Chronicles from a Caribbean Cubicle Podcast

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...

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 c...

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 dec...

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 ra...

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 com...

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...

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 supp...

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...

Companies obsess over documenting financial controls. They create detailed procedure manuals for operations. Yet when it comes to transferring strategic thinking between executives, most organizations fail spectacularly. The problem isn’t a lack of documentation. It’s documenting the wrong things entirely. The Six-Month Struggle Every Incoming Executive Faces Here’s a scenario playing out in board...

Will your organization survive the next 25 years? More importantly, are the decisions you’re making today planting the seeds of future irrelevance? The US Coast Guard wrestled with these questions and discovered something counterintuitive: to truly understand today’s challenges, you need to view them from 25 years in the future. Their Project Evergreen initiative proved this—but only after failing...

Annie’s hands trembled as she reread the email from her CEO. “Let’s talk about developing your strategic capabilities.” She’d just earned her MBA with honors, landed a promotion to Chief Marketing Officer, and crushed her Strategic Planning course with an A-. Now, three weeks before Christmas, her boss wanted to discuss her lack of strategic thinking. The meeting went poorly. “You’re just not bein...

Annie’s hands trembled as she reread the email from her CEO. “Let’s talk about developing your strategic capabilities.” She’d just earned her MBA with honors, landed a promotion to Chief Marketing Officer, and crushed her Strategic Planning course with an A-. Now, three weeks before Christmas, her boss wanted to discuss her lack of strategic thinking. The meeting went poorly. “You’re just not bein...

The Uncomfortable Truth About Good Leadership Two CEOs retired recently from similar-sized companies. Their departures couldn’t have been more different—and neither could the legacies they left behind. Michael’s farewell was everything you’d expect from a beloved leader. The board praised his “collaborative leadership style” in glowing terms. His team genuinely mourned his departure. Government of...

When disaster strikes, the language leaders choose reveals everything about their future. In late October 2024, Hurricane Melissa tore through Jamaica as a Category 4 storm, causing widespread devastation. Within days, business leaders across the island were using the same word: “recovery.” Getting back to where they were before the hurricane hit. But here’s the problem with that word—and why it m...

Transcript Ask most CEOs about their strategic plan and you’ll hear about vision statements, multi-year roadmaps, and quarterly KPIs. What you won’t hear is the one thing that actually matters: What do we believe has to be true for this to work? That missing question—the absence of a testable hypothesis—is why most strategic plans gather dust while organizations spin their wheels solving the same...

As a senior executive, you’ve delivered passionate presentations about your organization’s strategic vision. You’ve crafted compelling narratives about transformation, growth, and impact. Yet somehow, your message resonates in the boardroom but dies somewhere between middle management and the frontlines. Sound familiar? Most executives communicate like it’s 1995 - a pre-digital world. They craft o...

Transcript Imagine you lead a government ministry, department, or agency. As you approach the season for submitting annual reports and corporate plans, you realize something is missing. The very reason you entered public service is being lost in paperwork. This challenge isn’t unique to any single country—it’s a global phenomenon affecting government leaders worldwide, whether they’re working with...

Transcript When Good News Becomes a Business Risk: How Falling Crime Can Disrupt Your Strategy A Shift Few Leaders Expect Falling crime rates are usually celebrated as a sign of progress. Safer communities, stronger economies, and a brighter future—what’s not to like? Yet for business leaders, this kind of change can also be profoundly disruptive. If your company has been operating for decades in...

Transcript As a senior executive, you’ve probably felt the weight of expectation when it comes to inspiring your team. The board expects it. Your direct reports need it. But despite your best efforts—the carefully crafted presentations, the all-hands meetings, the motivational speeches—something isn’t working. Your people seem disengaged. They nod politely during strategy sessions, but you can sen...

Transcript When companies embrace long-term, aspirational strategic thinking, they often stumble upon a neglected truth: not all stakeholders have a voice. Some are silent—like the natural environment, social infrastructure, or even future generations. These sometimes non-human entities are easily overlooked because they don’t speak up, file lawsuits, or stage protests. Yet, their well-being may d...

As a member of the C-suite with a commitment to long-term success, you may find yourself at odds with the culture around you. You’ve come to realize that your role has subtly but fundamentally shifted. While others are chasing quarterly numbers, you’ve begun to see your job through a different lens: one of legacy-building. You’re being pulled into the future, tasked—whether formally or not—with th...

As a senior executive, one of your most crucial and delicate responsibilities is the communication of strategic plans to employees, board members, and key stakeholders. But how should you do it? Is it enough to share a dense, one-off report? Or can AI finally offer a way to transform this traditionally frustrating task into something more interactive and engaging? Most leaders dread this stage of...

“Inspiration in Leadership | Anchor Your Message in a Compelling Future” As a leader—whether in politics or business—you want to inspire people. You want them to care, commit, and go above and beyond. But earning this level of engagement is difficult. In fact, it’s one of the most elusive challenges in leadership. Inspiration, after all, isn’t automatic. It doesn’t come from holding a title or iss...

The Stability Trap Your organisation is doing well. Revenue is strong. Customers are satisfied. Partners are dependable. From the outside, all indicators suggest smooth sailing. But under the surface, a dangerous shift is taking place— short-term drift . Ironically, this subtle threat emerges not from crisis, competition, or disruption, but from long-term stability itself. Consider what has happen...

Transcript As a senior executive, you’ve probably felt the weight of expectation when it comes to inspiring your team. The board expects it. Your direct reports need it. But despite your best efforts—the carefully crafted presentations, the all-hands meetings, the motivational speeches—something isn’t working. Your people seem disengaged. They nod politely during strategy sessions, but you can sen...