Why I Stopped Reading Leadership Books: The Case for Contextual Intelligence in Leadership

By Tony Grayson, Tech Executive (ex-SVP Oracle, AWS, Meta) & Former Nuclear Submarine Commander

Published: November 24, 2024 | Last Updated: December 22, 2025

Context in action. I brought this group of executives to the flight deck of the USS Carl Vinson (CVN 70) to demonstrate what leadership looks like when the stakes are real. You can't simulate this environment in a conference room.

TL;DR — Key Takeaways

• Leadership books fail because they're optimized for likes, not results. Generic advice has the widest market—it sounds good in keynotes but falls apart when the mission is falling apart.

• Servant Leadership isn't always the answer. In crisis, teams need immediate direction, not consensus. Decisiveness measured in seconds, not consensus built over days.

• Directive Leadership isn't micromanagement. In high-stakes environments, it's often the most compassionate approach because it reduces uncertainty.

• Contextual Intelligence is the meta-skill. Knowing which tool to use matters more than mastering any single framework. Check the stakes, practice range, review the tool.

I don't read leadership books anymore.

It’s not because I know everything. It’s because I've learned enough to know the advice is often wrong. Not wrong in theory, but wrong in practice; wrong in the moment when it actually matters.

Leadership advice has become an industry. The people writing it need you to believe that leadership skills are teachable through their framework, their course, or their book. But generic advice has the widest market, so what gets published is optimized for likes, not results. It's designed to sound good in a keynote, not hold up when the mission is falling apart.

Take Servant Leadership. It's everywhere right now. The premise is attractive: Clear obstacles for your team. Ask what they need. Get out of their way. Put your people first.

Great advice. Until it isn't.

What Is Contextual Intelligence?

The core problem isn't the framework; it's the rigid application of it. Real leadership isn't about picking a single mode like Servant, Directive, or Adaptive Leadership. It is about

Contextual Intelligence.

Contextual Intelligence is the ability to recognize which leadership tool the situation demands in seconds, rather than relying on a static framework.

You don’t need to have run a reactor or served in a warzone to understand this, but you do need experience dealing with real stakes.

The Myth of Universal Frameworks

Servant leadership alone doesn't work in a crisis. Flooding. Fire. Reactor emergency.

In these moments, you don't ask the team what they need. You don't "clear obstacles." You give orders. Fast, clear, and top-down. Crisis leadership requires decisiveness measured in seconds, not consensus built over days. Asking "How can I support you?" is the wrong question when the ship is taking on water.

Every submarine officer learns this. The same person who spends months building trust and developing people must be able to flip a switch and become completely directive when the situation demands it—and then flip back just as quickly.

Most leadership development programs don't teach you how to do that. They teach you one mode or the other.

When Does Servant Leadership Fail?

There are specific scenarios where the popular "employee-first" narrative crumbles.

• When the mission requires spending your people: In longer deployments or higher tempos, a commanding officer can't always optimize for crew wellbeing. Sometimes the mission matters more. No leadership book wants to admit this, but anyone in the military or emergency services knows that leadership sometimes means making decisions that cost your people something.

• When someone needs truth, not support: Servant leadership says to clear obstacles. But sometimes the person is the obstacle. Sometimes the most important thing you can do is tell them something they don't want to hear. That's not clearing their path; that's standing in it.

• When the team needs direction, not facilitation: With a new crew or an uncertain situation, people are often looking around, waiting for direction. They don't need you to facilitate; they need you to decide.

I've watched leaders hide behind consensus. "What does the team think?" sounds collaborative, but sometimes it's just a way to avoid making the hard call. That's not democratic leadership. That's abdication dressed up as humility.

The Burden of Command: Decisiveness vs. Patience

Here's what no one writes about: the same action that makes you a hero in one situation makes you a liability in another.

We once had readings that indicated something might be wrong with the reactor.

Everyone wanted to leap into casualty procedures—that's the decisive thing to do, that's what we train for. But the physics didn't match.

So I waited. I watched. Nothing happened.

If I'd reacted, we would have pulled off station in the middle of a national mission.

Patience looked like hesitation, but it was judgment. No leadership book could have told me which one to choose, because the answer depended entirely on the context that only I had in that moment.

Transparency: Respect or Cruelty?

The modern corporate world idolizes transparency. But on a submarine, transparency can be a burden disguised as respect.

Before deployment, every sailor signs a form asking: If a crisis happens at home, do you want to be notified immediately? Almost everyone checks "Yes."

Then the Red Cross message comes in. A death in the family. A tragedy at home. Transparency says: give it to them. It’s what they asked for.

But what does that knowledge give them in that moment? They are trapped underwater.

They can't leave. They can't call. If I tell them, I am handing them a tragedy they have to carry alone, while operating a complex system, with no outlet for their grief.

Sometimes, leadership means holding that message in your safe until the mission allows them to deal with it. You carry the weight so they don't have to. Real leadership isn't being a clear glass conduit for every organizational tremor. It is acting as a shock absorber.

How to Build Contextual Intelligence

The real skill no one talks about is knowing which tool to pull and when. You won't get that from a framework. You build it by:

1. Checking the stakes: Ask, “What’s really at stake right now?” before you act. Is this a moment for consensus, or is the ship taking on water?

2. Practicing range: If you naturally lean back, practice stepping in fast on low-stakes decisions. If you naturally take charge, force yourself to wait.

3. Reviewing the "tool," not just the outcome: Don't just ask if the result was good. Ask if you used a hammer when you needed a screwdriver.

The people who've actually led through hard things (whether in Data Centers or on submarines) know this. They also know that the advice industry depends on you believing there's a shortcut. There isn't.

Servant leadership is powerful. So is directive leadership. The question isn't which one is right. The question is which one is right now.

Frequently Asked Questions (FAQ)

Who is Tony Grayson?

Tony Grayson is President & General Manager of Northstar Enterprise + Defense, former Commanding Officer of USS Providence (SSN-719), and recipient of the Vice Admiral James Bond Stockdale Award for Inspirational Leadership. He previously served as SVP at Oracle and held executive roles at AWS and Meta.

What is contextual intelligence in leadership?

Contextual Intelligence is the ability to recognize which leadership tool the situation demands—in seconds—rather than relying on a static framework. Developed as a leadership construct by researchers including Matthew Kutz, it integrates three core abilities: an intuitive grasp of relevant past events, acute awareness of present contextual variables, and awareness of the preferred future. Harvard professor Tarun Khanna described it in Harvard Business Review as the ability to understand the limits of applying management practices uniformly across different situations. It's a meta-skill that allows leaders to determine when to use Servant Leadership, Directive Leadership, Mission Command, or other approaches based on the immediate stakes and environment.

What is the difference between Servant Leadership and Contextual Intelligence?

Servant Leadership is a specific framework developed by Robert K. Greenleaf in his 1970 essay "The Servant as Leader," focused on prioritizing the needs of the team, clearing obstacles, and putting people first. Contextual Intelligence is a meta-skill that allows a leader to determine when to use Servant Leadership and when to use a more Directive approach based on the immediate situation. While Servant Leadership is one tool in the leadership toolkit, Contextual Intelligence is the judgment to know which tool to deploy and when—recognizing that no single framework works in all circumstances.

Why does Servant Leadership fail in crisis situations?

In a crisis (such as a reactor emergency, flooding, fire, or cybersecurity breach), the team needs immediate direction and clarity, not consensus. Servant Leadership's focus on facilitation, asking what the team needs, and clearing obstacles can slow down decision-making when speed is the critical factor for survival. Leadership research confirms that in times of crisis, swift decision-making is critical, and Servant Leadership's consensus-driven approach may lead to dangerous delays. As military commanders understand, crisis leadership requires decisiveness measured in seconds, not consensus built over days.

Is Directive Leadership bad?

No. Directive Leadership is often stigmatized as "micromanagement," but in high-stakes, high-ambiguity environments (like military operations, reactor emergencies, or critical infrastructure failures), it is often the most compassionate way to lead because it reduces uncertainty for the team. When people are looking around, waiting for direction in uncertain situations, they don't need facilitation—they need someone to decide. The key is knowing when to be directive and when to step back, which requires Contextual Intelligence rather than rigid adherence to any single leadership style.

Why do leadership books fail?

Leadership books fail because generic advice has the widest market, so what gets published is optimized for likes, not results. It's designed to sound good in a keynote, not hold up when the mission is falling apart. Real leadership requires contextual judgment that can't be reduced to a single framework. The core problem isn't any particular framework—it's the rigid application of it. Academic research spanning over 500 studies confirms that leadership does not occur in a vacuum, and context-free leadership theories are incomplete. As Fiedler's contingency model established in 1978, there must be a match between a leader's approach and situational factors.

How can I apply military leadership to business?

Military leadership isn't just about giving orders; it's about "Mission Command"—the Army's approach to command and control that empowers subordinate decision-making and decentralized execution appropriate to the situation. Originating from Prussian military doctrine after 1806, developed by Generals Scharnhorst, Gneisenau, and Clausewitz, Mission Command focuses on commander's intent rather than rigid processes. You can apply this by clearly communicating the "what" and "why" while letting subordinates determine "how," building trust through competence and shared understanding, and developing the judgment to know when to step in and when to step back.

What is Situational Leadership Theory?

Situational Leadership Theory was developed by Paul Hersey and Ken Blanchard in 1969, originally called "Life Cycle Theory of Leadership." The fundamental principle is that there is no single "best" style of leadership—effective leadership is task-relevant, and successful leaders adapt their style to the readiness and development level of their followers. The model identifies four leadership styles (Telling/Directing, Selling/Coaching, Participating/Supporting, Delegating) matched to four follower readiness levels. This aligns with Contextual Intelligence: the right approach depends on the specific circumstances and people involved.

What is the burden of command?

The burden of command is the weight of responsibility and accountability that comes with leadership authority. It includes the loneliness at the top (as peer groups shrink at higher levels), the human consequences of decisions, and the reality that second and third-order effects become more pronounced as you advance. What no one writes about: the same action that makes you a hero in one situation makes you a liability in another. Sometimes patience looks like hesitation, but it's actually judgment. The burden includes knowing when to act decisively and when to wait—a judgment call that no leadership book can make for you.

When should a leader choose patience over decisiveness?

A leader should choose patience over decisiveness when the physics don't match the perceived emergency. In submarine operations, for example, readings might indicate something wrong with the reactor, and everyone wants to leap into casualty procedures—that's the decisive, trained response. But if the underlying data doesn't support an actual casualty, reacting immediately could pull you off station during a critical national mission. Patience in that moment looks like hesitation but is actually contextual judgment. No leadership framework can tell you which to choose, that answer depends entirely on the context that only the leader has in that moment.

Why is transparency not always the right leadership approach?

The modern corporate world idolizes transparency, but sometimes transparency is a burden disguised as respect. On a submarine, if a Red Cross message arrives about a death in the family, the sailor asked to be notified—but they're trapped underwater. They can't leave or call. Giving them that information hands them a tragedy they must carry alone while operating complex systems with no outlet for grief. Sometimes leadership means holding that message until the mission allows them to process it. Real leadership isn't being a clear glass conduit for every organizational tremor—it's acting as a shock absorber, carrying weight so others don't have to.

How do you build contextual intelligence as a leader?

Building Contextual Intelligence requires deliberate practice across three areas: First, check the stakes before you act—ask "What's really at stake right now?" to determine if this is a moment for consensus or if the ship is taking on water. Second, practice range—if you naturally lean back, practice stepping in fast on low-stakes decisions; if you naturally take charge, force yourself to wait. Third, review the tool, not just the outcome—don't just ask if the result was good, ask if you used a hammer when you needed a screwdriver. This builds the 12 meta-competencies identified in Contextual Intelligence research, organized within the 3D Thinking Framework of hindsight, insight, and foresight.

What is Mission Command and how does it differ from Servant Leadership?

Mission Command is the military's approach to command and control that empowers subordinate decision-making through commander's intent, mutual trust, and decentralized execution. Originating from Prussian doctrine developed by Generals Scharnhorst, Gneisenau, and Clausewitz after 1806, it was formalized in U.S. doctrine through General Martin Dempsey's 2012 White Paper. Unlike Servant Leadership, which focuses on serving follower needs, Mission Command focuses on mission accomplishment through clear intent ("what" and "why") while empowering subordinates to determine "how." Both require trust, but Mission Command explicitly addresses high-stakes, rapidly-changing environments where decentralized execution based on shared understanding is essential. Read more about leadership psychology here.

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Tony Grayson is a recognized Top 10 Data Center Influencer, a successful entrepreneur, and the President & General Manager of Northstar Enterprise + Defense.

A former U.S. Navy Submarine Commander and recipient of the prestigious VADM Stockdale Award, Tony is a leading authority on the convergence of nuclear energy, AI infrastructure, and national defense. His career is defined by building at scale: he led global infrastructure strategy as a Senior Vice President for AWS, Meta, and Oracle before founding and selling a top-10 modular data center company.

Today, he leads strategy and execution for critical defense programs and AI infrastructure, building AI factories and cloud regions that survive contact with reality.

Read more at: tonygraysonvet.com