Skepticism and the Art of Questioning

It was the eminent Greek philosopher Socrates who first brought skepticism and the art of questioning to Western political and philosophical thought. In 399 BC, the leadership of Athens sentence him to death for this crime considering it to be ‘corrupting the morals of the youth of the city’. His prize student Plato also tried to understand the human condition and spread the concept of skepticism and questioning nature and existence. Indeed, Plato’s student Aristotle continued and spread the thought writing of human beings “desire to know” as a driving force in their existence. The desire to know expresses our humanity and it makes us human. Greek philosophical thought held the belief that by asking questions, we try to understand our world and ourselves. Fundamental questions such as “Who am I” and “Why am I hear?” define us as human beings.

Not only the Greeks recognized the importance of questioning their own society. French revolutionary Voltaire said “Judge a man by his questions rather than by his answers.” Philosopher Bertrand Russell had the same perspective saying “In all affairs it’s a healthy thing now and then to hang a question mark on the things you take for granted”.

Questioning ourselves, our lives, and our actions is not a new concept; TED founder Richard Wurman described himself as the consummate outsider. “My expertise has always been my ignorance–my admission and my acceptance of not knowing. My work comes from questions, not from answers.”

Scores of philosophers, writers, visionaries, and comedians have echoed the need to question that which is around us. If we do not ask or answer fundamental questions as individuals or as a society, we cannot understand ourselves or our world. Fundamental questions are critically important for humans. And from fundamental questions come secondary questions. They are no less important, practical questions. And so begins a process to understand an issue, concept, situation, premise, etc.

Questioning American society

The seemingly never ending transformation of American society makes it a civilization in search of its soul. Americans should consider the following question: “Who are we?” Well, a distinct answer can be found in every society, because every society raises people to serve its needs. This process has proven true throughout human history (cavemen, ancient Egypt, Industrial Revolution, Nazi Germany, etc.). Every society raises its population to serve its own needs. And it is the owners of that culture who decide what is needed in society.

Range of thought is generally limited by the dominant values of that society.

The owners of our cultural value system include government, NGOs, business, media, and education. Simply put, all these institutions shape an environment. And the environment creates people. Which of these entities has interest in people asking questions?
Government: There may not be a lot of interest in people asking questions of government or in government. Certainly, there will be some questions. But fundamental questions, whether from inside or outside of government, are disruptive to established processes. And bureaucracies tend to do well even on complex tasks by using established processes.

Business: Business has a love-hate relationship when it comes to questions. Innovative companies Google, Amazon, Space X, Silicon Valley, Disney, etc. have made their fortunes based on questioning conventional wisdom. Questions are always the first step towards innovating. On the other hand, questioning is often disruptive to everyday business practices and incorporates some element of risk. The vast majority of businesses take a “less risky” approach to everyday practices asking only the questions required to stay ahead of competition.

Media:
Does media help people to question the world around them? Possibly, but American media is often more concerned with pushing out information; and in fact, in American society the media has degraded to pushing out opinions vice information. This is not well received by the American public as evidenced by the fact that PEW and Gallop research polls over decades regularly indicate over 65 percent of Americans distrust the media.

Education: Educational institutions should be at least somewhat concerned with teaching children how to question.

Non government organizations: A non-governmental organization (NGO) is an organization that is neither a part of a government nor a conventional for-profit business. NGOs often do have a strong interest in questioning status quo.

We start out questioning life

The average child asks 40,000 questions between the ages of 2-5 (36,000 X 3 years = 12,000 per year or 1,000 per month, 33 per day). Those questions are first ones of fact (name of this or that) and then the more advanced questions of why (why is the sky blue?). The question of “why?” is a significant advancement for the brain recognizing that more than one answer is possible for a given question. Not coincidentally, this is also the period of greatest brain development in human beings. During these years, human brains develop over a quadrillion synapses. Questioning drops dramatically throughout school years into adulthood. Children at a young age have not yet developed mental models to fill in their gaps in understanding.i

Some people are naturally better at questioning. However, most of us have to actively work to question the standard operating procedures that become our daily lives.

How we learn not to question in the American Education System

Individualism and questioning. We criticize the American education system but it, in essence, is bound in a Socratic tradition that encourages individualism and independent thinking. I know the first reaction is often to think of our teachers as authority figures. And what has evolved in the US school system is a situation where authority figures ask questions.

There are a lot of cases that illustrate students in the US school system most definitely learn to question. At least some school systems in the US can claim credit in creating such lifelong questioners. Remember, America is the world’s leader in innovation. A number of world class innovators (e.g. Wikipedia founder Jimmy Wales, Amazon founder Jeff Bezos, Google cofounders Sergey Brin and Larry Page, Yahoo director, Marissa Mayer) attribute their success to the training to ask questions that was a product of Montessori school education.

Why don’t teachers shift to encouraging students to ask questions? To some degree they do but the process of allowing students to ask questions does two things:

• It transfers some power to the student who is now controlling conversation;
• It takes more time than just delivering a lecture.

Studies also show a whole range of additional negative issues relating to students not formulating questions:
• peer pressure
• racial and gender stereotypes
• cultural background
• economic well being

Studies have shown families with higher incomes were more likely to encourage their children to ask questions at school whereas children from modest backgrounds were encouraged to be more deferential to authority.

Peer Pressure in School For high school students there is a “self imposed” risk factor in asking questions and thereby exposing ignorance. A young high school student named Jack Andraka has appeared in TED talks and in the media. He recently became known for — at age 15 — developing a new and inexpensive way to screen for certain types of cancer. In an interview he spoke about not being encouraged to ask questions in school: “in my high school to be quote-unquote cool you’re typically very quiet and sit in the corner and you might snicker among your friends every now and then”.ii

So as you can see there are a lot of factors in the American society that limit how we (and our children) are taught to ask questions. There are some innovations making ground in schools designed to encourage children to ask fundamental and thoughtful questions. One such process recently highlighted in a Harvard University article is as follows:

Step 1: Teachers Design a Question Focus.
Step 2: Students Produce Questions.
Step 3: Students Improve Their Questions.
Step 4: Students Prioritize Their Questions.
Step 5: Students and Teachers Decide on Next Steps.
Step 6: Students Reflect on What They Have Learned.iii

In this activity students take ownership of the questioning cognitive process and are more inclined to think deeply about the subject.

But one cannot look at our educators and system in isolation. Compare it to other educational systems throughout the world. For example, the Confucian system of education is in place in much of Asia. And I want to say I’ve seen that system close-up. I’ve lived in Asia for a number of years and have very direct exposure to the educational system in many places. In many places, it is in its heart a Confucian system where the authority figure dictates the students learn facts and it is a disciplined environment. This is one of the reasons that America so dominates the world in innovation and China relegates itself to stealing technology.

Other Ways we learn not to question things

Experience: Many in the workforce have decades of experience. The experienced employees may be termed as technocratic thinkers. Like technical workers, they are trained as experts to solve problems in a particular area. It is this very often extensive experience that limits their ability to innovate. The experienced (technocratic) leadership in a typical organizational work environment creates a mental model for expected behavior. The acceptance of that mental model precludes or at least limits the ability to ask fundamental questions. Technocratic thinking and acceptance of the corporate mental model leads to few or even no questions about value, meaning, or purpose of the organization, its work, or processes.

People without out “expertise” in a certain area are often not bound by the limits of professional or institutional experience. They are free to challenge fundamental truths of anything.

• Inventor Van Phillips created the world famous Flex-Foot brand of prosthetic foot used by disabled Olympian athletes. His only knowledge of the subject was being dissatisfied as a double amputee.
• In 1902 Alabama native Mary Anderson wondered why no one had created a device to wipe the wind screen of a New York City bus she was riding in a snow fall. She was, of course, the inventor of the windshield wiper.
• Elon Musk had no experience designing rocket engines when he founded the company Space X and dramatically reduced the cost of going to space.

Environment Daily operations large organizations are generally not conducive to dynamic, wide reaching, and constant innovation. They might question a bit around the edges; meaning in the “how can we do this better?” But the need to be product driven in an economy (with technocratic experience) argues against elemental questioning, innovation, and change. Also, the daily operating environment does not provide for mechanisms to question existing processes. People at younger levels are not taught or even encouraged to question organizational processes or assumptions. A large organization often acts like a human body. Questions are disruptive to efficiency in standard operating systems. And just like the human body anti-bodies form and often attack the questioner. (Questioning is seen as counterproductive – it is answers that people want.)

Self interest How often have you heard “Hey boss, there is a new commercial software that can eliminate my job and the jobs of all the rest of the people in this branch. And it’s also efficient and cheap!” Well, if the answer is never, then join the club. It is a rare thing for humans to question anything that may have an answer that is against their own self interests.

Autopilot Unless trained to do otherwise, most brains actually start rejecting information from consciousness that is not relevant to daily life. Did you ever drive home and zone out during the trip? You are actually operating a motor vehicle at high speed and still cannot remember details of the trip. This very common human function of operating on “autopilot” reflects the brain’s ability to screen out information from consciousness thought. It should, therefore be no surprise when people similarly screen out information in their daily work lives.

Who asks Questions?

The first answer is most probably comedians. Does anyone ask more questions than comedians? How is it that stand-up comedians (or their writers) are so often able to make extraordinary insights into the most common of daily occurrences? George Carlin’s daughter Kelly wrote a book where she highlighted how her father felt like an outsider in life. Comedians often describe themselves as the stereotypical class clown. They are the classic outsiders. As a result, it lets them observe — as George Carlin did — human behavior. Artists and writers can also fall into this category; really, anyone who stops to observe and study the details of human behavior.iv

The same observation and questioning skills can also be said for academicians. The common criticism against academics is that they “live in an ivory tower”. They “ivory tower” concept is necessary as a disconnected place from which to observe, research, and study human society.

Now, noticing and observing the details of any situation are very important for questioning. So, for example, consider the oft used phrase to describe an optimist: “you’re glass is half-full.” AQ pessimist would say “The glass is half empty”. The observant person might note: “The glass is completely full: half water and half air”. It is jut a different way to perceive the obvious.

How we learn to ask Questions:

Whereas our educational system and some aspects of society may not completely prepare people to question all that around them; other aspects of our capitalistic society does. In America, businesses either excel at innovation and change or they ultimately fail. There is always someone trying to catch up to you, biting at your heels, trying to take your customers, expanding their business at your expense. This is true from the smallest home-based business to the largest corporate giant. Take Starbucks for example. After skyrocketing to fame in the high-end coffee business they were immediately challenged by Costa, Nero, and local cafés. Other food and even book distribution outlets added (e.g. McDonalds, Dunkin Donuts, Barnes and Noble) quality coffee to their services. The American economic and regulatory environment invites predatory behavior. And in order to thrive in that sort of environment a business must always be asking itself the right questions.

Americans do have the ability to question, and a regulatory environment that promotes innovation. Those two fundamental elements (+ hard work) are not standard components of all societies. This is one of the reasons that over the last two centuries America brought more innovation to the world than any other country. People in the United States have invented and developed so many technological wonders that have transformed all aspects of society from transportation to medicine to warfare and led to economic greatness.

Learning to formulate GOOD Questions

There is no secret to formulating good questions. It really is a function of three factors: organizing thoughts, attention to detail, and practice (personal training). I call the integration of these three factors establishing your own New Cultural Norm
The new norm is a Personal Culture of Inquiry.

1. Organizing thoughts

Step Back –
a. Have no assumptions as to why or how something should be
b. Keep your emotions in check. View the situation dispassionately
c. BE OBJECTIVE
d. Seek to understand what task or event is in front (or behind) you
Question from General to Specific
a. First seek to answer fundamental questions, then specific ones
EXAMPLE: After hearing a story I ask myself: “Why is this true?”
ANSWER: These 5 assertions (or statements) lead me to believe it could be true.

Establish the set of facts for each assertion. Inquire about all events that occurred during the relevant time frame, in chronological blocks of time. Establish all of the details in each of the chronological blocks to recreate the incident.
(Who, What, When, Where, Why, How)
• Exactly what occurred?
• When did it happen?
• Where did it happen?
• Who was present?
• Who else may know relevant information?
• How did it happen?
• Who did or said what? In what order?
• Why did it happen? Could it have been avoided?
• What is the evidence this happened?

WHAT IF (Favorite question for business – driver of innovation)
• Question your own set of facts. What of this or that really happened?
• Concept development
• Engage experts and expertise in other fields

2. Attention to detail

Time and attention to detail. Ever see one of those puzzles that has boxes within boxes? The question is how many boxes do you see? Almost always, the longer you look at the puzzle, the more combinations you can see and thus the more boxes become apparent. This can be said for whole range of brain exercises including “Where’s Waldo”? Well, this is very simply because the more we look at something, the more questions we can formulate about it, and the more answers we discover.

3. Personal Training (Practice)

Practice, practice, practice. Make organizing your thoughts and attention to detail a part of your daily life. In the beginning you will probably have to consciously make this effort. Train yourself in real and imaginary conversations. (i.e. John believes this. Why would that be? How would he know that? What are the facts? etc.)
Other aspects of building your Personal Culture of Inquiry
• Make mental notes about physical environment every time you walk into new surroundings
• Make the same mental notes about the appearance people you meet everyday
• Play the “what do I do if?” game in all surroundings. Mental preparation
• Prepare the same for interviews, discussions, etc.

Incorporate learning from all aspects of life. Open yourself to learning from colleagues with different backgrounds (peer-to-peer learning) Hacking or Maker sessions have been one of the great methods of learning to ask questions.

Think Like Leonardo DiVinci.


1. A More Beautiful Question (Warren Berger, Bloomsbury, USA, New York 2014)
2. Ibid
3. Rothstein, Dan, and Luz Santana. “Teaching Students to Ask Their Own Questions.” Harvard Education Letter. Harvard Education Publishing Group, Sept.-Oct. 2011. Web. 2 Jan. 2016.
4. A More Beautiful Question (Warren Berger, Bloomsbury, USA, New York 2014)

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