Chronicles from a Caribbean Cubicle Podcast
by Francis Wade
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
Episodes
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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...
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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...
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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...
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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...
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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...
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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...
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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...
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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...
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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.…
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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…
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The Strategy Handoff Crisis: Why Your Successor Can’t Think Like You Do
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...
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Why Your 2050 Strategy Must Start Today: Lessons from a 15-Year Failure
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...
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The YouTube Strategy School: Why Your MBA Didn’t Teach You Strategic Thinking
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…
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The YouTube Strategy School: Why Your MBA Didn’t Teach You Strategic Thinking
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…
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The Uncomfortable Truth: Good Leadership and the Transformational Non-Obvious
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...
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Stop Calling It Recovery: Why Your Business Needs a Different Word
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.”…
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Why Your Strategic Plan Is Probably Just an Expensive Wish List
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...
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Why Your Strategic Vision Falls Flat
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...
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Beyond the Annual Planning Checklist
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…
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When Good News Becomes a Business Risk
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…
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Why Your Strategy Isn't Inspiring Anyone
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...
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Beyond the Boardroom and Its Voices
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…
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Tumultuous Times? Learn to Persuade Others to Think Decades Ahead
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...
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Strategy Communication to Staff: One-Way Message or Two-Way AI?
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...
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Inspiration in Leadership | Anchor Your Message in a Compelling Future
“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...
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The Hidden Risk of Success: How Short-Term Drift Erodes Long-Term Leadership
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...
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How Your Staff Could Be Inspired By Your Strategy Using AI
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...
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Trauma-Proof Strategy: How to Tap Your Team’s Thinking with AI Prompts
As a CEO or senior leader, you’re responsible for steering your organization into the future. But if you’re being honest, you may feel like you’re falling short. The day-to-day noise is deafening. How can you rise above it all and think strategically—especially now, when AI tools like Large...
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Trauma-Proof Strategy: How to Tap Your Team’s Thinking with AI Prompts
As a CEO or senior leader, you’re responsible for steering your organization into the future. But if you’re being honest, you may feel like you’re falling short. The day-to-day noise is deafening. How can you rise above it all and think strategically—especially now, when AI tools like Large...
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Growing the Economy with a Grand Strategy: Four Unavoidable Truths
As a business leader, you’re tired of hearing about countries with stagnant economies. Perhaps your own nation is among them — stuck in low-growth mode, with seemingly no way out. Yet, you’re committed to finding answers. You’re ready for bold ideas, not short-term gimmicks. Here’s one worth your...
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From Vision to Victory: 8 Steps to Deliver Game-Changing Corporate Results
Imagine this: You’re the CEO of a growing company. You’ve gathered your executive team, ready to carve out a bold, breakthrough ambition. But there’s a moment of hesitation—you know someone will ask, “What’s the first step?” and you’re not quite sure how to respond. You’re not alone. Many leaders...
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The World’s Obsessed with Drama | Wise Leaders Leverage It for Long-Term Wins
Recently, I noticed two positive trends in Jamaica that haven’t exactly made the headlines. One is economic, the other social — and both are significant. Yet, they’ve flown under the radar. Why? It turns out, there’s a powerful leadership insight here. Let’s start with a quick story. On a recent...
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Choose Your Own Culture: The Role of Planning
Your company is chasing bold results—but something keeps getting in the way. Again and again, your corporate culture seems to sabotage your efforts. Should you push forward anyway? Or is this just the way things are? As a seasoned executive, you’ve seen a variety of workplace environments—some...
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Navigating Uncertainty: Step Back, Look Ahead, and Define Your True North
As a senior executive, you are no stranger to the relentless waves of change sweeping across North America. The onslaught of daily upheavals can feel overwhelming, making it tempting to believe that success hinges on reacting swiftly to each new development. But is this truly the most effective...
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The Leadership Trap: How Dominating Strategy Sessions Stifles Innovation
Smart CEOs instinctively understand that game-changing decisions require a unique context. But what exactly makes breakthrough strategic thinking different? And why do so many leaders struggle to get it right? In almost every strategic planning project I participate in, there’s a quiet…
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Sour Attitudes: Transforming Resistance Frees Up Commitment
As a leader, you have a clear vision of a brighter future for your enterprise. Yet, paradoxically, the more enthusiastic you become, the more resistance you encounter. How do you lead effectively when those around you refuse to be led? You notice negativity—cynicism, resignation…
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Trumpian Disruptions | Use Turbulence While Others Lose Their Minds
Donald Trump’s first weeks in office present the biggest distraction CEOs have ever witnessed. Apart from daily news explosions, there are material threats to their businesses. But is there a way for you to transcend continuous surprises? Many leaders believed that COVID-19 was the most…
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Think You Need a Comprehensive Strategy? Maybe Not.
Transcript Your company proudly touts its “comprehensive strategic plan.” But while its creators are satisfied with its depth and detail, perhaps it’s time to rethink. Narrowing its focus might just save it from failure. Somewhere in your email inbox, there’s a lengthy strategic document waiting…
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Lacking DeepSeek Impact in Your Strategy?
Transcript The world watches with anticipation as DeepSeek.com takes the lead in AI Large Language Models (LLMs). As a leader, you might wonder, “Why can’t my company achieve a similar breakthrough? What’s stopping us from uncovering game-changing insights?” As your team strategizes, you grow…
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Afraid to Be Lofty? | Expand, Then Compress Your Strategy
Transcript: A turbulent world demands game-changing strategies. Companies must stand out, yet executives quickly discover that setting exaggerated goals has its limits. How can you inspire staff and board members with ambitious aspirations while maintaining credibility? Case in Point: You...
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Every Leader’s Challenge | Transitioning Between Successive Visions
Transcript Jamaica’s economic future is once again in the spotlight. With elections on the horizon, the Prime Minister has unveiled the ASPIRE program. However, given the backdrop of past disappointments and widespread skepticism, one pressing question arises: How can leaders inspire others to...
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Transforming Vision Statements: Choosing the Right Vision for the Right Time
Transcript As a leader, you recognize the importance of inspiring your team with a compelling vision. Yet, you may find that your company’s vision statement, despite its lofty aspirations, fails to inspire meaningful change. How can you craft and communicate a future that genuinely motivates your...
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Jaded Staff: Why Past Corporate Change Projects Could Be the Issue
Transcript As a leader, you likely have ambitious goals for your team. But the more you share your vision, the more resistance you seem to face. So, how do you move beyond jaded staff members and their skeptical responses to new futures? A Real-World Example: Jamaica’s Key Challenges In a recent...
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From Panic to Purpose
Transcript / Article from a recent blog post Some companies that survived the pandemic now tout extreme agility as their superpower. But is this a sustainable approach? According to Jeff Bezos of Amazon, the answer may lie in focusing on what hasn’t changed, even amid turmoil. The Agility Debate...
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Master Planning for Complex Organizations: A New Approach to Achieve Exceptional Outcomes
If you’re part of a large public-sector organization or a multi-divisional private company, you probably operate within a framework of a “master plan.” This overarching strategy is meant to guide your organization towards its long-term objectives. Yet, despite the hard work, key milestones and...
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Avoiding Bad Strategy and Fake Retreats
Imagine this scenario: You’re a newly promoted executive involved in a strategic planning project and notice that one person is dominating the process. This individual is intelligent, but should you feel relieved or dismayed by their takeover? This is a public episode. If you'd like to discuss…
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Being Inspired in Public Sector Planning
As a leader in a government Ministry, Department, or Agency (MDA), you’re deeply committed to creating strategic plans that make a significant impact. However, it’s easy to get caught up in bureaucratic compliance, which can divert you from making the meaningful contributions you desire. So, how...
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The Power of Pre-emptive Strategic Planning
As a company leader invested in the future of your enterprise, it can be frustrating to see others content with handling issues only when they arise. How can you instill a culture of forward-thinking in your organization? In many local organizations, strategic planning is often viewed as a...
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Why End-of-Tenure CEOs Are a Danger
In the business world, the end of a CEO’s tenure often brings about significant challenges. As CEOs near the conclusion of their careers, a troubling pattern emerges: their actions can sometimes undermine long-term value and pose serious risks to the organization. This phenomenon is rooted in...
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Three Horizons for Strategic Thinking - a Guide for Long-Term Strategic Planning
As a proponent of long-term thinking in your company, you’ve likely encountered resistance. You may feel isolated, struggling to articulate the value of strategic foresight to colleagues focused on immediate concerns. This guide aims to provide you with a framework to effectively communicate the...
About this show
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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