Leadership

A collection of 42 posts

Leadership

The Prompt Leader [Part 2 of 5]

Remember the promise from yesterday? The best "prompt" isn't a prompt at all. We've been confusing prompts with context. They're not the same. Not close. A prompt is "Build a dashboard." Context is the entire universe of understanding that enables

Leadership

The Prompt Leader [Part 1 of 5]

Imagine a brilliant team delivering mediocre results. The same type of people excel elsewhere. Different leaders, different outcomes. What different? Not the people. The prompts. Here's what's breaking my brain lately: We've built incredible AI systems that respond brilliantly or terribly based on our

Leadership

The Prompt Leader [Part 0 of 5]

There's a meeting right now where everyone is lying. Including you. It's the talent review meeting. Someone's presenting slides about "capability gaps" and "hiring needs." Everyone's nodding. Everyone agrees: "We need stronger players." Here's

Leadership

Intelligence Theater

Nassim Taleb bombed every strategic planning session. He said, "To outperform trial and error intellectually, you need at least a thousand IQ points." Let that sink in... I used to think smart people had the edge. If you were brilliant enough, you could think your way past the

Leadership

The Competence Illusion

Who’s actually in charge here? Simple question. Should have a simple answer. The pilot flies the plane. The CEO runs the company. Someone has the whole picture. But watch what happens when you push on it… The pilot’s counting on air traffic control. Control’s watching software displays.

Analytics

Data Driven vs Data Inspired [Part 5 of 5]

Breaking Free Your team can escape. But not how you think. The answer isn't better data. It's better questions. Data driven asks, "What should we do?" Data inspired asks, "What's happening here?" That second question changes everything. Here's

Innovation

Data Driven vs Data Inspired [Part 4 of 5]

Why Smart Teams Stay Stuck Smart teams choose data-driven thinking. Even when they know better. It's not because they're dumb. It's because of how we reward teams. Here's what I mean. Two team members keep fighting about everything. Creative direction. Deadlines. Who

Analytics

Data Driven vs Data Inspired [Part 3 of 5]

Being Data Inspired Data inspired is different. Let me show you. Data driven sees: "Sales dropped last month. Run Campaign X again." Data inspired sees: "Sales drop every time we launch without testing messaging first." Notice the difference? Data-driven copy solutions. Data-inspired find principles. You look

Analytics

Data Driven vs Data Inspired [Part 2 of 5]

Analytics as Performance Theater Your team is sophisticated. They have dashboards. They track everything. But watch what they do. Sales drop. They review last quarter’s tactics. User traffic falls. They copy last year’s actions. Customer complaints rise. They use the same fix. This is data-driven thinking. "I&

Analytics

Data Driven vs Data Inspired [Part 1 of 5]

The Data Driven Trap Your team is underperforming. It might be because you're too focused on data. That sounds crazy. We've been told data-driven decisions are better, smarter, and more scientific. But watch what happens in most teams. The sales lead sees leads drop. They review

Leadership

Invisible Guardrails

Every organization struggles with ineffective procedures while wondering why smart people ignore "clear" instructions. We've created a paradox. The more we document, the less people follow it. The clearer our instructions, the more creative the workarounds. (You've seen this, right?) Humans are optimization machines.

Leadership

Locked Perception

Once you choose a story about why something happened, you stop looking for other explanations. ...and miss the real problems that will bite you again. "We failed due to poor execution" blinds you to systematic problems. "We succeeded due to great leadership" blinds you to lucky

Leadership

Frozen Lightning

Once you document a process, it's outdated—like trying to photograph lightning. Documentation creates a false sense of control. We think capturing the process means mastering it...  but processes are living systems. They evolve faster than we can describe them because they respond to unpredictable real-world conditions. By

Leadership

Small Teams Ship, Big Teams Sync

Adding a person to a project increases communication complexity exponentially, not linearly. A team of 4 has 6 communication paths. A team of 8 has 28. We optimize for collaboration without accounting for coordination costs. The math is brutal. More people means more meetings, alignment sessions, and "quick syncs&

Leadership

The Delegation Death Spiral

Managers think they're delegating. They're starting wars. They have a problem they don't want to think through. Without framework, direction or constraints, they hand it to someone else. Just "figure something out that I'll like." Staff think hard and return

Leadership

Ready Enough

"We need to be fully prepared before starting something important." Most people believe this. They're wrong. Think about planning dinner with friends: You check schedules You pick the perfect restaurant You make reservations Then reality hits: Someone runs late The restaurant loses your reservation The dish

Leadership

The Shadow Message

Your "metadata" speak louder than your words—especially in how you communicate. Every message you send has two layers: The words you choose. And the hidden metadata that reveals your true priorities. Your communication metadata includes: • Response time patterns • Channel selection • Time allocation • Communication frequency • Attention distribution These

Leadership

The Real Reason I Write

Most people think writing makes you smarter. They're wrong. Writing makes you realize how dumb you are. Every time I sit down to write, I discover new depths of my own ignorance. Things I thought I understood dissolve into confusion. Arguments I believed were solid crumble under scrutiny.

Leadership

The Clarity Tax

We've convinced ourselves that talking is faster than writing. It isn't. Think about your last meeting: "Can you clarify what we decided?" "That's not what I understood..." "Let me check my notes..." Important decisions bounce through endless meetings

Leadership

The Illusion of Clear Communication

You just finished a meeting. Everyone nodded in agreement. Then the follow-up emails arrive, and your heart sinks. Somehow, each person heard a completely different message. What you say matters far less than what others hear. This isn't a failure of communication — it's how communication works.

Leadership

Knowledge Isn't Numbers

Everyone collects data. Few understand how they learn from it. The difference between good and great data isn't information — it's metacognition. Here's what I mean: Two agencies track the same campaign metrics. The first uses data to adjust strategies. The second studies how it

Leadership

Intelligence In The Walls

Most companies get this backwards. They think intelligence flows from the top down. But the smartest organizations embed it in their walls. Look at Toyota's two-bin system — it manages inventory automatically, no managers needed. Or Google's testing frameworks that catch errors before humans do. Or hospital

Leadership

The Third Ear Principle

In 1962, during the Cuban Missile Crisis, Soviet submarine B-59 was ready to launch a nuclear torpedo. The standing order was that if three officers agreed, they could fire. Two said yes. But Captain Vasili Arkhipov did something different. He listened. Not just to words, but to what wasn'

Leadership

Stop Fixing, Start Refactoring

We call it "organizational baggage" and tell people to leave it at the door. But that's missing the point. What we label as baggage is actually cultural debt—accumulated over years within our teams and systems. It parallels technical debt in our codebases. Both are artifacts

Leadership

The Presence Paradox

We chase excellence to earn trust. But trust isn't earned through perfection... It's built in imperfect moments when we dare to stay together. In the end, it's simple: Character over competence.