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 Metaphor That Explains Everything

Want to see this pattern in pure form? Look at how different sports organizations develop talent.

Jamaica’s MVP Track Club has produced Olympic champions and world record holders whose careers span decades. Athletes like Shelly-Ann Fraser-Pryce and Elaine Thompson-Herah didn’t just win races—they sustained excellence well into their thirties, their bodies intact, their bank accounts healthy.

Meanwhile, the American collegiate athletics system—the NCAA—operates like a different species entirely. Talented high schoolers arrive with Olympic potential. Four years later, many flame out, never to compete internationally again. Bodies broken. Dreams abandoned.

Here’s what makes this fascinating: NCAA coaches aren’t incompetent. These are world-class professionals running billion-dollar programs with access to cutting-edge sports science. They track everything—times, splits, recovery metrics, nutrition, biomechanics.

Yet they’ve built a machine designed to extract maximum performance over four years, regardless of what happens afterward. The system optimizes perfectly—for conference championships, television contracts, recruitment rankings. And in the process, it systematically destroys the very athletes who make those outcomes possible.

MVP asked a different question entirely: What does success look like measured over a fifteen-year career instead of a four-year scholarship? The answer required sacrificing immediate gratification—forgoing certain meets, accepting slower progression, resisting the pressure to peak too early.

The NCAA doesn’t fail because its people are stupid. It fails because every incentive, every measurement, every reward structure points them toward short-term glory and long-term destruction. And every dashboard they monitor confirms they’re doing exactly what they’re supposed to do—right up until the athlete graduates broken.

Now here’s the uncomfortable question: Is your company running the NCAA playbook?

The Corporate Version of Athletic Destruction

Corporate history is littered with smart people making decisions that looked brilliant on every spreadsheet while quietly demolishing the foundation beneath them.

Consider the financial sector meltdowns of recent decades. Before the 2008 crisis, before Enron, before the savings and loan disasters of the 1980s, things looked spectacular. Quarterly earnings beat expectations. Risk models showed green lights. Executives earned accolades for innovative financial engineering.

The long-term destruction was being created from day one. Not by people too stupid to see it, but by systems designed never to look for it.

Why Intelligence Doesn’t Protect You

The trap works like this: The CEO who sacrifices this quarter’s numbers to protect next decade’s foundation doesn’t get applauded at the board meeting. They get questioned. Their judgment gets doubted. Their compensation takes a hit.

Meanwhile, the executive who delivers short-term wins—even by mortgaging the future—gets promoted, celebrated, interviewed by business publications.

This isn’t a failure of intelligence, discipline, or execution. It’s a design flaw in how success gets measured.

The answer isn’t working harder within the existing framework. It’s redesigning the framework itself. That requires confronting existential questions about what you’re actually optimizing for—and having the courage to challenge metrics that everyone agrees are “obviously” correct.

Three Techniques to Surface Hidden Disasters

Here are practical methods to force your leadership team to see beyond the quarterly mirage:

The Pre-Mortem Exercise

Gather your strategy team. Give them one instruction: Assume your current initiative has failed catastrophically fifteen years from now. Write the detailed story of exactly how and why.

Not vague organizational hand-wringing like “we didn’t execute well enough.” A specific, uncomfortable narrative that traces the chain of consequences from today’s confident decision to tomorrow’s wreckage.

The discipline is in the specificity. “We lost market share” is useless. “We optimized our pricing algorithm for immediate margin expansion, which slowly trained our best customers to view us as a commodity, which eroded pricing power, which forced us into a desperate discount spiral that destroyed brand equity and made us vulnerable to a well-funded competitor who simply waited us out” is useful.

The Second-Order Impact Map

Most strategy discussions evaluate immediate effects and stop there. “This restructuring reduces overhead by 18%.” Applause. Meeting adjourned.

The second-order map refuses to stop. It forces the room to keep pulling the thread: That cost reduction eliminates redundancy. Which reduces organizational resilience. Which means the next market shock hits harder. Which forces emergency measures. Which creates exactly the kind of chaos that drives your best people to competitors. Who use them to build what you should have built.

Keep pulling until the consequences become uncomfortable enough to reconsider the decision.

The Twenty-Years-Later Role Play

Identify the youngest person in your leadership team. They become a time traveler.

It’s twenty years in the future. A new generation of leaders asks them: “What was it like in that 2026 strategy session? What did your team decide?”

They respond with two scenarios. First, the courage scenario: “We confronted the hardest questions. We acknowledged uncomfortable truths. We made decisions that hurt short-term but protected long-term. Here’s how it played out.”

Second, the cowardice scenario: “We pretended things we knew weren’t true. We optimized for looking good rather than being good. We told ourselves comfortable lies. Here’s the price we paid.”

The technique works because it makes abstract future consequences feel visceral and immediate.

The Choice That Defines Leadership

Every organization faces the same fundamental question: Are you building an MVP or running an NCAA program?

Are you optimizing for sustainable excellence or spectacular quarterly performance? Are you protecting the foundation or mining it for short-term gains?

The smartest people in the room will keep making the worst decisions until the room itself gets redesigned. Until the metrics change. Until the incentives shift. Until the questions being asked force long-term consequences into immediate view.

The techniques exist. The choice is whether you have the courage to use them.

P.S. Five Prompts for Deeper Reflection

Use these with your preferred AI to explore how these patterns might be operating in your specific context:

“I’m a [your role] at a [your industry] company. We’re currently optimizing for [your key metric]. Help me identify what long-term value we might be destroying in the process. Be brutally specific about the chain of consequences I’m not seeing.”
“Run a pre-mortem analysis: It’s 2040, and the strategy we implemented in 2025 has failed catastrophically. Write the detailed story of how our decision to [your current initiative] led to our downfall. Don’t hold back on uncomfortable specifics.”
“I need a second-order impact map. Our first-order effect from [your decision] is [immediate outcome]. Help me trace at least five levels deeper into the consequences, particularly the ones that would take years to surface but would be devastating when they do.”
“Create a dialogue between my 2025 self and my 2045 self. The older version has lived through the consequences of [current strategic choice]. What would they tell me that I’m not willing to hear right now?”
“Analyze my industry through the NCAA vs MVP lens. Who in my competitive landscape is running the short-term optimization playbook? Who’s building for decades? What specific metrics distinguish them? What would it cost me to switch approaches?”

February 6, 2026

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 entirely.

The Six-Month Struggle Every Incoming Executive Faces

Here’s a scenario playing out in boardrooms worldwide: A seasoned executive departs. Their replacement inherits comprehensive transition materials—market analyses, strategic frameworks, financial models, implementation roadmaps, organizational diagrams, and risk assessments.

The incoming leader dedicates weeks to reviewing everything. They schedule meetings with key stakeholders. They take copious notes. They ask intelligent questions.

Six months later, they’re still struggling to make strategic calls with the confidence their predecessor demonstrated. They hesitate where the former leader acted decisively. They miss contextual nuances that seem obvious in hindsight.

What went wrong?

Nothing and everything. The documentation was thorough. The transition process followed best practices. But the handoff materials contained polished conclusions instead of strategic thinking itself.

This represents a fundamental misunderstanding about how strategic capability actually transfers between leaders.

What Your Transition Documents Are Actually Missing

Those transition binders look impressive. They contain everything a rational person would consider important: competitive threat assessments organized by market segment, positioning frameworks with detailed differentiation matrices, three-scenario financial projections, milestone-dependent implementation schedules, and comprehensive risk mitigation plans.

The critical gap? None of these materials explain how the organization arrived at its current strategic direction.

The genesis moment goes undocumented. Was the strategic pivot triggered by nearly losing a major client? Did a competitor’s unexpected move force a rethink? Did a board member ask an uncomfortable question that wouldn’t go away?

The discovery process remains invisible. What initial research contradicted long-held assumptions? Which sacred cows got sacrificed? When did the leadership team realize their comfortable worldview was dangerously wrong?

The human drama gets erased. That intense multi-day retreat where Finance and Operations clashed over resource priorities? Forgotten. The skeptical VP who opposed the initiative before becoming its most passionate advocate? Airbrushed out. The moment someone finally said what everyone was thinking but nobody wanted to acknowledge? Lost forever.

Most leadership teams justify these omissions with variations of: “That’s just internal politics. It’s unprofessional. The new executive needs our decisions, not our dirty laundry.”

This thinking is precisely backwards.

Why Messy Origin Stories Create Strategic Ownership

Consider two incoming executives facing the same strategic direction.

Executive A receives polished slide decks explaining the final strategic framework. Clean. Professional. Complete.

Executive B receives the full origin story: the triggering incident, the initial resistance, the data that changed minds, the fierce debates, the breakthrough moments, the implementation battles.

Three months later, both executives face pressure to abandon elements of the strategy. Market conditions have shifted. Key stakeholders are pushing for different priorities. Quick wins from alternative approaches look tempting.

Executive A, having only received conclusions, treats the strategy as inherited wisdom. They lack emotional investment. When challenged, they can recite the framework but can’t defend its foundations. They become susceptible to any argument that sounds reasonable because they never witnessed why alternative approaches were rejected.

Executive B, understanding the battle scars, responds differently. They know which assumptions were tested and survived. They understand which stakeholder concerns were addressed and how. They recognize which seductive alternatives were explicitly considered and rejected, and why. This knowledge creates conviction.

The messiness isn’t an embarrassing artifact to hide. It’s the mechanism that transforms a successor from a strategy executor into a strategy guardian.

Without origin stories, you’re handing someone a map without teaching them how to read terrain. They can follow the route you marked, but they can’t navigate when conditions change.

How Mental Models Beat Exhaustive Analysis

The second critical gap involves transferring strategic thinking patterns rather than strategic conclusions.

Your comprehensive transition documents provide analysis. What incoming executives actually need are the mental frameworks that generated that analysis.

Consider a healthcare organization undertaking strategic transformation. Traditional handoff approach: a 200-page document detailing market research, competitive positioning, customer segmentation, channel strategy, technology roadmap, and financial projections.

Alternative approach: “We’re becoming the Netflix of healthcare.”

That single sentence does more strategic work than 200 pages ever could. It instantly conveys: subscription relationships over transactional interactions, integrated digital experiences instead of fragmented touchpoints, platform thinking rather than service delivery, customer lifetime value over point-of-sale margins.

An incoming executive who internalizes this pattern can make hundreds of subsequent decisions aligned with strategic intent—without referring back to documentation. The pattern provides a mental model for evaluating new opportunities, prioritizing resources, and making trade-offs.

Analysis answers specific questions. Patterns teach strategic thinking.

Most transition documents fail here because outgoing executives don’t explicitly name the strategic patterns they’re using. These frameworks remain implicit—obvious to the departing leader but invisible to their successor.

Creating Genuine Strategic Urgency

The third missing element is the diagnostic story that explains why the current strategy became necessary.

Generic problem statements fill transition documents: “Market conditions are evolving.” “We need to maintain competitive advantage.” “Customer expectations are changing.”

These platitudes don’t create urgency. They create checkbox compliance.

Contrast that with a genuine diagnostic story: “Our analysis revealed we were Blockbuster in 2005. We had dominant market share, strong brand recognition, and profitable operations. We were also completely vulnerable. While we defended a dying business model, our industry’s Netflix equivalent was growing 40% annually. Our window for strategic response was roughly 18 months before our competitive position would become unrecoverable.”

That’s a diagnostic story with teeth. It explains why inaction represented an existential threat, not merely a missed opportunity. It creates urgency by making the stakes visceral and the timeline concrete.

Start Building Your Strategic Story Library Today

Most executives struggle to capture these three story types because they haven’t developed pattern recognition for what makes strategic stories effective. You need exposure to dozens of transformation cases before your mind identifies the underlying structures.

The solution? Deliberate practice with real business transformation narratives.

Start by studying how successful leaders explain their strategic pivots. Look for moments when executives describe “how we nearly missed this” or “why we became the [X] of our industry.” These moments contain the raw material for powerful strategic stories.

But finding quality transformation case studies scattered across YouTube and business media takes time—time most executives don’t have. That’s why platforms like StratCinema.org exist: to curate business transformation stories specifically for strategists developing this narrative fluency. Instead of algorithm-driven suggestions that keep you watching but not learning, you get carefully selected case studies that build pattern recognition.

Your next leadership transition deserves better than polished slide decks. It requires origin stories that create ownership, pattern stories that transfer mental models, and diagnostic stories that sustain urgency. Document these with the same rigor you apply to financial controls, and your successor won’t just execute your strategy—they’ll defend and evolve it.

P.S. Use AI to Capture Your Strategic Stories

Don’t have time to craft these stories from scratch? Modern AI tools can help you extract and structure the strategic narratives already in your head. Here are three sets of prompts—one for each story type—that you can use with any large language model to develop handoff materials that actually transfer strategic thinking.

Origin Story Prompts

“I need to document how our [specific strategic initiative] actually came together. Help me structure an origin story by asking me questions about: What triggered our initial concern? What was the ‘oh shit’ moment that made this urgent? Who were the initial skeptics and what convinced them? What data or insights contradicted our assumptions? What internal conflicts emerged during planning? Which alternatives did we seriously consider and reject? What breakthrough moment changed our approach? Walk me through these questions one at a time, then help me shape my answers into a compelling narrative that shows future leaders why this strategy emerged and what obstacles we overcame.”

Pattern Story Prompts

“Our strategy can be summarized as ‘[our approach]’ but I need to articulate the mental model behind it. Help me identify the pattern we’re following by asking: What successful company or strategy are we emulating? What’s our ‘[X] of [Y]’ statement? What core principle guides our decision-making? What trade-offs does this pattern naturally suggest? What does this pattern tell us to prioritize versus ignore? If someone internalized this pattern, what decisions would they make differently? Help me craft a concise pattern statement that transfers strategic intuition, not just strategic conclusions. Make it memorable enough that leaders can apply it without consulting documentation.”

Diagnostic Story Prompts

“I need to explain why our strategy was necessary—not just beneficial. Help me create a diagnostic story that conveys genuine urgency by asking: What complacent narrative were we telling ourselves before? What data revealed our vulnerability? What competitor or market shift threatened our position? What timeline were we facing? What would failure have looked like? What historical business failure does our situation resemble? Help me structure this into a narrative that makes inaction feel existential, not merely suboptimal. The goal is to transfer the visceral urgency we felt when we realized we had to transform.”

January 18, 2026

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 them from 25 years in the future. Their Project Evergreen initiative proved this—but only after failing spectacularly for 15 years first.

The Expensive Lesson: Brilliant Strategy, Zero Implementation

Imagine pouring 15 years into strategic planning. Your organization assembles the best minds, conducts sophisticated scenario workshops, and produces detailed roadmaps. The forecasts are prescient. The analysis is sharp. The strategies are comprehensive.

Then everything hits reality and dies on impact.

This was Project Evergreen’s painful trajectory. Every strategic plan they delivered landed, in their words, “like most additional work at an office with an already full plate: dead on arrival.” Inbox after inbox received these plans. Nearly all went unimplemented.

The Coast Guard had built “isolated, independent cogs” that required “considerable effort to forcefully engage into the many turning mechanisms” of actual organizational planning. Picture trying to force a rigid gear into machinery that’s already running—that’s what executing these strategies felt like for frontline teams.

Why did meticulously crafted strategies produce such dismal results?

The Question That Poisoned 15 Years of Planning

For a decade and a half, Project Evergreen asked what seemed like a perfectly reasonable question: “What should the Coast Guard do?”

If you’ve sat through strategic planning sessions, this probably sounds familiar. It’s typically the first question on the agenda. What should we do about artificial intelligence? How should we respond to digital transformation? What’s our climate change strategy?

The problem isn’t obvious at first glance. This question appears logical, even necessary. But it creates a fatal dynamic.

When you ask “What should we do?” you’re asking workshop participants—typically senior strategists and consultants—to prescribe solutions. These prescriptions then get handed down to implementers who weren’t in the room and didn’t shape the solutions. As the Coast Guard discovered, “the ideal people to do the job might not be in the room.”

This creates what I call supply-side strategy: strategists manufacture solutions and push them onto implementers. Those solutions arrive as rigid directives disconnected from operational reality.

The fundamental flaw isn’t that strategists are separated from implementers—there are simply too many implementers to fit in a retreat. The flaw is the question itself.

Present-Forward Thinking: Perfect for Tactics, Fatal for Transformation

That innocent-sounding question—”What should we do?”—invisibly locks your thinking into a present-forward orientation.

Present-forward thinking starts with today. It analyzes current problems, extrapolates existing trends, and prescribes solutions based on incremental projections. This approach works brilliantly for everyday management. It’s ideal for hitting quarterly targets, solving operational problems, and managing predictable challenges.

But for 25-year transformation? It’s disastrous.

Why? Because present-forward thinking generates tactical responses to current conditions. It can’t account for fundamental shifts in your organization’s operating environment. It can’t help you prepare for demands that don’t yet exist. It treats the future as a slightly modified version of today.

Case in point: In 2001, Kodak had abundant, recent evidence that digital photography was no threat to traditional business. The present-forward mindset dominated the thinking of executives and blocked the possibilities.

Managers use present-forward thinking each day because it’s the default mode for problem-solving. But that’s exactly why it fails for long-range strategy. This familiar mode becomes invisible, and organizations apply it to challenges it was never designed to address.

The Cognitive Shift That Changed Everything

After 15 years of failure, the Coast Guard discovered the fundamental shift required: from present-forward to future-back thinking.

This framework, developed by strategy theorists Mark Johnson and Josh Suskewicz, represents a complete cognitive reorientation. Instead of starting with today’s problems and projecting forward, you start with 2050’s probable demands and work backward.

The new question becomes: “What demands will the organization face?”

This isn’t semantic trickery. It’s a fundamentally different way of thinking about strategy.

When the Coast Guard made this shift, they began identifying what they call “robust strategic needs”—outcomes required by specific long-term futures, each demanding particular strategic responses.

Here’s the critical difference: prescriptive solutions constrain implementers. Strategic needs empower them.

Prescriptions say “do this.” Strategic needs say “accomplish this outcome”—and then trust implementers to craft solutions suited to their specific contexts and the evolving reality they’re navigating.

How Future-Back Thinking Works in Practice

Project Evergreen now runs workshops that map multiple plausible 2050 scenarios. They explore various futures the Coast Guard might face—different geopolitical landscapes, climate conditions, technological capabilities, maritime threats.

Then something critical happens. As the project team explained: “The solution space had to be left to the people who were actually going to implement the solution.”

Instead of receiving detailed instructions, implementers receive strategic needs. They’re asked to “deconstruct and then reconstruct” these needs for their specific operational contexts.

This approach works because objectives spanning 25 years can’t be prescribed with any accuracy. The future will unfold in unexpected ways. Game-changing strategies require flexible frameworks that can adapt as conditions evolve. Strategic needs provide that framework. Rigid tactical plans don’t.

The result: Project Evergreen became what they call a “backdoor strategic contributor”—guiding organizational direction without constraining operational flexibility.

The 2025 Payoff from 2050 Thinking

Here’s where this approach delivers immediate value.

Future-back thinking reveals which of today’s “urgent” priorities are actually superfluous. When you clearly understand the demands your organization will face in 25 years, some current problems simply fade in importance. The larger perspective exposes which fires are worth fighting and which will burn out on their own.

This prevents wasting resources on solutions that won’t address actual long-term demands.

It also transforms implementer motivation. Instead of following someone else’s prescriptions, teams gain the autonomy to design solutions matched to their reality. That autonomy—the flexibility to meet strategic needs in contextually appropriate ways—creates genuine engagement and inspiration.

Applying This to Your Organization

Consider your organization’s long-range planning through this lens.

The present-forward approach asks: “What should we do about immediate challenges?” This generates aspirational goals—”become industry leader,” “achieve digital transformation,” “reach carbon neutrality”—often disconnected from implementation reality. These sound impressive in board presentations but provide little practical guidance for teams expected to deliver them.

The future-back approach asks: “What demands will our organization face in 2050?” This identifies strategic needs that divisions must customize for their contexts.

For example, rather than prescribing “implement AI across all functions, ”you might identify a strategic need for “decision-making capabilities that scale with data complexity.” Different departments can then develop solutions suited to their unique challenges—customer service might deploy conversational AI, logistics might focus on predictive routing, finance might build automated risk assessment.

A flexible framework instead of a rigid mandate.

The Counterintuitive Truth

The Coast Guard’s expensive lesson offers a counterintuitive truth: you need tomorrow’s perspective to understand today’s priorities.

Organizations that begin with present-forward thinking remain trapped in tactical responses to current conditions. They mistake busy-work for strategy. They confuse detailed plans with transformation.

Organizations that embrace future-back thinking gain something more valuable: clarity about which current actions actually matter for long-term survival.

That 25-year horizon isn’t about predicting the future perfectly. It’s about developing the perspective to distinguish signal from noise in the present.

The question isn’t whether your organization will face existential demands by 2050. It will. The question is whether you’re building the strategic foundation today to meet those demands—or whether you’re sowing the seeds of irrelevance while obsessing over quarterly results.

The answer starts with asking a different question.

Source: Project Evergreen’s Long-Range Strategic Planning, United States Naval Institute

January 8, 2026

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, her boss wanted to discuss her lack of strategic thinking.

The meeting went poorly.

“You’re just not being strategic enough,” he said, arms crossed.

“Can you give me specific examples?” Annie asked, pulling out her notebook.

He waved his hand vaguely. “It’s hard to explain. I just know it when I see it.”

She pressed for details. He offered hollow phrases about “seeing the big picture” and “thinking long-term.” Nothing concrete. Nothing actionable. By the time she left his office, both were frustrated.

Now it’s January. Annie sits at her desk, surrounded by expensive textbooks and highlighted case studies, completely lost. She can recite Porter’s Five Forces backward. She built financial models that made her professors weep with joy. Yet somehow, she’s failing at the very thing her degree promised to teach.

The brutal irony? Her CEO can’t articulate what strategic thinking actually is because he developed the skill unconsciously, through years of pattern recognition. Annie can’t demonstrate it because her MBA systematically removed the very experiences that build strategic intuition.

They’re both trapped. And neither understands why.

The MBA’s Fatal Flaw

Annie isn’t alone in this predicament. Across boardrooms worldwide, formally trained managers struggle to translate their academic frameworks into real strategic insight. They possess intellectual tools but lack the deeper capability that separates strategic thinkers from strategic memorizers.

Here’s what business schools won’t tell you: becoming genuinely strategic isn’t about learning more frameworks. It’s about understanding that strategy professionals operate in three distinct seasons—and most never experience the first two.

Season 3: Creation and Mobilization
This is the visible season. Senior leaders gather to craft corporate strategy over one to three months. PowerPoint decks multiply. The C-Suite debates market positioning. Consultants bill impressive hours. This is what most people imagine when they picture “strategic work.”

Season 2: Focused Skill Building
Between major strategic initiatives, professionals identify capability gaps and target specific learning. They read journals, attend workshops, and study new frameworks. MBA programs excel at teaching a few basic Season 2 skills.

Season 1: Curiosity-Driven Exploration
This is the secret season. The forgotten season. The season where strategic intuition actually develops.

And it’s completely absent from formal business education.

Warren Buffett’s Secret Curriculum

To understand why Season 1 matters so profoundly, consider how Warren Buffett transformed Katherine Graham from overwhelmed newspaper heiress into one of America’s most respected CEOs.

In 1963, 46-year old Graham suddenly inherited control of The Washington Post after her husband’s death. She’d been a housewife with zero business experience. Now she faced a company, competitors, and boardroom dynamics she didn’t understand. Terrified but determined, she reached out to Buffett for guidance.

What happened next reveals everything about how strategic thinking actually develops.

Buffett didn’t send her to business school. He didn’t recommend management textbooks. He didn’t even explain financial statements, despite being one of the world’s greatest investors.

Instead, according to researcher Cedric Chin, Buffett quietly assembled a curated collection of annual reports from diverse companies across multiple industries. Then he sat with Graham and walked her through them, one by one.

But here’s the crucial detail: they didn’t analyze balance sheets or scrutinize financial ratios. They discussed stories. Why did this CEO make that decision? What pattern do you notice across these three retail failures? How did this manufacturer navigate technological disruption?

Over months of discussing hundreds of these narratives, Graham developed something more valuable than financial expertise. She built a mental library of business patterns—a sixth sense for recognizing strategic situations before they fully materialized.

The result? A powerful 28-year tenure that transformed The Washington Post into a media powerhouse.

Any MBA professor would dismiss Buffett’s approach as unscientific, inefficient, and impossible to grade. Yet it produced extraordinary results. Why?

The Ill-Structured Domain Problem

Corporate strategy isn’t like chess. Chess has clearly defined rules, limited possible moves, and objective evaluation of positions. Master chess by studying enough positions and you’ll reliably improve.

Strategy operates differently. It’s what cognitive scientists call an “ill-structured domain”—a field where:

The rules constantly change
Problems arrive with incomplete information
Multiple valid solutions often exist
Varying contexts determine which frameworks apply
Pattern recognition trumps analytical rigor

In ill-structured domains, you don’t become expert by memorizing frameworks. You develop expertise through massive exposure to varied cases, gradually building intuition about what patterns matter and which don’t.

This is why Annie’s MBA, for all its rigor, failed her. Business schools teach Season 2 skills in Season 2 format: structured, analytical, framework-driven. But strategic intuition develops in Season 1, through unstructured, curiosity-driven exploration of countless business stories.

Her professors taught her to dissect strategies. Buffett’s method taught Graham to recognize them in the wild.

Annie’s Accidental Discovery

Over the Christmas holidays, Annie found herself doing something she normally avoided: falling down a YouTube rabbit hole.

It started innocently. She’d always wondered why Apple’s iPhone crushed Blackberry, Nokia, and Ericsson—giants that seemed untouchable until they weren’t. A Google search led her to a documentary video. That led to another. And another.

Four hours later, having watched 21 videos spanning mobile phone history, product launches, and CEO interviews, she emerged with a strange new capability. She could now answer a question she’d never consciously considered: “What would I have done differently as CMO at Nokia?”

But immediately, guilt set in. Had she just wasted an evening on the digital equivalent of binge-watching reality TV or TikTok? Shouldn’t she be reading the Harvard Business Review journal articles sitting in her queue?

What Annie didn’t realize: she’d accidentally stumbled into Season 1 learning.

That “wasted” evening accomplished something her expensive Strategic Planning course never could. By immersing herself in multiple failure narratives, she began building the pattern recognition library that expert strategists draw from automatically.

One case study teaches frameworks. Twenty-one interconnected stories start building intuition.

Building Your Own Season 1 Practice

The transformation Annie needs won’t come from reading one more business book or taking another certification course. She needs to deliberately create her Season 1 practice.

Here’s what that looks like:

Consume voraciously, but with purpose.
Watch YouTube documentaries about business failures. Read long-form narratives about company transformations. Follow industry evolution stories across decades. The key isn’t passive consumption—it’s exposing yourself to enough varied cases that patterns start emerging naturally.

Ask the practitioner’s question.
Don’t just absorb stories. Constantly ask: “What would I have done as CMO/CEO/strategist/consultant in this situation?” This active engagement transforms entertainment into training.

Seek variety over depth initially.
Early in Season 1, breadth matters more than depth. Sample retail failures, tech disruptions, manufacturing transformations, and service industry evolution. Cross-industry patterns are often more valuable than industry-specific expertise.

Let curiosity lead.
Unlike Season 2’s targeted learning, Season 1 works best when you follow genuine interest. That four-hour YouTube session worked for Annie because she authentically wanted to understand mobile phone competition.

Connect consumption to creation.
Eventually, Season 1 exposure fuels Season 2 learning, which prepares you for Season 3 execution. But the sequence matters. Don’t rush to application before you’ve built sufficient pattern recognition.

The Real Competitive Advantage

When Annie returns to her next major strategic initiative—her next Season 3 moment—she’ll show up differently. Not because she learned new frameworks, but because she’s developed strategic peripheral vision.

She’ll recognize patterns her CEO can’t articulate but knows when he sees. She’ll spot familiar dynamics in unfamiliar situations. She’ll propose approaches that feel intuitively right, even if she can’t immediately explain why.

This is what her boss meant by “strategic thinking.” Not framework mastery. Pattern fluency.

And her company becomes the ultimate beneficiary. Now they have a CMO who brings genuine strategic intuition to every discussion—the kind of thinking that can’t be faked, purchased, or crammed before a meeting.

It just has to be grown, season by season, story by story.

———————————

P.S. You are invited to share in my compilation of strategy-related YouTube videos at StratCinema.org

P.P.S. This article is based on a column I wrote for the Jamaica Gleaner.

P.P.P.S. Here are some LLM prompts you can use for further learning.

Here are instructions and 5 prompts for readers developing strategic fluency:

Before Using These Prompts

Copy and paste this context into your LLM to get better responses:

“I’m developing strategic intuition by studying business cases, company failures, and industry transformations—an approach called Season 1 learning. Unlike traditional MBA education that focuses on frameworks, I’m building pattern recognition by exposing myself to many varied business stories. I’ll be sharing cases I’ve consumed (YouTube videos, articles, books, documentaries) and asking you to help me extract strategic insights and patterns. Your role is to help me think like a practitioner who must make decisions under uncertainty, not like an academic analyzing what already happened. Push me to identify what I would have done differently and what patterns I’m noticing across multiple cases.”

Prompt 1: The Practitioner’s Debrief

“I just watched/read [title/description of case]. Here’s what happened: [2-3 sentence summary].

Now help me process this as a strategist-in-training:

What was the critical decision point where things could have gone differently?
If I were [specific role: CMO/CEO/Head of Product] at that moment, what information would I have lacked that seems obvious in hindsight?
What would I have needed to believe or notice to make a better choice?
What’s one pattern here that might appear in completely different industries?”

Prompt 2: Cross-Case Pattern Recognition

“I’ve now consumed [number] cases about [general theme: tech disruption/retail transformation/product failures/etc.]. Here are brief descriptions of 3-5 of them: [list cases with 1-sentence descriptions].

Help me identify:

What strategic pattern appears in at least 3 of these cases?
What does this pattern look like in its early stages, before the outcome is obvious?
When this pattern appears, what are the hard-to-see warning signs?
What would ‘seeing this pattern early’ have enabled in each case?
In what completely different context might I encounter this same pattern?”

Prompt 3: The Mental Library Builder

“I want to add this case to my ‘mental library’ of strategic patterns: [describe case].

Help me catalog it effectively:

What’s the one-sentence ‘pattern name’ I should remember this case by?
What are the 2-3 specific details that make this pattern recognizable in real-time?
Which other cases in my library does this connect to or contradict?
If I’m in a strategy meeting and this pattern is emerging, what question should I ask to test if it’s really present?
What’s the ‘inverse’ of this pattern—what does success look like when someone navigates this well?”

Prompt 4: The Scenario Transfer

“I just studied how [Company X] failed at [situation]. Now help me practice transferring this insight:

Imagine I’m [specific role] at a company in a completely different industry—say [name specific industry]—and I’m seeing these three signals: [describe 3 current business signals].

Could the pattern from [Company X]’s failure be emerging here?
What would I need to investigate to confirm or rule out this pattern?
If it IS the same pattern, what would I do in the next 30/90/180 days?
What would cause me to be wrong about this pattern applying?
What other patterns from my library might explain these signals better?”

Prompt 5: The Strategic Intuition Audit

“I’ve been doing Season 1 learning for [time period]. I’ve consumed approximately [number] cases covering [list topic areas].

Help me audit what strategic intuition I’m actually building:

Based on what I’ve described, what are the 3-4 patterns I seem to be recognizing most readily?
What types of strategic situations am I probably still blind to?
Where are the gaps in my mental library? (What industries, failure modes, or strategic contexts am I under-exposed to?)
Given my role as [your actual role], which 5 specific case types should I prioritize consuming next to build practical pattern recognition?
How would I know if I’m moving from ‘consuming cases’ to ‘recognizing patterns in real-time’?”

How to Use These Prompts

Start with Prompt 1 after every case you consume. Use Prompt 2 weekly after you’ve accumulated several cases. Deploy Prompt 3 when a case feels particularly instructive. Use Prompt 4 monthly to practice transferring insights to your actual work context. Run Prompt 5 quarterly to ensure your Season 1 practice is building genuine strategic intuition, not just entertainment consumption.

Note – this article is based on a column written for the Jamaica Gleaner.

December 21, 2025

The Uncomfortable Truths 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 officials attended his retirement celebration. By every visible measure, he’d been a success.

Sally’s exit was more muted. The board called her tenure “necessary but difficult.” Several executives had departed during her five years at the helm. Her farewell event was notably subdued compared to the celebration Michael received.

But here’s where the story gets interesting.

Six months after Michael left, his company announced a major restructuring that eliminated the divisions he’d protected for a decade. Millions of dollars in shareholder value evaporated. Within a year, 50% of the workforce was gone.

Six months after Sally left, her company reported record profits from the strategic pivot she’d championed over fierce internal opposition. When an unexpected crisis hit shortly after her departure, the organization adapted with unusual speed and turned the disaster into an opportunity.

The pattern reveals an uncomfortable truth about leadership that most of us would rather not confront.

The Questions Leaders Ask Themselves

Each executive had been asking themselves fundamentally different questions throughout their tenure. These questions were invisible to outsiders and perhaps even unconscious to the leaders themselves. But they had profound effects on performance and organizational capability.

Michael achieved unanimous board approval and high satisfaction scores by proposing only moves people were comfortable with. His instinct was always to adjust proposals until opposition disappeared. Board meetings were harmonious. His team was content. Everyone liked working with him.

Sally generated regular conflict by advocating for positions she might be wrong about—market exits, controversial partnerships, challenging restructuring efforts. She created tension in boardrooms and pushed her team beyond their comfort zones.

Michael was beloved. Sally was respected. And only one of them transformed their company.

In the day-to-day reality of organizational life, we’d all prefer to work with a Michael. It’s just easier. Less stressful. More comfortable. But when you step back and look at the big picture, the Sallys of the world achieve something fundamentally different—they build organizations capable of thriving in uncertain futures.

From Management Excellence to Leadership Impact

The irony is that Michael rose through conventional management success. He delivered immediate results. He worked long hours. He built people’s skills. Everyone appreciated his collaborative style, and he accumulated a long list of admirers throughout his career.

But what made him an excellent manager became deadly when he stepped into the CEO role.

His “nice guy” instinct—so valuable when managing projects and building teams—became a liability when leading organizational transformation. He sought comfort over conflict. He adjusted strategies until opposition disappeared. Board meetings remained harmonious, but no one challenged weak ideas. Everyone was smiling while the company slowly lost its competitive edge.

Only after his retirement did the damage emerge in stark financial terms and workforce devastation.

Sally took a different path. She prepared for C-suite roles deliberately—hiring executive coaches, engaging in intensive leadership development, and training herself to ask a fundamentally different question: “What am I willing to be wrong about?”

This wasn’t just a philosophical exercise. She actively sought out perspectives that challenged her thinking, including using AI tools to stress-test her assumptions and identify blind spots in her reasoning.

As CEO, she pushed for market exits, restructures, and strategic pivots that sparked genuine debate. Board meetings became intellectually rigorous rather than comfortable. Her management team was forced to think independently rather than seek consensus.

When that crisis hit after her departure, the company was ready. Years of her tough choices—the re-engineering projects, the technology integration, the market repositioning—had already built adaptive capacity into the organization’s DNA. The crisis didn’t create team strength. It revealed the resilience her uncomfortable decisions had forged.

What Transformed Sally’s Leadership

A former vice president who worked under Sally explained the shift this way: “Sally never asked what we were willing to do. She told us what she believed we could do, then demanded proof. At first we resisted—some of us vocally. But eventually, we became more than we thought possible. We discovered capabilities we didn’t know we had.”

That insight became the foundation of Sally’s leadership philosophy: people don’t discover their capacity through comfort. They discover it by confronting challenges they initially believe are beyond them.

This realization required Sally to make a conscious decision about what kind of leader she would be. She stopped optimizing for board approval and started advocating for market reality. She stopped asking what people would volunteer and started demanding what they could become.

It wasn’t about being difficult for its own sake. It was about holding up a mirror to the organization’s potential and refusing to settle for the comfortable status quo.

Three Principles for Transformational Leadership

From this fundamental insight, Sally developed three operating principles that guided her leadership decisions:

Advocate for what others won’t see. Not the obvious moves everyone agrees on, but the non-obvious plays that data suggests and comfort resists. This means being willing to be the voice in the room that says, “I know we’ve always done it this way, but here’s what the market is actually telling us.”

Demand what others won’t give. Not what people volunteer to do, but what you genuinely believe they’re capable of becoming. This requires a deep confidence in human potential combined with the courage to ask for more than people think they can deliver.

Test what others won’t risk. Not consensus-driven certainties, but hypotheses you’re willing to be wrong about. This means running controlled experiments with strategic bets, learning from failures, and iterating quickly rather than waiting for perfect information.

These principles aren’t about being contrarian or difficult. They’re about recognizing that transformation—real transformation—requires someone to push beyond the boundaries of organizational comfort.

The Legacy Question

Here’s the question every leader should be asking: Ten years from now, will your successor be building on your legacy or repairing what you avoided?

The companies thriving in 2035 won’t be led by consensus-builders like Michael, despite how beloved they were. They’ll be led by leaders like Sally—people willing to make boards and teams uncomfortable in service of genuine transformation.

This isn’t an abstract theoretical point. It’s playing out in real time across industries. The organizations that thrived through the pandemic weren’t those with the most harmonious cultures—they were those whose leaders had already pushed them to build adaptive capacity through uncomfortable changes.

Your Next Move

This week, starting tomorrow, challenge yourself to do something concrete: Choose one strategic position you believe in but haven’t voiced because it risks discomfort.

Don’t ask yourself if the board will like it. Don’t wonder if your team will resist it. Instead, ask yourself: Am I willing to be wrong about this?

If the answer is yes—if you genuinely believe it’s worth testing even though you might be wrong—then you have your next leadership move.

Because here’s the final uncomfortable truth: the farewell speech that will eventually be given at your retirement is already being written. Every decision you make today, every time you choose comfort or conflict, consensus or transformation, is adding another line to that speech.

Managers chase comfort and celebrate short-term wins. Leaders pursue transformation by demanding more than people thought they could give—and building organizations capable of thriving long after they’re gone.

The question isn’t whether you’ll be liked or loved. The question is whether you’ll be needed—because you built something that couldn’t have existed without your willingness to make people uncomfortable in pursuit of something greater.

What will your legacy be?

—————————————

This article is based on a column published in the Jamaica Gleaner.

December 8, 2025

Ep 32 – From Idea Overload to Execution – A Strategist’s Guide to Prioritization

This is a free preview of a paid episode. To hear more, visit longtermstrategy.substack.com

Your organization has 37 brilliant projects. You have bandwidth for maybe 5.

Now what?

This is the reality facing leaders everywhere: expensive master plans that deliver impressive lists of initiatives but zero guidance on which ones to actually pursue. Meanwhile, your CEO expects magic, your budget is maxed out, and that critical board meeting is in two weeks.

Sound familiar?

This episode tackles one of strategy’s most brutal challenges: how do you prioritize when everything seems important and resources are painfully limited?

Joined by Ivana Wilson, founder of Wilson Business Consulting and expert in opportunity framing, Francis Wade and his guest unpack the story of “Stephanie”—a VP of strategic planning stuck with 37 projects from an expensive master plan and no roadmap for execution.

This conversation exposes the hidden traps of poor prioritization and reveals a systematic approach to cutting through the chaos.

You’ll discover:

* Why “let’s start everything and see what works” destroys value faster than doing nothing

* The real cost of scattered execution (spoiler: it’s not just wasted money)

* A proven framework for organizing idea overload into executable strategy

* How to build decision-driven roadmaps that preserve flexibility while driving focus

* The art of strategic sequencing: when to say “not now” to protect “yes” for the right projects

The hard truth: Most organizations fail not because they lack good ideas, but because they try to execute too many at once. The companies that win? They master the discipline of strategic prioritization.

Stop drowning in possibilities. Start executing with purpose.

Here is the video version of the free excerpt.

For a limited time, the full video below the paywall will be available on StratCinema.

December 7, 2025

Stop Calling It Recovery: Why Your Business Needs a Different Target

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 matters far beyond Jamaica’s shores.

“Recovery” assumes your old business model was viable. For most organizations, it wasn’t. That’s why they’re calculating hurricane damage for the third time this decade, why they’re responding to their fourth supply chain crisis in two years, why they’re addressing the same vulnerabilities again and again.

The word matters because it shapes the destination. And if that destination is simply “back to normal,” you’re planning to fail in exactly the same way next time.

The Recovery Trap

Let me be direct: If your post-crisis strategic plan looks like “restore operations to pre-crisis levels,” you’re planning to fail again.

Recovery language creates a dangerous illusion. It suggests there was a golden era you need to return to—a time when the business was humming, customers were happy, and growth was steady. Then the crisis hit and disrupted everything.

But that’s fiction.

The truth most leaders know but won’t say out loud: Your business had fundamental vulnerabilities long before the crisis made them visible. The hurricane, the pandemic, the market shock—it didn’t create your problems. It revealed them.

You already knew your supply chain was too dependent on a single source. You already knew your physical infrastructure couldn’t handle severe weather. You already knew your cash reserves were too thin. You already knew your team’s digital capabilities were years behind competitors.

The crisis just made these truths undeniable.

So when you talk about “recovery,” what are you actually recovering to? A fragile business model? An outdated strategy? An eroded competitive position? A workforce unprepared for what’s coming?

That’s not a plan. That’s a delusion.

What Transformation Actually Looks Like

Let’s look at what organizations that escaped this trap actually did.

Sony, Post-War Japan: When Sony emerged from the devastation of World War II, they didn’t try to rebuild Japan’s pre-war electronics industry. That industry was based on cheap labor and imitation of Western products. Instead, Sony’s founders asked a different question: “What could Japan become if we built for the world that’s coming?”

They invested in miniaturization technology when everyone said radios had to be large. They pioneered the transistor radio when the market didn’t exist. While Japan was rebuilding roads, they built global distribution networks.

Sony didn’t recover. They transformed into something their pre-war selves couldn’t have imagined.

The defining moment came in 1955 when Bulova proposed a massive deal that would have guaranteed immediate revenue. Co-founder Akio Morita refused: “If we accept, they will be promoting the Bulova name. In five years, no one will remember Sony. But if I spend 50 years selling Sony-branded products, I will build a brand that lasts for decades.”

That’s the difference between recovery thinking and transformation thinking.

Indonesia, Post-Tsunami: After the 2004 tsunami devastated Aceh province, killing over 160,000 people in Indonesia alone, the government didn’t just rebuild the fishing villages that were destroyed. They relocated entire communities to higher ground, created early warning systems that didn’t exist before, and diversified local economies away from single-industry dependence.

The new Aceh wasn’t a recreation of the old one. It was designed for a future where tsunamis would happen again—but with radically different outcomes.

New Orleans, Post-Katrina (A Counter-Example): What happens when you choose recovery over transformation? Look at New Orleans after Hurricane Katrina in 2005.

The city spent billions rebuilding in the same flood-prone areas, restoring the same vulnerable levee systems, recreating the same economic dependencies. Twenty years later, the city remains vulnerable to the same threats. The recovery was successful. The transformation never happened.

That’s the cost of choosing the wrong word—and the wrong destination.

The Question That Changes Everything

Here’s what transformational thinking looks like in practice:

Instead of asking “How do we get back to normal?” you ask a different question: “If we were building this business from scratch today, knowing what we know about technology, climate, markets, and geopolitics, what would we build?”

This isn’t theoretical. Jamaica is facing exactly this choice right now.

Since 2009, Jamaica has been working toward Vision 2030 Jamaica—a national development plan with the ambitious goal of achieving developed-country status by 2030. It was a bold, comprehensive framework covering everything from education to economic policy to social development.

But as Prime Minister Andrew Holness acknowledged in late 2024, many of its original aspirations are now beyond reach. Jamaica won’t become a developed country in the remaining years of the plan.

Yet Vision 2030 did something crucial: it demonstrated that long-term thinking is possible, even in a country accustomed to short-term crisis management. It planted the seeds of what comes next.

Vision 2050: Transformation, Not Restoration

What Jamaica needs now—and what your organization likely needs too—is a Vision 2050.

Not a recovery plan. Not a restoration strategy. A transformation roadmap.

A Vision 2050 should be hard-hitting enough that it forces uncomfortable questions. What does a mid-century resilient organization look like in a world of climate chaos, technological disruption, and geopolitical instability? What capabilities must we build? What dependencies must we eliminate? What assumptions must we abandon?

It should be detailed enough that you can work backward to inform today’s decisions. If we need X capability in 2050, what must we start building in 2025? If Y vulnerability will be fatal in 2040, what must we eliminate now?

And it should be transformative, not restorative. The goal isn’t to get back to 2024. The goal is to leapfrog to something that would have been impossible to imagine in 2024.

The Opportunity Crisis Creates

Here’s the paradox: Crisis is the only time most organizations have permission – the full freedom – to transform.

In normal times, there’s too much momentum, too many stakeholders invested in the status quo, too many reasons to optimize rather than revolutionize. Crisis breaks that inertia. It creates a brief window where fundamental change becomes possible—even expected.

Hurricane Melissa offers Jamaica this opportunity. Your next crisis—and there will be one—offers it to you also.

The question is whether you’ll use it for recovery or transformation.

Recovery is easier. It’s more comfortable. It doesn’t require you to question fundamental assumptions or abandon familiar approaches. You can point to what existed before and say “let’s get back to that.”

Transformation is harder. It requires admitting that what you’re losing wasn’t worth preserving in its current form. It demands imagination about futures that don’t yet exist. It means making irreversible decisions based on incomplete information.

But only one of these approaches positions you for the world that’s actually coming.

The Fork in the Road

Every organization facing disruption stands at a fork in the road. One path leads back. One path leads forward. They’re labeled with different words.

One sign says “Recovery.”

The other says “Transformation.”

The choice reveals everything about what comes next—and whether you’ll be having this same conversation after the next crisis hits.

Choose the right word. It determines your destination.

——————————-

This article is based on a column published in the Jamaica Sunday Gleaner Business Section by Francis Wade

November 23, 2025

Unreliable Inspiration | Engage Others with Category Design Like Fosbury

Imagine your executives are adopting a dangerous belief: people only perform when threatened by crisis. When the building is on fire, performance soars. When competitors attack, teams mobilize. When survival is at stake, magic happens.

This point of view sounds plausible, but it should worry you.

Yes, crises can bring out extraordinary levels of commitment and sacrifice. But as a leader, you should be suspicious. Must your employees face an existential threat to deliver their best work?

Or is this just cynicism masquerading as realism?

Consider it an admission of leadership failure. Deep down, you don’t want to manufacture drama to fire people up. And you don’t want to hype fake urgency (“This is our make-or-break moment!”) just to get people moving.

Fortunately, there’s a source of “clean” inspiration available to you: perpetual category design.

Case in Point

Until the 1968 Mexico Olympics, the world accepted certain limits on high jump techniques. Jumpers went over the bar face-down, in variations of the straddle or scissors technique. Going head-first or face-up? Unthinkable.

In fact, USA Olympic coach Payton Jordan warned that such a technique would “wipe out an entire generation of high jumpers because they will all have broken necks.”

Yet a time traveller from the 1992 Olympics would be utterly confused. By then, 100% of jumpers were defying Jordan’s accepted wisdom, arching backwards over the bar in what became known as the Fosbury Flop.

What had happened?

Dick Fosbury created a new category of high jump. Working almost alone as a high school student, he experimented with an approach that took advantage of recently introduced foam landing pits. Over time, he transformed from a mediocre athlete into a 1968 gold medallist who revolutionized his sport forever.

And no, there wasn’t a crisis afoot. No Olympic committee threatened to eliminate high jump. No injury forced his hand. He was simply a college student on track to become a civil engineer, competing in an era when track and field offered few monetary rewards.

He innovated because the possibility excited him.

Your Employees Want This

In your organization, there’s a special kind of employee who understands this possibility. They’re frustrated because executives don’t. You’ll hear them complain that leadership thrives on the adrenaline of surprise disruptions, that short-term firefighting crowds out long-term thinking.

They’ll point out something more troubling: crisis-addiction actually creates more crises. It’s a self-fulfilling prophecy.

Consider the pattern: organizations that lurch from emergency to emergency often discover their problems took years to develop. The talent shortage that hits during a critical launch. The technology debt that cripples during expansion. The cultural dysfunction that surfaces when pressure mounts.

These weren’t surprises. Someone saw them coming. Someone raised concerns. But leadership was too busy fighting the last fire to prevent the next one.

Category Design as Alternative

What if those organizations had practiced category design instead?

Category design is a strategic planning method for achieving breakthroughs rather than incremental improvements. It involves creating and dominating brand new business categories, rather than competing in existing ones crowded with rivals. By seeking to make a fundamentally different kind of impact, a new category unlocks fresh value.

Some organizations are forced into new categories others define. Think of how Netflix forced Blockbuster to reckon with streaming, or how Tesla pushed traditional automakers toward electric vehicles. These transitions are painful when someone else designs the new category.

A tiny few don’t wait for crisis or competitive pressure. Instead, they design new categories proactively, committing themselves to long-term transitions. With pre-emptive actions, they craft a new landscape while others are still defending the old one.

Perpetual Category Design

However, there’s a tendency for companies to over-focus on single innovations, treating competitive advantage as if it were a one-time occurrence. The best companies think differently.

They always have a 15-30 year vision and strategy in play, working behind the scenes where competitors can’t see it. As soon as they accomplish a major milestone, they revise their plans and set new targets.

This is the only way to transcend the human tendency to leap big hurdles, then lose the capacity to imagine further obstacles. Without perpetual category design, organizations stagnate after victories, endlessly reciting prior successes. Their constant chest-beating gets in the way of fresh thinking.

To help your organization avoid this trap, follow these steps inspired by the Category Pirates:

Name the current category game. What category are you and your competitors playing in today? What are its defining rules and assumptions?

Dive deep into unmet needs. What do your customers or stakeholders truly need that no one is adequately addressing? Where is everyone solving the wrong problem?

Frame a new point of view. What different lens or perspective reveals new possibilities? What becomes possible when you reject conventional wisdom?

Name your new category. Give your different approach a memorable name that captures its distinctive value.

Build a long-term vision and strategy. Map the 15-30 year journey from here to category leadership. Make it concrete enough to guide decisions.

You may not replicate the high energy of crisis response. Few can sustain that.

But you will have defined something more valuable: a sustainable, renewable source of motivation. When done well, it creates immediate action that feels as urgent as emergency response—without the accompanying disaster.

Crisis creates urgency by making the present unbearable.

Category design creates urgency by making the future irresistible.

Go Deeper: LLM Prompts for Category Design

Prompt 1: Diagnose Your Crisis Addiction “I lead a team/organization in [your industry]. Help me identify signs that we might be addicted to crisis-driven performance. Ask me 5-7 diagnostic questions about our leadership patterns, planning practices, and team behaviors. After my responses, analyze whether we’re running on crisis energy vs. sustainable inspiration.”

Prompt 2: Map Your Current Category “I work in [describe your industry/sector]. Help me clearly define the category game my organization is currently playing. Ask me questions about: (1) what business we think we’re in, (2) who we compete with and how, (3) the rules everyone follows, and (4) what ‘winning’ looks like. Then show me the invisible assumptions constraining our thinking.”

Prompt 3: Discover Unmet Needs “Act as a strategic interviewer helping me uncover unmet customer/stakeholder needs. I serve [describe your audience]. Ask me probing questions about: what they hire us to do, what they settle for, what they complain about, and what they’ve stopped asking for. Help me see the gap between what we deliver and what would truly transform their situation.”

Prompt 4: Design Your New Category “Based on this context [paste your responses from prompts 2 and 3], help me brainstorm 3-5 potential new category positions for my organization. For each option: (1) name the new category, (2) explain how it’s fundamentally different from our current category, (3) describe the distinctive value it unlocks, and (4) identify the biggest obstacle to getting there.”

Prompt 5: Build Your Fosbury Moment “I want to create a ‘Fosbury Flop’ innovation in my field. Like Dick Fosbury, I want to question a fundamental assumption everyone accepts. In my industry [describe], help me identify 3-5 ‘sacred cows’—techniques, practices, or beliefs that everyone follows but no one questions. Then help me imagine what becomes possible if we challenge each one.”

Prompt 6: Create Your 15-Year Vision “Help me draft a compelling 15-year vision for category leadership. I want to shift from [current category] to [new category concept]. Ask me about: our unique advantages, the milestones we’d need to hit, the capabilities we’d need to build, and the legacy we want to leave. Then help me write a vivid 2-paragraph vision that makes this future feel irresistible to my team.”

This article is based on a column written for the Jamaica Gleaner.

November 9, 2025

Chronicles from a Caribbean Cubicle 2025-11-09 09:19:17

Why Playing It Safe Will Erase Your Leadership Legacy

The conventional wisdom says: stay focused, deliver on your core responsibilities, don’t overstep. But the leaders who’ll be celebrated a generation from now are ignoring that advice entirely.

Picture this: You’re running a major public sector organization. Every performance indicator is green. Your board loves your quarterly updates. Senior leadership regularly commends your results.

Yet when you walk through the communities you serve and talk to regular people, they describe the same chronic problems that existed half a decade ago.

“Nothing’s really changed,” they tell you. “The issues we complain about? Still there.”

Here’s what you know that they don’t: Many of these problems have simple tactical fixes. But implementing systematic, lasting solutions? That’s brutally difficult.

Why? Because the real challenges don’t respect organizational boundaries. They sprawl across multiple departments, agencies, and jurisdictions. Solving them requires something most job descriptions never mention: delivering results beyond your formal authority.

When Excellence Becomes the Enemy

The most dangerous trap in public sector leadership isn’t outright failure. It’s what we might call “compliant mediocrity.”

This happens when leaders optimize for their own metrics, hit their assigned targets year after year, and consider themselves successful—within narrow confines.

But something’s missing. Despite their achievements, they feel perpetually drained. Their work doesn’t inspire. While they collect their paychecks, their legacy quietly dissolves because the work that truly matters doesn’t sit neatly inside their control. Instead, it lives in the uncomfortable spaces between organizations.

These boundary-spanning problems—crime, economic stagnation, infrastructure decay, climate resilience—remain unsolved because government systems reward predictable, controllable ambitions over transformative ones.

A small group of public sector leaders, however, have discovered a different path.

The Cross-Agency Coordination Model

Consider a successful example: a national security coordination body designed to span multiple stakeholder organizations. Rather than operating as a single agency, it functions as a coordinating mechanism that brings together defense chiefs, police commissioners, anti-corruption directors, and senior civil servants in quarterly sessions that enforce collaboration and mutual accountability.

This sounds impossibly complex. Bureaucratic chaos waiting to happen.

The secret ingredient? A secretariat led by someone with deep institutional knowledge—decades of service across multiple ministries, connections throughout the civil service, and the credibility to cut through red tape.

Leaders like this see past surface-level problems. They understand that when infrastructure fails in your neighborhood, it’s rarely one agency’s fault. They recognize these as complex challenges that cross organizational boundaries and demand cooperation.

Sometimes, this requires personal trust built over years that transcends hierarchy and formal mandates.

Here’s what these cross-boundary initiatives do differently:

Begin with citizen outcomes, not organizational outputs. This means multiple stakeholders working simultaneously toward shared final results, regardless of difficulty. Think of national development frameworks that require whole-of-government approaches.

Develop shared strategic hypotheses. These groups craft testable theories about what might work, and every stakeholder buys into the same hypothesis. This alignment is invisible but essential.

Create distributed ownership. Few thoughtful observers believe complex social problems can be solved by single agencies. For example, the pipeline that leads people into the criminal justice system involves education, social services, mental health, employment, and community development—not just law enforcement.

Deploy data surgically. By targeting specific areas and measuring them with modern tools, these coordination bodies receive rapid feedback and can adjust quickly.

This list isn’t exhaustive. But the fundamental shift is enormous: committing yourself to citizen outcomes that can’t be mapped to your organization chart or short-term results requires courage.

Three Immediate Actions

1. Redefine How You Measure Success

Stop asking: “Did I meet my targets?” Start asking: “What outcome do citizens actually need—and who else must I engage to deliver it?”

This single reframe changes everything.

2. Cultivate One Strategic Partnership This Quarter

Identify the single senior leader whose work intersects with your biggest bottleneck.

Don’t request a generic “collaboration meeting.” Instead, bring value to the table: “I have data on [specific challenge] that affects both our organizations. Can we review it together?”

This mirrors the trust-through-transparency approach used by successful cross-agency bodies.

3. Launch One Cross-Boundary Experiment

Select one problem requiring multi-agency partnership. Design a small, 90-day pilot with concrete metrics.

Approach your leadership and secure explicit permission to “test and learn” across boundaries they may guard carefully.

For instance: “Can we reduce youth reoffending by 15% if we coordinate case management across education, justice, and corrections for 20 young people?”

The Memorial Test

Two decades from now, nobody will remember your Q3 performance ratings.

They’ll remember whether violent crime decreased in their city. Whether young people found pathways to employment. Whether communities became more resilient to natural disasters.

You face a choice: operate within comfortable boundaries and deliver forgettable results, or cross organizational lines and create something that endures.

The question isn’t whether you can collaborate across silos. It’s whether you’re willing to be remembered for something beyond meeting targets.

Six Strategic Prompts for Cross-Silo Leadership

Prompt 1: Define Your True Impact Zone

“I lead [your organization]. Our formal mandate covers [state scope]. But the outcomes stakeholders actually need are [list 3-5 challenges].

Analyze: What’s the highest-impact outcome I should pursue that requires collaboration beyond my current organizational boundaries? Map which other agencies must participate and why.”

Prompt 2: Chart Your Collaboration Landscape

“I want to address [specific cross-cutting challenge, e.g., chronic homelessness or youth workforce development].

Create a stakeholder map showing: (1) Which organizations control relevant budgets, authority, or data, (2) Each organization’s current incentive structure, (3) Where natural friction points exist, (4) Which ‘connector’ leaders I should approach first.”

Prompt 3: Build Your First Strategic Experiment

“Using evidence-based delivery frameworks, help me design a testable 90-day strategic hypothesis for [boundary-crossing problem].

Include: (1) The specific measurable outcome we’re testing, (2) The minimum viable partnership (which 2-3 organizations must coordinate), (3) Key assumptions we’re validating, (4) Early warning indicators that signal we need to pivot, (5) How to present this as a ‘safe-to-fail’ experiment to leadership.”

Prompt 4: Draft Your Trust-Building Approach

“I need to engage [counterpart at another organization] about collaborating on [challenge]. They’re likely skeptical because [explain context: past failures, territorial concerns, resource limits].

Write a 200-word email or meeting opening that: (1) Leads with evidence they care about, (2) Frames the challenge as shared rather than ‘my request,’ (3) Proposes a low-risk exploration, (4) Acknowledges their constraints to build trust.”

Prompt 5: Navigate the ‘Not My Responsibility’ Response

“I’m encountering resistance to cross-boundary work. The objections are: [list specific pushback like ‘that’s outside my role,’ ‘we lack capacity,’ ‘that’s Agency X’s territory’].

Provide: (1) A reframe for each objection that shifts from ‘mandate compliance’ to ‘stakeholder outcome delivery,’ (2) Examples from successful cross-agency coordination that show how leaders navigated similar resistance, (3) A compelling case for how this enhances (not threatens) institutional reputation.”

Prompt 6: Track Progress Across Organizational Lines

“I want to monitor progress on [cross-cutting outcome] involving [list 3-4 organizations]. Currently, each tracks different metrics that don’t create a coherent picture.

Design: (1) A simple dashboard with 4-6 shared metrics all organizations can feed, (2) A quarterly reporting rhythm that minimizes bureaucratic burden, (3) How to make this data transparent for public accountability without making organizations defensive.”

Note: Expect targeted insights specific to your context and constraints.

This is a longer version of my recent column in the Jamaica Gleaner.