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

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.

Frameworks don't fail in theory. They fail in context.

I don't read leadership books anymore.

Not because I know everything. Because I've learned enough to know the advice is often wrong. Not wrong in theory. 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, their book. Generic advice has the widest market. Specific, contextual truth doesn't scale. So what gets published is optimized for likes, not results. It's designed to sound good in a keynote, not hold up when everything is falling apart.

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

Great advice. Until it isn't.

The Myth of Universal Frameworks (vs. Contextual Intelligence)

The core problem is simple: real leadership isn't about picking a single framework like Servant, Directive, or Adaptive Leadership. It is about Contextual Intelligence, the ability to recognize which tool the situation demands in seconds, not days.

You don’t need to have run a reactor or served in a warzone to understand this, just experience dealing with real stakes and real consequences.

Servant leadership alone doesn't work in a crisis. Flooding. Fire. Reactor emergency. You don't ask the team what they need. You don't clear obstacles and get out of the way. You give orders. Fast, clear, top-down. Crisis leadership requires decisiveness measured in seconds, not consensus built over days. "How can I support you?" is the wrong question when water is coming in.

Every submarine officer learns this. The same person who spends months building trust, developing people, listening...that person has to flip a switch and become completely directive when the situation demands it. And then flip back. The leadership development programs don't teach you how to do that. They teach you one mode or the other.

When Servant Leadership Fails

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

• When the mission requires spending your people: Longer deployments. Harder tempo. A commanding officer can't always optimize for crew wellbeing. Sometimes the mission matters more. That's the job. No leadership book wants to say that out loud because it doesn't fit the modern narrative. But anyone in the military or emergency services knows that sometimes, leadership means making decisions that cost your people something. And you carry that.

• When someone needs truth, not support: Servant leadership says to clear the obstacles. But sometimes they are the obstacle. Sometimes the most important thing you can do for someone 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: New crew. Uncertain situation. Everyone is looking around, waiting for someone to say something. They don't need you to ask what they need. They need you to tell them what's happening and what to do next. Executive leadership sometimes means being the person willing to decide when no one else will.

I've watched leaders hide behind consensus. "What does the team think?" sounds collaborative. 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.

I've watched decisiveness save lives. I've also held back when every instinct said act.

We once had readings that indicated something might be wrong. 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. It would have been very hard for what the readings suggested to actually be happening.

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. It was judgment. And no leadership book could have told me which one to choose, because the answer depends 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 a simple question: 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 actually give them in that moment? They are trapped underwater. They can't leave. They can't call. They can't fix it. If I tell them, I am handing them a tragedy they have to carry alone, while operating a nuclear reactor, 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.

The same logic applies to the boardroom.

I see leaders confuse "honesty" with "transferring anxiety." You know a re-org is coming. You know a major client is threatening to walk. If you share that raw uncertainty with the team before there is a plan, you aren't empowering them. You are paralyzing them.

Real leadership isn't being a clear glass conduit for every organizational tremor. It is acting as a shock absorber. You absorb the ambiguity and the fear so your team has the stability to execute. That isn't lying. It's protection.

Support vs. Sabotage

I've watched a young officer fumble through something I could've fixed in ten seconds. It was painful to watch. The team was getting frustrated. I could feel them looking at me, waiting for me to step in.

But I didn't. Because that officer needed to struggle, that's how people learn. The "leadership" move was to step back when everything in me wanted to step forward.

I've kept someone in a data center delivery when they wanted off. They felt overwhelmed. The caring answer looked like yes—pull them off, reduce the pressure, show you're a supportive leader.

But the right answer was no.

They needed to get through it, not around it. They needed to learn that they could handle more than they thought. They did. And they were different after—more confident, more capable. If I'd let them walk away, I would have told them I didn't believe they could do it. That's not support. That's sabotage dressed up as kindness.

 How to Actually Build Contextual Intelligence (as a Leader)

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:

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

• Practicing both modes on purpose. If you naturally lean back, practice stepping in fast on low-stakes decisions. If you naturally take charge, force yourself to wait.

• Reviewing decisions after the fact. Don't just review the outcome; review the choice of tool. Did I use a hammer when I needed a screwdriver?

You don’t need combat for this...you need real stakes, honest after-action reviews, and the humility to admit when you picked the wrong tool.

The people who've actually led through hard things 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. So is adaptive leadership. The question isn't which one is right. The question is which one is right now, for this team, in this situation, with these stakes.

And if someone's selling you a framework that answers that question for you, they're selling you something that doesn't exist.

So I don't read leadership books anymore. Not because the principles are wrong.

Because the principles aren't the hard part. The hard part is knowing when to abandon them.

That's not teachable in a post, including this one.

Tony Grayson

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