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Five Habits of the Master Thinker: How to Upgrade Your Mind

Who has the time for slow thinking and rigorous analysis? The work is piling up, pressure is mounting, and deadlines are looming. How can we still get useful results if we need to make quick judgments and fast decisions? Randy Pherson, a former CIA analyst, got asked that question a lot. In response, Pherson devised the Five Habits of the Master Thinker. Granted, not everyone is an analyst. But once developed, the five habits of the master thinker can improve everyone’s ability to reason more instinctively and make better decisions. Here’s how we can upgrade our minds.

What Are the Five Habits of the Master Thinker?

The Five Habits of the Master Thinker are practices analytic thinkers will apply instinctively when they have to think quickly on their feet. They’re based on Pherson’s 2013 paper of the same name and were born out of Structured Analytic Techniques, SAT for short.

SATs are qualitative methods used by intelligence analysts to diagnose a problem, challenge their thinking, or anticipate future scenarios. I’ve covered three examples, Premortem Analysis, Red Team Analysis and Deception Detection in previous essays. The techniques aim to mitigate human biases and generally improve the rigour of analyses.

In essence, Pherson identified the core principles across the various SATs and distilled them into a single set of five habits of the master thinker worth cultivating.

Thinking, Habits and Mastery

Now before we dive into the habits themselves, let’s take a moment to consider the meaning of the key terms: thinking, habits and mastery.


According to critical thinking advocate David T. Moore, thinking “involves objectively connecting present beliefs with evidence in order to believe something else”. We’re essentially running a series of simulations in our heads. At best, we discard ideas that might cause us harm while we build upon those that will make life better. There are plenty of ways to deal with someone cutting us off in traffic. Not all of them get us home safely.

Cognitively, we have an intuitive system of thinking that relies on time-saving mental shortcuts. It enables us to solve complex problems quickly. When determining the distance to the car in front of us, for example. The slower part of our brains is much better suited for deliberate judgments, such as deciding whether we should get an electric car with automatic emergency braking.

While intuitive decisions are often flawed, deliberate solutions are time-consuming and resource-intensive. In a perfect world, we’d want our thinking to be lightning-fast and 100% objective. This is where habits come in.


James Clear, the author of Atomic Habits: Tiny Changes, Remarkable Results, defines habits as “the small decisions you make and actions you perform every day”. He notes that our lives are essentially the sum of all our habits combined. They add up. While habits tend to be unconscious, we can develop or change them for the better.

When it comes to our reasoning, we could say that the sum of our thinking habits determines the quality of our thinking. There are detrimental ones, such as defaulting to the supposed group consensus without giving an issue independent thought. And productive ones, such as those that put us on the path to becoming the eponymous master thinker.


That leaves us with the concept of mastery. Here’s one way to think about it: When we’ve mastered something, we’ve reached the state of unconscious competence. With ample practice and experience, we no longer need to think about what we’re doing and how. It just works, and almost by itself so. A skilful pianist doesn’t ponder the next note she will play. An expert driver shifts gears instinctively.

Similarly, a master thinker would be someone who unconsciously yet objectively connects present beliefs with evidence to believe something better. He or she must cultivate the key habits needed to instinctively evaluate information and pick the ideas that move things forward. Mastering our mind is a much more abstract and elusive skill than driving. That means we have to pick our habits even more carefully.

Five Habits of the Master Thinker

The key to becoming an expert thinker is to nurture those practices that will make the most difference when time is in short supply. So without any further ado, let’s get into them.

1. Challenge Your Key Assumptions

Our thinking and judgments stand and fall with the quality of our assumptions. An assumption is something we consider to be the case, even if we don’t have any proof (yet). Based on past experience, our mind constantly makes assumptions about the world. When visiting a Tesla store1, for example, we might assume the following: That neck-tattooed salesman in the ice cream-stained suit is not trustworthy.

What saves us time and energy can lead to wrong conclusions if our assumptions remain unchallenged. Unfortunately, they’re often implicit. So how are we supposed to challenge assumptions if we’re unaware of them? The short answer is that we can’t, which is why Pherson suggests starting by working in a team and questioning each other’s hypotheses.

Ideally, this collaborative approach matures to a culture with a healthy competitive angle. Once you expect your thinking to be challenged in such a way, you’ll pay more attention to what you assume to be true and why. That car salesman, why exactly do we think he’s not trustworthy? What evidence is there except for looks and a feeling? How — if at all — does this affect our decision about buying a Tesla?

2. Consider Alternative Explanations

Humans crave explanations. Try making a claim such as Everyone should own a Tesla and wait for the inevitable question: Why? Not all explanations are made equal, though. The availability heuristic can cause us to prefer the one that comes to mind first. However, the most obvious explanation for a phenomenon isn’t necessarily the correct one.

According to Pherson, it pays to instinctively look beyond the most obvious explanations. This is to avoid confirmation bias; when we ignore evidence that goes against a prior belief. And because the evidence situation may change; i.e. the most likely explanation could become the least likely one. To the very least, Pherson notes, a master thinker treats the possibility that their preferred explanation is wrong as a hypothesis on its own.

Regarding our car dealership example, what other feasible explanations exist for the salesman’s appearance and demeanour? Are they mutually exclusive? How would that change our judgement about him and the dealership?

3. Look for Inconsistent Data

This master thinker habit is purportedly the most beneficial in terms of time saved. In an everyday context, we can think of inconsistent data as conflicting information from different sources. If we come across substantial evidence that contradicts one of our explanations, we might be able to discard it and concentrate on a different one instead. Wittgenstein’s Ruler is a good place to start when it comes to matters of judgements.

As Pherson notes, looking for inconsistent data is the most difficult habit to develop. Not only do we need to have generated a set of alternative hypotheses. We must also develop a sense of what sound evidence looks like and how to use it to evaluate the veracity of our explanations.

That salesman is now chatting up a customer as if she was his wife. Now he’s hugging a kid eating ice cream. What do you mean, Tesla doesn’t even employ salespeople?

4. Focus on Key Drivers

Key driver is another term frequently used in analytic circles. It simply refers to the main factors that influence how things have been going or how they will go. Market growth for electric cars, for example, is driven by battery development, the availability of charging stations and gas prices. Changes in automotive painting technology…not so much.

If we practice watching for driving factors when we have time to think, we’ll be able to identify them more instinctively on occasions when we’re in a hurry. An untrained mind is likelier to spend an unreasonable amount of time thinking about trivial issues. The master thinker prioritises the factors that impact an issue the most.

So if it’s not neck tattoos and ice cream stains, what really drives our purchase decision? The reliability of the car, its price and the service quality will probably have a bigger impact on whether we’ll be happy with our purchase.

5. Consider the Overarching Context

Context is vital. In the English language, I’ll get the door, has an entirely different meaning depending on whether it’s said in your family home or on a construction site. The overarching context of our judgments and decisions matters in the same way. The master thinker intuitively considers the circumstances and conditions of an issue.

It goes without saying that this should be done before launching into an analysis. This habit entails looking at the big picture first. A few minutes to orient ourselves and reflect on the situation as a whole can once more save us time down the road. Only then is it time to consider the details and incorporate them back into said picture.

Taking a moment to reflect on the overarching context and what we’re trying to achieve would’ve saved us some time at the dealership. With the other habits combined, it would’ve kept us from getting all hung up on irrelevant details. The neck-tattooed manager of the Tesla store agrees as he greets us warmly.

* * *

In summary, to earn the title of a master thinker we must develop the following five habits:

  1. Challenge our assumptions by practising collaboratively with others
  2. Consider alternative explanations to mitigate our biases
  3. Look for contradicting information to save valuable time
  4. Keep our eyes on key drivers to reason more efficiently
  5. Assess the overall context before launching into judgment.

Closing Thoughts

Becoming a master thinker is an aspirational goal. True expert thinkers know the limitations of their minds. They leverage collaboration to mitigate biases and invest in cultivating reasoning habits when they have time to think deeply.

The five habits of the master thinker are born out of SATs. It makes sense that Pherson suggests regularly using them to “engrain new habits of thinking critically” in our minds. To learn more about the methods, check out his Handbook of Analytic Tools & Techniques or the CIA’s own Tradecraft Primer. But even without these analytic tools, verbalising our thought processes and writing them down will aid the development of our habits.2

In any case, cultivating new thinking patterns takes time. Start small by focusing on one or two of the five habits. Doing it imperfectly is better than not doing it at all. To channel James Clear: Every time we question an assumption, come up with alternative explanations or wonder what’s driving a problem, we’re casting a vote for our new identity as a master thinker.


  1. I am not affiliated with Tesla in any way. Rest assured, Tesla doesn’t even know I exist.
  2. Feel free to use this list of habits as a cheat sheet. Look them up for practice when you have time, then gradually try doing without them.