Things to Think About

Quick Summary: Ask and answer a broad range of questions before committing to starting a business.


The Internet, news stories, and folklore pant an overwhelmingly positive image of the entrepreneur/startup world.  Overnight millionaires and billionaires, driving $250,000 sports cars seem commonplace.  Looking below the covers, the reality is quite different.  Success is the exception, not the norm.  Despite the many obstacles, many individuals take the plunge and never look back.  Before taking the plunge, it is only prudent to test the water.  Asking a diverse set of questions, and answering them objectively is the best approach in making this, potentially life-changing, decision.

This article, unlike the other 610-plus articles in this collection, only presents questions.  It does not provide answers or advice.  Every would-be entrepreneur should think about each of them.  The questions were compiled over the last several years from Executive MBA students attending the Executive MBA Program at the Michael J. Coles College of Business at Kennesaw State University (Georgia).  The students prepared the questions prior to a panel discussion that was part of the program’s Entrepreneurship unit.  The questions were directed to a panel of four or five entrepreneurs who responded to the questions in an open, three-hour dialogue.  The quality of the questions and sincere interest of the students have made these sessions quite worthwhile to all of those in attendance. 

The entrepreneur panel members background and focus covered all four corners of the business spectrum from business to business, to business to consumer focus -- offering either products or services.  The company size, maturity, and success of the entrepreneurs varied as well.  This diversity lead to wide-ranging answers to the questions.

There is a wealth of information available from multiple sources on the Internet and in bookstores regarding entrepreneurship.  Every major city has multiple incubators, shared-space facilities, meet-ups, and sponsored activities that cover almost every conceivable aspect of starting a business.  Consultants, mentors, and serial entrepreneurs are also available to help – many provide their guidance on a pro bono basis.  The KSU Panel Forum provided a unique opportunity for individuals with widely varying experiences and goals to hear from and interact with each other and entrepreneurs living the life.

There seems to be one consistent and powerful recommendation that virtually every entrepreneur agrees with: Find a Mentor!  Be careful in selecting a mentor.  Many people will willingly offer you advice and their intentions will be noble.  However, individuals that you have a previous personal relationship may be more focused on positively supporting you than providing you with the candid feedback that you (desperately) need.  Many others, with good intentions, may offer you their best advice that, unfortunately, could be totally wrong for you!  For example, a retired senior executive that has spent their entire career in corporate America probably has a wealth of experience and wisdom.  Unfortunately, most of it may not be applicable to your startup situation.  Many of the questions listed below will be very hard for you to answer.  You may not know the answer or may not WANT to objectively answer the question.  In these situations, a mentor that has gone through startup issues, whether successful or not, can help you look in the mirror and think through the issues surrounding the questions. 

Understandably, most entrepreneurs focus on securing the necessary funds to start and run their businesses.  There is no question that cash is important.  There is, however, one thing that is far more important than cash.  It is the entrepreneur’s time.  An entrepreneur must think of every hour as a silver bullet; once fired it is gone forever.  Spending the appropriate amount of time, at the right time, is critical.  Re-work and correcting mistakes are obviously costly.  Many of the questions listed below should help an entrepreneur think about and prioritize issues, and hopefully, avoid the mistakes of others.

This article fits perfectly into the first business stage category included in the CxO-Atlas website collection: “Thinking About Starting a Business”.  Assuming the would-be entrepreneur decides to move forward, their answers to these questions will help them as they move to the second stage: “Committed to Starting A Business”.  The questions are divided into multiple (but overlapping) categories.

Clearly, the overall number of questions (94) appears to be overwhelming, and the answers may not be obvious.  However, the commitment to start a business requires a very serious decision that demands careful consideration.  Two facts must be kept in mind.  First, most businesses do not survive to see their fifth anniversary.  Second, “overnight success” commonly takes ten years!  However, knowing and living through the reality of the situations, when asked, entrepreneurs most often say “I would do it again.”

Taking the Plunge

  1. Where did you get your idea or concept for the business?
  2. What drove you to be an Entrepreneur vs. working for "the (wo)man?" - Did becoming an Entrepreneur be what you thought it would be like?
  3. If you worked in the corporate world before, how did you make the transition?
  4. How much did you know about starting your own business prior to executing and how did you teach yourself along the way?
  5. How did you go about identifying your target market?
  6. How did you verify that there's demand for your product/service and that it was a viable business idea?
  7. What were some key activities you did to identify a need?
  8. As a serial entrepreneur, I'm sure you have new ideas for businesses often: How did you know when you had a good enough idea to pursue?
  9. What are the best organizational tips you can provide to someone starting their own business?
  10. How many times did you "go back to the drawing board" from initial idea to opening the doors for business?
  11. What was the best resource that helped you during the concept phase?
  12. What criteria did you use to decide to leave existing employment to start your business?
  13. Did you or could you have started your existing business part-time?
  14. What advice would you provide someone if they were going to start their business idea part-time?
  15. What was the biggest challenge during that transition?
  16. What do you consider to be the most difficult part of starting a new endeavor, ideation (it seems difficult to come up with something truly niche these days), business planning (cost and profitability analysis), or implementation (getting all the pieces in place and setting them in motion)?
  17. Is right now the right time to begin a business? Why or why not?
  18. If you have a million ideas, how do you know which is the one you should focus on creating your business around? What if multiple seem great? How can you evaluate to know which is going to be successful so you're not in the hole and unable to feed your kids? Once you do pick one to go with, how do you then determine which resources you'll need?


  1. How did you end up in the line of work that you are in?
  2. Did you always want your own business?
  3. Did you have a corporate background?
  4. What was the single moment when you knew you were going to 'make it'?
  5. What are the non-work habits that help you with your work-life balance?
  6. What is the best advice you received recently, and that you still follow?
  7. What are your characteristics and skills you possess that made you a successful entrepreneur?
  8. What was harder than you thought it would be as an entrepreneur? Easier than you thought it would be?
  9. How much of networking with others influenced your business?
  10. If there was a skill outside the typical business school subjects that you think is critical to starting a business, what would it be?
  11. Regarding family and friends working in your business, what has been the challenges that you have faced?
  12. How did you gain the courage to venture out on your own?
  13. To what do you contribute your success?
  14. What time do you wake up in the morning? (I have heard that successful people start their day early...0430ish).
  15. What was non-negotiable for you during this journey?
  16. What has the work-life balance journey looked like for you? from the beginning until now?
  17. I see a lot of people on LinkedIn who claim to be Entrepreneur's but seem like they're just really good at Marketing themselves: what's the difference between someone who's good at BS'ing and a successful Entrepreneur?


  1. What motivates you?
  2. Where do you get your motivation from?
  3. What inspired you to become an Entrepreneur?
  4. Assuming that any of these entrepreneurs left a corporate job to pursue their own company, what gave them the confidence to take the risk of walking away from their old career path?
  5. What was it that made you start your own business? What was it about your product/service that made people wanted to buy it?
  6. What was your defining moment when you wanted to start your own business?
  7. What is more important in deciding to have your own business: your passion and desire to do what makes you happy or your rational thinking and an idea which will be profitable for sure?


  1. Is what you set out originally to do with your own business what you are still doing today, or did it evolve?
  2. In the past few months, what was the smallest change you made that has had the biggest positive result?
  3. How did you build your clientele?
  4. What was your approach to recruiting and building your team at the initial stage of launching your company?
  5. How did you grow your team and bring great people on board when starting out if you are not able to offer potential team members high salaries or job security?
  6. What are some nice to haves - maybe not crucial, but some things you still need to consider?
  7. How do you ensure your idea will be irresistible to people?
  8. How can you co-create with your target customer to ensure the best product/solution?


  1. Do you have any personal regrets due to the sacrifices you made in your life while trying to build a business?
  2. If you have failed in previous attempts to create your own business, when did you know to throw in the towel, and what is different about your current business to make it successful where the previous business(es) failed?
  3. If you could time travel back to day one of your startup and have 15 minutes with your former self to communicate any lessons learned, what would you tell yourself?
  4. What was your biggest mistake? How did you deal with it? What would you have done differently? What did you learn?
  5. If you could have given yourself a piece of knowledge or advice when you started what would that be?
  6. Were there any "mistakes" that you made that were actually blessings in disguise? (i.e. if you hadn't learned that lesson it would have impacted you negatively with more at stake in the future)
  7. Which opportunities should you have followed; what pitfalls would you have avoided?
  8. What was the biggest challenge in the first year of operating? In the second year?
  9. How many friends did you lose and how many enemies did you make?
  10. If you closed the business tomorrow what would your next venture be?
  11. What did you learn from your biggest failure?
  12. What's a bad decision you made as an entrepreneur that you would advise an aspiring entrepreneur to avoid?
  13. What are some of the lessons learned you can share in starting your business?
  14. What did you spend too much time doing during your first year?
  15. Is there something you wish you educated yourself on before you started your business? Something you wish you knew before you got started that you now have learned.
  16. What were some of the hardest lessons you learned when starting businesses that you wish you could do over again?
  17. What's the biggest mistake you see entrepreneurs make that MUST be avoided to be successful?
  18. When do you know it's time to walk away from a business idea?
  19. If you were given a chance to use a time machine to transport you to a business opportunity that you had in your life, What is the business? What would you do different this time around?
  20. What was the most important failure you have ever had? (What did you "fail" at that in hindsight has helped you the most)

Revenue / Cash / Funding

  1. What was a key component of your business plan? What component do you wish you would have included in your business plan?
  2. How did you go about establishing an initial budget for your business?
  3. How did you determine how much money you would take home in the beginning (or when you could start taking money home) too support your family and how has that evolved?
  4. What is your rating on a scale of 1-10 on the importance of cash flow?
  5. Was your focus on revenue early on or were you primarily focused on margin throughout each phase of your growth?
  6. How long did it take for your business to make a profit?
  7. Outside of friends and family, what are good ways to finance your business starting out?
  8. Would you recommend taking capital investment funding or trying to remain self-funded if you had it to do over again?
  9. How do you find your funding source when looking for investors?
  10. Do you have a rule of thumb you used to determine how much of your own capital (i.e. - what % of your personal savings) you'd limit your investment in the business to?
  11. How did you determine the funding source and why did you decide on the source you did?
  12. Did any of your start-ups require a capital investment from investors? 
  13. How much money did you personally invest in your business before making a dime?
  14. What are some good non-typical ways of raising the initial capital investment for your business?

General / Miscellaneous

  1. Is Atlanta still a great place to launch a company or has it become a small pond with too many (big & little) fish?
  2. What is the maximum number of partners you'd recommend one have in business?
  3. How much time did you invest in researching the idea that you had before initiating the new business?
  4. If you have an idea for a business and are presenting to potential investors, what is stopping them from taking your idea you have presented and creating a business themselves?
  5. How much formal market study did you complete before activating your business?
  6. If my idea involves a product, how do I know who I need to hire to help me out? How do you pick a business partner?
  7. How do you patent before you actually have a working product, so your idea doesn't get stolen?
  8. What makes your company stand apart from others like yours? What innovative efforts are being made to make the company better? What problem(s) does your company solve?
  9. What differences do you see between a not-for-profit entrepreneur and a for-profit startup?
  10. Where can an entrepreneur put his/her business up for sale?



Article Number : 3.010006   

A Handy Reference Guide for Executives and Managers at All Levels.

9 Volumes 42 Chapters ~689 Articles

Browse Select Read Download



The weight of your world does not have to be on your shoulders.
The articles in this site will help to lift that weight from your shoulders.
Pick an article similar to how you pick a route on a page of an atlas.
There is no need to look at other articles, just as you ignore other pages in an atlas.
It is easy to start a business but it is hard to run. Bumps and unexpected sharp turns in the road are always present.
Others have traveled the road before you; learn from them. This site may help.