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On Being An Entrepreneur: Questions Every Business Leader Should Ask


Sitting on the edge of my bed trying hard to stifle my tears, I realized I would have to leave the company I had founded. I was faced with making one of the toughest decisions of my life. As an entrepreneur, I felt that giving up my business was like losing a child. My deepest fear was that if I left the business, I would be letting down my colleagues, my partners and my investors. I turned to my friend and said, “If I turn away from this business, these people will think I’ve failed them and that scares me.” I was convinced that if I didn’t turn this company into a multi-million-dollar business, then no one would have faith in me again. Then my friend, an entrepreneur herself, gave me the best advice an entrepreneur could ever receive. She said, “You’re wrong about that, those people will all be asking, ‘Gee, I wonder what exciting thing he’ll be up to next!?'” She was reminding me that the most important attribute of being an entrepreneur is the ability to recover from your failures and start over again. Guidance like that is invaluable.

So, to whom do entrepreneurs turn when things go wrong, or when they want to make their current success even greater? Most often, entrepreneurs are isolated by their position as founder or leader of their organization. There are few people that they can turn to or even talk to about their business’ ups and downs. Business leaders have slipped into the belief that asking for help is a sign of weakness. That couldn’t be further from the truth. Successful entrepreneurs surround themselves with credible and enthusiastic advisors. These teams of advisors include financial advisors, business leaders, and legal advisors, as well as executive and life coaches. The importance of support for any businessperson is very underrated. No person is an island and the more support a leader can arrange around him/her, the stronger that person will become.

As I sat on my bed all those years ago, I didn’t even know executive and entrepreneurial coaches existed. If I had, I would have worked with one to ensure a smoother transition from one situation to another. Coaches can be important guides through periods of transition, as well as during periods of quiet reflection. Entrepreneurial coaches are an awesome resource of support and experience that can assist you in developing your own innate talents as an entrepreneur.

Over my career as a serial entrepreneur, I have stumbled across several golden questions that have been exceptionally useful to me. I ask myself these questions before I start a business, and frequently during my involvement in that business. Below is a list of sixteen questions that you should ask yourself. The answers will provide you with a head-start in getting your business to perform at its best.

Sixteen Important Questions Every Potential Leader Should Ask Him/Herself:

  1. How well do you know your business and industry? Are you an expert in your field?
  2. Have you hired the best people you can afford? Second-rate people produce second-rate work. Employ people that you know will be better at doing the work than even you can.
  3. Do you have a plan? Have you written a business plan incorporating your marketing and financial plans? Write it in several formats – one line, one paragraph, one page, one document, etc.
  4. Can this business scale and grow without your hourly attention? Can your idea grow to survive your absence? After all, that’s why we create businesses; so we don’t have work all the time.
  5. Does everyone in the business have a specific role? Are the roles and responsibilities for every person in the business clearly defined? This is most important for partners and senior managers.
  6. Is there more money in your account each month than the previous month? This is what separates businesses from hobbies.
  7. Have you given careful thought to how you package your products and services? Help clients to decide what they want and then get out of their way.
  8. What have you chosen as the company identity? Create a culture based on the identity of the company – choose the identity carefully.
  9. What agreement do you have with your investors? Investors are only interested in returns. Don’t believe it if they tell you differently.
  10. How do you and your people spend your time? Which activities are leading to profits and which to expenses? Activity doesn’t equal productivity.
  11. How do you manage expenses and liabilities? Cost-conscious and value-conscious are both important, but are not the same thing.
  12. What is your company and personal focus? This is an entrepreneur’s biggest challenge; staying focused. Don’t try too many things at once (if you do decide to do many things, know that they will only perform at 50%).
  13. Who is the competition and what are they doing? There is no such thing as NO competition!
  14. How do you balance work with relaxation? Burnout is a process, not an event. It can sneak up on you.
  15. Do you really enjoy the business you’re in? To truly love what you do, you must do what you love.
  16. What self-improvement education are you undergoing to improve your skills and expertise? Are you on a course? Are you working with a coach? In general, being the best entrepreneur that you can be might ultimately involve handing over the business to people that can run it better than you can. This is a tough decision to make and is the number-one reason why companies fail; the inability of the founders to curb their egos. Working with a coach will help you understand the issues of the business from an objective point of view.

Author Richard Banfield

As CEO, Richard leads Fresh Tilled Soil’s strategic vision. He’s a mentor at TechStars and BluePrintHealth, an advisor and lecturer at the Boston Startup School, and serves on the executive committees of TEDxBoston, the AdClub’s Edge Conference, and Boston Regional Entrepreneurship Week.

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