How to Upgrade Your Critical Thinking Skills for a Sharper Mind

As humans, we typically operate on cognitive autopilot. We rarely stop and reflect on how we interpret information and create mental models which replicate our perception of reality.

But when our mental models fail to match reality, we simply ignore reality and operate throughout the day on implicit assumptions. These are not conscious choices. Our mental models allow us a simple way to cope with reality, yet we fail to confront reality when it is different than our mental model. Essentially, we have unknowingly created a ready-made default mechanism. 1

So, what can we do?

We must first take time to reflect on our critical thinking skills. By simply understanding how you interpret and perceive information differently than everyone else is a great first step. To truly upgrade your critical thinking skills, you must examine how thoughts arise in your mind and how they got there.

Critical thinking is about asking yourself how you make choices. We can choose to believe something we hear or see; however, why do we choose to believe something we hear or see?

As a Red Team Member in the U.S. Army, I will explain how I upgrade my critical thinking skills using Colonel John Boyd’s OODA Loop as a framework for critical thinking. I will then demonstrate practical ways to upgrade your critical thinking skills for a sharper mind using tools and techniques from the University of Foreign Military and Cultural Studies (UFMCS) Center for Applied Critical Thinking (also known as the Red Team school) and The Applied Critical Thinking Handbook (also known as The Red Team Handbook).2

What is critical thinking?

Critical thinking can be explained in a number of ways. Let’s quickly examine a few definitions:

  • “Critical thinking is a process, the goal of which is to make reasonable decisions about what to believe and what to do.” – Robert Enis
  • “Critical thinking means developing an ever better worldview and using it well in all aspects of your life. The essence of critical thinking is questioning and arguing logically.” – Gary Jason
  • “Critical thinking is searching for hidden assumptions, noticing various facets, unraveling different strands, and evaluating what is most significant. It implies conscious, deliberate inquiry, and especially it implies adopting a skeptical state of mind.” – Sylvan Barnet and Hugo Bedau

To me, critical thinking is as follows:

“Critical thinking is observing the world with an open and skeptical mindset with the goal of exploring all alternatives objectively (as much as possible). It is our ability to orient our mental models to view reality through an emotionless lens seeking the truth by questioning our own assumptions and deconstructing arguments logically. It is our ability to identify gaps and uncover what is missing to improve our quality of decisions. Finally, it is our ability to unravel different strands of significant information through a continuous stream of feedback so that we continuously destroy and create new mental models allowing us to act closer to reality.” – Dr. Jamie Schwandt

Critical thinking framework: OODA Loop

I use John Boyd’s OODA Loop as a framework for critical thinking. It is similar to Swarm Intelligence, where we use simple rules to allow the collective intelligence to emerge. The simple rules are Observe, Orient, Decide, and Act.

The OODA Loop is a high-speed decision making and feedback process in four stages: Observe, Orient, Decide, and Act.3 The OODA Loop is a continuous feedback loop where the objective is to go through the loop faster than your opponent.

I use simple rules provided within the OODA Loop to assist me in speeding up my critical and creative thinking abilities. However, do not confuse the word “simple” with “simplistic” as the OODA Loop uses simple rules within a complex system (which is exactly what the OODA Loop is).

The key to the loop is feedback. The OODA Loop is similar to Double-Loop Learning, where the goal is to modify decision-making in light of new experience.

Double-Loop Learning is the first loop uses goals or decision making rules, the second loop enables their modification… hence, double-loop.4

Chris Argyris writes about Double-Loop Learning in Teaching Smart People How To Learn,

“A thermostat that automatically turns on the heat whenever the temperature in a room drops below 68 degree is a good example of single-loop learning. A thermostat that could ask why am I set to 68 degree? and then explore whether or not some other temperature might more economically achieve the goal of heating the room would be engaged in double-loop learning.

The overarching guide for my use of the OODA Loop is as follows:

I will talk about this more in the How-To Guide: Tools to Apply the Critical Thinker’s OODA Loop section below.


It’s about seeking truth. Here we should seek to follow a concept introduced by Immanuel Kant as a way of evaluating motivations for actions – called the Categorical Imperative. Kant defines a categorical imperative as an absolute or an unconditional requirement that must be obeyed in all circumstances and is justified as an end in itself. For example, “Act only according to the maxim whereby you can, at the same time, will that it should become a universal law.” For more information, visit the Categorical Imperative.

Imagine you can physically remove yourself from your body and objectively view how you make decisions. It’s like pulling your mind from your body.

This is essentially solving problems by working backwards. A simple example of this method is working backwards to solve a math problem.

For example, solve the following problem: “I think of a number and add three to it, multiply the result by 2, subtract 4 and divide by 7. The number I end up with is 2. What was the number I first thought of?” To solve, read the problem backwards. You start with: 2 x 7 = 14. Then take 14 + 4 = 18. From there take 18 / 2 = 9. Then take 9 – 3 = 6. Finally, the number you first thought of was 6.

Moreover, Reasoning Backwards can be viewed through the lens of deduction. I prefer deduction over induction and here is why:

An example of Inductive Reasoning is: this raven is black, that raven is black, all ravens are black.

Deductive Reasoning is: All ravens are black, that raven is black, therefore it is black.

We make deductions from laws to see what should happen and then experiment to see if our prediction was right. Think about it this way… to test whether a burner is hot, we must touch the burner first using Inductive Reasoning; however, if we were to use Deductive Reasoning, we would first predict the burner to be hot and would realize there is not need to touch it.

One last benefit of Reasoning Backwards is that it forces our linear and logical mind to catch things we wouldn’t normally catch. For example, read the following sentence:

After reading this sentence, you will realize that the the brain doesn’t recognize a second ‘the’.

Now read the sentence again, this time read it backwards. Did you notice that you missed the second ‘the’?

The UFMCS uses this as the single most important idea to enable critical thinking. For example, prior to taking on an issue, we should first think independently and reflectively, then write down our thoughts (which assists us in shaping and refining them), then share them in a disciplined manner. This takes us from divergence to convergence.

Boyd described a thought experiment in a presentation called Strategic Game of ? and ?. Through the process of Destructive Deduction (analyze and pull apart mental concepts into discrete parts) and Creative Induction (using these elements to form new mental concepts) we can create a new mental model that more closely aligns with reality.

Part 1 of his question:

“Imagine that you are on a ski slope with other skiers…that you are in Florida riding in an outboard motorboat, maybe even towing water-skiers. Imagine that you are riding a bicycle on a nice spring day. Imagine that you are a parent taking your son to a department store and that you notice he is fascinated by the toy tractors or tanks with rubber caterpillar treads.”

Part 2:

“Now imagine that you pull the skis off but you are still on the ski slope. Imagine also that you remove the outboard motor from the motorboat, and you are no longer in Florida. And from the bicycle you remove the handle-bar and discard the rest of the bike. Finally, you take off the rubber treads from the toy tractor or tanks. This leaves only the following separate pieces: skis, outboard motor, handlebars and rubber treads.”

What do you imagine could be created using the remaining parts? A Snowmobile

Let’s now turn our attention to the four simple rules within the OODA Loop.

Think of how we use sensors and gather information. In an ant colony, this is where ants shoot pheromones to signal others when they have found food.

Here we are detecting events within our environment and identifying change (or lack thereof). This could also be identified as Locate or Perceive (think swarming tactics or artificial intelligence).


  • Find out what is really there.
  • Observe first and gather data.
  • Identify the uncommon and common things. As Sherlock Holmes famously said, “What is out of common is a guide.” A great video on this point is The most unlikely threat from the hit movie Men in Black – watch the following…
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