Chronicles from a Caribbean Cubicle Podcast

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 Language Models (LLMs) are reshaping the game? In the past, you likely comforted yourself with a familiar be...

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 Language Models (LLMs) are reshaping the game? In the past, you likely comforted yourself with a familiar be...

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 time. A few weeks ago, I watched a YouTube video from a university research day featuring Michael Lope...

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 find themselves in this exact spot—excited about what could be , yet uncertain about how to turn ambit...

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 trip to Trinidad — my first in nearly ten years — I was surprised by how well the country was doing. Th...

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 vibrant and inspiring, others toxic and draining. You know how much culture matters. Yet, you might still...

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 path forward? Is there a smarter, more strategic way to navigate the turbulence? If these questions have...

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 conversation with the top leader before we begin: “Don’t dominate the discussion.” It’s a simple directive, but n...

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, despair—permeating different levels of the organization. It’s not just an issue at the lower levels; even executives in...

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 significant disruption of their careers. The world came to a halt and took years to return to normal. But today,...

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 to be read. It’s so long and dense that you haven’t even glanced at it. You’re not alone—no one has. Re...

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 weary of the same old excuses—yours included. Stakeholders demand answers. Why isn’t your organization mak...

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 anticipate breakthroughs during strategic planning retreats. Instead, you’re met with the same old ideas. Why?...

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 embrace a new direction when another, prior “new direction” is still fresh in people’s memories? From a p...

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 team to take action? The Challenge of an Inherited Vision Statement Imagine you’re a newly promoted CE...

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 discussion among thought leaders, three major issues emerged as Jamaica’s toughest challenges: crime, l...

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 Critics of long-term strategic thinking argue that it stifles flexibility. They believe leaders must pr...

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 targets may still be missed. How can you ensure that your organization achieves significant, measurable r...

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 this with other subscribers or get access to bonus episodes, visit longtermstrategy.substack.com/subscrib...

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 can you truly make a difference? This is a public episode. If you'd like to discuss this with other sub...

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 luxury—an activity to be deferred until more stable times, when there’s ample time and money. For others, it’...

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 several behavioral tendencies that intensify over time, but they aren't easy to spot. This is a public epi...

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 importance of long-term strategic planning (LTSP) and engage others in this crucial mindset. This is a...

Your company has a long history of putting together strategic plans. And you have diligently read them all in a search to understand the intentions of prior leaders. But as you look them over you are concerned. There are lots of todo lists, action items, and budgets, but the underlying plan seems to lack something important - a strategy. You can’t quite explain why this is the case, but you can te...

You love your national sport. Seeing the Jamaican (or West Indian) flag soar above a global stage fires you up. But you also see that in football and cricket, we’ve fallen. Could it be about long-term thinking? When the West Indies men’s cricket team dominated the world in the 1980s and 90s, other countries envied them. They all tried to catch up, but Australia’s response was unique. They decided...