Category: Strategy

Picture a familiar scene in a non-profit organization. A hotel conference room. Flip charts on easels. A two-day offsite that everyone has blocked out on their calendar and quietly dreaded.

The exercises begin. Strengths, weaknesses, opportunities, threats. Stakeholder maps. Priority matrices. The team engages dutifully, filling in the boxes, generating the language that planning retreats are supposed to generate.

Then comes the afternoon slump – and it is not just fatigue from the morning’s work. Something more specific has happened. The conversation has drifted away from the reason the organisation exists. Words like “competitive positioning” and “market capture” are appearing on the sticky notes, and they feel borrowed – like wearing a suit that belongs to someone else.

Nobody says anything. Everyone is willing the process to work.

A document emerges by the final session. The board receives it at the next meeting. And within a few months, it occupies a shelf or a folder, largely untouched.

This is not a story about poor facilitation or disengaged leadership. It is a story about using the wrong instrument for the job.

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Where These Frameworks Actually Come From

Management strategy as a discipline has a particular genealogy. The models that dominate executive education – the competitive analyses, the positioning matrices, the market share battles – were developed with a specific type of organisation in mind: businesses that survive or collapse based on their ability to outperform rivals and make profits.

The evidence is in the curriculum. Academic research suggests that the vast majority of MBA case material is drawn from industries where competition is the central organising tension. The mental model underneath most strategy training treats the world as a contest. There is a prize. There are opponents. The goal is to win more than you lose.

That framing is genuinely useful for firms operating in those conditions. The urgency of a competitor threatening your revenue is real, and tools designed around that urgency have genuine motivating power.

But take those same tools into a cooperative, a trade association, a government agency, or a development organisation, and something goes wrong almost immediately. (The same applies to a monopoly.) The animating force – the rival who might take what is yours – does not exist in the same way. Frameworks engineered around that force become awkward, like running software on a system it was never designed for.

The afternoon energy drop at your retreat was not a morale problem. It was the sound of a square peg meeting a round hole.

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The Timeframe Problem Nobody Talks About

The mismatch runs deeper than vocabulary, though.

Competitive strategy is built around a particular relationship with time – specifically, a short one. The frameworks that dominate business education are oriented toward near-term results: quarterly performance, annual targets, the speed of response to a market threat.

Mission-driven organisations often operate under an entirely different time logic. A land trust working to preserve ecosystems, a credit union serving underbanked communities, a health institution building public capacity – these organisations are answerable to timescales that most competitive strategy tools cannot even see.

When a long-horizon organisation runs its strategy through a short-horizon framework, something gets quietly distorted. The institution begins optimising for the measurable and the near-term, while the foundational commitments – the ones that justify the organisation’s existence – drift into the background.

The Co-operative Group in the United Kingdom offers a sobering case study. Once among the most significant member-owned enterprises in the world, the Co-op entered the 2010s in serious trouble. An investigation into its near-collapse revealed a decade of decisions shaped by competitive growth logic: major retail acquisitions, banking mergers, rapid diversification across sectors. The goal had been scale – more market presence, more revenue streams, more assets.

What the organisation had not been tracking with the same rigour was whether any of this expansion was coherent with what a cooperative is actually for. Its governance was member-based. Its legitimacy came from community trust. Its identity was inseparable from a set of values about how business ought to be conducted.

By the time a £1.5 billion hole appeared in the banking arm, the institution had been operating with someone else’s strategy for years. The tools it had borrowed rewarded growth metrics. They had no mechanism for asking whether growth was serving the mission – or consuming it.

The same drift appears in organisations across every sector.

• A humanitarian agency that chases high-visibility donor projects at the expense of quiet, unglamorous long-term work.
• A professional body that adds revenue streams until its membership can no longer articulate what the body stands for.
• A regional development authority that reports on outputs while the underlying social fabric it was created to strengthen continues to fray.

In each case, the damage is slow and largely invisible inside the planning documents that caused it.

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Planning Built Around Purpose

What these organisations need is not a modified version of competitive planning. They need a process that begins with a different assumption — that strategy is about protecting and advancing a purpose across time, not about positioning against opponents.

1. Such a process starts with an honest reckoning with the present. Before any direction is set, the organisation needs to understand where it actually stands – not just financially, but in terms of mission integrity. How is trust held among the people the organisation serves? When has the institution historically drifted from its purpose, and what triggered those moments? What resources – financial, relational, reputational – are genuinely available?
2. From that foundation, a long horizon is established. Somewhere between fifteen and thirty years is typically productive. This might feel uncomfortably distant, but the distance is the point. It shifts the planning conversation away from quarterly anxieties and toward the questions that actually define an institution’s legacy.
3. With a target horizon in place, the team explores a range of possible futures rather than committing to a single premature forecast. The world in twenty-five years will be shaped by forces that cannot be predicted with precision – demographic shifts, technological change, political reconfigurations, ecological pressures. Scenario thinking does not pretend otherwise. It builds the capacity to navigate uncertainty rather than deny it, and it asks the organisation to identify which kind of future best allows its mission to flourish.
4. From a single chosen scenario, the planning process works backwards. If the organisation needs to be in a certain condition twenty-five years from now, what does the ten-year mark look like? The five-year mark? What must be in place, and by when? What are the big tradeoffs which need to be made? This backward mapping turns an inspiring long-term vision into a logical chain of necessary steps, each grounded in the one that follows it.
5. Only after that work is complete does it make sense to design a short-term action plan – because now there is a genuine strategic context for it. Immediate decisions are no longer just reactive. They serve something larger. Here, further tradeoffs must be made.

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The Question Underneath the Question

The mechanics matter, but the conceptual shift matters more.

Competitive strategy is structured around the question: How do we beat them? Purpose-driven strategy is structured around a different one: How do we remain who we are, and do what we exist to do, across the years ahead?

These produce very different conversations – different discussions at leadership retreats, different criteria for investment decisions, different definitions of success that get embedded in the culture over time.

Cooperatives, civil society organisations, public institutions, and social enterprises are not inferior versions of private companies. They are different kinds of institutions altogether, built on different social contracts, accountable to different stakeholders, and serving purposes that exist precisely because markets and competitive logic have limits.

The strategy process these organisations use should reflect that – not apologise for it.

When the next retreat in your non-profit ends with a document that finally stays off the shelf, it will be because the planning process started from the right place: not how do we win, but how do we endure, and why does it matter that we do.

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

Go Deeper: Five Prompts for Further Exploration

The argument in this article points to a gap — between the strategy tools most executives have been given and the organisations they are actually leading. The five prompts below are designed for use with any AI assistant (Claude, ChatGPT, Gemini, or similar). Each one picks up where the article leaves off. Copy, paste, and adapt the parts in brackets to your own context.

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Prompt 1: Diagnose Your Own Organisation

For the reader who finished the article thinking — “this is us.”

I lead a [cooperative / government agency / NGO / family business / religious institution / statutory body] in [country/region]. Based on the argument that most strategy frameworks were designed for competitive, profit-first organisations, help me diagnose whether my organisation has been using the wrong strategy tools.

Ask me five diagnostic questions — one at a time, waiting for my answer before moving to the next — that will reveal whether our strategy process is genuinely built around our mission and long time horizon, or whether we have been borrowing competitive frameworks that don’t fit.

After my five answers, give me an honest assessment of where we stand, and identify the single most dangerous misfit between the tools we are using and the organisation we actually are.

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Prompt 2: Rebuild the Co-op’s Strategy — Non-Competitively

For the reader who found the Co-operative Group case study instructive and wants to go deeper.

The UK Co-operative Group’s near-collapse in 2013 has been attributed to governance failure and poor management. But a different diagnosis is possible: the Co-op was a mission-first, member-owned organisation that had adopted competitive private-sector strategy logic — chasing scale, acquisitions and market presence — instead of building strategy around what a cooperative is uniquely positioned to do.

Assume you are a strategy advisor brought in to the Co-op in 2005, before the Britannia merger and the Verde pursuit. Using only non-competitive strategy tools — scenario planning, category design, mission integrity analysis, and long-horizon thinking — build the outline of the strategic conversation the Co-op’s leadership should have been having. What questions should have been on the table? What 20-year opportunity was sitting unclaimed? What slow-moving threats should have been named? What would a purpose-first Co-op strategy for 2005–2030 have looked like?

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Prompt 3: Design a Purpose-First Strategy Retreat

For the reader who is planning — or dreading — their next strategic planning offsite.

I need to design a two-day strategy retreat for the leadership team of a [describe your organisation type and size]. Our previous retreats have used standard frameworks — SWOT analysis, competitive positioning, priority matrices — and the resulting plans have consistently ended up on shelves.

The core problem is that those frameworks were designed for profit-first, competitor-facing businesses. We are a mission-first organisation with a long time horizon and no direct rival whose defeat would constitute success.

Design a full two-day retreat agenda that replaces competitive frameworks with purpose-built alternatives. Include: the opening question that reframes the entire conversation; how to run a scenario planning session for a non-technical audience; how to do backward mapping from a 25-year horizon to a 90-day action plan; and how to end the retreat with commitments that will actually survive contact with the following Monday morning.

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Prompt 4: Make the Internal Case for Long-Term Thinking

For the reader who agrees with the argument but now has to convince a board or senior team that doesn’t.

I have read an argument that mission-driven organisations — cooperatives, government agencies, NGOs, religious institutions, family businesses — are systematically underserved by MBA-derived strategy frameworks because those frameworks were built for competitive, profit-first firms. I agree with this argument. My organisation is [describe it briefly].

The problem is that my board and senior leadership are not yet convinced. Several members have strong private-sector or MBA backgrounds and default to competitive strategy language. Others simply don’t see the urgency of changing our planning approach.

Help me build the internal case. Give me: three concrete examples of organisations like ours that failed — or significantly underperformed — because they used competitive strategy frameworks that didn’t fit; three compelling questions I can put to the board that will expose the mismatch without triggering defensiveness; and the single most persuasive one-paragraph argument I can make for why this matters now, not eventually.

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Prompt 5: Apply Category Design to a Non-Competitive Organisation

For the reader intrigued by the article’s reference to category design as an alternative strategic tool.

Category design is a strategy framework developed primarily for technology and consumer companies. Its core idea is that instead of competing within an existing market, an organisation defines and dominates an entirely new category — changing what problem it is seen to solve and becoming the obvious answer to a question that previously wasn’t being asked.

I want to explore whether category design can be applied to a non-competitive organisation. My organisation is [describe: sector, size, core mission, approximate age, geographic context].

Walk me through a category design thinking process adapted for a mission-first organisation. Specifically: What category does my organisation currently occupy in the minds of the people it serves — and is that the right one? What problem could we redefine ourselves as the unique solution to? What would it mean for us to own a category rather than compete within one? And what is the 10-year version of success if we got this right?

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A note on how to use these prompts: each one is a starting point, not a single exchange. The most productive approach is to begin the conversation, push back on the AI’s first response, add specifics about your own organisation, and treat the output as a thinking partner rather than a finished answer. Prompt 3 in particular benefits from iteration — run it once, then ask the AI to make the agenda harder, more honest, or more specific to your sector.

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:

1. 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.

2. 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.

3. 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.

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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:

1. “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.”
2. “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.”
3. “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.”
4. “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?”
5. “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?”

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.

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

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P.S. Here are prompts for use in your faovorite LLM.

These prompts are designed to help you shift from a “present-forward” mindset to “future-back” strategic thinking based on the article’s core lessons.

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1. The “Future-Back” Visioning Prompt

“Imagine it is the year 2050. Describe three major environmental, technological, or social demands my [industry/role] will face. Based on these 2050 demands, work backward to identify one ‘strategic need’ I must begin addressing today to remain relevant, focusing on outcomes rather than specific tools.”

2. Signal vs. Noise Filter

“Review my current top five professional priorities. Using the ‘future-back’ lens from the US Coast Guard’s Project Evergreen, analyze which of these are merely tactical responses to today’s ‘noise’ and which align with long-term ‘signals’ of 2050. Suggest which I should deprioritize.”

3. From Prescription to Empowerment

“I am currently planning [Project Name]. Instead of asking ‘What should I do?’, help me rephrase my goals into ‘strategic needs.’ Create a list of high-level outcomes that define success for this project while leaving the specific ‘how-to’ implementation flexible for changing future conditions.”

4. The “Anti-Kodak” Stress Test

“Identify a current success or ‘proven’ method in my business that feels indispensable today. Act as a contrarian strategist from the year 2050 and explain how over-reliance on this specific success could lead to my future irrelevance. What flexible capability should I build instead?”

5. Implementation Gap Bridge

“I have a long-term strategy to [Insert Goal], but it feels ‘dead on arrival.’ Help me deconstruct this rigid plan into ‘robust strategic needs’ that my team can actually implement. How can I shift from pushing solutions to empowering my team to solve for future demands?”

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Transcript

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.

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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:

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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.”

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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?”

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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?”

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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?”

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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?”

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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’?”

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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.

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

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.

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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.”

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