Originally published in The Whirl of ReOrientation on April 30, 2025.
As global uncertainty accelerates—whether through geopolitical tensions, economic disruptions, or AI and technological shifts—traditional decision-making frameworks are increasingly falling short. Enter Red Teaming, a disciplined, meta-approach to thinking that challenges assumptions, mitigates cognitive biases, and fosters critical thinking. Originally honed in military contexts, Red Teaming is now proving indispensable in the business world, offering a structured way to navigate the unpredictable and ensure organizations remain agile, innovative, and resilient.
I want to draw on insights from four recent episodes of the No Way Out podcast, featuring Colonel (Ret.) Steve Rotkoff, a pioneer in Red Teaming education and former director of the University of Foreign Military and Cultural Studies (UFMCS); Dr. Gary Klein, a renowned cognitive psychologist whose work on naturalistic decision-making has saved lives in high-stakes environments; Dr. Inês Hipólito, a neuroscientist and philosopher whose research on the Free Energy Principle, active inference, and complex systems theory provides a neurological foundation for Red Teaming; and Dr. Eduardo Salas, a leading expert in team science whose work has transformed how teams collaborate in high-stakes industries. Together, their perspectives offer a comprehensive framework for understanding why Red Teaming, supported by cognitive, neurological, and team science principles, is essential for thriving in today’s uncertain landscape.
What Is Red Teaming, and Why Does It Matter?
At its core, Red Teaming is a meta way of thinking designed to improve decision-making by encouraging divergence before convergence. As Rotkoff explains, “You’re going to get as many ideas onto the table before you decide which is the best idea.” This principle ensures that the best ideas rise to the top, regardless of their source, by separating the quality of an idea from the seniority or persistence of its proponent. Red Teaming employs tools like liberating structures, anonymity, and role-playing to mitigate groupthink—a pervasive human tendency to self-censor in the presence of perceived authority.
A Red Team, by contrast, is a specific group assembled to tackle a particular problem using Red Teaming methods. For example, Verizon has integrated Red Teaming into its strategy group, adapting the methodology to fit its corporate needs. The distinction is critical: Red Teaming is the overarching philosophy, while a Red Team is the tactical application of that philosophy.
Dr. Gary Klein’s work on naturalistic decision-making complements Red Teaming by emphasizing the cognitive dimension of decision-making. “The cognitive dimension is largely invisible,” Klein notes. “It’s not a set of steps to follow. It’s what you have to know in order to follow those steps effectively, to know when to depart from those steps, when to modify those steps.” Dr. Inês Hipólito’s neuroscience perspective adds a deeper layer, explaining that the brain operates under what is known as active inference, a corollary to the free energy principle, actively predicting its environment to minimize uncertainty. “The brain is actively making predictions about what is the most likely cause of what it is perceiving in the world,” Hipólito says, highlighting the brain’s energy-efficient drive to reduce surprise.
Dr. Eduardo Salas brings the perspective of team science, emphasizing that effective collaboration is not innate but must be cultivated. “Collaborative teamwork does not come naturally,” Salas asserts, debunking the myth that teams automatically know how to work together. His 40 years of research demonstrate that teamwork requires deliberate development, management, and reinforcement, particularly in high-stakes environments where errors can be costly. Salas’ work aligns with Red Teaming’s goal of fostering diverse perspectives, as both approaches aim to enhance decision-making through structured, evidence-based practices.
In a VUCA world, the stakes of poor decision-making are higher than ever. Businesses face unprecedented challenges—supply chain disruptions, rapid technological change, and shifting consumer behaviors—that demand a more adaptive approach. Rotkoff’s work with the UFMCS was born out of a recognition of this reality in the military context, following the unexpected challenges of the Iraq War in 2004. The establishment of UFMCS aimed to embed Red Teaming into military culture, addressing the failure to challenge assumptions and hear dissenting voices—a lesson that applies equally to business.
The Business Case for Red Teaming: A Multidisciplinary Perspective
The lessons from the military are directly applicable to business, and the combined insights from cognitive psychology, neuroscience, and team science provide a robust rationale for Red Teaming. Rotkoff notes, “This idea of better decision-making, bringing people into the room, groupthink mitigation, alternative futures—all that stuff is really universally applicable.” According to Rotkoff, companies like Nextdoor and the Department of Energy have adopted Red Teaming to address complex challenges, from social media dynamics to rare earth mineral strategies.
Rotkoff shares an example of a software company that used Red Teaming to identify vulnerabilities in its financial strategy, recommending diversification away from Silicon Valley Bank—a suggestion initially dismissed but later validated by the bank’s crisis. This underscores Red Teaming’s ability to reveal weak signals, which Hipólito explains as a failure of the brain’s predictive models to update when relying on outdated priors. Red Teaming forces the brain to confront these discrepancies, reducing prediction errors and enhancing adaptability.
Salas’ team science perspective highlights why Red Teaming is critical for organizational success. He notes that innovation and knowledge generation often come from multidisciplinary teams, a finding supported by data from economists over the past decade. “Breakthroughs come from multidisciplinary teams,” Salas explains, citing industries like aviation, healthcare, and oil and gas where human performance reliability is paramount. In these high-reliability organizations, errors can lead to catastrophic outcomes, making effective teamwork essential. Red Teaming enhances this by ensuring that diverse perspectives are leveraged, preventing the kind of groupthink that can lead to costly mistakes.
Klein’s work further illustrates the importance of updating mental models, a process Red Teaming facilitates. In a story about an F-4 pilot transitioning to an A-6, Klein describes how a landing signal officer helped the pilot overcome a flawed mental model through experiential learning. The pilot was used to flying from the centerline of the F-4, and upon his transition to the A-6, his seat was now left of the aircraft centerline. This F-4 sight picture is problematic when landing an A-6 on an aircraft carrier. This aligns with Hipólito’s emphasis on the brain’s need to update its predictive models and Salas’ focus on shared mental models in teams. Salas explains, “We use the shared mental model idea… to convince commands that it matters,” noting its role in transforming Navy training practices after the USS Vincennes incident.
Red Teaming also fosters cognitive diversity, a key driver of innovation, which is supported by the brain’s need for multi-stability (Hipólito) and the team’s need for task interdependence (Salas). Ponch highlights a common pitfall: “They hire diverse folks to become a new organization, and then they just continue to do what they normally do.” Red Teaming ensures that diverse perspectives are actively leveraged, aligning with Salas’ continuum of task interdependence—from groups with low interdependence to teams requiring high coordination. “The higher the task interdependence, the more I need your expertise, your information to complete the task,” Salas says, emphasizing the need for competencies like psychological safety and collective efficacy in true teams.
Red Teaming in Action: Tools for a VUCA World, Enhanced by Team Science
Red Teaming offers a suite of practical tools to navigate uncertainty, enhanced by cognitive, neurological, and team science insights. Here are a few highlighted in the podcasts:
Divergence Before Convergence: Red Teaming encourages a wide range of ideas before narrowing down to the best ones, ensuring innovative solutions aren’t stifled. Neurologically, this fosters divergent thinking (Hipólito), while team science shows that multidisciplinary teams drive innovation (Salas).
Anonymity and Weighted Feedback: Techniques like dot voting and “Think-Write-Share” allow participants to contribute without fear of judgment, reducing social conformity bias (Hipólito) and fostering psychological safety (Salas). Rotkoff’s exercise at the New York Federal Reserve, where leaders anonymously wrote down organizational lies, revealed hidden truths that wouldn’t surface otherwise.
Pre-Mortem Analysis: Klein’s pre-mortem technique, where teams imagine a plan has failed, leverages counterfactual thinking (Hipólito) to flag potential mistakes and increase insights. Salas’ emphasis on debriefing complements this, as it provides a structured reflection process to learn from past actions, enhancing shared mental models.
Role-Playing and Four Ways of Seeing: Red Teaming’s role-playing uncovers blind spots by forcing alternative perspectives, aligning with the brain’s need for attunement (Hipólito) and the team’s need for coordination (Salas). Klein’s shadow box technique further enhances this by allowing participants to see scenarios through an expert’s eyes, improving alignment with expert thinking.
Assumption Analysis: Rotkoff stresses monitoring critical assumptions, a process supported by Klein’s Situation Awareness Calibration Card and Salas’ focus on shared mental models. Salas notes, “The more you structure the reflection… the better you are,” highlighting debriefing’s role in aligning team understanding and reducing surprise.
Tactical Decision Games (TDGs): Klein’s TDGs train leaders to make decisions under uncertainty, building resilience through speculative thinking. Salas’ simulation-based team training complements this, providing a practical way to practice competencies like communication and situational awareness, as seen in aviation’s Crew Resource Management (CRM).
Salas’ work in team science adds a critical layer with his emphasis on the team lifecycle: pre-brief, perform, debrief. “Teams that pre-brief (plan), perform, and debrief outperform those that don’t,” he says, citing industries like aviation and nuclear power. This disciplined routine aligns with the OODA loop’s focus on continuous learning and adaptation, ensuring teams can plan, execute, and assess effectively. Salas’ work on aviation Crew Resource Management (CRM), which includes competencies like decision-making, communication, and adaptability (DAMCLAS), has saved lives in aviation by fostering these skills, demonstrating the power of structured team training over superficial team-building activities.
The Urgency of Red Teaming in Today’s Context: Building Resilient Teams
The podcast discussions, recorded in the context of the 2023 Israeli-Palestinian conflict, underscore the urgency of Red Teaming. Rotkoff points to historical failures—like the 11th Attack Helicopter Regiment’s dismissal of a warning during Operation Iraqi Freedom—as evidence of the cost of failing to imagine alternative scenarios. Hipólito frames this as cognitive entropy, where closed systems collapse by refusing to exchange information, while Salas highlights the human cost in high-reliability organizations where poor teamwork leads to errors.
In business, companies like Kodak and Blockbuster failed to adapt to weak signals, a failure Hipólito likens to a “psychosis” of being out of touch with reality. Salas notes that organizations often operate as “teams in name only,” falling prey to myths that teamwork comes naturally or that they’re already doing it effectively. “You have to develop it, manage it, support it, reinforce it,” he stresses, emphasizing the need for evidence-based practices like Red Teaming to break these myths and build true collaboration.
The rapid pace of change—exacerbated by global events and technological disruptions—demands that organizations adopt Red Teaming to hedge against uncertainty. Salas’ work with the Navy’s TADMUS program after the USS Vincennes incident, alongside Klein’s contributions, transformed training by focusing on turning “a team of experts into an expert team.” This involved creating shared mental models, a concept Salas used to change Navy practices, aligning with Red Teaming’s goal of fostering collective understanding and adaptability.
Building a Red Teaming Culture: Integrating Team Science Principles
To harness Red Teaming’s power, organizations must build a culture that integrates its principles with team science insights. Leadership is key: toxic leaders can stifle efforts (Rotkoff), while supportive leaders sustain behaviors over time (Salas). “The challenge today is how to sustain these behaviors over time… that’s a top management issue,” Salas notes, pointing to the role of reward systems and organizational conditions in reinforcing teamwork.
Red Teaming must be simple and replicable, as Rotkoff and Klein emphasize with intuitive tools like “Think-Write-Share” and shadow box. Salas adds that team training, not team building, is the key to skill development. “Team building is necessary but not sufficient,” he says, advocating for simulation-based training and debriefing to build competencies like collective efficacy—the confidence that a team can achieve its goals, a powerful predictor of performance.
Finally, Red Teaming should be an ongoing practice, aligning with the OODA loop’s emphasis on continuous reorientation (Rotkoff), the brain’s need to update models (Hipólito), and the team’s need for structured reflection (Salas). By continuously challenging assumptions and preparing for alternative futures, organizations can build resilience, avoiding the cognitive entropy that leads to obsolescence.
Conclusion: Red Teaming as a Strategic Imperative, Grounded in Science
As uncertainty accelerates, Red Teaming, enriched by cognitive insights from Gary Klein, neurological foundations from Inês Hipólito, and team science principles from Eduardo Salas, is a strategic imperative. By fostering cognitive diversity, mitigating groupthink, and building resilient teams, Red Teaming equips organizations to thrive in a VUCA world. The combined insights from these experts serve as a clarion call for leaders to embrace Red Teaming as a science-backed approach to navigating complexity, ensuring adaptability and innovation in an ever-changing landscape.
Make sure you download a a free copy of the Flow System Guide and check out The Flow System. Quick note: Nigel recognized the value of the Red Teaming tools and techniques I was using when he and I started working together, and this—Red Teaming combined with Lean and Agile—from my perspective, is where The Flow System emerged.
