Agility Under Fire

“In the midst of chaos, there is also opportunity.” —Sun Tzu

In the Army, we had a saying: “No plan survives first contact with the enemy.” That mindset shaped my leadership—whether serving in Special Forces units or the 101st Airborne. Success in combat—and tech—hinges on agility, rapid decisions, and empowered teams.

Applying Military Agility to Tech Leadership

In modern military operations, plans change the moment they’re put into motion. Elite units don’t follow rigid plans—they adapt. The OODA Loop (Observe, Orient, Decide, Act) keeps them ahead—driving both battlefield success and tech innovation.

Microsoft’s security teams apply this approach daily to stay ahead of cyber threats. They observe threats, orient by assessing vulnerabilities, decide on countermeasures, and act by rolling out patches.

The same framework helps tech teams stay agile:

• Product Development: Observe user behavior, orient with data, decide on improvements, and act through rapid iteration.

• Incident Response: Observe system disruptions, orient by evaluating business impact, decide on response priorities, and act with precise recovery execution.

Three Field-Proven Tactics for Agile Leadership

Agility in leadership isn’t just about reacting fast—it’s about designing systems that drive smart, rapid decision-making. The military excels at structured flexibility, balancing autonomy with oversight. In tech, the same principles fuel innovation, resilience, and execution speed. These three battle-tested tactics help leaders build adaptable, high-performing teams.

1. Decentralized Decision-Making: Speed Up, Scale Up, Win More

Bottlenecks kill agility. As General Stanley McChrystal noted in Team of Teams, those “closest to the problem, armed with insights, are best equipped to act decisively.”

To decentralize effectively, tech leaders must:

• Identify which high-impact decisions need executive input and which can be streamlined. Focus leadership where it adds the most value.

• Empower teams while ensuring accountability. Grant authority with clear ownership, performance metrics, and feedback loops.

• Eliminate needless approvals that slow execution. Use automation, self-service, or pre-approved thresholds to remove bottlenecks.

• Set budget, compliance, and metrics boundaries, then let teams operate freely. Guide with principles, not rigid controls.

Decentralization accelerates execution, but some areas—compliance, crises, and major investments—still need central oversight. The key is knowing when to empower teams and when to intervene. Leading companies strike this balance:

• Amazon’s “two-pizza teams” operate autonomously, reducing decision lags and accelerating product delivery—famously launching Amazon Prime in just 111 days.

• Spotify’s squad model distributes ownership of specific functions to cross-functional teams, slashing bureaucracy and enabling continuous innovation.

• Basecamp empowers small teams with complete decision authority, reducing oversight costs and increasing customer responsiveness.

2. Commander’s Intent: The Secret to Fast, Smart Execution

“Never tell people how to do things. Tell them what to do, and they will surprise you with their ingenuity.” —General Patton

Great leaders know when to step in and when to step back. Military commanders set the mission and trust their teams. Tech leaders should too—define the vision, guide, and let teams execute.

For tech organizations, this means:

• Prioritizing strategic outcomes over rigid processes.

• Trusting teams to navigate execution challenges.

• Providing clarity on “why” and “what” while letting teams determine “how.”

A strong commander’s intent answers three questions:

1. What does success look like? (Measurable outcome)

2. Why does it matter? (Strategic purpose)

3. What are the guardrails? (Key constraints)

Case Study: Netflix’s engineering culture thrives on trust. Leaders set clear objectives—like improving streaming performance—but leave execution to small teams. This autonomy enabled rapid innovation, such as their Chaos Engineering approach.

3. Gaining Ground-Level Insights: The Directed Telescope Approach

Military leaders use trusted sources to stay informed—without micromanaging.

For tech leaders, this means:

• Building trust with truth-tellers at all levels.

• Encouraging candid, constructive dissent.

• Testing assumptions against real-world data.

Implementation Strategies:

• Hold skip-level meetings to bypass filtered reports.

• Rotate leadership in team discussions.

• Use anonymous channels to encourage honest input.

• Engage with customers firsthand—calls, user testing, or support tickets.

Example: Microsoft executives exemplify this by engaging directly with frontline employees to ensure that leadership decisions align with reality.

Overcoming Agility Roadblocks

Applying military agility to tech means overcoming these challenges:

• Leaders reluctant to decentralize → Start with small wins: Delegate low-risk decisions, then expand autonomy as trust builds.

• Unclear objectives slow execution → Define commander’s intent: A clear end state, purpose, and constraints.

• Fear of failure stifles innovation → Reframe failure as a learning opportunity: Encourage experimentation and celebrate insights from setbacks.

Evolving as an Agile Leader

I’ve seen leadership evolve firsthand. Early in my career, I relied on structured decision-making. Over time, I learned that true agility demands flexibility. Great leaders know when to take the wheel and when to trust others to steer. This transformation involves:

• Developing self-awareness to identify personal agility blockers.

• Embracing continuous learning and adaptation.

• Establishing explicit feedback loops to improve decision-making.

Leaders can overcome agility barriers like fear of failure, resistance to change, and micromanagement by:

• Using 360-degree reviews to gain diverse feedback.

• Running regular retrospectives to refine team processes.

• Leveraging anonymous surveys to uncover unfiltered insights.

Self-Assessment: Your Agility Check

• What personal leadership habits might be hindering agility?

• How can you create a safe space for constructive dissent?

• What mechanisms can you implement to foster continuous learning?

The Power of Decentralized Leadership

A key lesson from both military and tech leadership is that true power comes from distributing authority. Special Operations teams succeed through adaptability, trust, and decentralized execution—not rigid command structures.

Tech leaders who embrace this—empowering teams, clarifying intent, and fostering diverse perspectives—create organizations that react swiftly and innovate continuously.

Take Action Today

These principles aren’t just theory—they’re battle-tested for real-world success. Get started with three simple steps:

• Delegate one decision today that you’d typically handle yourself.

• Define a clear Commander’s Intent for an upcoming project.

• Get unfiltered frontline feedback from your team within 48 hours.

Agility isn’t a one-time shift—it’s a mindset. Build it, refine it, and make adaptability your edge.