Charles Blain

Marketing

The Messy Middle

Consider this: 95% of your marketing "leads" will never buy from you. Not because you failed. Because they were never shopping—they were learning. Or killing time. Or avoiding their boss. Or playing a complex game of "what if I had money." Google calls it the

Innovation

What's Your Chocolate?

That client who keeps complaining about the same thing? The miscommunication that happens every Tuesday? The "glitch" in your process that everyone works around? You might be walking past your biggest breakthrough. Percy Spencer discovered microwave cooking because his chocolate bar kept melting at work. But nobody mentions

Innovation

The User Conspiracy

In 1953, Rocket Chemical Company aimed to create a rust-prevention solvent for nuclear missiles. The plan was simple. The execution... wasn't. It took 40 attempts. They failed thirty-nine times before they cracked it. They named it WD-40—Water Displacement, 40th formula. The brand became the failure count. But

Leadership

The Motte and Bailey (Part 5 of 5)

You can't fix what you won't admit is broken. Here's the uncomfortable truth: we've built systems that reward retreat. The motte and bailey isn't a communication problem. It's an evolutionary adaptation to organizational schizophrenia. Remember the high performer

Leadership

The Motte and Bailey (Part 4 of 5)

Every softened word is a diluted currency unit. Your organization is experiencing hyperinflation. "Strategic" means nothing when it also means "follow SOPs."  "Critical" applies to 70% of projects—all documented per process.  "Innovation" means "change that fits the existing framework."

Leadership

The Motte and Bailey (Part 3 of 5)

Here's why both sides need the retreat: Leaders need deniability. Teams need survival. Your company is insane. And everyone's pretending it's normal. Monday morning: "Be strategic! Take ownership! Drive innovation!" Monday afternoon: "Did you follow the SOP? Where's the

Leadership

The Motte and Bailey (Part 2 of 5)

"Psychological safety"? Look closer. It's a blame culture wearing a Halloween mask. Every meeting has invisible scoreboards. Who gets blamed when reality hits? Who covered their ass best? Who left paper trails? Motte and bailey isn't communication failure. It's blame insurance. "

Leadership

The Motte and Bailey (Part 1 of 5)

The Unnamed Pattern There's a trick in every meeting. Once you see it, you can't unsee it. Medieval castles had two parts: the bailey (where life happened—farms, markets, mess) and the motte (ugly hill, stone tower, miserable but impregnable). Attack coming? Abandon the bailey. Run

Leadership

The Prompt Leader [Part 5 of 5]

Here's the plot twist I've been holding back... The best teams don't wait for better prompts. They prompt their leaders for what they need. (Think about it. When's the last time someone on your team prompted YOU?) Remember Part 1? Those brilliant

Leadership

The Prompt Leader [Part 4 of 5]

The three promised intelligence boosters? They're hiding in plain sight. AI performance breakthroughs come from the same three things. They work on humans too. 1. Tool Calling → Empowered Execution When GPT-4 hits its limits, it calls specialized tools: Calculator for math, Browser for current events, and Database for

Leadership

The Prompt Leader [Part 3 of 5]

Do you remember that hidden "system prompt" I mentioned? (Hold that thought because that's where it gets weird...) Your team isn't making decisions. They're pattern-matching. Like AI. (Stay with me.) LLMs don't "think." They predict the next word

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