Charles Blain

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

Marketing

Colorblind Metrics

It's wild that we've been making the same mistake for years. Ancient Greek philosophers had a word: techne—the art of making things. They knew something we've forgotten: knowing HOW to count isn't the same as knowing WHAT counts. Stay with me…

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

Innovation

The Juicero Effect

Here's a story that'll make you laugh and cry. Juicero raised $120 million to build a $700 WiFi-connected juicer that squeezed pre-made packets. When reporters discovered you could squeeze the packets by hand, the company collapsed overnight. I mean... by hand. Like, with your actual hands.

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.

Marketing

Manual Override

I've been in digital marketing since the early 2000s, and I've seen this movie before. (Spoiler alert: we're watching it happen again.) The future of advertising changes again in 2026. ByteDance's virtual influencers are already here. Google's bringing ads into

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

Context Collapse

Every email you send misses 90% of your meaning. Tone, timing, and shared history are gone. Digital communication strips away the context that makes human interaction work. This is context collapse... Digital tools didn't create context collapse. They revealed it. We've assumed others see what we

Innovation

System Resistant

Why do we stay stuck in chaos? It feels good to be the hero. It feels good to be needed. But that addiction costs us in wasted effort and missed automation opportunities. When everything breaks and you fix it, people notice. They thank you. They need you. That feels better

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

Judgment Bottleneck

AI writes code. No-code builds apps. Templates solve design. The creative spark, that "what if" moment, has never been cheaper to test. But finishing? That's still expensive. The last 20% resists automation because it's where human messiness meets human needs. Edge cases aren'

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&

Innovation

Why Nothing Ever Gets Simpler

Organizations can only add complexity, never subtract it. Every new process gets layered on top. Every "improvement" becomes permanent baggage. Nobody's job description says "remove things", only "add solutions". This is the hidden law of institutional physics. Complexity is a one-way ratchet.

Marketing

You Can't Control Emergence

There's a marketing campaign running right now that's about to backfire spectacularly... and the team who created it has no idea. Complex systems produce behaviors none of their parts intended.  Your campaigns interact in ways you never designed.  Messages combine, recombine and impact your customers in

The Automation of Honesty

Machines don’t have egos to protect. They just report what they see. No spin. No excuses. This scares us. We want truth that makes us look good. But automated systems show what actually worked, not what we hoped worked. We resist this honesty because it’s uncomfortable. But organizations

Catching Intelligence [Part 5 of 5]

How do we build systems that reward truth over comfort? Most teams say they want the truth... (they really don't). Then they punish those who tell it. I've watched brilliant people learn to stay quiet... not because they lack insights, but because speaking up felt dangerous.

Catching Intelligence [Part 4 of 5]

The Difference Between Being Right and Being Useful Being right feels good. Being useful changes everything. Socrates was considered the wisest man in Athens not because he had the most answers, but because he asked the questions that revealed everyone else's ignorance—including his own. In business, we&