War Games in the Boardroom: A GC’s AI Playbook for Red Teaming

Sitting at my desk, surrounded by neatly stacked legal briefs and compliance documents, I sometimes reflect on the vast, unforgiving desert where I first learned the art of Red Teaming. As a Marine helicopter pilot, I participated in exercises designed to test our resilience, strategy, and adaptability. The stakes were high in the desert: a misstep in planning or execution could mean the difference between mission success and failure, or worse. Today, as a General Counsel, I strive to employ the same discipline and critical mindset to “red team” my legal work. While the terrain has shifted from dunes to boardrooms, the principles remain the same—anticipate threats, test weaknesses, and build strategies as robust as the aircraft I once flew.

In the military, every mission begins with a briefing. We’d gather in a hot, cramped tent, poring over maps and intelligence reports, preparing for a simulated attack from the Red Team. Their role was to think like the enemy, exploiting our vulnerabilities and testing our defenses. As the General Counsel, the mission briefing involves understanding the legal and business landscape. The "enemy" might be opposing counsel in litigation, regulatory scrutiny, or an unforeseen compliance gap. My tools are no longer flight plans and radar systems but statutes, case law, and AI-powered legal technology.

The first step in any effective Red Team exercise is preparation. Before tackling a legal issue, I use AI tools to simulate opposing perspectives. For example, when reviewing a contract, I increasingly use AI-powered analysis to surface ambiguities or clauses that could be exploited in a dispute. It’s akin to scanning the desert for enemy ambush points. The AI doesn’t replace my judgment—it enhances it, allowing me to anticipate challenges that may not be immediately apparent.

The Red Team’s job in the desert was to attack us where we were weakest. They might feint an air assault to distract us from an approaching convoy or exploit gaps in our perimeter defenses. Similarly, my role as General Counsel is to anticipate how our legal strategies could be attacked.

When reviewing a litigation brief, I imagine the opposing counsel sitting across the table, dissecting my arguments. AI assists in this by generating plausible counterarguments or highlighting inconsistencies in reasoning. For instance, if we argue for dismissal in any employment matter, I’ll use AI to predict potential responses from plaintiffs’ attorneys. This process forces me to confront uncomfortable truths about my case's weaknesses, ensuring that every argument is fortified before it ever reaches the courtroom.

Contracts, too, undergo rigorous testing. AI contract review tools act as a Red Team, identifying vague terms or risky clauses. For example, if a force majeure clause in a vendor agreement doesn’t adequately protect against supply chain disruptions, the AI flags it. This mirrors the military practice of running scenarios to see where a plan might collapse under pressure. The result? Contracts that are as resilient as a well-fortified base.

Flying over the desert, we often encountered unexpected challenges—sudden sandstorms, mechanical failures, or enemy fire. These moments taught me the value of adaptability and thorough preparation. In the corporate world, regulatory compliance presents similar unpredictability. Laws evolve, regulators shift their focus, and enforcement trends emerge without warning.

To red-team our compliance programs, I use AI to simulate regulatory scrutiny. These tools analyze policies against the latest legal standards, identifying gaps that could trigger penalties or enforcement actions. For example, when reviewing our company’s DEI initiatives, I rely on AI to ensure alignment with Title VII of the Civil Rights Act. The process is not unlike conducting a pre-flight inspection: every bolt and rotor must be checked to ensure the aircraft is mission-ready.

Stress-testing compliance programs also means preparing for worst-case scenarios. Just as we trained for emergency landings in hostile territory, we simulate a corporate crises—such as a data breach or environmental incident—to evaluate our response plans. These drills expose vulnerabilities, allowing us to address them before the real-world equivalent of “enemy fire” strikes.

In the desert, success depended on trust and collaboration. Pilots, mechanics, and ground crews worked seamlessly, each person fulfilling their role with precision. In my legal team, the same principle applies. Red Teaming is not a solo effort; it requires input from diverse perspectives.

AI fosters collaboration by breaking down silos of information. For instance, we integrate input from IT, legal, and risk management teams when evaluating cybersecurity risk. AI synthesizes their insights, identifying patterns and risks that might go unnoticed. It’s akin to coordinating air and ground units during a mission; each perspective strengthens the overall strategy.

Accountability is another cornerstone of Red Teaming. In the military, after-action reviews ensured that every mistake was analyzed and lessons were learned. As a General Counsel, I conduct similar reviews after major legal projects. AI tools help by providing data-driven insights into what worked and what didn’t. Whether tracking litigation outcomes or analyzing the effectiveness of compliance initiatives, these reviews ensure continuous improvement.

The desert taught me that no plan survives first contact with the enemy. Flexibility and innovation were essential to adapting to changing conditions. In the legal world, AI is the innovation that allows me to adjust. It acts as a compass and a co-pilot, guiding me through complex terrain.

For example, AI helps me anticipate shareholder concerns in corporate governance by analyzing proxy statements and SEC filing trends. It’s a proactive approach, much like using reconnaissance drones to gather intelligence before a mission. Similarly, AI-powered litigation tools can predict case outcomes based on historical data, allowing me to adjust strategies before stepping into the courtroom.

However, just as advanced avionics didn’t replace the need for skilled pilots, AI doesn’t replace the need for experienced legal counsel. The tools are only as effective as the person wielding them. My judgment, honed in the cockpit and the courtroom, remains the ultimate arbiter of decisions.

After every Red Team exercise, we debriefed to identify what went right, what went wrong, and how we could improve. As General Counsel, I apply the same rigor to my legal work. AI aids in this by providing detailed analytics, whether tracking how a judge has ruled on similar motions or identifying recurring issues in compliance audits.

These insights fuel continuous improvement, ensuring our legal strategies remain agile and effective. I carry a mindset from the desert: never assume you’ve won the battle—always prepare for the next.

Red Teaming in the desert was about more than testing strategies; it was about fostering a mindset of vigilance, adaptability, and continuous improvement. General Counsel need to bring that mindset to their desk every day. Whether reviewing contracts, crafting litigation strategies, or stress-testing compliance programs, there is a continuing need to approach each task with the same discipline and determination I once applied to flying missions.

AI has become a modern-day GC co-pilot, helping anticipate challenges, analyze risks, and refine strategies. Yet, the core principles remain unchanged: prepare thoroughly, test rigorously, and never stop improving. The desert taught me that resilience isn’t built in comfort; it’s forged in adversity. That lesson serves me well, whether I’m navigating a sandstorm or the complexities of corporate law.

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