Think You Need a Comprehensive Strategy? Maybe Not.

Your company proudly touts its “comprehensive strategic plan.” But while its creators are satisfied with its depth and detail, perhaps it’s time to rethink. Narrowing its focus might just save it from failure.

Somewhere in your email inbox, there’s a lengthy strategic document waiting to be read. It’s so long and dense that you haven’t even glanced at it. You’re not alone—no one has. Reading it would take hours, and your plate is already full.

Deep down, you worry that months—or even a full year—might pass before you carve out time to review it. But while the plan gathers digital dust, you don’t question the good intentions behind its creation. You may have even contributed some ideas early on. Yet, because you weren’t part of the team that finalized the document, its nuances escape you.

The responsibility for crafting the final version fell to a group of well-meaning colleagues who embraced the idea of being “comprehensive.” And therein lies the potential problem.


From Strategic Plan to Wishlist

What if the plan is less of a strategy and more of a wishlist? Think of a child’s letter to Santa: an ambitious catalog of hopes, many of which are unlikely to come true.

The issue isn’t that the individual ideas in the plan are bad—on the contrary, you probably support most, if not all, of them. The problem lies in the fallacy that “more is better.” In strategy, this belief can be dangerous. It’s easy for leaders to fall into the trap of saying “yes” to every new proposal, particularly in the C-suite.

But this “yes to everything” mindset often results in an unattainable dream masquerading as a plan. Failing to say “no” plants the seeds of failure.

Perhaps this pattern is familiar. It might even explain your reluctance to engage with the document. After all, a strategy overloaded with too many good ideas often adds up to a bad one.


A Case in Point: Apple’s Comeback

Consider Steve Jobs’ return to Apple in 1997. One of his first moves was to cut most of the company’s product lines. By focusing on a single ecosystem, Apple transformed itself into the world’s most valuable company.

This example highlights the power of focus. Now, how should you respond to your own bloated strategic plan?


Announce: The Process Isn’t Finished

Reject the current wishlist and restart the planning process with a fresh approach. A helpful tool to guide this next phase is Peter Compo’s Strategy Triad, which comprises three components:

  1. Aspiration – Your primary objective.
  2. Bottlenecks – The key obstacles standing in the way.
  3. Tasks and Policies – The actions needed to address the bottlenecks.

Use this framework in your next strategy session to sharpen your focus. Here’s how:

  1. Start by selecting your single most critical objective.
  2. Identify the bottlenecks preventing success and narrow down to the few actions required to overcome them.
  3. Move on to the next objective, applying the same process.
  4. Eliminate wishlist items that don’t directly address the bottlenecks.
  5. Prioritize a small number of high-impact initiatives that fit your resources and budget.

While this streamlined approach seems logical, expect resistance.


Handling Pushback

Objection #1: “This Will Be Too Difficult”

Narrowing the plan means forcing tough choices. Colleagues with conflicting priorities will have to confront their differences in open discussions, which can create tension.

The solution? Use a neutral facilitator. A skilled, impartial moderator can help navigate disagreements, ensuring the group reaches consensus without losing focus or momentum.

Objection #2: “This Will Take Too Long”

Don’t assume you can resolve these challenges in a quick meeting. Instead, dedicate a full day to an offsite session with your top 20 leaders. Away from daily distractions, work together to identify the few key initiatives that will “bust” the bottlenecks and achieve your goals.

While this approach requires time upfront, it’s an investment. Begin by showing how many hours would be wasted trying to execute the original wishlist. By narrowing the focus, you’ll save time overall and boost the odds of success.


Why It Works

An overly broad strategic plan is often overwhelming. Your colleagues may avoid engaging with it for the same reasons you do—it feels unrealistic and demotivating. By narrowing the scope, you create a plan that feels achievable and inspires action.

Think of it as a Minimum Viable Strategy. A focused plan speeds up implementation, concentrates energy, and delivers visible results. Success, in turn, builds momentum, paving the way for even greater achievements.

When it comes to strategy, less is often more. Toss the wishlist, narrow the focus, and watch your organization thrive.

Afraid to Be Lofty? | Expand, Then Compress Your Strategy

A turbulent world demands game-changing strategies. Companies must stand out, yet executives quickly discover that setting exaggerated goals has its limits. How can you inspire staff and board members with ambitious aspirations while maintaining credibility?

Case in Point: You anticipate breakthroughs during strategic planning retreats. Instead, you’re met with the same old ideas. Why? Tentative thinking holds everyone back.

You want your team to think in lofty, inspirational terms. But motivating bold action in just a few hours is a tough challenge. Even when the business urgently needs leadership, making courageous moves is easier said than done.

You wonder, “Is there a way to escape the extremes?” Can you encourage big thinking without retraining your senior team? Try the strategy compression technique.

Establish Equity with Ground Rules

Imagine this: A CEO interrupts a retreat to make a surprise announcement. After much deliberation, he’s decided on the “perfect” targets and timelines. Cutting the discussion short, he commands, “Focus on how we get there.”

At first glance, it seems efficient. In reality, it’s bullying.

By hijacking the process, the CEO forces colleagues into a subordinate role, stripping them of their ability to make meaningful decisions. To prevent this, establish ground rules that ensure equity during the retreat.

These rules should define how discussions are conducted and decisions made. Include pre-defined steps to address rule violations.

A CEO should recognize their unique role. They think about strategy daily, unlike others who need more time to shift into strategic thinking. Patience is key.

Overcoming Old-Style Thinking

Many executive teams lack experience with effective game-changing strategic planning. Yet, they’re all too familiar with the pitfalls of lofty goals—and the ridicule that follows when aspirations seem unrealistic.

This fear prompts leaders to think small, focusing on three-to-five-year horizons. During retreats, this mindset stunts ideation, limiting creativity. Instead of seizing opportunities for bold, pre-emptive thinking, they settle for mundane logic and uninspiring goals.

What’s the cost?

Look at Blackberry, Nokia, and Ericsson. They once dominated the mobile phone market but lost their edge due to overly cautious thinking. Despite vast resources, these companies fell into comfortable ruts, leading to their decline.

To change expectations, inform your team that they’ll be engaging in game-changing, pre-emptive planning. Then, introduce the Expand-Compress Technique.

The Expand-Compress Technique

Once you’ve set the right tone, choose a target year 15-30 years in the future. A horizon like 2050 forces the team to move beyond business-as-usual thinking.

Start by brainstorming a range of desired outcomes that collectively form a breakthrough vision for that year.

Next comes the magic: creating milestones from the present to 2050. These should be realistic. How? Backcast from the future to the present, and develop mini-plans to achieve these milestones. The result is a “Merlin Chart.”

Now, take a collective pause. Ask, “How can this chart be compressed?”

This is a delicate step. Why?

If a CEO pushes too hard, the plan becomes unrealistic, breaking the cause-and-effect logic of the Merlin Chart. However, a cohesive team can challenge assumptions from various perspectives—finance, operations, marketing, etc. The chart belongs to everyone.

Compression isn’t about being reckless. It requires rigor to avoid unrealistic goals. The aim is to stretch the model without breaking it.

When done right, every participant can stand behind the compressed Merlin Chart. By negotiating timelines and trade-offs openly, the resulting strategy becomes a shared vision. This ownership significantly boosts the likelihood of successful implementation.

The Result

While contentious, the compression process allows you to aim for lofty aspirations. By blending bold vision with careful planning, you can inspire your team to reach new heights.

Every Leader’s Challenge | Transitioning Between Successive Visions

Jamaica’s economic future is once again in the spotlight. With elections on the horizon, the Prime Minister has unveiled the ASPIRE program. However, given the backdrop of past disappointments and widespread skepticism, one pressing question arises: How can leaders inspire others to embrace a new direction when another, prior “new direction” is still fresh in people’s memories?

From a political standpoint, the announcement has generated predictable headlines. Unsurprisingly, it hasn’t captured much interest beyond the loyal party base. Despite accurately reflecting the aspirations of most Jamaicans, the ASPIRE program has yet to ignite widespread optimism. Few believe this initiative will significantly alter the economic landscape. But is this response solely due to poor timing?

No one is satisfied with Jamaica’s sluggish economic performance. As such, it’s difficult to argue against the intent behind the ASPIRE program. A revitalized economy is urgently needed. However, the lack of enthusiasm for the program points to deeper issues. What lessons can organizational leaders glean from the Prime Minister’s challenge?

The Burden of Previous Failures

Every organization needs a clear vision to move forward. Leaders often feel an urgency to launch their initiatives as quickly as possible. Yet, in their haste, they sometimes overlook a critical step: addressing the legacy of previous efforts.

When introducing ASPIRE, the Prime Minister bypassed the unresolved struggles of Vision 2030 Jamaica and the unfulfilled promises of the 5-in-4 project. (They were launched in 2009 and 2016 respectively.) This omission is not unique to him; leaders often face difficulties transitioning from one ambitious vision to the next. However, these challenges are amplified when prior efforts have left a trail of unfulfilled expectations.

Jamaicans have seen multiple attempts to rally the nation around shared economic growth objectives. Yet, many remain skeptical, with some pursuing opportunities abroad in search of a better life. The problem lies in the failure to properly address and learn from past shortcomings. When launching a new vision, ignoring previous failures is a mistake that erodes trust and engagement.

Closing the Loop

As someone who enjoyed Carnival in my younger years, I learned valuable advice from Trinidadian friends: “Don’t try to replicate last year’s experience.” Each new event should be approached on its own terms. This wisdom is profoundly relevant to leadership. Humans are at their best when inspired by fresh opportunities rather than weighed down by past successes or failures.

So, how can leaders effectively inspire their teams while navigating the shadows of prior disappointments?

  1. Acknowledge Successes and Failures: Recognize that each previous effort is a mix of achievements and setbacks. Be transparent about both.
  2. Celebrate Contributions: Publicly thank participants and highlight stories of dedication and accomplishment. Empathize with those who experienced disappointment.
  3. Extract Lessons Learned: Share the insights gained from past efforts. Demonstrate the value of those experiences, even if the original goals weren’t fully met.
  4. Position the New Vision in Context: Frame the new initiative as a natural progression informed by prior feedback. Skilled communicators can emphasize that the new vision is not a rejection of the old but an evolution built on collective experience.

These practices are rooted in effective change management. They not only foster engagement but also encourage the discretionary commitment of time, energy, and attention—resources that leaders depend on to achieve their goals.

Consider historical examples, such as the independence movement in India. Mahatma Ghandi and his followers’ quest for justice called for immense sacrifices, ultimately costing hundreds of lives. While today’s challenges may not carry such dire consequences, visionary leadership still asks for sacrifices. In a climate of past disappointments, skepticism is natural, and leaders must tread carefully.

A New Strategy for Sustained Leadership

In the modern world, people expect more than inspiring rhetoric. They demand a practical strategy that addresses obstacles, such as talent shortages or previous missteps. Followers scrutinize new visions against past outcomes, grappling with two key questions:

  • Logical Concerns: What makes this initiative different? Why should it succeed where others failed?
  • Emotional Concerns: Do my leaders understand my disappointment? Do they take responsibility for past failures and empathize with my reluctance to trust again?

Launching a new vision without addressing these concerns risks deepening cynicism. Leaders who skip over the logical and emotional barriers of the past will find it increasingly difficult to inspire genuine commitment. Instead, leaders must intervene with honesty, empathy, and a clear plan.

For example, Nelson Mandela’s leadership in post-apartheid South Africa provides a powerful blueprint. Emerging from prison, Mandela confronted the nation’s painful history with sober honesty. His vision of reconciliation didn’t gloss over atrocities but sought to unite both victims and perpetrators under a shared future. His authenticity and empathy helped forge a new path for the country.

Some leaders may argue that achieving results requires force and urgency. However, true inspiration cannot be compelled. To galvanize others toward a bold new future, leaders must address the past openly, demonstrate empathy, and rebuild trust. Only then can they rally people to make the sacrifices needed for transformative change.

From Panic to Purpose: Building Strategy Around What Matters Most

Some companies that survived the pandemic now tout extreme agility as their superpower. But is this a sustainable approach? According to Jeff Bezos of Amazon, the answer may lie in focusing on what hasn’t changed, even amid turmoil.

The Agility Debate

Critics of long-term strategic thinking argue that it stifles flexibility. They believe leaders must prioritize adaptability, mastering the art of the pivot to stay afloat.

Adherents to this philosophy often chase short-term gains, juggling endless opportunities and quick fixes. Unfortunately, this leaves little room for deep reflection or meaningful answers to big questions. The result? A constant state of urgency that might, ironically, hinder growth.

Is this short-sighted?

Emergencies do demand immediate action, but the adrenaline rush of reactive leadership can become addictive. Could this obsession with rapid responses undermine long-term success?

Here’s Bezos’s take:

“I very frequently get the question: ‘What’s going to change in the next 10 years?’ And that is a very interesting question; it’s a very common one. I almost never get the question: ‘What’s not going to change in the next 10 years?’ And I submit to you that that second question is actually the more important of the two.”

In other words, lasting success comes from building a strategy around stability rather than unpredictability.

Anchoring to Customer Needs

Tony Ulwick offers a framework to understand stability through unmet needs, which drive people to take purposeful action—what he calls “Jobs to Be Done” (JTBD).

For example, before hamburgers became the most popular fast food, other regional choices like hot dogs, tacos, fish and chips and noodles dominated as go-to quick meals. Today, there’s a broad menu of options, but the underlying job remains the same: satisfying immediate hunger with a fast, affordable solution.

This stability extends to other industries. A trendy restaurant might offer an innovative menu, but it still relies on timeless needs—good food, quick service, and affordability.

Yet, when disruptions arise, some leaders lose sight of these enduring truths. Consider a cafe owner, struggling with sales, who decides to sell branded apparel alongside lunch. Such zigzag responses might miss the mark entirely.

Instead, here’s a better way forward:

  1. Acknowledge unmet needs and JTBDs remain constant.
  2. Identify how disruptions are creating new obstacles for customers.
  3. Diagnose opportunities to remove those obstacles.
  4. Act swiftly before competitors do.

Take, for instance, many countries’ ongoing ATM crisis. As banks close branches to cut costs, customers face immense frustration over fewer functional ATMs. Despite this glaring issue, few financial institution have stepped in with viable solutions.

As the holiday season amplifies the problem, even the central banks have expressed concern. A bank that truly understood its customers’ JTBDs—secure and convenient access to cash—could innovate and dominate.

Why hasn’t this happened?

The Missing Emotional Connection

Some public-sector professionals demonstrate genuine passion for serving citizens. Their enthusiasm helps them deeply understand and empathize with people’s needs. They aren’t just doing a job—they’re solving problems they care about.

In contrast, private-sector leaders often lack this emotional connection. Their focus tends to be transactional, driven by profits. Customers’ needs become tools for financial gain, not ends in themselves.

This mindset falls short.

If leaders could develop a deeper empathy for customers’ challenges, they’d unlock a surprising source of competitive advantage. This applies across sectors, including non-profits and government organizations, where relevance remains crucial for funding and support.

Disruptions, rather than being excuses for frantic pivots, can become opportunities to reconnect with core customer needs. By anchoring your organization to JTBDs, you can stand out meaningfully.

Winning the Long Game

When leaders embrace stability over chaos, they discover depth rather than desperation. Customers notice, and their loyalty follows.

As Bezos reminds us, long-term success doesn’t come from guessing what will change but from staying true to what won’t. Build on this foundation, and you’ll always have a winning strategy.


Intrigued? Take a moment to visit my long-form content, in text, audio and video. Click here: https://longtermstrategy.info

Ep 22 – Strategy Across Silos | Master Planning Redefined

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

Have you ever seen strategic master plans gather dust on a shelf? Or, have you ever poured your heart into a master plan only to see it fall flat?

Strategic Master Plans make sense but they rarely work in practice. If this echoes your experience, don’t miss this episode.

We’ll tackle the reasons why these efforts promise so much but deliver so little. We’ll examine the issue through the lens of Dr. Peter Compo, author and strategy theorist.

You’ll hear why strategic master plans which offer no more than wishlist-style thinking do more harm than good. We’ll also look at reasons why the EndPoint Method includes certain steps which invite difficult conversations and challenging tradeoffs.

The episode draws heavily on Peter Compo’s book The Emergent Approach to Strategy.

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Transforming Vision Statements: The Right Level of Vision for the Right Time

As a leader, you recognize the importance of inspiring your team with a compelling vision. Yet, you may find that your company’s vision statement, despite its lofty aspirations, fails to inspire meaningful change. How can you craft and communicate a future that genuinely motivates your team to take action?

The Challenge of an Inherited Vision Statement

Imagine you’re a newly promoted CEO. Among the many responsibilities you’ve inherited is a vision statement. While it might look passable on paper, it has yet to inspire you, let alone your team, to embrace new behaviors or think differently.

It’s not that you lack vision yourself—after all, your success is built on envisioning possibilities and pursuing them. But translating that personal energy into an organizational vision that resonates with others is a different challenge altogether. Should you simply rewrite the vision statement, or is there a better way to achieve meaningful impact?

Here’s a fresh approach to this age-old leadership dilemma.

Understanding How Vision Truly Works

A powerful vision fundamentally transforms how we experience the present. Think about the difference between a Friday afternoon in the office and a Sunday afternoon. The former often feels better—not because of the immediate circumstances but because of our anticipation of the weekend. This sense of future anticipation changes how we perceive the present moment.

That’s the kind of shift you want to inspire in your stakeholders. You want them to feel energized by the future you’re describing, just as you are. The hallmark of success is when individuals take initiative, make sacrifices, and go beyond their job descriptions—not because they’re told to, but because they’re inspired to.

But here’s the hard truth: a traditional vision statement alone cannot deliver this kind of transformative impact.

Rethinking Vision: Introducing the Three Levels

Most organizations begin with what can be termed a “Level 1 Vision”: a concise, polished statement, often a few sentences or paragraphs, that attempts to summarize the future. However, these statements are frequently vague, generic, and uninspiring. They might sound nice but leave people either indifferent or skeptical. Some may even feel the statement describes what the organization has already achieved, rendering it irrelevant.

A better approach is to think of the Level 1 Vision as just the “headline” of a more detailed vision framework. Here’s how to expand it.

Building a Level 2 Vision

To create a meaningful vision at this level, gather your leadership team for an offsite retreat and focus on a specific long-term horizon—typically 15 to 30 years in the future. Work together to describe a vivid picture of what success looks like at that time. This Level 2 Vision goes beyond a brief statement; it provides several pages of detail, potentially including visuals, videos, or other media to bring the future to life.

The key here is collaboration. By involving your leadership team, you not only create a shared sense of ownership but also tap into a wider pool of creativity and ambition. A well-crafted Level 2 Vision should reflect the aspirations of your entire C-suite, energizing everyone involved.

However, many organizations stop at this stage. While the Level 2 Vision is more compelling than a simple statement, it often becomes an overwhelming list of aspirations. Without prioritization (and reduction), it risks becoming unrealistic, leading to cynicism rather than inspiration. Some employees may even dismiss it as “the CEO’s wish list.”

To avoid this pitfall, you must take the next step.

Evolving to a Level 3 Vision

The “Level 3 Vision” transforms lofty aspirations into a credible, actionable plan. This involves narrowing down the vision to a focused set of achievable targets supported by a strategic roadmap.

This process requires tough conversations. Your leadership team will need to negotiate priorities, confront trade-offs, and align on a clear path forward. Engaging a skilled facilitator can help ensure these discussions are productive and lead to consensus.

The outcome is a vision that stands apart from your competitors. A Level 3 Vision includes:

– Specific, measurable results: Clearly defined goals with tangible metrics.

– Milestones: Key achievements along the journey to the ultimate vision.

– A strategic pathway: A roadmap showing how to get from the present to the desired future.

– Team alignment: Full buy-in from your leadership team, ensuring commitment to execution.

With this, your vision evolves from an abstract dream into a realistic plan that inspires action.

Communicating Across the Three Levels

Once your Level 3 Vision is established, it’s crucial to communicate it effectively. Each level of vision—Level 1, Level 2, and Level 3—has a role to play depending on your audience and context.

For example, a Level 1 Vision offers a concise, memorable summary. Think of Vision 2030 Jamaica’s tagline: “…the place of choice to live, work, raise families and do business.” It’s short, evocative, and easy to recall.

A Level 2 Vision, on the other hand, provides more depth. Vision 2030 Jamaica expands on its tagline with four National Goals and 15 Outcomes, offering stakeholders a richer understanding of the country’s aspirations.

Finally, a Level 3 Vision delivers the detailed roadmap necessary to ensure credibility and guide execution.

By mastering these three levels, you can tailor your communication to inspire stakeholders while maintaining clarity and focus. Avoid the mistake of using the wrong level for the audience or situation, which can lead to confusion or disengagement.

Conclusion

Transforming vision statements into actionable, inspiring frameworks requires more than polished language. By embracing a three-level approach, you can align your team, inspire stakeholders, and chart a credible path to the future. Choose the right level of vision for the right moment, and you’ll not only communicate your aspirations—you’ll make them a reality.

Jaded Staff: Why Past Corporate Change Projects Could Be the Issue

As a leader, you likely have ambitious goals for your team. But the more you share your vision, the more resistance you seem to face. So, how do you move beyond jaded staff members and their skeptical responses to new futures?

A Real-World Example: Jamaica’s Key Challenges

In a recent discussion among thought leaders, three major issues emerged as Jamaica’s toughest challenges: crime, literacy, and high energy costs. Yet, they also agreed that the public is jaded, worn out from unmet expectations and dashed dreams. Like employees in many organizations, there’s a deep-seated cynicism that has taken hold.

For CEOs and government leaders, the typical response has been to “stay positive” or “push harder.” However, when there’s a legacy of failure, these well-meaning platitudes can often make things worse.

Let’s explore this dynamic through Vision 2030 Jamaica, a national development plan that, despite its initial inspirational promise, has become a barrier to achieving new aspirations.

A Picture-Perfect Start

Recently, the Prime Minister announced that Jamaica is unlikely to achieve “developed country” status by 2030. News outlets highlighted this as a failure of Vision 2030, the nation’s first comprehensive National Development Plan. However, there’s a deeper, more complex story here.

When Vision 2030 was introduced in 2009, it was an exemplary initiative by the standards of that time. The effort achieved something rare: bipartisan hope, even during the global financial crisis. Other countries, as well as the United Nations, took note, asking Jamaica for guidance on how to foster broad participation and consensus.

Today, with the benefit of hindsight, we can see the gaps in how Vision 2030 was managed. This isn’t surprising with 20-20 hindsight—leaders today are way more knowledgeable and experienced than they were 15 years ago. But more importantly, this plan, which once inspired, has become an obstacle to future goals. Why?

Why All Projects Need a Decisive Closure

If you’ve led a team through change, you may have wondered why your staff remains skeptical, despite your best efforts. Here’s a potential explanation for why cynicism persists.

Imagine a scenario: a boyfriend who cheats once may not repeat the mistake. But if he never apologizes or makes amends, the relationship suffers, even if his partner doesn’t speak up.

The same principle applies here: any Jamaican government aiming to promise a bright future must confront Vision 2030’s shortcomings. This is also true for all the organizations that contributed to its creation, including NGOs, businesses, political parties, and community groups.

Consequently, avoiding a confrontation with Vision 2030 would be a mistake. Any promising vision for the future must build on the successes and address the shortcomings of this plan. Here’s how to approach this task.

Resetting or Retiring an Organization’s Vision

Just as a relationship marred by betrayal needs to be reset or ended, a corporate vision sometimes needs a refresh or complete halt. Using Vision 2030 as a guide, here are steps to consider:

1. Acknowledge Both Successes and Failures

– Begin by reaching a consensus on what went well and what didn’t. This fosters learning and promotes transparency.

2. Reset or Retire the Vision

– With a shared understanding, decide together whether to rejuvenate the vision or move on altogether. This buy-in is critical.

3. Establish a New Horizon

– After addressing past shortcomings, use the renewed energy and insights to set a fresh, achievable goal.

“The truth will set you free” is more than a cliché. Embracing hard-earned lessons often strengthens an organization, just as scar tissue becomes tougher than uninjured skin. In Jamaica’s case, celebrating some achievements of Vision 2030 may help lay the groundwork for future progress.

For instance, one of Vision 2030’s significant contributions has been the integration of monitoring practices across government entities. This has fostered a disciplined reporting system among over 100 government organizations and affects more than 100,000 civil servants. This level of alignment is rare, even in exemplary private sector companies.

Your leadership team should appreciate this capability, as it’s an essential foundation for any future large-scale initiative. Without such discipline, major change efforts would struggle to gain traction in Jamaica.

Vision 2030 has created a powerful engine for transformation, one that shouldnt be ignored or downplayed. Neither should it be reinvented. As such, any brand new national vision, such as one for 2060, is bound to falter without first addressing the strengths and weaknesses of its parent: Vision 2030.

It’s natural for C-suite leaders or board members to feel impatient and want to leave past challenges behind. But bypassing these issues isn’t the answer. By addressing and learning from previous failures, leaders can transform their teams’ skepticism into optimism and create a pathway toward genuine, lasting change.

In short, to move forward, embrace a clear-eyed look at what has come before. For leaders dealing with jaded staff, acknowledging past disappointments is a necessary key to unlocking a motivated, engaged workforce, ready to tackle the future.

This article is based on a Jamaica Gleaner column from November 10, 2024.

Beyond Repeated Failure: Defining a Strategy Triad

Studies consistently show that most strategic plans fall short.

The reasons are varied, but a common mistake stands out: teams often assume they understand “strategic” planning, only to end up misguided, compromising their organizations’ success. Often, what they call a “strategic plan” lacks real strategic thought.

How Missteps Occur

If you’ve ever reviewed a company’s strategic plan, you’ve likely seen a list of ambitious goals. They may be grouped in catchy ways, but as you read through, doubts surface. Why?

You sense the organization may lack the resources or focus to achieve all these objectives simultaneously. The longer the list, the more you suspect it may be abandoned when daily issues arise, with lofty goals slipping out of view.

Redefining “Strategic”

One way to prevent this common pitfall is to rethink how we use the term “strategic.” Today, the label “strategic” is often used casually to signal importance, so much so that it’s lost its impact, and audiences tune it out. This isn’t just a communication issue. When teams invest time in a strategic retreat, they expect the final plan to be truly strategic, yet often that’s not the case.

Typical brainstorming sessions encourage a mix of ideas and positive intentions without much structure. The result is often an extensive report of hopeful outcomes, which can look similar to other plans within the industry—ultimately, another reason for failure.

Enter the Strategy Triad

Peter Compo’s book *The Emergent Strategy* introduces a helpful redefinition of “strategic” by proposing a triad approach:

1. Aspiration: A meaningful, challenging goal that requires effort and won’t happen automatically.

2. Bottleneck: The main obstacle preventing the organization from achieving its aspiration(s).

3. Guiding Principle: A decision-making rule to help navigate actions that address the bottleneck.

Consider a store aiming to increase profits. If the biggest bottleneck is low brand recognition, the guiding principle could be to improve brand awareness through multiple channels—online, in-store, and through partnerships.

Applying the Strategy Triad

At a recent strategic planning retreat, a leadership team was challenged to apply the triad. Initially, it was difficult; identifying bottlenecks from new perspectives required collaboration and creativity, especially without cross-functional data, which led them to rely on firsthand experiences. Yet, they successfully defined bottlenecks and guiding principles that empowered employees to align their daily choices with the strategic plan. This alignment is what leaders want but is often rare.

Why Alignment is Rare

Leadership teams often avoid the challenging, healthy conflict required to build a robust strategy triad. They may take the easier path, creating lists of goals rather than diving into critical strategic planning. Alternatively, when discussions become too heated, leaders may intervene prematurely, cutting off debate and limiting essential buy-in.

To achieve meaningful alignment, it’s important to work through differing viewpoints until agreement is reached. Though challenging, this process builds the intellectual and emotional commitment needed for successful execution. By persevering through difficult conversations, leaders can significantly improve their strategic plans’ success and longevity.


Francis Wade | Not everything is strategic | Business | Jamaica Gleaner

Ep 21 Navigating Cultural Drift: Fixing Leadership and Strategy Before It’s Too Late

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

What happens when leadership goes off-course and starts undermining the very culture that made your company successful? 

In this thought-provoking episode, Francis Wade teams up with Barry Eustance, an expert in aviation and corporate transformation, to tackle a problem that many executives face but few know how to fix: cultural drift. 

Together, they explore how leadership styles can erode the foundations of a company, drawing on powerful real-world examples like Boeing’s notorious safety lapses. 

Through candid discussions, they reveal why culture is fragile, how neglecting it can lead to catastrophic outcomes, and the vital role that long-term strategy plays in maintaining organizational health. 

Whether you’re navigating corporate politics or looking to preserve your company’s mission, this episode will help you spot the early warning signs and build a culture that thrives—before it’s too late.

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Elevate Underperforming Boards: Prioritizing Board Self-Examination

Imagine you’ve joined a board, only to discover it’s deeply mediocre. This is your third meeting, and it’s becoming clear that the issues you sensed in the first two weren’t incidental—they’re ongoing. How do you address this underperformance?

Luckily, you aren’t the only one who’s noticed. Some members recognize that long-standing issues have held the board back for years, and while they’ve tried initiating change, nothing has stuck. These are complex, systemic challenges that won’t be resolved by casual discussions, pep talks, or a thoughtful email. Swift, strategic action is needed. But how?

I recently encountered insights from consultant A. Cecile Watson that shed light on why boards need their own strategic approach. Her perspective inspires these key reasons for why your board must implement a self-care plan.

Why Boards Should Prioritize Self-Examination

Boards are often envisioned as serving the organization’s needs. If all members align with this vision, things should function smoothly. Small differences can be ironed out, much like in the “Form-Storm-Norm-Perform” teamwork model, which illustrates the stages groups move through to achieve high performance.

However, boards today face a high-pressure environment, dealing with complex VUCA (Volatile, Uncertain, Complex, and Ambiguous) issues from the outset. While they might receive briefings, individual and group development often gets overlooked in the rush to deliver.

This traditional expectation—that boards serve swiftly, even if under-informed—faces scrutiny in Watson’s latest article. She argues that boards must practice self-reflection and strategy if they’re to excel. Smart people on a board don’t guarantee a high group IQ or EQ; in fact, group performance can suffer if proactive measures aren’t in place.

What does your board need? A new level of self-care. Watson suggests that boards operate as a kind of strategic unit, managing their performance preemptively. Failing to do so only perpetuates mediocrity.

The Case for Board Self-Strategy

Typically, boards focus on “strategic planning” for their organization’s future. Watson’s approach takes this one step further: boards must also strategize for themselves. As a unit, they need the space to address their own evolution.

This doesn’t mean ignoring corporate planning. In fact, I’ve previously recommended that board members actively engage in their organization’s strategic retreats, where they contribute to shaping long-term goals.

Yet, once these retreats end, some boards must adapt as well. For instance, one board I worked with chose to refresh its membership, reducing both the average age and tenure of its members to bring new perspectives aligned with the strategic plan.

In another case, a board had grown complacent. Members showed up sporadically, often unprepared. This lack of accountability permeated the organization, undermining its standards and culture.

Unfortunately, board evaluations alone rarely spark transformation. Instead, Watson advocates for a written Board Strategy, a guiding document that steers the board’s actions.

Creating a Strategy for the Board

Watson advises boards to define a vision for themselves and set measurable milestones to ensure the plan stays on course. While this may sound overwhelming for already busy board members, it’s ultimately about cultivating the right mindset, not rigidly following a checklist.

Adopting these principles can help your board become resilient, better equipped to navigate future challenges, and able to avoid the slow slide into mediocrity that affects many corporate teams.


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This post was based on an article published in the Jamaica Gleaner.