Category: Strategy

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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.

Posted on

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.

Posted on

Why Your Strategic Plan Is Probably Just an Expensive Wish List

And how one Jamaican leader used scientific thinking to crack a problem everyone else had given up on

Ask most CEOs about their strategic plan and you’ll hear about vision statements, multi-year roadmaps, and quarterly KPIs. What you won’t hear is the one thing that actually matters: What do we believe has to be true for this to work?

That missing question—the absence of a testable hypothesis—is why most strategic plans gather dust while organizations spin their wheels solving the same problems year after year.

Dianne McIntosh and Jamaica’s Citizens Security Secretariat (CSS) discovered this the hard way. Their story reveals how treating strategy like a scientific experiment—not a sacred document—can unlock progress that seemed impossible.

The Problem with Most Strategic Plans

Here’s the uncomfortable truth: calling something a “strategic plan” doesn’t make it strategic.

Most planning exercises produce elaborate action lists. Deploy new technology. Improve customer service. Expand into new markets. These aren’t strategies-they’re activities. And activities without an underlying theory about why they’ll work are just expensive guesses dressed up in PowerPoint.

Real strategy requires what Dr. Peter Compo describes as a central rule: a single guiding choice that directly addresses the system’s bottleneck—the critical constraint standing between you and your aspiration. A true strategy is not a laundry list of initiatives but a clear, testable bet about how overcoming that bottleneck will unlock progress. The central rule can then be tested, adapted, or abandoned as evidence accumulates.

Why don’t more leaders think this way? Because genuine strategic thinking is genuinely hard. It demands:

  • Making peace with incomplete information
  • Committing to multi-year time horizons
  • Accepting you might be wrong
  • Following evidence even when it contradicts your initial beliefs

Most executives understandably retreat to the comfort of detailed plans and busy work. At least that feels like progress.

When Reality Breaks Your Beautiful Plan

When Jamaica formed the CSS to tackle violent crime, they followed the standard playbook: multi-sectoral coordination, justice reform, community programs. Their flagship initiative? Train 99,000 parents of at-risk youth through the Parenting Commission.

It was comprehensive. It was ambitious. It was wrong.

The program failed spectacularly—burning through a million euros in EU funding before collapsing under the weight of insufficient capacity and entrenched behavioral patterns. The target was fantasy, not strategy.

This is where most organizations double down on the original plan or blame “execution failures.” The CSS did something different: they admitted their hypothesis was flawed and went looking for a better one.

The Question That Changed Everything

Tony Anderson, then Commissioner of Police, posed a challenge that redirected their entire approach: “When are you going to do something about the few schools producing most of our criminals?”

That question sent McIntosh’s team into Jamaica’s education data for the first time. What they found confirmed Anderson’s instinct—but revealed something far more important.

The data exposed the bottleneck: children leaving primary school reading at Grade Two level, many traumatized, seeking achievement and belonging in criminal gangs instead of classrooms.

This wasn’t about parenting programs. The constraint was literacy and unaddressed trauma in the education system itself.

Suddenly, the CSS had a testable hypothesis: If we close learning gaps and treat trauma in vulnerable schools, we can predictably reduce the pipeline of youth into criminality.

That’s a hypothesis you can build experiments around. That’s a hypothesis that points to specific interventions. That’s a hypothesis that, if wrong, tells you exactly where your assumptions broke down.

The Scientific Approach to Strategy

The CSS’ turnaround demonstrates a replicable four-step process:

First: Treat Your Plan as a Temporary Hypothesis

Stop calling it “the strategy” and start calling it “our current best guess.” The CSS abandoned their parenting program quickly because they viewed it as a testable assumption, not a political commitment. This requires intellectual humility—and organizational culture that rewards learning over face-saving.

Second: Let Data Reveal the True Constraint

The CSS didn’t commission a new consulting study. They analyzed existing school inspection reports and educational outcomes data. The constraint revealed itself: students trapped in learning failure, falling further behind each year.

Theory of Constraints teaches that every system has one primary bottleneck limiting performance. Your job isn’t solving every problem—it’s identifying which constraint actually matters, then exploiting it relentlessly.

Third: Build a Cause-Effect Model You Can Measure

The CSS formalized their new hypothesis as the Inter-Ministerial School Support Strategy (IMSSS). Success became concrete: move a child from Grade One to Grade Four reading level in ten weeks.

This shift is critical. Unlike short-term police operations that yield immediate metrics, social development requires years to show results. But intermediate indicators—reading level improvements, trauma treatment completion—let you track whether your hypothesis is working long before final outcomes appear.

You’re not waiting five years to discover you were wrong. You’re testing assumptions continuously.

Fourth: Institutionalize the Learning Process

Borrowing from Tony Blair’s UK government, the CSS established itself as a delivery coordination center—managing the “science of delivery” across multiple ministries.

Why does this matter? Because one-off experiments don’t create lasting capability. You need institutional mechanisms that turn hypothesis testing into organizational DNA.

Does Your Plan Have a Hypothesis?

Most strategic documents hide their assumptions rather than stating them explicitly. You can fix this today with a simple diagnostic.

Take your current strategic plan and ask an AI to analyze it using these prompts:

  1. What’s our stated long-term objective?
  2. What are our top five proposed actions?
  3. What cause-and-effect chain connects these actions to that objective? (State it explicitly: “We believe X leads to Y because of Z”)
  4. What’s the implicit hypothesis? (“The constraint preventing our success is…”)
  5. Are these actions surgical interventions testing our hypothesis—or just business-as-usual activities we hope will help?
  6. Can you state our central strategic hypothesis in one clear, testable sentence?

If the AI can’t find a clear hypothesis, neither can your team. You’re operating on hope, not strategy.

The Ultimate Test

After running this analysis, ask yourself one question McIntosh would recognize:

“If we executed this plan perfectly and still failed to achieve our goals, would we know exactly which assumption was wrong?”

If you can’t answer “yes”—if you can’t pinpoint the specific cause-effect belief that would be disproven—then you don’t have a strategic hypothesis. You have a prayer disguised as a plan.

But if you can articulate what would have to be true, what evidence would prove you wrong, and what you’d learn from failure—then you’re thinking scientifically.

The CSS didn’t contribute to reducing Jamaica’s violent crime by 40% through willpower or resources. They did it by treating strategy as science: form a hypothesis, design experiments, follow the evidence, adjust ruthlessly.

Your constraints are different. Your bottleneck isn’t literacy or trauma. But your challenge is identical: stop planning and start hypothesizing.

The evidence is waiting to tell you what’s actually true. The only question is whether you’re ready to listen.

This article is based on my recent Jamaica Gleaner column.

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Why Your Strategic Vision Falls Flat (And How AI Can Fix It in 10 Minutes)

As a senior executive, you’ve delivered passionate presentations about your organization’s strategic vision. You’ve crafted compelling narratives about transformation, growth, and impact. Yet somehow, your message resonates in the boardroom but dies somewhere between middle management and the frontlines.

Sound familiar?

Most executives communicate like it’s 1995 – a pre-digital world. They craft one message and assume it will resonate equally across all levels of the organization. Unfortunately, they remain trapped in a predictable pattern: the C-Suite is energized, department heads are cautiously optimistic, supervisors are skeptical, and frontline staff are mentally planning their next vacation.

This enthusiasm gap has killed more strategic initiatives than market downturns, budget cuts, or competitive threats combined.

But what if you could access an AI assistant that never tires of brainstorming and never judges your half-formed ideas? Some executives are already discovering this secret weapon. What follows are three 10-minute prompting strategies that require only copying, pasting, and customization. By the end, you’ll have created a new Super Colleague who works for free.

The Level-Specific Translator

Your strategic passion resonates at the top, wavers in the middle, and completely dissolves at lower organizational tiers. One-size-fits-all messaging simply cannot work when you’re speaking to executives worried about market position, managers concerned about operational changes, and frontline employees focused on daily workflows.

Start with this basic prompt:

“I need to communicate our strategic initiative to different levels of my organization. Here’s our core message: [INSERT YOUR MESSAGE]. Please create 4 versions tailored for: 1. Senior executives (focus on strategic impact) 2. Middle managers (focus on operational changes) 3. Supervisors (focus on team implications) 4. Frontline staff (focus on daily work impact). For each level, address their specific concerns and use language they relate to.”

To deepen this approach, upload relevant strategic documents, previous planning frameworks, and organizational assessments. But go further.

Great communication begins with genuine empathy for your audience. Modern tools like Jobs to Be Done and Design Thinking can take you into your staff’s actual experience. Once there, you can tap into deeper motivations than just “getting a paycheck.”

Feed these insights into your AI and ask it to generate multiple message options. This gives you choices rather than hoping your first attempt works.

The Resistance Detector

Even with perfect messaging, you should expect skepticism. While employees nod politely in meetings, their real objections remain unspoken, quietly sabotaging your efforts. You’re fighting invisible resistance because people won’t voice their true concerns publicly.

Use your AI to anticipate objections before they derail your initiative:

“I’m rolling out strategic initiatives in my [TYPE OF ORGANIZATION]. Based on typical employee concerns, what are the likely unstated objections from: 1. Middle managers worried about implementation 2. Supervisors concerned about their teams 3. Frontline staff skeptical about change. For each group, identify their top 3 unspoken concerns and suggest how I should address them in my communication.”

Feed in data from employee surveys, focus groups, and engagement metrics. Your AI Super Colleague will analyze every piece simultaneously—a feat no human consultant can match.

Expect some surprises. You’ll also receive specific strategies to address lurking issues before they become problems, helping you craft proactive responses rather than reactive damage control.

The Tactical Action Generator

If you’ve gained traction with the above methods, congratulations—but you’re far from finished. Strategic success relies on thousands of individuals taking specific actions that fall well outside business-as-usual operations.

That’s the entire point of strategic transformation.

Now you need concrete activities that departments can integrate into their operational plans:

“Our organization is pursuing [INSERT SPECIFIC STRATEGIC GOAL]. We are a [TYPE OF ORGANIZATION] with departments including [LIST DEPARTMENTS]. For each department, create 3-5 specific actions they can take in the next 90 days that directly contribute to this goal. Make sure each action is SMART and requires minimal additional resources.”

The specific answers won’t be perfect, but they’ll accelerate your thinking exponentially. You’ll move from abstract strategy to concrete tactics in minutes rather than months.

Beyond Traditional Consulting

Skeptics might argue these are questions leadership teams discuss regularly. True—but we know that fresh perspective can shake up stale thinking considerably. Your AI Super Colleague brings unlimited patience, vast knowledge synthesis, and zero political agenda to strategic planning.

Unlike human consultants who deliver recycled frameworks, AI generates organization-specific insights. Unlike internal brainstorming that gets trapped in groupthink, AI challenges assumptions. Unlike expensive advisory relationships that drain budgets, AI provides unlimited strategic thinking support.

The transformation isn’t just about better communication—it’s about democratizing access to strategic thinking tools that were previously available only to organizations with massive consulting budgets.

Start Today

Your AI Super Colleague is waiting, ready to transform how you bridge the gap between strategic vision and organizational reality. While others struggle with the same old enthusiasm gaps and communication breakdowns, you can become the leader who finally cracks the code on organization-wide alignment.

The prompts are here. The technology is accessible. The choice is yours. Why not start today?

This article was inspired by one that was published in the Jamaica Gleaner.

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Live on Substack #3: Unmasking the Strategy Success Trap

Unmasking the Strategy Success Trap: Why Booms Lead to Busts!

How should your company react to amazing success? Join us for a spirited conversation diagnosing the fatal strategic missteps of companies that went through unearned booms during COVID-19.

We reveal why giants like Peloton and Fiverr abandoned their profitable, long-term business models to chase massive, temporary demand.

We explore how this pursuit of tactical success led to impulsive, nearsighted decisions—such as Peloton becoming a capital-intensive manufacturing/logistics operation—which guaranteed a crash and painful layoffs. Discover the critical difference between “structural change” (permanent) and “cyclical noise” (temporary).

Learn the essential discipline of long-term strategy. A sound strategy must act as a risk-management tool during good times, allowing companies like Amazon and Uber to leverage windfalls to build a lasting, sustainable advantage.

True success is measured not by the peak of a boom, but by the depth of a normalization the company can survive. Prepare your company for the threat of a disruption brought about by success beyond its wildest dreams.

This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit longtermstrategy.substack.com/subscribe

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Ep 31 – Escaping the Short-Term Trap

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

You have a hunger for game-changing results. As a CEO, board member, or strategic planner, you aspire to produce big results. While you know methods that work, you still find yourself drifting back into short-term thinking in these tumultuous days. Without daily activities guiding you toward a True North—a preferred long-term destination—you run the risk of being sucked into the 24-hour news cycle or latest drama.

How do you build the strategic muscles necessary to withstand even daily shocks and surprises?

The opposite of conventional strategy is true. Stop chasing short-term survival; outsiders and technology cannot save you from constant disruption. Conventional wisdom demanding “twice the results in half the time” is fundamentally flawed. Real game-changing success requires robust long-term strategic muscle.

We expose the 25 fatal obstacles infecting C-suites with short-term thinking, providing definitive ‘obstacle knowledge’ so you can become a robust, different kind of strategist who can preemptively design for disruption.

Tune in to join me in tackling this wicked problem. I’ll share the approach we took to designing the Long-Term Strategy Conference 2025 held in June.

I’m Francis Wade and welcome to the JumpLeap Long-Term Strategy Podcast.

P.S. Here’s a LLM prompt you can copy and paste into an LLM to deepen your understanding:

Act as a strategic planning consultant. I just listened to a podcast about long-term strategic planning. Here’s the core insight I learned: “Big results need years. Long time frame and big results go together. If you try to commit to big goals on short time frames, it doesn’t work.”

My current strategic planning challenge is: [DESCRIBE IN ONE SENTENCE YOUR BIGGEST STRUGGLE WITH LONG-TERM THINKING IN YOUR ORGANIZATION].

Based on this insight, identify three specific symptoms in my organization that indicate we’re stuck in short-term thinking. Then suggest one concrete conversation starter I can use this week to begin reframing our strategic discussions.

P.P.S. Want more? For subscribers, I have generated at least 5 more prompts, available below the paywall.

Show Notes

https://strategyconf.fwconsulting.com/conference-topics-2025/ – The full list of 25 Obstacles

The full video is available below for subscribers. So are the other LLM Prompts mentioned above.

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Beyond the Annual Planning Checklist: How Government Executives Reclaim Inspiring Purpose

Imagine you lead a government ministry, department, or agency. As you approach the season for submitting annual reports and corporate plans, you realize something is missing. The very reason you entered public service is being lost in paperwork.

This challenge isn’t unique to any single country—it’s a global phenomenon affecting government leaders worldwide, whether they’re working within established national development frameworks or considering creating one.

A Case Study in National Vision: Jamaica’s Experience

To understand this dynamic, consider Jamaica’s Vision 2030—one of the world’s most comprehensive national development plans. For over 16 years, more than one hundred government organizations have submitted detailed annual plans to parent ministries, creating a rigorous process that private sector executives often admire. It represents a remarkable achievement in sustained strategic execution.

Dr. Wesley Hughes, the plan’s architect, originally envisioned something transformational. In his forward to the Vision 2030 document, he wrote: “Today, our children have access to technologies that were once considered science fiction. They seek opportunities to realize their full potential. This Plan is to ensure that, as a society, we do not fail them.”

Hughes continued: “We have a duty to ourselves, to the sacrifices of past generations and to the hopes of future generations, to preserve the best of our country and to transform the worst. The outcome in 2030 is dependent on the decisions we make today.”

However, as insiders know, even the most well-intentioned national frameworks can become sources of bureaucratic dread rather than inspiration. How does this happen, and what can leaders worldwide learn from this experience?

The National Vision Compliance Trap

The primary problem—whether in Jamaica or any country with strategic planning processes—is that organizations typically complete their internal plans before “aligning” them with the national vision. Compliance checking becomes the final step rather than the foundational starting point.

This approach is fundamentally backwards, like deciding to travel somewhere before determining why the journey matters.

Consequently, civil servants feel constrained rather than inspired by their national development framework. For countries without established national plans, this offers a crucial lesson: the implementation process matters as much as the vision itself.

Universal Principles for Government Leaders

Whether you’re operating within an existing national framework or considering developing one, the solution involves reclaiming strategic voice through fundamental questions:

“What does our country need from this organization to accomplish our national vision?”

“What game-changing outcomes aren’t explicitly captured in current planning but have become critical?”

“What goals should influence the next (or first) iteration of national planning?”

Reconnect with Original Purpose

Study Dr. Hughes’ approach as a model. He didn’t create Vision 2030 as bureaucratic compliance exercise—he crafted it as a covenant with future generations. Government leaders worldwide can apply this principle by:

  • Returning staff to the original purpose behind strategic frameworks
  • Connecting teams with the deeper reasons they joined public service
  • Making inspirational founding documents part of organizational culture
  • Recognizing that most public servants want to accomplish more than mere survival

From Following to Leading: The Jamaica Model and Beyond

Jamaica’s experience offers both cautionary tale and opportunity. The country now stands at a unique inflection point—with remaining years in the Vision 2030 timeline that could become its finest contribution to national development.

This mirrors a broader truth: research shows humans overestimate short-term potential while underestimating long-term possibilities. Strategic initiatives often build momentum gradually, achieving exponential impact toward their timeline’s end.

For countries without national development plans, Jamaica’s experience suggests several critical design principles:

  • Start with inspirational purpose, not compliance requirements, and convert these into frequent practices.
  • Build implementation processes that energize rather than drain participants.
  • Create feedback loops that celebrate progress toward transformational goals.
  • Design planning cycles that connect daily work to generational impact.

The Global Leadership Choice

Whether you’re working within Jamaica’s Vision 2030, another country’s national framework, or considering developing strategic planning processes, the fundamental choice remains the same.

The question isn’t whether you have authority to lead transformational change—you do. The question is whether you have courage to use it.

Right now, government leaders across the globe face this choice. Will you spend your tenure perfecting compliance reports? Or will you use strategic planning as foundation for breakthrough leadership?

Dr. Hughes designed Vision 2030 to prevent society from failing its children. His vision applies universally: every government leader has opportunity to ensure their work serves future generations rather than mere bureaucratic efficiency.

Lessons for Countries Without National Plans

Jamaica’s experience offers valuable insights for nations considering comprehensive strategic planning:

  1. Start with inspirational architecture like Hughes created—connect planning to generational responsibility.
  2. Design implementation processes that inspire rather than constrain participants.
  3. Build momentum systems that recognize long-term strategic initiatives often achieve greatest impact at timeline’s end.
  4. Create cultural integration that makes strategic thinking part of daily organizational life.

History won’t remember executives who filed the most thorough paperwork. It will remember those who transformed their area of responsibility when game-changing leadership mattered most.

The choice, and the legacy, are yours—whether you’re building on Jamaica’s model or creating your own path toward national transformation.

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When Good News Becomes a Business Risk: How Falling Crime Can Disrupt Your Strategy

A Shift Few Leaders Expect

Falling crime rates are usually celebrated as a sign of progress. Safer communities, stronger economies, and a brighter future—what’s not to like? Yet for business leaders, this kind of change can also be profoundly disruptive. If your company has been operating for decades in an environment shaped by insecurity, what happens when that reality suddenly shifts?

Jamaica offers a striking example. For years, high levels of violence defined everyday life and business practices. Many firms adapted, building their operations on an assumption of danger. Now, crime is falling. If this trend proves durable, the very foundations of corporate strategy in the country could be shaken.

The same dynamic applies globally. Whether it’s crime, inflation, regulation, or even cultural norms, long-standing conditions shape business models. When those conditions change, the leaders who cling to old assumptions often suffer the most.

Beyond Skepticism: Could the Change Be Real?

History encourages caution. In Jamaica, crime dipped after the 2010 “Dudus crackdown,” when nearly a hundred criminals were eliminated or fled. The effect was temporary; crime rebounded. Understandably, leaders today hesitate to celebrate.

But current indicators suggest something different. The Citizens Security Plan (CSP), launched in 2020, has applied coordinated interventions across policing, communities, and schools. These are not random shifts but measurable, systemic efforts. According to Dianne McIntosh of the Citizens Security Secretariat (CSS), the downward trend was predicted and intentional, not accidental.

If this approach is sustainable, Jamaica may be entering a new era. For business leaders, that requires more than casual observation—it demands strategic reconsideration.

When Old Assumptions Become Dangerous

Executives often claim to have “a long-term plan.” Sometimes it exists only in their heads; other times it’s reduced to lofty mission statements. But when tested, many leadership teams struggle to articulate a coherent strategy. That’s manageable when conditions remain stable. It’s perilous when they change.

Falling crime isn’t just a social good—it’s an economic shock. Studies suggest that Jamaica’s high crime rate has shaved 2–4% off annual GDP growth. If that burden is lifted, the economy could expand in ways that reward some sectors while destabilizing others.

Consider Colombia. Between 2002 and 2010, murders and kidnappings plummeted. While the country as a whole benefited, one sector suffered: private security. With half a million armed guards—more than the army and police combined—the industry had thrived on fear. When violence declined, demand collapsed. Firms that assumed the old reality would last indefinitely faced sudden disruption.

The same could happen anywhere. Companies built on entrenched conditions may discover that their core business model no longer fits.

Lessons from a Pandemic Surprise

This pattern isn’t limited to crime. In 2017, a financial services client dismissed the idea that their country was ready for online banking. They imagined digital adoption as a distant event.

In discussions, I encouraged them to carve out an actual timeline: a 10-year goal. Then the COVID-19 pandemic hit. Overnight, physical branches closed, and the digital future arrived.

Fortunately, the company had at least sketched out a plan. They accelerated it, shifting in months what they thought would take a decade. Those without foresight were left scrambling.

The lesson is clear: change rarely arrives on schedule. Leaders who prepare for disruption—whether it comes from crime rates, technology, or global crises—are positioned to adapt. Those who rely on yesterday’s success become their own worst enemy.

Why Foresight Matters Now

Harvard professor Clay Christensen once observed that organizations grow addicted to what made them successful. They defend the familiar rather than exploring the new. This is comforting but risky.

If crime falls sustainably, a country like Jamaica will experience profound change. Real estate values could climb. Tourism could expand. Consumer confidence could rise. Yet industries tied to fear—private security, certain insurance products, or defensive real estate designs—may shrink.

Globally, the principle is the same: whenever a long-standing challenge begins to ease, leaders must ask, what happens to us if the world really does change?

Turning Good News into Strategic Advantage

Falling crime is an undeniable win for society. But for business leaders, it’s also a challenge. The question is not whether to celebrate, but whether to adapt.

Here are three steps to consider:

  1. Validate the Data
    Don’t rely on rumors or short-term headlines. Understand the leading indicators, the policies behind them, and whether the change is likely to last.
  2. Stress-Test Your Model
    Ask how your operations, costs, and markets would shift if the old assumptions disappeared. If your business relies on high levels of fear, inflation, or any entrenched condition, prepare alternatives.
  3. Rebuild Before You’re Forced To
    Waiting until the change is undeniable often means it’s too late. Instead, use foresight to redesign your company around the future that could emerge.

The Bottom Line

A safer society is a gift. But it is also a test of leadership. True foresight requires seeing risks where others see only triumph.

The companies that thrive will be those willing to let go of outdated assumptions and embrace a new normal—even when the news is good.

This article is based on a column I wrote for the Jamaica Gleaner published on Sep 14, 2025.

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Why Your Strategy Isn’t Inspiring Anyone (And How AI Can Fix It)

As a senior executive, you’ve probably felt the weight of expectation when it comes to inspiring your team. The board expects it. Your direct reports need it. But despite your best efforts—the carefully crafted presentations, the all-hands meetings, the motivational speeches—something isn’t working.

Your people seem disengaged. They nod politely during strategy sessions, but you can sense their minds wandering. The quarterly results suggest they’re just going through the motions rather than truly buying into your vision for the future.

Your first instinct might be to blame yourself. Maybe you need better presentation skills, more charisma, or additional leadership training. But before you sign up for another executive coaching program, consider this: the problem might not be you at all.

The Outdated Playbook

Most organizations still rely on industrial-age methods to communicate their strategic vision. The playbook hasn’t changed much in decades:

Step one: Leadership team crafts a comprehensive strategic plan during an off-site retreat.

Step two: Create a polished presentation and distribute lengthy PDF documents.

Step three: Hold a company-wide meeting where the CEO delivers an inspiring speech.

Step four: Trust middle managers to cascade the message down through their teams.

Step five: Hope the enthusiasm lasts more than a few weeks.

This approach assumes that inspiration works like a broadcast signal—send it out once, and everyone receives it clearly. But that’s not how human psychology works, especially in our current information-saturated environment.

Consider this reality check: the average employee finds more engagement in a one-minute Tik Tok video than in most hour-long corporate strategy presentations. This isn’t a reflection of shortened attention spans—it’s about relevance and interactivity.

Rethinking Employee Activation

Instead of trying to temporarily pump up your workforce, focus on creating what consultant Amie Devero calls “activated” employees. These are people who either genuinely care about your company’s future or have discovered how their personal aspirations align with organizational goals.

In most companies, roughly half the workforce falls into one of these categories naturally. They want to contribute meaningfully and grow professionally. The challenge is that traditional communication methods only effectively reach about 10% of non-executive staff members.

Why such a low connection rate? Most employees simply lack the background or time to digest complex strategic documents. Even when materials are well-written and intentions are good, the gap between executive thinking and front-line understanding remains vast.

When leaders notice this disconnect, they often make things worse by trying harder with the same failed methods. They speak louder, write longer documents, and add pressure on middle managers to better “sell” the message.

But what does a truly activated employee look like in practice?

They regularly reference the company vision when making decisions. They have genuine curiosity about strategic initiatives and how their work contributes. Most importantly, they feel connected to colleagues around shared purpose rather than just shared tasks.

The question becomes: how do you create this level of engagement systematically?

The AI-Powered Solution

Recent advances in artificial intelligence offer a completely different approach to vision and strategy communication. Large Language Models—sophisticated chatbots that can engage in natural conversation—have opened new possibilities for organizational learning.

More specifically, there’s a subset called Source Language Models that work exclusively with materials you provide. Think of it as creating a custom search engine that only knows about your company’s strategy documents, leadership videos, planning materials, and related content.

Unlike general-purpose AI that draws from the entire internet, these focused systems answer questions using only your uploaded materials. This means employees can have detailed, accurate conversations about your specific strategic vision without getting generic business advice.

The practical applications are remarkable. An employee wondering how their department fits into the five-year plan can get instant, detailed answers. Someone curious about market assumptions underlying your strategy can explore those topics in depth. A team member with ideas for improvement can understand exactly where their suggestions might fit.

Modern platforms can automatically generate supplementary materials from your core documents: podcast-style audio summaries for commuters, interactive quizzes to test understanding, visual mind maps showing strategic connections, and even video presentations that break down complex concepts.

Beyond Traditional Engagement

This AI-powered approach addresses several problems with conventional vision communication:

Personalized pacing: Instead of forcing everyone to absorb information at the same rate during meetings, people can explore strategic concepts at their own speed and depth.

Continuous availability: Rather than limiting strategic discussion to quarterly all-hands meetings, employees can engage with your vision whenever questions arise in their daily work.

Interactive learning: Instead of passive consumption of presentation slides, people can ask follow-up questions, explore specific areas of interest, and test their understanding.

Identifying blind spots: As employees interact with your strategic materials, they often surface insights that leadership teams miss. Front-line workers frequently spot emerging technologies, customer trends, or operational challenges that could reshape your industry.

When this happens at scale, you essentially gain access to a tireless strategy consultant who knows your business intimately and never sleeps. Your AI system becomes increasingly valuable as more employees engage with it, asking questions that reveal both strengths and gaps in your strategic thinking.

The Leadership Shift

This approach represents a fundamental shift in how we think about inspirational leadership. Instead of placing the entire burden on executives to be charismatic communicators, it creates systems that meet each person where they are.

Some employees learn best through detailed written analysis. Others prefer audio explanations during their commute. Still others need visual frameworks to understand complex relationships. An AI-powered system can serve all these learning styles simultaneously.

The result is genuine activation rather than temporary motivation. When people can explore your vision on their own terms, at their own pace, they develop deeper understanding and stronger commitment.

As a leader, this doesn’t diminish your role—it amplifies your impact. Instead of being limited by your personal bandwidth and communication style, you can reach every team member in ways that resonate with their individual needs and interests.

The future of vision communication isn’t about becoming a more inspiring speaker. It’s about creating more engaging, accessible, and interactive ways for people to connect with your company’s purpose, strategy and direction.

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Hard to engage staff on vision/strategy? Do it in your sleep with AI.

Tired of staff surveys on company vision and corporate strategy showing disengagement despite your best efforts? You’re not alone. Most leaders think they need to be more “motivational” – but that’s backwards.

The real breakthrough? Creating systems where people motivate themselves. And AI is making this easier than ever.

Join us for a short presentation where we’ll share real experiments from leaders who’ve transformed their strategy communication from painful struggle to effortless system.

You’ll discover why your current approach isn’t working and see a completely different way to inspire your team – one that works even if you’re not a natural motivational speaker.

Spoiler alert: this has to do with setting up systems that produce profound engagement with the help of AI.

Thank you to everyone who tuned into my live video! Join me for my next live video in the app.

Amie Devero

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