1.0 Introduction

Ever feel like the pace of technology demands SUPERHUMAN decision-making abilities?

You're not alone.

After 30+ years in technology leadership, I've seen brilliant CIOs crash and burn NOT because they lacked technical knowledge, but because they couldn't make decisions at the speed business demands.

One moment stands out vividly...

I was consulting with a Fortune 500 company when their Technology Director– let's call him Alex – faced a critical decision about an aging e-commerce platform. His team had identified serious performance issues and proposed a migration that required temporarily limiting some customer features.

The business team was pushing back HARD.

Alex froze. He wanted more data. More analysis. More meetings.

While he deliberated for WEEKS.

The cost of the delay:  Help lines swamped with complaints.  Thousands of aggravated customers.  Lost contract renewals.  Reduced market share. 

The difference wasn't technical expertise. It was DECISION VELOCITY.

Today, I'm pulling back the curtain on the framework that separates extraordinary technology leaders from the merely competent ones: The OODA Loop.

2.0 The REAL Power of OODA

You might think OODA (Observe, Orient, Decide, Act) is just another cute acronym. It's NOT.

Developed by Air Force Colonel John Boyd, it's a battle-tested methodology that gives you a competitive advantage through superior decision-making speed and quality.

But here's the part most people miss...

The goal isn't just to cycle through OODA once. It's to create a CONTINUOUS LOOP that works faster than your competition's decision cycle.

When your OODA Loop operates at higher velocity, you can:

• Respond to threats before they become crises

• Seize opportunities while others are still analyzing them

• Adapt to changing conditions while competitors remain stuck in outdated approaches

I've implemented this with dozens of technology executives, and the results are nothing short of transformative.

One leader I worked with reduced critical incident response time within 90 days. Another unlocked more value by accelerating technical decisions that had been stalled for months.

But to harness this power, you need to understand each component deeply and how they work together.

3.0 OBSERVE (See Reality Without Filters)

Most CIOs think they're good observers. Most are WRONG.

Effective observation means perceiving reality without the filters of:

• Preconceived notions

• Cognitive biases

• Ego protection

• Political considerations

I worked with a healthcare technology consulting leader who insisted that their security practices were solid despite several near-misses. His team was afraid to challenge him, and he filtered out warning signs that contradicted his beliefs.

We implemented three observation practices that changed everything:

1. Get Other Opinions: He appointed a trusted team member to actively seek and highlight vulnerabilities and contradictory data

2. Assumption Audit: A weekly review of the assumptions underlying key decisions

3. Fresh Start: Monthly sessions where the team approaches problems as if seeing them for the first time and asks “would I do things differently”.

Within weeks, they uncovered significant security gaps that had been rationalized away and implemented fixes before a breach occurred.

Your observation advantage comes from seeing what others miss – especially what they deliberately avoid seeing because it's uncomfortable.

4.0 ORIENT (Apply the Right Mental Model)

Orientation is where most technology leaders go wrong.

It's not just about processing what you've observed – it's about choosing the correct mental model through which to interpret that information.

Your mental models are shaped by:

• Your technical background

• Past experiences (especially traumatic ones)

• Cultural heritage

• Organizational history

• Leadership style

A brilliant leader I coached kept approaching every problem as a technical challenge because that's where his expertise lay. Team struggling? Apply more sophisticated project management tools. Board communication issues? Create more detailed technical documentation.

Her orientation was LIMITING his effectiveness.

We expanded his mental models to include:

• People-centered leadership frameworks

• Stakeholder influence mapping

• Business value creation models

• Organizational psychology perspectives

The breakthrough came when she reoriented a persistent delivery problem from "We need better tracking tools" to "We have a cross-functional collaboration issue."

This single reorientation unlocked a solution that had eluded her for MONTHS.

The secret to superior orientation? Maintain a diverse toolkit of mental models and consciously choose which to apply rather than defaulting to your comfort zone.

As the renowned polymath Charlie Munger said: "To the man with only a hammer, every problem looks like a nail."

5.0 DECIDE (Make the Call)

Here's where technology leaders often get stuck in the mud.

The decide phase isn't about reaching perfect certainty – it's about making a choice with the best available information within the necessary timeframe.

After studying hundreds of technology executives, I've identified three decision-making styles that consistently fail:

1. The Perfectionist: Requires complete information and zero risk before deciding

2. The Consensus Seeker: Won't move forward without universal agreement

3. The Lone Ranger: Makes decisions in isolation without input

The OODA-optimized approach? Decisive but adaptable decision-making.

One director that I worked with was paralyzed about a major ERP implementation. Every decision required extensive analysis, multiple approvals, and exhaustive risk mitigation.

We implemented a simple decision framework:

• If reversible → decide quickly with adequate information

• If irreversible → increase analysis time but still set a firm decision deadline

• If urgent → use the 70% rule (decide when you have 70% of ideal information)

• If non-urgent → determine if decision can be broken into smaller, reversible steps

The impact was immediate. Decisions that previously took weeks now happened in days or hours. The project timeline accelerated significantly.

Remember: In technology leadership, a good decision now almost always beats a perfect decision later.

6.0 ACT (Execute With Speed and Conviction)

This is where the rubber meets the road.

Many technology leaders excel at planning but struggle with execution. They develop brilliant strategies that never see the light of day.

Action in the OODA Loop isn't just about doing something – it's about moving with sufficient speed and commitment to impact the situation before it changes again.

I worked with a start-up CTO who was brilliant at spotting emerging technologies and developing adoption strategies. Yet somehow, her organization was always playing catch-up with competitors.

The issue? Her "actions" consisted primarily of:

• Creating detailed implementation plans

• Establishing comprehensive governance frameworks

• Developing extensive risk mitigation strategies

All valuable activities – but by the time her team actually IMPLEMENTED anything, the competitive advantage had disappeared.

We shifted his approach to focus on:

1. Minimum Viable Actions: Identifying the smallest steps that would yield meaningful results

2. Parallel Processing: Initiating action while planning continues

3. Time-Boxing: Setting non-negotiable deadlines for moving from planning to action

The result? His team launched a new set of security features to market in three months, capturing several new clients and getting a letter of intent to acquire!