Navigating Uncertainty: Step Back, Look Ahead, and Define Your True North

As a senior executive, you are no stranger to the relentless waves of change sweeping across North America. The onslaught of daily upheavals can feel overwhelming, making it tempting to believe that success hinges on reacting swiftly to each new development. But is this truly the most effective path forward? Is there a smarter, more strategic way to navigate the turbulence?

If these questions have crossed your mind, you are not alone.

For many leaders, it feels as though the world has downed a double shot of espresso. Major disruptions that once occurred sporadically now seem to arrive in rapid succession, sometimes multiple times in a single day. In the past, convening an emergency meeting may have provided some sense of control. However, this approach is no longer sustainable. Constant crisis management is an exhausting, reactive cycle that diverts energy from long-term strategic imperatives. Forward-thinking executives are realizing that a different approach is required—one that prioritizes a steady course over continual reaction.

The End of a Comfortable Status Quo

Canada has long enjoyed a privileged economic relationship with the United States, a stable partnership that many organizations assumed would remain unshaken. For decades, Canadian businesses could rely on predictable trade policies and seamless access to the U.S. market, much like cyclists drafting behind a peloton leader.

But today, that certainty has eroded. The political landscape in the United States has grown increasingly volatile, resembling a cantankerous relative prone to unpredictable outbursts. Just as you wouldn’t stake your business on the hope that an erratic family member will suddenly become reliable, Canadian firms can no longer afford to take U.S. stability for granted. Instead, they must develop contingency plans that mitigate risks and reduce dependence on a single, unpredictable partner.

This shift is causing ripples throughout the entire supply chain, affecting customers, suppliers, distributors, and regulators on a global scale. Many Canadian executives are realizing that simply reacting to daily shocks is not a viable strategy. The smarter move is to step back and reassess their long-term direction.

Lessons From the Chaos

More business leaders are awakening to some hard but valuable lessons. While these insights have always been available in theory, firsthand experience has proven to be the ultimate teacher.

Lesson #1: The pace of disruption is too fast for deep analysis of every crisis.

The sheer speed at which events unfold means there is little time for comprehensive assessments of each disruption. Many executives now recognize that this state of volatility is not a passing phase—it is likely to persist for years, regardless of political leadership changes.

Lesson #2: Few organizations engage in rigorous scenario planning.

Despite repeated warnings about potential disruptions—such as Trump’s supporters actively promoting Project 2025—many assumed these threats would never materialize. As a result, they failed to anticipate today’s challenges and are now scrambling to adapt.

Lesson #3: Structural changes require years of planning and execution.

Adjusting supply chains, diversifying markets, and securing alternative resources take far longer than many executives expect. Consider Tremcar, a Canadian manufacturer of tanker trailers. The company relies on aluminum imports from the U.S., but retaliatory tariffs could jeopardize its operations. While Canada has domestic aluminum production, sourcing materials locally requires significant logistical adjustments. What seems like a straightforward shift is, in reality, a complex, long-term endeavor.

This challenge extends beyond Canada. In Jamaica, a transformation that has been years in the making is now disrupting the courier industry. Amazon’s recent introduction of free shipping to Jamaica may appear to be a win for consumers. However, for companies like MailPac, ShipMe, and DHL—whose business models revolve around importing goods for local shoppers—this shift presents a major existential threat.

If these firms did not foresee this change and adjust their strategic planning accordingly, they now face an uphill battle. This underscores a critical reality: businesses that fail to anticipate disruption are left scrambling to survive when it arrives.

Finding Stability Amid Chaos

It is easy to assume that your industry is an exception, that the disruptions affecting others won’t impact you. However, rather than relying on luck, a wiser course of action is to take proactive steps to future-proof your business.

The most effective way to navigate uncertainty is to step back from the daily noise and adopt a long-term perspective. This requires more than a vague vision statement or an inspiring corporate mantra—it demands a clearly defined True North that serves as a guiding principle for decision-making over the next 15 to 30 years.

This level of strategic foresight may seem daunting, especially in an environment where rapid changes create the illusion that long-term planning is futile. However, consider the analogy of air travel: throughout a flight, an airplane is off-course the majority of the time. Yet, through continuous small corrections, it reaches its intended destination.

Your organization must do the same.

Instead of allowing the turbulence of current events to dictate your direction, use these disruptions as an impetus to sharpen your strategic focus. Employees, stakeholders, and investors may feel unsettled by the uncertainty around them, but a well-defined True North provides the stability and clarity needed to move forward with confidence.

By resisting the urge to react to every headline and instead anchoring your organization in a steadfast long-term vision, you create a roadmap that ensures sustainable success—regardless of the chaos that may unfold along the way.

The Leadership Trap: How Dominating Strategy Sessions Stifles Innovation

Smart CEOs instinctively understand that game-changing decisions require a unique context. But what exactly makes breakthrough strategic thinking different? And why do so many leaders struggle to get it right?

In almost every strategic planning project I participate in, there’s a quiet conversation with the top leader before we begin: “Don’t dominate the discussion.” It’s a simple directive, but not always easy to follow. Sometimes, we even have to step in to maintain the right balance.

But why should you, as the top executive, take this advice seriously?

After all, you think about corporate strategy more than anyone else on your team. You’re the only C-Suite leader who oversees all functions, ensuring cohesion across departments. So why would we suggest that you take a step back when crafting a game-changing strategy?

Not a Search for Quick Solutions

Your leadership team is already well-versed in emergency thinking. Every week or two, you gather to brainstorm solutions to immediate problems. Like a general, you take the lead, act decisively, and hold colleagues accountable. Their role is to execute and report back at the next meeting.

While each team member focuses on their own responsibilities, you oversee everything. If you miss a meeting, progress often slows. You are the driving force.

But experience shows that game-changing strategy sessions should NOT follow this familiar script. Instead, the entire team must shift from a “Present Forward” problem-solving mindset to a “Future Back” perspective—one that envisions what’s possible before determining how to get there.

To make this shift, you must deliberately set aside old habits. Now is the time to:

  • Diagnose the current situation without rushing to fix anything.
  • Identify external patterns and trends that are easy to overlook.
  • Surface long-term challenges that could take decades—not days—to solve.

If you dominate the discussion, you disrupt this transition from urgent problem-solving to visionary thinking. In doing so, you risk becoming the biggest obstacle to creating the new context your company needs to move forward.

This isn’t easy to do. But why?

Embracing Complexity

You likely agree—weekly meetings aren’t the place for major strategic decisions. Why?

Breakthrough decisions require leaders to engage directly with complexity. This is true for any company large enough to have a leadership team of specialists.

Many executives recognize this and don’t attempt to tackle complex strategic issues in a regular meeting. Instead, they set aside dedicated time to create a different kind of conversation—one that allows them to go deeper than ever before. This approach is the only way to uncover the radical insights that drive game-changing strategy.

But achieving this depth of thinking isn’t about making a long wish list, writing a report, or hiring consultants to do the work for you. These approaches often obscure complexity rather than address it. Similarly, if you dominate the discussion, you limit the depth of insight your team can generate.

Instead, embrace a different approach.

Distributed Logic

To tackle complexity as a team, you must commit to achieving true breakthrough thinking. Start by crafting a vivid, detailed vision of your organization 15 to 30 years into the future—one so specific that it forces you into bold new strategies.

A game-changing strategy isn’t a simple checklist. It’s a multi-layered, interconnected set of decisions. Because of this, only a fully engaged C-Suite team can create it. No single leader, no matter how visionary, can develop it alone.

When executives work together in this way, they generate the insights needed to make the right strategic choices. Given the high stakes, this type of collaboration becomes the most meaningful form of team-building available.

Unlike traditional exercises involving ropes, ladders, and artificial challenges, this is not a simulation. The decisions made in strategic planning have real and immediate consequences. It’s the equivalent of making a U-turn in an oil tanker—slow, deliberate, and high-impact.

The Leader’s Role: Facilitating the Shift

So, what is your role as the top leader?

If a powerful strategic context is to emerge, you must actively facilitate its creation. This may feel uncomfortable at first. You may be used to being the driving force behind decisions. But stepping back to create space for collective insight is the true mark of leadership.

This is the only way to bring about a “Future Back” mindset at scale—perhaps for the first time within your C-Suite.

If your team struggles to navigate today’s global disruptions, don’t double down on quick fixes. Instead, create a larger, future-focused context—one that fuels powerful, game-changing decisions.


This article is based on a Gleaner article published on March 16th 2025.

Ep 26 – Seth Godin – Stuck in Stale Strategy? Seeing Systems Holding You Back

Your company is built on systems – a whole bunch of systems which are intertwined.

Understanding how they work together is critical for any strategic changes you want to make.

However, you have also seen system diagrams. They look awful, with too much detail, and don’t capture the essence of what happens at any level of the organization. Plus, they take forever to build.

So you know you need to have this knowledge but how do you begin to grab hold of it so you can use it in your strategy? Where is the practical application?

Tune into this episode to hear from me and my special guest, Seth Godin, as we tackle and even try to solve this wicked problem together.

Plus – if you enjoy Seth’s work in this area, here’s a new experiment. I opened up a NotebookLM-like page on Cobundle – https://strategyconf.fwconsulting.com/resources-ep-26-with-seth-godin-strategy-and-systems/.

YouTube Chapters

0:00 – Introduction: Why Systems Thinking Matters

2:00 – The Invisible Systems That Control Your Decisions

5:00 – The Danger of Ignoring Systemic Change (Yahoo vs. Google)

9:00 – How Companies Get Stuck in Old Ways of Thinking

12:00 – Walmart’s Smart Decision to Delay Competing with Amazon

16:00 – Why Traditional Strategy Tools Are Failing You 20:00 – How to Help Leaders See Their Own System Blind Spots

25:00 – The Power of Storytelling in Strategy

31:00 – The Role of Emotion in Driving Change

37:00 – Breaking Free: How to Build Strategy That Actually Works

41:00 – Final Insights & How to Apply This to Your Work

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

Ep 25 – Drowning in Data | How AI Can Rescue Strategy

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

You are a facilitator or sponsor of strategic planning offsites. Recently, you noticed that it’s become easier than ever to gather pages of interesting and pertinent information about client companies. You’re pleased…this is a far cry from the days when you were forced to walk in empty-handed because the company had nothing to offer you.

But now you have a new problem. The best clients are collecting a ton of information, and providing it to you in buckets. You want to go through all of it but with limited time and resources, you can’t.

You don’t want to fake it until you make it…but what else can you do?

Tune into this episode to hear from me and my special guest, Dan Bruder, as we solve this wicked problem together.

To watch or hear 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.

Lacking DeepSeek Impact? | Why Uncovering Strategic Insights Defeats CEOs

The world watches with anticipation as DeepSeek.com takes the lead in AI Large Language Models (LLMs). As a leader, you might wonder, “Why can’t my company achieve a similar breakthrough? What’s stopping us from uncovering game-changing insights?”

As your team strategizes, you grow weary of the same old excuses—yours included. Stakeholders demand answers. Why isn’t your organization making a significant impact?

You try to explain: “We lack capital, time, talent, cutting-edge technology, and a Silicon Valley-style culture.” But then, along comes DeepSeek—achieving disruptive success with limited funding, relatively low expertise, cultural disadvantages, and only a few years of effort.

What sets them apart? And more importantly, how can your organization—whether for-profit or nonprofit—create revolutionary strategies consistently? Here are three critical lessons.

1) Prioritize Powerful Insights

A closer look at DeepSeek reveals that they overcame significant obstacles through superior strategy.

To outsiders, it might seem like magic.

Before their recent breakthrough, prevailing wisdom suggested that such an achievement was impossible. However, a deeper examination shows that the Chinese team pieced together a set of unique features. Each individual element may have seemed ordinary, but together, they formed a disruptive force.

This suggests that other teams—perhaps even yours—could have done the same.

A crucial factor in their success appears to be their ability to harness the smallest unit of innovation: a single insight. These insights, while seemingly minor on their own, can combine to create transformative change.

But the key question remains: Can your team do the same? Let’s examine how your corporate strategy is built. Insights should drive your company forward, but if you’re not achieving game-changing results, something needs to shift.

2) Let Go of “Big Man” Thinking

Many CEOs assume they don’t have a strategy problem. They believe they already possess all the insights necessary—derived from their own expertise.

To justify this, they point to their colleagues’ lack of strategic contributions.

“Not one of them has ever come up with a truly strategic insight!” they argue, frustrated by a team that focuses solely on immediate problems. However, they fail to acknowledge that the company itself rewards this behavior.

In some cases, they might be right.

As the CEO, MD, or Chair, you are one of the few people with a comprehensive view of the business. Naturally, strategy falls under your responsibility.

But this could also explain why groundbreaking strategies are so rare.

Think of your company as an intricate system—too complex for any single person to generate all the insights it needs. No outsider, even with extensive reports, can fully grasp its nuances.

Instead, your leadership team must collectively produce DeepSeek-level strategy. But they can’t do this while stuck in the usual mindset and corporate culture.

If you want breakthrough thinking, take a fresh look at your management team. Then, take action to unlock the insights you need.

3) Run a Workshop to Unlock Your C-Suite’s Potential

If you have a generous budget and time to spare, long-term training and coaching are excellent investments. But if, like most, you need results sooner, organize a face-to-face workshop designed to tap into your leadership team’s best thinking. Why?

You won’t extract transformative insights through surveys, bonuses, or one-on-one interviews. Nor will you uncover them in your usual problem-solving meetings.

Instead, take a lesson from crafting a great ChatGPT prompt.

To get quality responses, you feed an AI model relevant data, structure your question carefully, and then hit <Enter>. The chatbot delivers an insightful answer—often one you hadn’t considered.

Now, imagine doing the same with your C-Suite.

Through multiple trials, I’ve found that leadership teams can be “prompted” to generate their own breakthrough insights. How? By structuring an insight-oriented workshop.

Here’s how to run a high-impact session:

  1. Craft sharp prompts. Formulate precise questions that challenge conventional thinking and address the root cause of strategic roadblocks.
  2. Supply relevant data. Provide internal company information and credible local market insights.
  3. Introduce external trends. Share macro trends that neither you nor your competitors can control but must adapt to.
  4. Leverage consulting shortcuts. Introduce fresh analytical frameworks used by top consulting firms to accelerate strategic thinking.
  5. Encourage AI integration. Use LLMs to help your team think beyond their usual constraints and generate breakthrough ideas.

By combining the insights from this session into your next strategic plan, you’ll position your company for game-changing success.


Breakthrough strategy isn’t reserved for Silicon Valley startups or billion-dollar enterprises. With the right approach, any organization—including yours—can generate innovative insights that lead to transformational success. The key is fostering a culture that prioritizes insights, moves beyond individual genius, and taps into the collective intelligence of your leadership team. Do this, and your company might just be the next DeepSeek.


This article was inspired by a column I wrote for the Jamaica Gleaner.

For long-form content on game-changing, pre-emptive long-term strategy, visit https://longtermstrategy.info

Sour Attitudes: Transforming Resistance Frees Up Commitment

As a leader, you have a clear vision of a brighter future for your enterprise. Yet, paradoxically, the more enthusiastic you become, the more resistance you encounter. How do you lead effectively when those around you refuse to be led?

You notice negativity—cynicism, resignation, despair—permeating different levels of the organization. It’s not just an issue at the lower levels; even executives in the C-suite can fall into this trap. In some cases, their negativity makes them unapproachable.

Perhaps this shouldn’t be surprising. Even when a project promises benefits for all, resistance still arises.

The Hidden Roots of Resistance

A striking example comes from Dr. Dana Meadows, who led a 1993 workshop on ending global hunger. The attendees, all committed to the cause, surprisingly resisted discussions on vision.

Some argued that talking about vision was futile. Others believed it was dangerous. A few went so far as to say that confronting their deepest hopes for the planet was too painful because it highlighted the vast gap between dreams and reality.

Meadows was astonished. Something deeper was at play.

She concluded that as children, we freely dream of happy futures. However, over time, cynical adults suppress this ability. Many learn to surrender after repeated disappointments.

By adulthood, this pattern becomes ingrained. We withhold our hopes, dreams, and aspirations, fearing further disappointment.

In organizations, this mindset creates a reinforcing cycle of cynicism. Eventually, visionary thinking is stifled altogether.

The Leadership Dilemma

How should you, as a leader, respond? Your instinct might be to push forward with urgency: “Let’s just get on with it.” Or you might try to keep things practical: “Don’t overthink this.” You may even remind employees of the importance of financial stability.

At first glance, this seems reasonable. But in reality, this mindset undermines game-changing innovation.

One common leadership response is to become the “Cheerleader-in-Chief.” If that role doesn’t appeal to you, there’s a more effective way to achieve a positive outcome—without forced enthusiasm.

A Reality-Based Vision Strategy

Recently, two clients challenged me to refine how I help companies develop long-term vision and strategy. Each wanted a method to engage their top 40+ managers before formal strategy sessions.

I reflected on my time as a McKinsey consultant, where my team—young, highly educated, and expensive—was brought in to provide external expertise. We justified our fees by working late nights and accessing hard-to-find knowledge worldwide.

Today, however, the knowledge gap has narrowed. Many companies have in-house MBAs from the same institutions as top consulting firms.

With this in mind, I designed a workshop to tackle the company’s toughest issues, identified through surveys, interviews, and focus groups. These issues were reframed as challenges for teams to solve. Using data from internal sources, the Jamaica Gleaner, ChatGPT, and other references, employees applied structured frameworks, similar to those used by consulting firms. The result? A set of real-time reports with actionable insights.

Insider Advantage

How did these teams perform?

Having worked on both sides of the consulting table, I can confidently say that insiders have a distinct advantage. Their reasoning is superior because they account for resistance from within the company.

After all, they work with these resistant colleagues daily. Their solutions are more practical and more likely to be implemented successfully. But this is just one way to navigate organizational cynicism.

Building Resilience from Within

Most organizations neglect the need to cultivate internal resilience. Employees are left to deal with their own struggles—depression, frustration, bitterness—without structured support. 

This lack of mental health training leaves individuals vulnerable. Even those who believe in the company’s vision can become disillusioned, trapped in a cycle of negativity.

Yet, solutions exist. Therapy, coaching, group training, self-help, and personal development programs offer ways to strengthen resilience. These are not abstract or unsolvable issues. Companies can—and should—take deliberate action.

Turning Resistance into Commitment

In today’s world, leaders don’t need to surrender to cynicism. By acknowledging resistance and equipping employees with the right tools, organizations can transform hesitation into commitment. A thoughtful, reality-based approach to vision and resilience-building paves the way for sustainable success.


Interested in long-form content on these topics? Join my podcast/newsletter page – https://longtermstrategy.info

Ep 24 Employees Want In! | How AI Fixes the Participation Gap w Dan Bruder

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

Your company is committed to engaging staff in implementing the next strategic plan. Like most, you realize that their involvement is important.

But the company is big…large enough that you can’t talk to everyone. Not effectively. But you’d like to give each person a chance to contribute. And be heard.

How can you pull off this seemingly impossible feat? And how can you do so…at scale?

Tune into this episode to hear from me and my special guest, Dan Bruder, as we solve this wicked problem together. We’ll look at the ways AI can be used to drive employee engagement at scale.

To watch or hear 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.

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.