Leading Under Pressure:

What does military leadership teach boards about governing risk under pressure?

We gathered senior military veterans from across the branches of the military to explore this topic. Mary O'Brien, Robert Skinner, Erick Turasz, and moderator Patrick Huston provided valuable insights available in the key takeaways and video below.

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KEY TAKEAWAYS

Balanced Risk Taking

• “Be aggressive but not reckless.” Directors should focus on calculated risk-taking. Excessive caution can stall innovation, while moving too quickly without preparation can create significant operational and strategic risk.
• “No friction, no traction.” Constructive friction in the boardroom is healthy. Fast alignment may signal insufficient challenge, debate, or examination of downside scenarios.
• “Find a way to yes.” Boards should encourage management teams to identify mitigation strategies rather than defaulting to risk avoidance or organizational paralysis.

Good Leadership Requires Clarity and Discipline

• Effective governance requires creating maneuver space early enough to adapt before risks become crises.
• Planning for worst-case scenarios through “rock drills,” rehearsals, and contingency exercises is more valuable than preparing for best-case conditions.
• Organizations need the right technology, tools, and training in place before a crisis occurs, along with a clear understanding of how those capabilities mitigate risk.
• “Pressure” is not one condition. Boards should distinguish between the following and act accordingly:
• pressure tied to keeping people safe and operational
• pressure created by resource constraints and budget tradeoffs
• pressure created by deadlines and manufactured urgency
• Scenario planning, contingency reviews, and crisis simulations improve decision-making when information is incomplete.
• Organizations should “educate for the known and train for the unknown,” particularly in cyber and operational resilience.

Supply Chain and Technology Risks

• Modern logistics risk now extends beyond physical infrastructure to software supply chains, chips, and geopolitical dependencies.
• Boards should evaluate whether the organization has hidden single points of failure tied to countries, suppliers, software providers, communications infrastructure, or technology dependencies.
• Red-teaming data flows and supplier relationships can expose vulnerabilities before adversaries or disruptions exploit them.
• Red-teaming should also include organizational procedures, workforce readiness, and professional development to ensure teams have the right training and visibility into emerging risks.
• Boards overseeing AI, cyber, autonomous systems, and emerging technologies should view operational resilience and geopolitical exposure as inseparable issues.

Boards Must Define Intent

• “Commander’s intent” provides a strong governance framework by clearly defining objectives, unacceptable outcomes, priorities, and decision boundaries while empowering teams to act.
• Management teams should understand how far they can move decisively without waiting for additional approval during fast-moving events.
• Excessive escalation to senior leadership slows organizational response times and weakens adaptability.
• CEOs and executive teams should independently document their understanding of strategic intent and compare alignment gaps across leadership teams.

Crisis Readiness

• Boards should regularly ask “what if” questions and evaluate preparedness for communications outages, supply chain disruptions, cyberattacks, and geopolitical shocks.
• Crisis playbooks should exist before an incident occurs, including escalation paths, decision authorities, and operational contingencies.
• “After-action reviews” remain underutilized in corporate governance. Organizations often fail to systematically capture lessons learned after major events.
• Effective after-action reviews require candor, humility, accountability, and a culture where expertise is valued over hierarchy.

AI Governance and Workforce Readiness

• Boards should understand where and how AI, especially agentic AI, is being deployed across the enterprise.
• Governance teams should assess whether employees understand the legal, operational, and reputational risks associated with AI tools and autonomous agents.
• Simply deploying AI technology without workforce training can increase operational risk and reduce effectiveness.
• Organizations should prepare for AI-related reputational events, including misinformation, leaks, activist campaigns, and brand attacks that could materially impact the company.

Culture Determines Risk

• Leadership teams should create environments where employees can raise concerns without fear of blame.
• Organizations should distinguish between:
• blameworthy failures tied to integrity or willful misconduct
• failures caused by capability gaps, insufficient resources, or complexity
• “praise-worthy failures” tied to responsible experimentation and innovation
• Boards should incentivize transparency, learning, and early escalation of emerging risks rather than only rewarding short-term success.
• One of the strongest indicators of governance effectiveness may be whether meaningful disagreement is surfaced and addressed constructively.

Questions Boards Should Bring Back to Their Organizations

• Where are our hidden single points of failure across technology, suppliers, communications, and geopolitics?
• Do management teams understand the board’s strategic intent and decision boundaries during crises?
• Have we recently rehearsed our response to a major cyber, AI, supply chain, or reputational event?
• Are employees empowered and incentivized to raise risks and challenge assumptions early?

SPEAKERS

Mary O'Brien

Lt. Gen. USAF (Ret.); Director, National Digital Trust Company, Operation Homefront, Tharros; Co-founder and CSO, OperativX

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Lieutenant General (ret.) Mary O'Brien, NADC.CD, is an independent director, board advisor, and strategic consultant, specializing in the intersection of national security and dual-use cyber, AI, and autonomous technology...

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Bob Skinner

Lt. Gen. USAF (Ret.); CXO Revolutionaries Advisory Board, Zscaler; Founder, Skinner's Strategic Solutions LLC

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A career cyber and communications leader, Skinner most recently served as director of the Defense Information Systems Agency and commander, Joint Force Headquarters–Department of Defense Information Network, leading global unified network operations and cyber defense for the Department of Defense...

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Erick Turasz

Vice President—Strategic Partnerships, Global Guardian

As vice president of strategic partnerships, Erick Turasz helps Fortune 500 companies and affluent families implement a full range of domestic and international duty-of-care safety, medical, and security services...

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MODERATOR

Patrick Huston

Brigadier General, U.S. Army (Ret.); General Counsel & Advisory Board, Ondas Holdings; Member, FBI’s AI Task Force

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Gen. Patrick Huston, NACD.DC, is an experienced attorney, advisor, and board member. He’s a renowned technology lawyer focused on artificial intelligence (AI), quantum computing, and cybersecurity...

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