficient funds to operate and grow. For example, learning about cash flow can help you manage income and expenses more effectively, preventing many potential shortfalls.

Financial literacy helps you in making informed investment decisions. Knowing how to analyze financial statements or understanding the concept of return on investment can guide you in allocating resources wisely, ensuring every dollar is put to its best possible use.

Learning Agility

The ability to learn from experiences and apply those learnings to new situations is a vital characteristic of successful entrepreneurs. They are open to feedback and continuously aim for improvements.

One entrepreneur with high learning agility can quickly understand new problems and craft effective solutions. This adaptability can be a startup’s greatest asset, helping it navigate the unpredictable waters of the business world.

Learning agility encourages a mindset of continuous improvement. Agile learners always seek new knowledge and experiences, which can lead to innovative ideas and practices. This continuous evolution can give a startup a competitive advantage in the marketplace.

Personal Questions for You as a Future Entrepreneur

Let’s start with personal questions about yourself as a future entrepreneur and business owner.

Prepare Yourself as a Startup Entrepreneur

Successful entrepreneurs, before everything else, prepare themselves for the startup process. To start and build your own business, you must learn as much as possible about yourself and know what you want to achieve.

1. Do you believe there is some pattern or formula to becoming a successful entrepreneur?
2. What is your favorite aspect of being an entrepreneur?
3. How can you achieve personal growth?
4. What are your personal values?
5. Do you feel some self-doubt about your next steps?
6. How will you deal with fear and doubt?
7. Can you accept risks and sacrifices?
8. How can you achieve a suitable work-life balance model?
9. What routines and daily habits do you follow each day?
10. How do you define success? What are your entrepreneurial career goals?
11. What will be a business success for your own business? What are your business goals?
12. What are your most important technical skills?
13. Do you have one business idea or more that will help you in easier pivoting later?
14. What do you work on now as a startup entrepreneur?
15. How much time will you need to finish it?
16. What do you think about future customers?
17. How do you spend time preparing your first product or service?
18. Do you spend your time with your future or potential customers?

Your Competencies as a Startup Entrepreneur

Competencies are something that will make a difference between successful and unsuccessful startup companies. A good entrepreneur needs different competencies to build a successful business.

19. Do you know your competencies?
20. Do you have all the competencies you need for your small business?
21. Do you need to add more competencies to your company?
22. How will you add more core competencies and new skills that you need for your small business?
23. What about knowledge?
24. How can you build knowledge for your business?
25. How will you share knowledge in your company?
26. How will you implement new technology and knowledge in your company?

Your Leadership and Vision as a Startup Entrepreneur

Successful businesses require strong leadership and vision from entrepreneurs. These are soft skills important for success. As a business owner, your role extends beyond founder or CEO. You’re also a leader whose vision will chart your company’s future. Balancing these roles is challenging but crucial for your startup’s success.

Visionary leadership is about seeing the invisible and making it visible. It’s about imagining an inspiring future for your startup and then mobilizing your employees to turn that dream into reality. Many entrepreneurs forget about this at the startup stage. As a business owner, your vision acts as a compass, guiding your team’s efforts and aligning everyone with your business goals.

27. Can you notice some changes in your vision before you start to work on its achievement?
28. How can you ensure all employees follow your vision?
29. Is what you do bringing you closer or farther away from your vision?
30. Do you need, and what do you need to change in the way that you are following to be closer to your vision?

Your Salary

The salary of a startup entrepreneur isn’t fixed and can fluctuate based on various factors. It’s a delicate balance between supporting small businesses’ growth and meeting entrepreneurs’ personal financial needs.

31. How will you pay yourself?
32. How much salary do you want to be paid at the startup stage?
33. What are the industry standards related to the wage?
34. Do you think you are paid too much or too little as a startup entrepreneur?
35. How are you looking at your products as a collection of features or a collection of benefits?

Productivity

Productivity means doing more things in less. Or better results in a shorter time. Follow these 60 productivity rules that will help you to improve your productivity.

36. Do you have and use a to-do list?
37. How did you succeed in implementing your to-do list?
38. Do you succeed in finishing on time and with the right quality of all your work tasks?
39. What about your team and your own to-do lists? Are they finishing everything on time and with the right quality?

Business Model and Pivoting

Entrepreneurs find that achieving their business and personal goals will be easier when they know what they must do. So, you must develop a business plan to help you achieve your vision.

Business model

Developing a business model is a critical step for your startup business journey. It acts as a roadmap, outlining how your startup will create, deliver, and capture value.

40. Ask and answer the following questions:
41. Do you have a business model?
42. Is that model a sustainable one?
43. How do all elements add value to your startup? Can you translate it into an executable business plan?

Pivoting

Remember that changing and adjusting your small business journey is important to entrepreneurial success. Pivoting means you need to implement change in the direction where you lead your startup. As a startup entrepreneur, you will have many pivoting activities.

These questions you must ask yourself here:

44. Do you know what pivoting is?
45. Do you know when you will need to pivot?
46. Is there a need for pivoting?
47. What will you need to pivot?
48. What will come after pivoting?

What and How Will You Sell?

Knowing what you will sell and how you will market and sell is important. This is one of the biggest challenges for startup business owners. So, you must start with your customers in mind and develop an effective sales funnel.

Customers and Market

Understanding your customers is the cornerstone of a successful startup and your whole business journey. As a successful entrepreneur, the more you know about your customers, the better equipped you are to meet their needs and exceed their expectations. With this knowledge, you will build better products and services and implement marketing strategies to bring results to your small business.

Important questions to ask yourself about customers are the following:

49. Can you see how the customer uses your products or services?
50. Do you know the customer’s pain points and desires that will guide your product development process?
51. Are you improving on an existing product or introducing innovation into the marketplace?
52. Are they satisfied with your products and services?
53. Are they asking you about when they can buy your products or services?
54. Can you notice some additional problems in their questions?
55. How much is your customer ready to pay you to solve the problem that your product or service solves?
56. What real value do you offer your customers as a startup entrepreneur?
57. What is your unique value proposition?
58. Does your product or service have customer validation?
59. How do you build a successful customer base?
60. How does your startup market or plan to market its products or services?
61. What is your startup’s PR strategy?
62. What is your startup’s social media strategy?
63. What is the cost of a customer acquisition?
64. What is the projected lifetime value of a customer?
65. What advertising will you be doing?
66. Should you try to launch to a niche or entire market segment?
67. Have you missed a new customer segment or special market?
68. How large is the potential target market (in units or dollars)?
69. Is it growing, stable, or decreasing?
70. What percentage of the market do you have?
71. What is your competitive advantage?
72. How do you plan to sustain your competitive advantage?
73. What market research did tell you about your target market?

Sales Funnel Related Questions

Designing an effective sales funnel will define your path to success. Here is how you can keep your sales funnel always full.

Here are the important questions to ask:

74. Do you understand your sales funnel as a startup entrepreneur?
75. Do you know the conversion rates in your sales funnel?
76. Is everything in your sales funnel as it needs to be?
77. What is the typical sales cycle between awareness and purchasing?
78. Do you need to change something?
79. If you need to change something in your sales funnel, how will you change that?
80. When was the last time you tested your sales funnel?

Managing Your New Company

Managing a whole new venture or company effectively is important for startup entrepreneurs. From setting clear goals through team building and leadership to risk management, every business will require management processes.

Human Resource and Team Building

To become a successful entrepreneur, you must surround yourself with high-quality people who will increase your business potential energy. Depending on the growth rate of small businesses, successful entrepreneurs must sometimes work on hiring managers who will help them continue growing.

The following questions to ask yourself regarding human resources and team building are essential:

81. Do you have the right resources and relationships?
82. What type of people do you need that will help you to execute your business plan?
83. Do you know such people that will fit your business?
84. Where will you find them for your business?
85. How will you attract potential hires and target candidates from your company?
86. How will you keep them in your company after attracting and selecting them?
87. What company culture do you want to build to attract and retain the best employees?
88. How will they affect your work and your business?
89. What next steps will you need to take for your business?
90. Are you ready to sacrifice your life for the team you are building?
91. How big does the team you are building need to be?
92. Can you succeed without them? How will you support employees in their everyday jobs?

Process Management

Your processes are doing the job inside your company. If they fail, your business will also fail. So, designing your business processes and continuous improvement is crucial for your success as a startup entrepreneur.

Now, let’s look at what questions you must ask yourself here:

93. Have you designed all your business processes?
94. How do your processes operate in a real environment?
95. Are there some bottlenecks in your processes?
96. What are the bottlenecks?
97. What do you need to do to eliminate those bottlenecks?

Key Performance Indicators

Key Performance Indicators (KPIs) are indicators that will tell you if you achieve what you have expected to achieve. Here is how my measurement system saves me from big failure.

When it comes to KPIs, essential questions to ask are the following:

98. What are your key performance indicators?
99. How can you follow and measure your key performance indicators?
100. According to those key performance indicators, how do you decide as a startup entrepreneur?
101. How much time will you need to decide according to those key performance indicators?
102. Can you follow up on your key performance indicators if you are out of your business building?

Finance

As a business owner, financial literacy is important for your tomorrow’s success. You must know how to manage one of the scariest resources for every business: finances. Financial literacy refers to understanding various financial elements like cash flow, balance sheets, income statements, and financial planning.

Startup Costs

Startup costs are the expenses you will have while creating your new business. These costs can be divided into two main categories: (1) one-time costs,which are the initial costs necessary to start your business (legal fees, permits, and licenses, branding (like logo design), website setup, initial inventory purchase, and more) and ongoing costs, or recurring expenses that you’ll face in the regular operation of your business (rent or mortgage payments, utilities, employee salaries, marketing and advertising expenses, and insurance).

Important questions to ask yourself about startup costs are:

103. How much capital will you need as a new business owner?
104. Have you made a financial analysis of your small business?
105. How do you determine your startup costs and other expenses?

Cash Flow

Cash flow refers to the movement of money in and out of your business. It measures your business’s liquidity and ability to cover its costs.

Positive cash flow means your business’s liquid assets are increasing, enabling you to settle debts, reinvest in your business, return money to shareholders, pay expenses, and provide a buffer against future financial challenges.

Here are some questions to ask related to the cash flow:

106. Do you understand the cash flow and its significant impact on your business?
107. What is your projected monthly cash flow?
108. Why is it important to do a monthly cash flow analysis?

Financing Your Startup

Financing a startup refers to securing capital to start and grow your business. This funding covers startup costs, from initial expenses like office space and equipment to ongoing costs such as salaries, marketing, and product development.

So, the questions to ask yourself are the following:

109. How will you find that capital to finance your business startup?
110. How will you raise capital for your own business?
111. Are there some other options to raise funding for your business?
112. Are there some potential investors that will be interested in your business?
113. How will your business repay that money if you borrow them?
114. Can your financial strategy inside your business plan generate sufficient profits and growth rates for your own business?

As a Startup Entrepreneur, You Will Need to Build a Business, not a Product.

Many entrepreneurs put their whole focus on products and services without thinking about building the business. Yes, you must design and create a business, not the product. Here is how you can start to build a business, not the product.

Here are the questions to ask here:

115. Do you enjoy your work as a startup entrepreneur?
116. How do you spend your time for enjoyment when you are not occupied with your startup?
117. Do you have time for enjoyment?
118. If you are absent from your business for a month, can your company continue to operate in the same way as if you were there?
119. Do you know why your business can continue to operate without you?
120. Do you know why your business can’t continue to operate without you?
121. What must you do to ensure your business will continue operating even without you?

Frequently Asked Questions