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.

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.

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.