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.

Ep 23 – Conflicting Visions – the Invisible Threat that Unites Goals

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Why You Should Listen to This Episode of the Jump Leap Long-Term Strategy Podcast

Picture this: you’re in the middle of a critical strategic planning retreat. Your team has crafted bold visions for the future, but now comes the toughest part—choosing the path forward. Limited resources, competing priorities, and mounting pressure make every option feel like a gamble.

In this episode of the Jump Leap Long-Term Strategy Podcast, host Francis Wade and special guest Dr. Peter Compo, author of The Emergent Approach to Strategy, tackle this exact dilemma. Together, they break down the messy realities of decision-making in high-stakes environments, offering practical tools and transformative insights.

Here’s what you’ll gain:

* Actionable Frameworks – Learn why most strategies fail and how Peter’s “Strategy Matrix” can help you evaluate options effectively.

* Real-World Lessons – Dive into examples, like the fictional Arturo’s challenge, to see how disciplined decision-making can overcome bottlenecks.

* The Jazz Analogy – Discover how the improvisation of jazz mirrors the blend of structure and creativity needed in strategy.

This episode isn’t just about theory. It’s about equipping leaders with the tools to navigate complexity, make bold choices, and design strategies that inspire and deliver results.

Whether you’re a CEO, facilitator, or team leader, you’ll leave with a clear understanding of how to tackle the toughest strategic decisions. Tune in and learn how discipline, creativity, and trust can transform your approach to planning.

Click play and take the first step toward game-changing strategy.

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

To watch the full episode, join JumpLeap as a subscriber. This supports the work I’m doing on long-term strategic planning. It appears below the Subscribe signup box.

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.


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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.

To watch the full episode, join JumpLeap as a subscriber. This supports the work I’m doing on long-term strategic planning. It appears below the Subscribe signup box.