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Oct 25, 2021

Asking “What If?” and Five Other Lessons in Red Teaming from the Joint Special Operations Command

Written by: Chris Blake



  • What if the ship you have been tracking for weeks, suspected to be full of illicit weapons, turns out to be a local fisherman?
  • What if the target compound, where the terrorist leader is hiding, isn’t his family home – but instead is full of armed ISIS fighters?
  • What if your “just-in-time” supply chain fails at an overseas juncture, outside your direct control?
  • What if your “sure bet” acquisition turns out to be a disaster of a company, one that’s rife with cultural issues and hidden financial challenges?
  • What if your well-intentioned strategy was founded upon faulty assumptions that went unchallenged – because they came from the top of your organization?


What If?

This simple, but powerful, question can make all the difference between success or failure. It can drive a team towards adaptive, flexible, and responsive leadership. It has, many times over, been the sole reason that elite military organizations and top tier businesses avoid failure and catastrophe.

“What if?” should be at the heart of an organization’s Red Teaming efforts. But asking “what if?” is not sufficient on its own. Through my time as a military Intelligence leader in the Joint Special Operations Command (JSOC), I have found five key concepts are critical to effective red teaming, especially in volatile, uncertain, and ambiguous circumstances.


Lesson 1: Leverage PRE-MORTEM ANALYSIS – Answering “What If?” With the Worst Possible Outcomes

The mission has failed. Lives were lost. Military objectives were left unmet. Why? Asking these hard questions before embarking on an operation – by assuming failure and evaluating the potential root causes – is a powerful approach to predicting problems. Gary Klein describes this red teaming exercise as a Pre-Mortem Analysis. By creatively considering how a chosen strategy, plan, or operation could possibly fail, and then painstakingly breaking down why the failure occurred, teams can implement proactive steps to address critical vulnerabilities or blind spots before the first round is shot – or the first dollar is invested.

This is easier said than done; to effectively conduct a Pre-Mortem Analysis, teams must consider a few other lessons.


Lesson 2: Employ Adversarial Empathy – “Act As If…”

In the Intelligence Community, a phenomenon known as “mirroring” serves as a foundational concept and cautionary warning that underpins all analysis, planning, and red teaming efforts. Mirroring, or the mirror-image fallacy, occurs when we evaluate threats, vulnerabilities, and risks from our own, rather than the adversary’s, perspective.

Red teaming must be founded in an adversary-centric approach – whether that adversary is Al Qaeda, Al Shabaab, or your firm’s closest market competitor. Professional empathy is a powerful tool and putting yourself “in the shoes” of those who could potentially upend your strategy or disrupt your operation enables you to see the same situation in a new light. But to do this effectively, you must see the whole problem, not just the readily evident surface effects. It’s important to “act as if” you’re the enemy to see the whole operating picture and execute effectively.


Lesson 3: Consider the Iceberg Effect – Endeavor to See the Whole Problem

At first glance, a potential problem may seem small and insignificant – a passing phenomenon with no apparent impact on you or the task at hand. But like an iceberg, this may be but a fraction of the whole. In red teaming, thoughtful and careful consideration of what lies beneath an issue can make the difference between dismissing something – like an anomalous earnings report in your due diligence analysis leading up to a merger – or keying in on a potential risk that nearly went unconsidered.

The best way to guarantee that your decision-making process succeeds is to ensure that your organization has an established, objective, end state-focused process in place to consider such potential threats.


Lesson 4: Focus on the Process – Build Red Team Structure, Support, Objectivity, and Repeatability

As leaders, the systems and practices we put into place must work not just in times of ease and routine, but also in the midst of crisis. Red teaming, by its nature, requires an insider’s perspective and an outsider’s objectivity; that kind of autonomy can’t happen without the right level of empowerment and support from the top.

In JSOC, tactical plans for high-risk operations are always red teamed by an objective team of elite military professionals who ensure that potential pitfalls are not overlooked by the assault force planners who will lead the operation. This process, wherein peers and colleagues “check each other’s homework” works because everyone knows that this red team effort is a critical, unemotional, and structured component of the Commander’s decision-making process that happens every time there is a complex life-and-death decision at hand. Overt and declarative support from the top of an organization, coupled with structured and objective techniques and a well-defined repeatable process, give these evaluations the power and impact needed to make red teaming work.


Lesson 5: Ask “What Else?” – Consider Competing Hypotheses

When a situation is complex enough to warrant red teaming, it’s safe to assume that success or failure hinges on a multitude of potential pitfalls rather than one glaring risk. Asking “what else?” – and evaluating a range of competing hypotheses about root causes beneath risks at hand – ensures that your leadership team doesn’t get overly focused on one potential hazard at the expense of another. In the military and Intelligence Community, asking “what else?” is a tried-and-true structured analytical technique called analysis of competing hypotheses. Applying analytical rigor and objective consideration across a range of potential assessments ensures that bias and premature decision-making doesn’t impede objective and fulsome consideration of all possible factors at play.


Applying Red Teaming Lessons Learned

Red teaming doesn’t happen on its own. Asking hard questions, objectively challenging assumptions, and finding flaws in a team’s plan require individual and organizational knowledge, skill, courage, and support. In the military, leaders are trained in red teaming techniques and learn how, when, and why to employ red teaming methodologies. But the military doesn’t hold a monopoly on complex problems and hard decisions. McChrystal Group's Red Team Solutions equip organizations with the tactical, strategic, and environmental tools, methods, and transformations required to compete and flourish in today’s complex business world, and give you tools your competitors are not using for their decisions.