INTRODUCTION TO 

RED TEAM THINKINGTM

WORKBOOK 

DON’T OUTSOURCE THINKING! 

© 2023 TRUTHINKING CORP. 

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RED TEAM THINKING BOOT CAMP®

The general who wins a battle makes many calculations in his temple ere the battle is 

fought. The general who loses a battle makes but few calculations beforehand. Thus 

do many calculations lead to victory, and few calculations to defeat. 

~ Sun Tzu 

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INTRODUCTION TO RED TEAM THINKING 

Red Team Thinking is a cognitive capability that helps you: 

1. Engage critical thinking 

2. Enable distributed decision making 

3. Encourage diversity of thought 

4. Identify and understand threats and opportunities 

5. Make better decisions faster in your complex world 

6. Develop The Three Cs: Clarity, Capability, and Culture 

Red Team Thinking relies on a set of battle-tested applied critical thinking and 

groupthink-mitigation techniques that were originally developed by the military and 

intelligence agencies to meet the challenge of today’s volatile, uncertain, complex, 

ambiguous, and hyperconnected operating environment. Let’s unpack what these tools 

can do for you and your organization: 

Engaging critical thinking: Survey after survey has revealed that applied critical thinking 

is fast becoming one of the most essential skills for leaders today – and one of the most 

difficult to find. While critical thinking was once an essential part of post-secondary 

education in many countries, that is no longer the case. Colleges and universities have 

increasingly focused their curricula on more specialized courses that are ostensibly 

designed to prepare students for their future careers in relatively narrow fields. 

Unfortunately, this narrowed focus often leaves graduates without a practical 

understanding of how to think and make decisions in the real world. Red Team Thinking 

will help you develop these essential skills and use them every single day. 

Enabling distributed decision making: Distributed decision making means allowing 

frontline leaders – those at the coalface who have the best visibility and the most current 

information – to make decisions themselves in order to respond effectively in real time 

to the challenges and opportunities they are facing. Doing so makes organizations for 

adaptable, more resilient, and better able to cope with new developments and changing 

circumstances. In the military, this approach is referred to as mission command, or 

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Auftragstaktik by the Germans who pioneered this concept in 1800s and used it with 

great effect in World War I and World War II. Since then, other nations have tried hard 

to emulate this approach by giving lower-ranking officers the authority to think for 

themselves and modify their orders if necessary to achieve the desired outcome. 

Businesses around the world are also waking up to the benefits of this approach, but 

most still struggle to implement it. Red Team Thinking helps leaders do just that by 

showing them how they can give their subordinates the tools they need to make good 

decisions for themselves – and the confidence to allow it. 

Encouraging diversity of thought: Diversity and inclusion are hot topics in almost every 

workplace today. Companies and other organizations say they want to promote diversity 

and inclusion. Many spend a great deal of time and money on training and awareness 

programs. Most make a conscious, and often well-publicized, effort to promote and 

recruit individuals from diverse backgrounds. However, what most organizations don’t 

do is actually listen to the diverse perspectives and ideas these people bring to the table. 

That’s a shame, because listening to different perspectives is one of the keys to good 

decision making. The best idea can’t win if it is never even heard. That is why Red Team 

Thinking includes an array of techniques designed to help you surface ideas and insights 

from their entire team – because as the head of our D&I practice, Ellie Cloke, likes to 

say, “Diversity without inclusion is delusion.” 

Identifying and understanding threats and opportunities: One of the greatest fears every 

leader faces is the fear of the unknown. Not knowing what you don’t know makes it hard 

to sleep at night, let alone move forward with confidence. Red Team Thinking will help 

you see potential risks that lie ahead and uncover opportunities you might have missed 

so that you avoid the former and take advantage of the latter. 

Making better decisions faster in today’s complex world: The aim of all these things is 

to help individuals and organizations consistently make good decisions as quickly 

possible. Speed is essential because things change quickly in today’s world. What was 

the right decision yesterday, may not be the right decision tomorrow. A leader must 

make sure that the choices they have made remain sound and be prepared to modify 

their plans when necessary. That is why we refer to decision making as a practice, not a 

process. A process has a start and a finish; a practice is something you do regularly that 

improves your performance over time. The tools and techniques you will learn in this 

course are designed to help you make good decision making second nature. 

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What Red Team Thinking Is 

Red Team Thinking is both a mindset and a set of tools. The tools of Red Team Thinking 

are drawn from the tradecraft of intelligence analysts and the research of cognitive 

psychologists. They are designed to challenge assumptions, pressure-test plans, surface 

alternative perspectives, generate new options, and ensure that the best ideas win, 

regardless of where they come from in an organization. They work well enough by 

themselves, but the real power comes from coupling these techniques with a Red Team 

Thinking mindset. Adopting a Red Team Thinking mindset means taking nothing for 

granted. It means thinking the unthinkable, questioning the unquestionable, and being 

willing to challenging everything – not for the sake of argument, but in order to ensure 

that the decisions you make are really the best ones. Once you start looking at the world 

with this critical eye, you will be amazed at what you see. You will be stunned to discover 

how poorly thought out many plans are, how little people think about the second- and 

third-order impacts of their decisions, and how much what passes for planning is really 

just kicking the can down the road. It’s like taking the Red Pill and seeing through The 

Matrix. Once you do, you can’t unsee it. Gaining that penetrating insight will help you 

help you see more clearly, too. 

Red Team Thinking is both a science and an art. The science of Red Team Thinking is 

rooted in cognitive science and the psychology of decision making. For centuries, it was 

assumed that human beings generally made the best decisions possible with the 

information they had available. But in the past few decades, researchers have found that 

is simply not the case. They have discovered an uncomfortable truth: Each of us, no 

matter how smart, or well-educated or well-intentioned we may be, is unduly influenced 

by a dizzying array of cognitive biases and logical fallacies that skew our decision making 

and lead us in unintended directions without us even being aware of it. Red Team 

Thinking not only makes us aware of these biases and fallacies, but also offers us a means 

of overcoming them. The art of Red Team Thinking lies in deciding which tools and 

techniques to use under which circumstances. Red Team Thinking tools are like the clubs 

in a golf bag. Each one has its own purpose and using them effectively involves more 

than just knowing how to swing them correctly. You also must know where and when to 

use them. Successful use of Red Team Thinking also depends not just on knowing when 

to use these tools, but also when to stop using them and act. 

Red Team Thinking is about embracing change. Red Team Thinking is predicated on the 

understanding that there is no end state for any company and no equilibrium in the 

marketplace. Change is the only constant. No matter how dominant or great an 

organization or business is today, the only way it can stay great is to continue to evolve. 

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As MIT management guru Peter Senge wrote in his seminal work The Fifth Discipline, “a 

corporation cannot be ‘excellent’ in the sense of having arrived at a permanent 

excellence; it is always in the state of practicing the disciplines of learning, of getting 

better or worse.” 

What Red Team Thinking Is Not

Red Team Thinking is not an excuse for inaction. General George S. Patton famously 

said, “A good plan, violently executed now, is better than a perfect plan next week.” But 

an unexamined plan will never be as good as one that has been subjected to critical 

analysis. Red Team Thinking can be used to provide an in-depth, formal analysis when 

that is merited, but these tools and techniques are designed to be used quickly and 

efficiently without slowing down the decision-making process or preventing a decision 

from being made when one is required. 

Red Team Thinking is not fortune-telling. Some of the Red Team Thinking tools are 

designed to help you understand the different ways in which the future could unfold so 

that you can modify your plans to better ensure success or mitigate the impact of 

potential failures. But none of them are a crystal ball. The only way to avoid surprise is 

to expect the unexpected. 

Red Team Thinking is not negative or cynical. There is a big difference between being 

critical and being negative, just as there is a big difference between being sceptical and 

being cynical. These are important distinctions. Sceptics ask tough questions to make 

sure they are making the right choice and moving forward in the best direction; cynics 

ask tough questions to undermine confidence and cast everything in a negative light. 

Red Team Thinkers should always be sceptical, but they should never be cynical. You 

should always use these tools in a constructive and collegial manner, and you should 

teach your clients to do the same. Otherwise, they run the risk of alienating their 

colleagues, making it impossible for them to listen to their analysis and learn from their 

insights. 

Red Team Thinking is not a panacea. Red Team Thinking is not a replacement for a good 

product or a compelling service, but it can help to make a company’s products and 

services better. Red Team Thinking cannot overcome the business cycle, but it can help 

a company better weather its ups and downs. Red Team Thinking cannot prevent new 

competitors from entering the marketplace, but it can help a company respond more 

effectively when they do. Red Team Thinking cannot change an organization that does 

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not want to evolve, but it can provide powerful insights and guidance to those that do. 

Red Team Thinking is not a replacement for good leadership, but it can make a good 

leader great. 

The Origins of Red Team Thinking 

Red Team Thinking’s roots run deep – all the way back to the Greek philosopher Socrates 

(c. 470-399 B.C.E.), who used probing questions to challenge the prevailing wisdom of 

his contemporaries and uncover powerful truths. This was really the start of critical 

thinking, but it did not end there. 

During the European Renaissance Pope Sixtus V created the office of the advocatus 

diaboli or “devil’s advocate” in 1587 C.E. to deliberately challenge candidates for 

sainthood. This appears to be the first instance of an organization developing a formal 

process for challenging its own thinking in a contrarian way, but it was not the last. 

In the early 1800s, the Prussian military developed a new concept called Kriegsspiel or 

“wargaming” that it used to stress-test strategies through tabletop exercises before 

implementing them on the battlefield. To do this, Prussian officers divided themselves 

into two groups. One group played the Prussian side, represented on the gameboard 

by pieces painted in their national color, blue. They were the blue team. The other side 

played enemy, represented by red game pieces. They were the red team. This is where 

the terms red team and red teaming originate. It is also the first example of an 

organization using a formal, deliberate process to stress-test its own strategies, and 

militaries around the world soon adopted this approach once they saw how effective it 

could be. During the Cold War, for example, the United States military and intelligence 

agencies set up red teams to get inside the head of their Soviet adversaries to try to 

understand their thinking and anticipate their moves on the global geopolitical 

chessboard. 

In the wake of the terrorist attacks of September 11, 2001, and the disastrous wars that 

followed them, the American military and intelligence agencies began using a similar 

approaching to challenge not just their strategies and plans, but also the assumptions 

and beliefs that informed these strategies and plans in order to make better decisions. 

They called this approach decision-support red teaming. 

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RED TEAM THINKING BOOT CAMP®

”Red teams are established by an enterprise to challenge aspects of that very 

enterprise’s plans, programs, assumptions, etc. It is this aspect of deliberate challenge 

that distinguishes red teaming from other management tools.” 

~ U.S. Department of Defense 

This formal red teaming approach proved to be tremendously valuable and was rapidly 

adopted by allied militaries and intelligence agencies around the world. However, it also 

created its own challenges. Formal red teaming: 

• Requires outside facilitators or a dedicated, in-house team 

• Requires extensive training 

• Can be time-consuming 

• Can create political challenges within an organization 

• Can slow down decision making if not conducted in a focused and disciplined 

manner 

Red Team Thinking was created to overcome these deficiencies and enable individuals 

and organizations to employ these game-changing tools and techniques more easily and 

effectively. 

Red Team Thinking, in contrast: 

• Does not require a separate red team 

• Can be used informally with a small, ad-hoc group or even individually 

• Easier to learn and simpler to practice 

• Works at every level of an organization 

• Does not require buy-in from others 

• Is fast and adaptable, allowing you to make better decisions faster 

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WHY WE NEED RED TEAM THINKING TODAY 

“In 2025, analytical thinking, creativity, and flexibility will be among the most soughtafter skills.” 

~ World Economic Forum (October 2020) 

“All humans think, but few consciously focus on the process of thinking.” 

~ Training Industry (March 2022) 

“Demand for ... higher cognitive skills will grow.” 

~ McKinsey (June 2022) 

Applied critical thinking and decision making are two of the most needed skills in the 

world today. Demand for these skills is so high because we now live and work in a world 

defined by: 

• Volatility 

• Uncertainty 

• Complexity 

• Ambiguity 

• Hyperconnectivity 

This was the case before the present pandemic, and the world has only become more 

volatile, more uncertain, more complex, more ambiguous, and more hyperconnected 

since Covid-19 first emerged. 

The other reason we need Red Team Thinking is because most organizations die from 

self-inflicted wounds. If you study the history of business you will find few corporations 

that went bankrupt because of a new competitor or a new technology; rather, it was their 

reaction to that new competitor or new technology (or lack of reaction) that destroyed 

their business. Others have fallen victim to internal politics and infighting. Red Team 

Thinking is designed to combat complacency, overcome inertia, and help companies 

think disruptively about their own business before someone else disrupts them. 

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THE PSYCHOLOGY OF RED TEAMING 

You believe you know what goes on in your mind, which often consists of one 

conscious thought leading in an orderly way to another. But that is not the only way 

the mind works, nor indeed is that the typical way. Most impressions and thoughts 

arise in your conscious experience without your knowing how they got there. 

~ Dr. Daniel Kahneman 

Red Team Thinking is based on the latest research in neuroscience, cognitive 

psychology, and human decision making. Scientists and psychologists working in these 

fields have identified to forms of thinking. 

• System 1 Thinking: Automatic, intuitive, instinctual. 

• System 2 Thinking: Deliberate, methodical, analytical. 

Dr. Daniel Kahneman, who won the Nobel Prize for his work in this area, calls System 1 

Thinking “a machine for jumping to conclusions.” System 2 Thinking is much more 

rigorous and reliable. But there is a problem: “Its operations are effortful, and one of its 

main characteristics is laziness, a reluctance to invest more effort than is strictly necessary. 

As a consequence, the thoughts and actions that System 2 believes it has chosen are 

often guided by ... System 1.” 

That leads us to make some very bad decisions, both as individuals and as organizations. 

Why? Because all of us – no matter how smart we are, no matter how well-educated we 

are, no more how experienced we are, no matter how successful we are – fall victim to a 

dizzying array of cognitive biases and heuristics that skew our thinking in ways we are 

not even aware of. 

• Cognitive Bias: Cognitive biases are inherent, systematic errors in our thinking 

that follow predictable patterns. 

• Mental Heuristics: Heuristics are often-unconscious mental shortcuts that help us 

make quick decisions — though not necessarily correct ones. 

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Making good decisions becomes even more difficult in organizations, particularly in 

large, complex ones like militaries or multinational corporations. In addition to acting as 

an echo chamber of cognitive bias, the hierarchical nature of organizations creates 

additional challenges, including: 

• Groupthink: The tendency to value consensus at the expense of independent, 

critical thinking and constructive debate. 

• Satisficing: The practice of making a decision by choosing the first available option 

that works – even if it is not the best one. 

• Bureaucracy: The creation of overly complicated internal processes that slow 

down decision making and discourage consideration of multiple options. 

• Internal Politics: The games people play in the workplace at the expense of the 

organization they are supposed to be serving. 

• Careerism: The tendency to make decision based on what is most likely to protect 

or promote one’s own position, rather than on what is best for the organization as 

a whole. 

How does Red Team Thinking help? 

Red Team Thinking helps overcome cognitive bias, mitigate groupthink, and improve 

organizational decision making by: 

• Offering tools to counter unconscious biases 

• Engaging “System 2” thinking 

• Providing techniques to surface alternative perspectives 

• Allowing all voices to be heard 

• Forcing you to challenge your own assumptions 

• Leveraging the wisdom of the group to overcome the blind spots of the individual 

• Enabling you to make better decisions faster in today’s complex world 

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THE RED TEAM THINKING TOOLKIT 

There are many different tools in the Red Team Thinking toolkit. They include analytical 

techniques, imaginative techniques, and contrarian techniques. 

Analytical Techniques 

These tools are designed to break a strategy, plan, or problem down into its underlying 

assumptions, stress-test these assumptions, and also identify both the different ways the 

plan could unfold and the critical stakeholders that could contribute to its success or 

failure. Examples include: 

• Six Strategic QuestionsTM: A tool for ensuring that your strategy is solving the right 

problem and will lead to the desired outcomes. 

• Assumptions ChallengeTM: A technique for identifying and challenging the stated 

and unstated assumptions upon which a plan or strategy is based. 

• Alternative Futures Analysis: A method for looking at the different ways a plan 

could unfold. 

• Influencer EngineeringTM: A tool designed to identify key stakeholders who could 

influence the success or failure of a strategy or initiative, as well as the 

opportunities that exist to increase their support or blunt their opposition. 

Imaginative Techniques 

These tools are designed to uncover the ways in which a plan could fail in order to ensure 

that it does not, explore the ways future events could impact your organization positively 

or negatively, and help you examine a problem from the perspective of key stakeholders. 

Examples include: 

• PreMortem Analysis: A technique for figuring out how a plan could go wrong and 

exposing the hidden weaknesses in it. 

• Four Ways of Seeing: A tool designed to examine an issue from the point of view 

of key stakeholders. 

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• Swan DiveTM: A systematic method for exploring the ways in which a future event 

could play out or impact a particular plan. 

Contrarian Techniques 

These tools are designed to leverage contrarian thinking to surface new options and 

ideas, regardless of where they come from within an organization, while also preventing 

self-inflicted wounds. Examples include: 

• Devil’s TroikaTM: A technique designed to stress-testing strategies, plans and 

hypotheses before committing to one of them. 

• Weighted Anonymous FeedbackTM: A system for assessing what people really 

think of an idea or option. 

• The Enemy WithinTM: A tool designed to expose the things an organization is doing 

to defeat itself. 

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LIBERATING STRUCTURES: Think/Write/Share 

One thing a person cannot do, no matter how rigorous his analysis or heroic his 

imagination, is to draw up a list of things that would never occur to him. 

~ Thomas Schelling 

To further support the concept of Red Team Thinking, we use a number of simple 

groupthink mitigation techniques called Liberating Structures. A core principle of Red 

Team Thinking is to start with divergent thinking and move toward convergent thinking 

in order to ensure that the best idea wins, regardless of where it arises from within the 

organization. Too often, people with good ideas keep them to themselves. Often, this is 

because they conflict with those espoused by others above them in the organizational 

hierarchy. In other cases, this self-censorship is the product of a lack of confidence. Either 

way, the only way to make sure the best idea gets a fair hearing is make sure that all 

ideas are on the table. 

The most basic of these techniques, and the most important, is called Think-Write-Share. 

This technique may seem very simple, but it was originally developed by the U.S. Army 

and is based on some very powerful neuroscience. Here’s how it works: 

STEP 1: Start by asking team members to think about a problem or question. 

STEP 2: Have each person write down their thoughts. 

STEP 3: Then share them with the group. 

This sequence is important because, too often, people working together in groups are 

in a rush to share their ideas. They are eager to demonstrate how smart they are or 

establish their expertise with the topic under consideration. Red Team Thinking is not 

about intellectual grandstanding; it is about taking the time to consider everybody’s 

ideas fully. 

More importantly, taking a minute to think before writing or speaking forces everyone to 

engage System 2 thinking. By requiring a short amount of time for silent reflection at the 

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beginning, team members have a chance to consider their responses before sharing 

them with the group. 

Writing those responses down is important, too, because it forces people to “own” their 

answers. It is far easier to equivocate when people are just blurting out the first thing 

that comes to mind. This method also forces people to pre-commit to an idea and not 

modify their thinking based on what they hear from the rest of the group. Moreover, 

neuroscience has demonstrated that the act of writing deepens cognition, further 

engaging System 2 thinking. That is why you may often find that you change or modify 

your initial answer when you start writing it down. 

The final step, sharing, is essential because a key aim of Red Team Thinking is promoting 

diversity of thought and moving from divergent thinking to convergent thinking. 

Thinking first, then writing down your ideas enables full focus when others are sharing 

their ideas, this is called active listening. This means making a conscious effort to hear 

not only the words that the other person is saying but also the complete message being 

communicated. In order to do this, you must pay attention to the other person very 

carefully. This doesn’t often happen, as people are usually thinking about their own 

responses or who will get picked next. However, with Think-Write-Share, you can pay 

more attention to each speaker because you have already taken the time to think and 

write down your own thoughts. 

Because this method is so easy to use and so powerful, we use Think-Write-Share as part 

of almost every other Red Team Thinking tool and technique. Even if you are working by 

yourself, there is still value in taking time to reflect, then writing those reflections down – 

even if you share them with no one other than yourself. If nothing else, you can look back 

on them later to see how close your initial thoughts were to hitting the mark. 

If you are a leader, you can use this method in meetings with your team to: 

• Surface diverse ideas and perspectives (CLARITY) 

• Engage System 2 thinking (CAPABILITY) 

• Ensure that everyone’s voice is heard (CULTURE) 

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SIX STRATEGIC QUESTIONSTM

Strategy is about making choices. 

~ Michael Porter 

Human beings are natural problem solvers. When we are presented with a problem, 

most of us start trying to solve it before it has even been fully articulated. Few of us take 

the time to consider whether it is even problem worth solving in the first place. Even if it 

is, our haste can prevent from fully considering the implications of our solution. 

To make sure that does not happen, a number of strategic planning processes have been 

developed. While these can help organizations make better strategic decisions, these 

processes are often reduced to a series of boxes to be checked by planners. Moreover, 

in many organizations, the processes that do exist are often subverted by the public 

musings of senior leaders, which are too often taken as direct orders — even when they 

are not intended as such. 

When this happens, the work of planners becomes focused anticipating what senior 

leaders want to see rather than on what the organization needs to succeed. 

To combat this dangerous tendency, we have developed a simple exercise you can 

conduct at the start of any planning discussion to make sure you are heading in the right 

direction: Six Strategic Questions. 

Six Strategic Questions is based on a simple practice developed by the U.S. Army’s elite 

Delta Force. Whenever Delta is given a new mission, its officers ask themselves a series 

of questions designed to determine what success would look like. By beginning with a 

clear picture of the desired end-state, they are better able to formulate an effective plan 

for achieving those results. 

We have taken those original questions, modified them to be more broadly applicable, 

and added several additional questions to help planners think more holistically about 

the problem they are trying to solve, consider other options, weigh the opportunity 

costs, and ensure that the team is aligned on the correct course of action. 

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Before beginning work on any strategy or plan, or before red teaming an existing 

proposal, ask yourself the following six questions: 

1. What is the problem we are trying to solve? 

2. Is it the right problem? 

3. If we do this, what are we choosing not to do? 

4. If this plan is executed, what will our organization look like? 

5. If this plan is executed, what will our key stakeholders look like? 

6. If this plan is executed, what will the operating environment look like? 

You can use Six Strategic Questions in your organization to: 

• Stress-test strategies and plans (CLARITY) 

• Create alignment and ensure everyone is rowing in the same direction (CLARITY 

and CULTURE) 

• Develop new strategies and plans (CAPABILITY) 

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MORE WAYS TO START USING RED TEAM THINKING 

The easy way out usually leads back in. 

~ Peter Senge 

Here are some additional things you can begin doing right now to apply start using Red 

Team Thinking to make better decisions today, both for your organization and for 

yourself: 

1. CHALLENGE YOUR ASSUMPTIONS 

• Make a list of the stated and unstated assumptions that underly your plan or 

strategy. 

• How certain you are that they will prove true? 

• What could you do to help make sure they do prove true? 

• Develop options in case they don’t. 

2. CONTEMPLATE FAILURE 

• Imagine that your plan or strategy fails spectacularly. 

• Working backwards, ask yourself how this failure occurred? 

• What could you do to avoid that? 

3. CONSIDER THE ALTERNATIVES 

• Don’t just go with the first viable idea that occurs to you. 

• Force yourself to come up with another viable alternative. 

• Weigh your options and see if there is a third way that includes the best elements 

of both. 

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Continue Your Training 

There are many opportunities for you to continue your Red Team Thinking training and 

learn all the other RTT tools and techniques: 

• Training for yourself: If you want more Red Team Thinking training for yourself, or 

want to become a Certified Red Team Leader, join our Red Team Coaching 

program, offered in partnership with Coaching.com. 

• Training for your organization: If you want Red Team Thinking training for your 

organization, bring us in to lead a Red Team Thinking Workshop and find out how 

Red Team Thinking can help you become one of the disruptors, rather than one 

of the disrupted. 

• RTT Online Community: Join our online community and be part of the growing, 

global cadre of Red Team Thinkers! 

To learn more, please visit: redteamthinking.com 

WELCOME TO THE INSURGENCY! 

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