Red Team: How to Succeed by Thinking Like the Enemy: Summary & Key Insights

Red teaming at its core is a systematic approach to challenging assumptions. It began as a military term during the Cold War, when NATO and U.S. strategists realized that traditional exercises often reinforced what commanders already believed. They simulated “blue” forces (friendly units) fighting “red” forces (the enemy). But over time, some officers noticed that the red side often played its part too predictably—mirroring American logic rather than truly emulating Soviet thinking. So the concept evolved. A genuine red team would think as the adversary thinks, creatively, aggressively, in order to expose the weaknesses in blue team plans.

When I immersed myself in military archives and conducted interviews with practitioners, I saw that red teaming is not primarily about cynicism—it’s about empathy. To red team a plan is to inhabit another worldview and uncover what those living within it would exploit. The practice takes many forms: from physical penetration testing of security systems to ideational challenges to policy decisions. But all share the same essence: they create an independent structure inside the organization tasked with asking, “What if we’re wrong?”

Organizations often confuse red teaming with simple devil’s advocacy, but the difference is substantial. Devil’s advocacy is rhetorical; red teaming is procedural. It is embedded in the structure, designed to produce actionable insights. It requires autonomy, methodological rigor, and leadership willing to accept discomfort. Its aim is to prevent catastrophic surprise—the kind that occurs when blind confidence meets complex reality.

My research into U.S. and allied armed forces revealed that the military has been both the birthplace and the laboratory of red teaming. After the failures of operations like Desert One and the initial difficulties in Iraq, commanders recognized a flaw in their command culture: decisions were made in insulated rooms, filtered through hierarchy, and rarely subjected to adversarial stress tests. To change that, the U.S. Army formally institutionalized red teams through the University of Foreign Military and Cultural Studies at Fort Leavenworth. There, officers were trained not to plan operations—but to challenge them.

A compelling example is found in the Joint Warfighting Centers’ exercises, where red teams simulate enemy tactics, information warfare, and even cultural behaviors unfamiliar to American planners. Their purpose is not to embarrass commanders but to sharpen them. When red teams question an assumption—say, that local populations will react positively to foreign troop presence—they do so to prevent real-world miscalculations. As one general told me during an interview, “Our red team saved lives by forcing us to see how our plan looked from outside.”

The lesson from military red teams is that structured dissent must have legitimacy. The best units treat red teams as partners in truth-seeking, not as intruders. They understand that strategic surprise comes from overconfidence, and humility, though uncomfortable, is the warrior’s best defense.