Continuous entrepreneurial success is determined by a combination of factors. The skill of asking questions is considered to be one of the most important tools for success.

This is the reason why it is so vital to understand the basics of asking yourself good questions.

Why it is so important for entrepreneurs of asking questions:

  • If an entrepreneur wants to innovate he must ask questions and keep on innovating. Innovative entrepreneurs continuously ask questions. As Peter F Drucker said: “Entrepreneurs innovate. Innovation is the specific instrument of entrepreneurship.”  Also by Peter F Drucker: “This defines the entrepreneur and entrepreneurship – the entrepreneur always searches for change, responds to it, and exploits it as an opportunity.”
  • Asking questions is the most effective way of learning, exploring the unknown, and adapting to change. Through exploring the unknown with an attitude of continuous learning, the entrepreneur will understand the importance of adapting to change and find new, improved methods of managing his business. As Dennis Waitley  said is this regard: “Continuous learning is the minimum requirement for success in any field”.
  • Asking questions helps the entrepreneur gain deeper insights into the challenges facing his business, and assists with making better decisions. Peter F Drucker once said: “Wherever you see a successful business, someone once made a courageous decision.”
  • Asking questions triggers deeper thinking that increases understanding and thus helps with the learning process by getting more information. Albert Einstein has said: “The world as we have created it is a process of our thinking. It cannot be changed without changing our thinking.”  To emphasise the importance of thinking Thomas A Edison said: “Five percent of the people think; ten percent of the people think they think;  and the other eighty-five percent would rather die than think.


Asking questions is therefore the only way to get new information, to learn, to improve, and to innovate. Without these it will not be possible for entrepreneurs to develop a sustainable business. That is the reason why asking questions is so vital for business success.


Many different questions can be asked to improve the business of the entrepreneur. Asking the right questions is a vital skill that all entrepreneurs can and should develop to resolve any challenge. To assist I would like to give my personal preference of questions to be asked.  Due to the fact that the entrepreneur’s business and personal lives are so closely related, questions must focus on both personal and business related issues.


Some of these questions can be asked daily, whilst others at intervals, depending on the specific circumstances.

About Meaning in life: it is important to be sure that your business adds meaning to your life. There should be no conflict between what you do in business, and what gives personal meaning

  • What is it that gives meaning to my life?
  • What makes every day worth living?
  • What do I want out of life?


About Myself: I must understand myself and my identity in order to successfully promote my business to clients and stakeholders.

  • Who am I?
  • What defines me?
  • What is my identity?


My big Why: this is one of the most vital questions. Make sure to get clarity.

  • Why am I here?
  • Why am I in this business?


About my Mindset: we tend to forget the influence our mindset has on business success. It may be a blindspot, so make sure to understand and manage it.

  • Do I have a positive mindset?
  • Do I have any limiting beliefs?


Life is about having a positive attitude and being grateful. Manage and monitor it daily, improve it continuously.

  • What am I grateful for today/now?


Personal life and business is about personal and business development.

  • What improvements have I made today in my personal or business life?
  • What new knowledge did I gain today?
  • How can I do what I love doing, more effectively and efficiently?


Values are our guidelines to test every action or decision we make. One can never be sure enough that these are in harmony.

  • Are my decisions in line with my values?


Optimization of time is vital for success in any career or business. How time is spent and ways to improve the use of time must be monitored daily.

  • Did I keep to my time sheet?
  • Did I plan the optimal use of my time today?
  • Where and how can I improve the use of my time?


Business and personal goals are an important part of our destiny, make sure that every action taken daily is directed towards your goals.

  • Did I make progress towards my goals today?
  • Why not?
  • What can I do to make more progress?


Life and success is not only about yourself, it is also about community and making a contribution towards others.

  • What contribution did I make to improve the wellbeing of somebody today?
  • Did I radiate positive energy today towards other people?


One of the important contributing factors towards self-actualization is the integration of personal, business and social life. That is the reason why some questions in this regard are important.

  • Do I spend enough quality time with my family?
  • Do I spend enough quality time with my friends?
  • Am I satisfied that I optimally integrate the time I spend in my business and my personal life?

Asking yourself relevant and good questions is a crucial skill which can and should be developed. Study material is available to assist you master this skill.

Asking regular questions to guide and monitor yourself is a habit. One of the problems we encounter is that although we realise the importance of developing or having good habits – we so seldom stick to them, or do what we are supposed to do.

These three quotes from experts illustrates the point:

  • “Successful people are simply those with successful habits”. Brian Tracy
  • “Habits change into character.” Ovid
  • “Depending on what they are, our habits will either make us or break us. We become what we repeatedly do.” Sean Covey

I do hope that you realise the importance of mastering the skill of asking yourself good, relevant and regular questions. This skill will definitely assist every entrepreneur to grow his business to the next level.