75 Startup Questions To Ask Entrepreneurs Before Launching Your Own Business

by Jul 15, 2023

Successful young entrepreneurs ask lots of questions before launching their venture. Founders must be in the know, so create a long list of questions to ask successful entrepreneurs during your planning process. Entrepreneurship requires continuous personal growth so don’t be afraid to ask questions while preparing to execute your startup phase.



75 Startup Questions To Ask Entrepreneurs Before Launching Your Own Business




Successful entrepreneurs wonder why and how. A naturally thoughtful and inquisitive nature leads to questions which leads to creating the building blocks of business development.

An entrepreneur asking questions before embarking on their venture is very similar to the continued need learn and ask questions before deciding a new hire or when seeking an investor. The questions change. The inquisitive nature and thought behind crafting the questions does not. 


Ask lots of questions. Discover. Absorb all that you can, which will in turn, help you think for yourself and come to conclusions that work for you. You don’t know everything – no one does – so asking questions is positive. 


Your time is limited though, so think of it as a budget and don’t waste time asking for information that won’t help. 

You’ll use the information you collect to help craft your business plan and goals. Asking questions is a sign of strength and intelligence. Entrepreneurs are always learning. It’s part your launch but also an ongoing part of risk management. 

The question and answer process serves many additional purposes. 

  • It validates your idea.
  • Creates your proof of concept
  • Answers concerns
  • Offers practical advice
  • Strengthens your network
  • Helps you define your target audience
  • Helps you understand your target audience
  • Leads you to an action plan & execution timeline
  • Helps you assess, then minimize risk
  • It helps you create a positive entrepreneurial experience.




Image of young lady pointing



Question asking tips for new or young entrepreneurs


It’s okay to ask questions as you think of them, but it helps to have a purpose.

If your opportunity is planned, think through what you want and need out of the conversation. Jot your questions down as you would for any other interview situation so you don’t forget. 

Be clear and specific. Be a good listener. Take notes. 

Many entrepreneurs use this time to learn and to reflect. You want to use these takeaways in your business planning asap. 


It’s your opportunity to interview a founder!


You want to understand how they began their entrepreneurial journey, and you want their 20/20 insights that may help you avoid common or unexpected pitfalls. Ask about: 

  • How they got started 
  • Early failures and successes
  • How they handled operations as business grew
  • How they survived in the red
  • Early, wise investments into technology or support services
  • Communication tips
  • Networking tactics that work
  • Marketing tactics that work
  • Accountability
  • How they remain confident and energized
  • Motivating factors


Startup questions to ask an entrepreneur 

Launching a business requires a lot of preparation, as you know. Every minute and every piece of material has a value – a cost. Maximize your investment by learning all that you can from those who have been there. The conversation will be as motivating and inspiring as it is educational.


– What inspired you to start this business?


– Where did the idea for your business come from?


– How did you know it was a winner?


– Have you ever felt unsure of a decision you made?


– How do you deal with self-doubt? 


– How about doubt from others?


– To what or whom do you owe your success?


– What’s been your most satisfying about this journey?


– What’s the most rewarding aspect of starting your own business?




Making Candles




William Arthur Ward


– What do you enjoy most about entrepreneurship?


– What is the most difficult or unenjoyable part of working your business?


– What advice would you give to someone who is starting their own business?


– What was your biggest aha moment so far?


– How do you define of success?


– How do you measure success?


– What do you think are the most important skills or qualities for a small business owner?


– When did you know it was time to focus on your business full-time?


– What are the most common mistakes that new business owners make?


– What did your initial business plan look like?


– What does your typical workday look like?



More questions to ask entrepreneurs!


– What inspired your company and brand names?


– How did you decide on the location for your business?


– How did you protect your idea from the competition?


– How do you market your business?


– What’s been your most effective marketing strategy? Why?


– Has your target market changed? How? 


– What marketing tactics are helping you acquire new customers and retain existing ones? 


Use these questions as they are or use them as a guide and develop your own. 

There is no right question to ask or correct number of questions to ask. 

This is your time to take and absorb. 




Quote image by Michael Hyatt "Asking questions is one of the best ways to grow as a human being."




Hurdles for business owners


– What are the biggest challenges you’ve faced as a small business owner?


– What was the toughest moment in your business journey? How did you get past it?


– What key lessons did you learn throughout your entrepreneurial journey?


– What are the biggest mistakes first-time entrepreneurs can make?


– What are some difficult choices you had to make to get where you are?


– Looking back, what would you have done differently?


– Did you ever have to choose between innovation or integrity?


– How do you manage risk in your business and what strategies do you use to mitigate potential risks?


– What were some of the biggest financial challenges you faced when starting your business?


– What are some common but avoidable financial mistakes that I should consider?


– What advice do you give aspiring new or young entrepreneurs who are struggling to manage their finances?


– How did you fund your business in the early stages and what financing options do you recommend for a startup?


– How did you manage your cash flow and ensure you had enough funds to cover expenses?


– What financial tools do you recommend I use to manage my finances as a new entrepreneur?


– What are some key financial ratios or indicators that you use to assess the health of your business?


– What strategies have you used to reduce costs and increase profitability?



Albert Einstein



Developing the venture – and adventure! 

Allow their success to inspire you to dream big!


– What drove your sales in the beginning?


– How did you effectively scale?


– How did you handle fast growth? What were your biggest challenges?


– How do you plan on growing your business in the future?


– Could you evaluate the ups & downs of your business as they happened so that you could change course?


– How has your business shifted over time?


– What KPIs do you use to measure your business success?


– What do you consider to be the most important factors and influences that will shape the future of your company? 


– What consumer, industry or world problems are you currently trying to solve?


– How did you initially differentiate your business from others in the market? How about now?


– What do you believe sets your product or service apart from your competitors?


– What are your plans for growth or expansion in the future?





Quote by Indira Gandhi - "The power to question is the basis of all human progress."




The list of questions continues!

Learn as you cultivate this new relationship. 


– How do you connect with people that support your business?


– What soft skills are most helpful?


– How do you get noticed without being a pest?


– Do you use social media to network?


– Who and what inspires your entrepreneurial ventures?


– Who do you look to for guidance and mentorship?


– Do you belong to business associations or online groups?


– Should I attend industry conferences or workshops? Which ones?


– How can I boost my communication skills?


– How can I boost my leadership skills?


– How can I be a better team player with my network and vendors?


– How did you optimize your LinkedIn and social media profiles?


– How do you stay on top of industry trends?


– What do you read? What do you recommend?


– What websites, blogs and podcasts are most helpful to you and why?


Execute against self-care goals too

Part of your strategy must include executing self-care goals. You want your best self in place while representing and taking care of your business!


– What motivates you to keep going?


– How do you balance your personal life with the demands of running a business?


– How do you manage your work-life balance?


– How do you manage business stress and prevent burnout?


– Who or what inspires you to take care of yourself?


– Do you use vision boards, affirmations, or manifesting techniques?


– What apps or strategies help you take care of you? 



Questions are a start to and a continuation of your process. As you clarify your vision and mission and steps in your business plan, you define your business goals, and then start turning questions into actions. 

What you learn often has lifetime value. 

Stay in touch with those advising or mentoring you. You want to build a relationship, and showing appreciation will go a long way as you ask for continued recommendations. They can continue coaching and act as an outlet to help you further brainstorm, define your next steps and fine tune your actions to ensure success. You got this.


Check out 17 Free Resources for Small Businesses to Leverage Year-Round

BLOG CATEGORY: Entrepreneurship

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