Ep 27 – Missing Insights | How to Find Breakthrough Strategies in the C-Suite

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

You are convinced that your company or client needs a game-changing strategy. But you have also worked with them to see that their thinking is pedestrian. Ordinary. Run of the mill. Business as usual.

You realise that one element which is lacking is a set of powerful insights. Without them, you’ll always be stuck no matter how well they do at implementation.

And if a competitor comes along, like Deep Seek, you’ll be disrupted.

Tune into this episode to join me in tackling this wicked problem.

And here’s a resource I mentioned for scanning future trends:

https://www.futuresplatform.com/

Here is the complimentary video excerpt for free subscribers. The full video is behind the paywall below.

Ep 27 – Missing Insights | How to Find Breakthrough Strategies in the C-Suite

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

You are convinced that your company or client needs a game-changing strategy. But you have also worked with them to see that their thinking is pedestrian. Ordinary. Run of the mill. Business as usual.

You realise that one element which is lacking is a set of powerful insights. Without them, you’ll always be stuck no matter how well they do at implementation.

And if a competitor comes along, like Deep Seek, you’ll be disrupted.

Tune into this episode to join me in tackling this wicked problem.

And here’s a resource I mentioned for scanning future trends:

https://www.futuresplatform.com/

Here is the complimentary video excerpt for free subscribers. The full video is behind the paywall below.

Ep 27 – Missing Insights | How to Find Breakthrough Strategies in the C-Suite

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

You are convinced that your company or client needs a game-changing strategy. But you have also worked with them to see that their thinking is pedestrian. Ordinary. Run of the mill. Business as usual.

You realise that one element which is lacking is a set of powerful insights. Without them, you’ll always be stuck no matter how well they do at implementation.

And if a competitor comes along, like Deep Seek, you’ll be disrupted.

Tune into this episode to join me in tackling this wicked problem.

And here’s a resource I mentioned for scanning future trends:

https://www.futuresplatform.com/

Here is the complimentary video excerpt for free subscribers. The full video is behind the paywall below.

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 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 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

Trumpian Disruption: Use Turbulence While Others Lose Their Minds

Donald Trump’s return to office has created an unprecedented distraction for CEOs. The daily whirlwind of headlines isn’t just noise—it brings real threats to businesses. So, how do you rise above the chaos and stay focused?

Many leaders thought COVID-19 was the biggest disruption of their careers. The world froze, and recovery took years.

But today, the relentless shocks coming from the U.S. make the pandemic seem mild in comparison. This is disruption on another level.

Some executives have responded by diving headfirst into crisis mode. They react to every shock, chasing after short-term fixes. Running on adrenaline, they believe sheer effort will get them through.

But a few leaders have realized that constantly playing firefighter isn’t just exhausting—it’s dangerous.

The Braddock Trap

History provides a warning: General Edward Braddock’s misstep at the Battle of the Monongahela (1755). When French and Native forces ambushed his troops, he abandoned his command post and charged into battle. He was shot and killed, leaving his soldiers leaderless. The British suffered heavy losses, and the war dragged on.

How can you avoid making the same mistake with your company?

Recognizing the Real Threat

Fortunately, you aren’t facing bullets. But your business does face existential risks—competition, regulation, new technology, and shifting customer expectations.

If you fail to lead, the consequences are real: layoffs, lost market share, declining shareholder value. Even your personal legacy is at stake.

But leadership doesn’t mean rushing into the fray. When you lose sight of the big picture, you abandon your role as a strategic leader. Instead, you need to fight your instinct to react impulsively and take a step back. Will you?

The solution lies in skills you likely didn’t master in school: foresight, strategy, and discipline.

You weren’t promoted for these skills, but today, they are essential. Admitting you need to strengthen them is the first step.

Set a Long-Term Course

History is full of companies that focused too much on short-term fires—only to collapse later.

Jack Welch’s tenure at General Electric set up his successor for failure, wiping out billions in value. Boeing’s leadership sacrificed safety, leading to catastrophic failures. Wells Fargo’s obsession with sales numbers fueled massive fraud.

Short-term goals are fine, but without a long-term vision, they can be disastrous.

Disruptions like Trump 2.0 push leaders into short-term thinking. Here are two common responses:

  1. Hit Pause on Strategy. Some leaders believe it’s impossible to plan for the future right now. They assume once things settle, they’ll return to long-term thinking.This logic is gaining traction in boardrooms. Executives point to COVID-19 as “proof” that focusing on immediate concerns is the right call.But what if Trump’s first month back is just the beginning of four years of upheaval?
  2. Use Disruption to Strengthen Long-Term Vision.Consider Nintendo. In the 1960s, declining playing card sales forced a shift. Instead of panicking, the company embraced change—experimenting with toys, arcade games, and eventually launching the NES in 1985. That move revitalized the gaming industry and transformed Nintendo into a global powerhouse.The lesson? Disruption can fuel reinvention.

The challenge isn’t choosing a destination. The real difficulty is getting stakeholders to commit to a 15- to 30-year vision—while chaos rages around them.

True leaders use today’s turbulence to build tomorrow’s success.

Learning from History

Take the collapse of the West Indies Federation in 1961. It was a devastating setback for regional unity. But instead of giving up, Jamaica channeled the disruption into its independence movement. Self-determination didn’t die—it just took a new path.

Most leaders, in both government and business, lack the skills to avoid the Braddock trap.

Be different. Warren Buffett put it best: “Be fearful when others are greedy, and be greedy when others are fearful.”

Now is the time to resist knee-jerk leadership. Step back, set a long-term course, and let today’s chaos propel you toward a future worth building.

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.