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Building a Red Teamer’s Library

By Michael Rogan

We have all heard the saying: “All readers are leaders.” Well, if you want to be a Red Teamer or think like a Red Teamer, then you must be a reader. Red Teamers generally read from a broad range of academic disciplines. This article posits that anyone can improve their knowledge to make better decisions by reading and reflecting on the wisdom available in books relevant to Red Teaming.

Red Teaming is both a mindset and a skillset that helps individuals and organizations make better decisions. Red Teaming is the artful application of structured analytical tools and techniques that can provide commanders an independent capability to fully explore alternative plans, operations, and concepts in the context of the operational environment and from the perspectives of partners, adversaries, and others. 

As Colin Gray states in Another Bloody Century, the study of war is ultimately about “context, context, context.”  Thus, the Red Teamer must research and study the anticipated and actual operational environment. During this preparation, humility is critical. Hubris is the Red Teamer’s nemesis. Another essential quality for the Red Teamer is to not mirror image or take an ethnocentric perspective towards another culture. Strategic empathy is cognitive; it is not sympathy. 

I could provide a few books that are essential reading for the South China Sea, the Korean Peninsula, or the Baltics, but the list of recommendations in this article is more about gaining a Red Teamer’s mindset to think better about operational and strategic problem sets. Red Teaming is ultimately about better thinking. A better thinker is a better planner, operator, communicator, and leader.

As a foundational text, every Red Team student receives a copy of the Red Teaming Handbook. This handbook is an aide-memoire that is a compilation of structured analytic techniques and tools. It also encourages the Red Teamer to increase their self-awareness, ability to reflect, and willingness to empathize with others. This handbook serves as a playbook, not a rulebook. The Red Teamer is encouraged to modify the techniques and tools as needed and not just blindly execute as written. 

The following 10 book recommendations are a starting point for building a Red Teamer’s library; each provides insight into the Red Teamer’s mindset:

1-The Logic of Failure by Dietrich Dorner  – This book is fundamental to understand why and how humans make errors in cognition. Dorner writes: “People court failure in predictable ways.” That statement is powerful and true. This book is a seminal work for Red Teamers as it spans the interrelated topics of complexity, systems thinking, modeling, and decision making.

2-Farsighted: How We Make the Decisions That Matter the Most by Steven Johnson   – This is an easy and enjoyable read. Johnson outlines a process employing mapping, predicting, and then deciding. He uses the SEAL Team Six raid on Osama bin Laden’s compound in Abbottabad as an example of a deliberate decision process. Johnson also relates how reading fiction allows us to empathize with characters who make full spectrum decisions with variables spanning multiple scales.

3-Thinking Fast and Slow by Daniel Kahneman   – Nobel Prize winning cognitive psychologist Daniel Kahneman eloquently describes the human brain’s two systems: System 1 (fast thinking) and System 2 (slow deliberate thinking). The big idea is that humans should slow down their thinking when making important decisions to avoid the trap of cognitive biases and experienced-based decision-making shortcuts (heuristics) that could lead them astray. 

4-Red Teaming: How Your Business Can Conquer the Competition by Challenging Everything by Bryce Hoffman – The author, who attended a UFMCS resident course in 2013, describes Red Teaming as it is taught in the Army’s schoolhouse. Hoffman explains the most basic and intuitive Red Teaming tools and how to effectively apply them. The target audience for the book is professionals in the business world. 

5-Superforecasting: The Art and Science of Prediction by Phillip E. Tetlock and Dan Gardner  – Tetlock uses Isaiah Berlin’s essay on the fox and the hedgehog to explain the qualities of a superforecaster. A hedgehog knows one thing; a fox knows many things. Thus, foxes make better predictions because they account for more variables and adjust as new information is revealed. Like a superforecaster, a good Red Teamer approaches a problem with an interdisciplinary and open-minded approach. 

6-Asking the Right Questions: A Guide to Critical Thinking by M. Neil Browne and Stuart M. Keeley (11th Edition) – There are many books on critical thinking. This is one of the best. It is clear, concise, and compelling (The three Cs is courtesy of Joseph McCormack, author of Brief). The chapter on logical fallacies is essential reading for the UFMCS lesson on argument deconstruction. Good questions are designed to gain insights, develop deeper understanding, and uncover flawed assumptions.

7-The Culture Code: The Secrets of Highly Successful Groups by Daniel Coyle – Culture for the Red Teamer may be civilizational or organizational. This book focuses on the latter. The two characters who most stand out for setting conditions to build great teams are retired Navy SEAL operator Dave Cooper and San Antonio Spurs coach Gregg Popovich. Cooper expresses the ideal conditions for conducting productive After-Action Reviews (AARs): “Rank switched off, humility switched on.”

8-On Grand Strategy by John Lewis Gaddis – A military professional must understand strategy. Period. A strategic thinker must understand strategy for the thinking to be strategic. Gaddis uses the timeless wisdom of historical literary classics (Sun Tzu, Machiavelli, and Tolstoy) to explain the relationship of ends (aspirations) which are infinite and means (capabilities) which are finite. Gaddis uses the framework of time, space, and scale to examine how the best grand strategists do strategy. Additionally, Gaddis does an outstanding job distilling Carl von Clausewitz for the general reader. 

9-Humble Inquiry: The Gentle Art of Asking Instead of Telling by Edgar Schein – Better group processes lead to better decisions, which improve the probability of a favorable outcome. As Americans, we tend to focus on tasks over relationships. This approach can get us in trouble when working with foreign partners. Red Teamers must consciously resist the gravitational pull of Western thought. 

10-The Return of Marco Polo’s World: War, Strategy, and American Interests in the Twenty-first Century by Robert Kaplan – Kaplan is the writer who best synthesizes the topics of strategy, culture, and geography. This volume is a collection of 16 essays by Kaplan that starts with one written for the Pentagon’s Office of Net Assessment in 2016 that appraises the strategic context of Eurasia. Everything written by Robert Kaplan is high quality and readable. This was chosen because it is topical and displays the contextual depth and breadth of his writing.

These are my recommendations to start building a Red Teamer’s library. The list is prioritized. Thus, I recommend starting at number one, but feel free to follow your intellectual curiosity. The list reflects my personal biases, in that it shows what I believe is most important for a Red Teamer. In true Red Team fashion, each of my colleagues has a different top 10 list, and I welcome debate and discussion on the merits of yours. 

Mike Rogan is a seminar leader at the US Army University of Foreign Military and Cultural Studies at Fort Leavenworth, Kansas. He is employed as a contractor by Yorktown Systems Group. Mike is a retired Special Forces warrant officer who instructs the 12-week Special Operations Campaign Artistry Program (SOCAP) course that awards its graduates the Red Team Leader additional skill identifier (ASI 7G). SOCAP is a resident course that is held annually from April through June, but it was conducted online this past year due to COVID-19. 

Approved for public release. Distribution is unlimited. The views expressed in this article are the personal views of the author and do not necessarily reflect the views of the military Services, the U.S. Army University of Foreign Military and Cultural Studies (UFMCS), or the DoD.


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