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Chronicles from a Caribbean Cubicle Podcast

There are significant challenges facing Caribbean companies. In the areas of strategic planning and productivity improvements, unique thinking is needed to break out of historical norms. But such thinking isn’t easy to find. Join me, Francis Wade, for some provocative insights into the way I see these problems. These are mostly audio editions of past Gleanr articles. longtermstrategy.substack.com

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The One Diagnostic Step Every Failed AI Rollout Skipped

There are two ways a board loses confidence in a CEO’s AI strategy. One is watching a rushed rollout blow up in public. The other is watching nothing happen, quarter after quarter, while rivals pull ahead. Leaders treat these as opposite sins — one of recklessness, one of paralysis. They are the same sin wearing two costumes. Consider a government vehicle-inspection office. For years, getting a…

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The Missing Rung: Why Your Innovation Efforts Remain Uninspiring and Empty

The Missing Rung: Why Your Innovation Efforts Remain Uninspiring and Empty As the person responsible for driving innovation in your organisation, you have probably sat through a version of this conversation more than once. The leadership team agrees that a new category is needed. Everyone nods. A workshop is scheduled. Consultants are hired, sticky notes are deployed, and three months later the…

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The CEO Who Solved Everything - But Inspired No-one

Transcript The CEO Who Solved Everything — and Inspired No One You are putting in serious effort to motivate your team — and it still isn’t working. The hours are long, the intent is genuine, and the results are stubbornly flat. Before you blame your communication strategy, your budget, or your personality, consider a different diagnosis entirely. Two fictional CEOs illustrate the problem. Marcus…

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Where AI Belongs in Strategy — and Where It Will Wreck You

In the early 1980s, McKinsey told my employer at the time, AT&T, that the global market for mobile phones would top out at roughly 900,000 subscribers by 2000. The actual number was 100 million. A decade later, AT&T paid $11.5 billion for McCaw Cellular to claw its way back into the market it had walked away from. Hundreds of America’s brightest minds had read the same report, nodded at the same…

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The Productivity Trap No Election Can Fix

There’s a number most government leaders would rather not think about. For Jamaica, it’s nine dollars. That’s the country’s productivity measured as output per hour worked — US$9. Barbados, a neighboring island economy, produces more than twice that. Panama produces five times as much. Most strikingly, Jamaica’s hourly output is only marginally ahead of Haiti’s — a country that has experienced…

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The Two Meetings That Turn Long-Term Strategy Into Motion

Most top executives can generate urgency around a quarterly target. The mechanisms are familiar: dashboards, deadlines, compensation levers. People move. But ask those same executives to build genuine momentum toward a grand aspiration which needs a fifteen-year horizon, and something strange happens. They show up. They nod. They wait for the pressure to pass. This isn’t insubordination. It’s a…

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Blue Ocean Strategy Has a Flaw Nobody Talks About

There is a book on the shelf of almost every serious executive in the world. It has sold over four million copies, been translated into 46 languages, and spawned an entire consulting industry. Its central idea is so compelling that once you hear it, you cannot unhear it. The book is Blue Ocean Strategy (BOS), published in 2004 by W. Chan Kim and Renée Mauborgne. The central idea: stop fighting…

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The Moment I Realised My Story Library Was Embarrassingly Small

There is a specific kind of professional humiliation that doesn’t arrive with a bang. It sneaks in quietly, while you’re nodding, performing competence, convinced the conversation is going well. Mine arrived fifty minutes into a live podcast recording with Seth Godin. I was mid-interview. The mic was hot. And somewhere between his twelfth and thirteenth story, I heard myself say — out loud, on the…

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Your Mission-Driven Organization Deserves Better Strategy Tools

Picture a familiar scene in a non-profit organization. A hotel conference room. Flip charts on easels. A two-day offsite that everyone has blocked out on their calendar and quietly dreaded. The exercises begin. Strengths, weaknesses, opportunities, threats. Stakeholder maps. Priority matrices. The team engages dutifully, filling in the boxes, generating the language that planning retreats are…

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When Excellence Breeds Failure: Why Your Best Team Might Be Building Your Worst Disaster

Picture this: A talented leadership team. Top-tier credentials. Flawless execution. Every metric trending green. And yet, five years later, the company is fighting for survival—or worse, gone entirely. This isn’t a story about incompetence. It’s something far more insidious. It’s about intelligent people trapped inside a system that rewards them for making precisely the wrong choices. The Athletic…

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