How to Conduct a Game-Changing 15-30-Year Strategic Planning Retreat

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You’re someone who is looking ahead to your next strategic plan. Why? You’re looking at the process, the activities that go into it, and the final outcome. And you’re wondering, is it too much to ask, or to expect that this one be a game-changer?

You’re familiar with companies that have launched transformational strategies, and they’ve taken over their …

Unraveling Strategy Amnesia

Have you ever left a strategic planning retreat feeling invigorated, only to find that the excitement fizzles out? Despite the initial enthusiasm and belief in the positive change that was about to ensue, weeks later, the essence of those profound discussions becomes a distant memory.

The baffling reality is this: a gathering of bright, dedicated individuals, all ardently striving to make a meaningful difference, encountered an unexpected descent post-retreat. The perplexity of this decline seemed insurmountable, leaving one pondering what went awry.

Thankfully, a recent book “Lead from the Future” by Johnson and Suskewicz sheds new light. These insights delineate a striking dichotomy in mindsets: “Past Forward” versus “Future Back.” Let’s delve into these divergent mental frameworks to illuminate the conundrum at hand.

The Dichotomy of Mindsets

The prevalent “Past Forward” mindset thrives on incremental advancements, rooted in dissecting past triumphs and failures. It’s the default mode for most managers navigating day-to-day challenges, leveraging their proven track records that propelled them up the ranks.

However, the milieu of a strategic planning retreat demands a paradigm shift, beckoning participants to embrace an unfamiliar “Future Back” approach. Here lies the crux: mastering this skill within a group setting remains uncharted territory for the average manager.

Sure, crafting lofty vision statements might seem within their purview. Yet, sculpting a comprehensive future and then backcasting it to the present demands a distinct skill set. It’s akin to acquainting oneself with an intricate dance just moments before the performance begins.

Initial struggles are commonplace with newfound skills. Yet, with perseverance, momentum gradually builds. Ideas cascade, intertwine, and gather pace, an exhilarating whirlwind of innovation and collaboration ensues.

The Fragility of Future Back Thinking

However, amidst this euphoria lurks a paradox unique to strategic planning assemblies.

Picture hurtling down a steep incline in a hastily assembled homemade go-kart…at breakneck speeds. The thrill is palpable, but the precariousness looms – at any moment, the framework could splinter apart.

Similarly, the pinnacle of a strategic planning retreat rests atop the fragile pedestal of a Future Back mindset. However, the buoyant euphoria often leads participants to overestimate its durability, a temporary high masking its ephemeral nature.

Regrettably, mere hours post-retreat, this Future Mindset evaporates. The commitments, decisions, and promises made during the meeting dissolve as the rigors of daily operations resurface, ushering back the Present Forward mentality.

Hence, navigating this transition demands astute tactics tailored for strategic planning retreats, steering teams from this transient mindset toward tangible implementation.

Constructing Resilient Frameworks

Envisage your next retreat as an arena for implementing these tactics:

– Visual Strategy Mapping: Transcend mere verbal articulation; employ diagrams to encapsulate the elusive strategic hypothesis underlying your deliberations.

– Actionable Projects: Define projects in tangible terms, delineating actionable steps for seamless execution.

– Project Descriptions: Elaborate on each project in written paragraphs, engraving its significance and rationale into the strategy.

– Sponsorship Assignments: Appoint sponsors for each project, fostering ownership and ensuring continuity beyond the retreat.

– Comprehensive Documentation: Record vital discussions and retain transcripts for future reference and sustenance of momentum.

These strategic pillars aren’t just conveniences; they stand guard against the pervasive “Strategy Amnesia” plaguing planning efforts. Deploy them to infuse accountability and anticipation into the implementation phase, steering clear of post-retreat disillusionment.

“Breaking Free from a ‘Past Forward’ Mindset: Navigating the CEO’s Transition

The transition from manager to CEO often proves to be an intricate journey, one that presents unique challenges to those stepping into this elevated role. Managers, typically adept at producing short-term results, find their focus honed on meeting quarterly or yearly targets.

However, a distinct realization dawns upon some top-tier executives – a profound responsibility transcending immediate successes. This newfound responsibility calls for the articulation of a vision. But it can’t be a hollow ‘vision statement.’ Instead, it must be a transformative, long-term destination capable of captivating and engaging stakeholders on a deeper level.

Yet, embracing this visionary aspect doesn’t come effortlessly for a new leader. Consequently, many opt for shortcuts, each carrying its set of pitfalls and limitations.

One shortcut involves redefining the concept of ‘long-term,’ squeezing it into the narrow confines of three to five years. The other shortcut involves padding the current plan with additional years, adding superficial layers that fail to address the underlying complexities. However, these superficial approaches inevitably pave the path to failure. Let’s delve deeper into the reasons behind this.

Comprehending Managerial Mindsets

At strategic planning retreats, managers engage in collaborative activities. Yet, beneath the action, a phenomenon unfolds, understood by only a few individuals.

Johnson and Suskewicz, in their book ‘Lead from the Future,’ introduce a compelling concept termed the ‘Past Forward’ mindset. This mindset characterizes managers elevated to the C-Suite based on their track record of delivering immediate results. It’s a mindset steeped in past experiences – leveraging prior triumphs and missteps to pave incremental pathways for future improvements.

Occasionally, amidst routine meetings, a contrary voice emerges, questioning the grander vision for the company’s trajectory. However, these inquiries often get sidelined, perceived as peripheral to the immediate agenda.

Fast forward to mandatory strategic retreats, met with groans by many attendees. These managers view the retreats as distractions diverting their attention from pressing targets.

Embracing a New Perspective

Consequently, most attendees walk into these retreats entrenched in the ‘Present Forward’ mindset, secretly yearning for swift remedies before returning to their ‘actual’ responsibilities.

Thus, engineering a shift – an imperative transition to what the authors term the ‘Future Back’ approach – becomes the order of the day. This approach necessitates envisioning credible, transformative futures – a significant departure from vague, traditional vision statements. It’s about precisely delineating new destinations that will, in turn, inform robust strategic plans.

While no standardized formula can usher in this transition universally, leveraging the dynamics of a cohesive team often bears fruit. A shift in mindset among a few can catalyze a ripple effect, influencing others to follow suit.

To initiate this paradigm shift, I recommend embarking on a deep dive into the current challenges. However, this isn’t about finding quick fixes; it’s about diagnosing issues and devising long-lasting solutions. Often, persistent challenges arise from long-ignored problems.

Previous executives, ensnared in the ‘Present Forward’ mindset, defer addressing these. They follow the Southwest Airlines’ IT fiasco of late 2022, which stemmed from repeated delays in system updates.

This diagnostic phase of the retreat is an unprecedented opportunity to confront long-overdue matters, liberated from the usual shackles of time constraints.

Anticipate witnessing a surge in collective energy as the C-Suite delves into long-term thinking, unloading pent-up frustrations. Additionally, this event inadvertently fosters a unique team-building experience.

However, sustaining the ‘Future Back’ mindset individually is a formidable challenge. Most CEOs need the collective support of a group setting to prolong this mindset beyond fleeting moments.

Top leaders thrive in such retreats, experiencing an intellectual shift beyond the confines of immediate urgencies. Here, the C-Suite collectively embodies the ‘Future Back’ mindset, embracing the vision of chief executives thinking on a collective scale.

This alleviates the pressure on CEOs to function as the solitary visionaries. For the duration of the retreat, they coalesce into a cohesive ‘Future Back Team,’ diverging from the solitary focus on ‘hitting numbers.’

Unfortunately, this transformational journey is transient in nature. Therefore, to solidify this unique mindset and embed it into the organizational fabric, I will delve into strategies for concretizing commitments. This must happen quickly: before this transcendent essence dissipates.

In my next article, I will address how to take strong next steps.

Injecting Insipid Plans with Strategic Essence

Ensuring your plan possesses a genuine strategy is crucial, yet sometimes, strategic plans lack strategic essence. Here’s why this happens and how to prevent it.

Imagine joining a new management team and attempting to grasp the existing strategic plan. You ask for documentation due to the confusing explanations from your new colleagues. However, reviewing the outputs from the last planning project doesn’t provide the clarity you seek. Instead, it overwhelms with numerous words and diagrams, leaving you feeling lost. The strategy fails to emerge from the pages.

But don’t worry—it’s not you. The issue lies in the strategy’s formulation. Often, strategic planning results in nothing more than a wish-list or a laundry-list.

The wish-list resembles a child’s letter to Santa—dreams of a pony, a helicopter, and a 65-inch television. Similarly, the strategic plan includes all good things imaginable without any hard choices being made.

Conversely, the laundry-list mirrors disorganized ad-hoc tasks lacking clear reasoning. Even when categorized for readability, their origin and purpose remain obscure. They reveal a lack of real thought.

But let’s not be too critical. While every strategic plan includes goals and action items, these lists miss conveying the essence of the chosen strategy. Consequently, they fail to distinguish it from plans in similar organizations.

At the core of a poor strategic plan a crucial element is missing—the strategic hypothesis. It might not be officially named as such, but its essence is critical.

To craft this essential hypothetical element, understand that strategic hypotheses, though sounding abstract, are simple in concept. Recognize that testing a strategy’s validity only happens through implementation—until then, it’s an educated guess, a hypothesis.

Why this approach? Because true strategic planning begins with incomplete information, lacking valuable historical data to predict success. Additionally, the human element and flawed communication within leadership contribute to unpredictability. Moreover, the ever-changing external environment adds another layer of variability.

This unpredictability poses challenges, making long-term strategic planning daunting for some executives. They find leaving things to chance easier than forging a hypothesis that demands multiple steps, significant investments, and years of effort.

However, positive examples exist of companies incorporating game-changing strategic hypotheses. Take Steve Jobs and Apple in 2000, during the Dot-Com Bust. Despite adversity, they formulated a 10-year strategic hypothesis—shifting from selling high-end desktops to interconnected devices like the iPod, iPhone, and iPad. This innovation led Apple from near-bankruptcy to become the world’s most valued company.

Jamaica’s GraceKennedy, in the 1990s, facing currency challenges, devised a 25-year vision (GK2020) to enter financial services and overseas markets. This move saved it from disaster and yielded monumental results.

In all strategic hypotheses, intricate links exist between proposed actions and desired outcomes. Apple and GK couldn’t guarantee success with limited information, yet their bold moves changed their trajectories.

So, can your executive team craft a game-changing strategic hypothesis? Though not easy, doing so could make all the difference.

How to Effectively Manage Cynical Employees

In every organisation, there are employees whose primary motivation is simply trading their time for a paycheck. Unfortunately, these individuals contribute to creating a negative and toxic work environment that is detrimental to the leadership team. Negativity takes over the corporate culture.

Is there a way to tap into greater motivation among your staff? As a C-Suite executive or board member, can you do more to provide your employees with a chance to discover meaning in their work?

One surprising revelation for many first-time managers is the prevalence of cynicism among their former, non-supervisory colleagues. In some cases, the majority of the workforce can be deeply cynical, and their negative outlook can be contagious.

Over time, this pervasive cynicism erodes a sense of purpose in the workplace, leaving only the newly hired employees with a glimmer of enthusiasm. Unfortunately, even these newcomers often lose their initial spark after a few months.

In response to this lack of meaning at work, employees may seek fulfilment in other areas of their lives, such as social media, gaming, religion, family, hobbies, vacations, side-hustles, or even consider resignation or migration. A handful may even end up feeling depressed.

However, it’s essential to view these responses as a positive sign. They reflect a fundamental human desire for a purposeful life, a concept echoed in Viktor Frankl’s book “Man’s Search for Meaning” and the movie “Life is Beautiful.”

Regrettably, many CEOs fail to acknowledge this deep-seated need and struggle to connect with their staff’s deeper aspirations. Here are some critical steps to address this challenge effectively.

1. Lead with Bold, Inspiring Goals

CEOs are often successful in inspiring their close C-Suite colleagues who naturally exhibit high self-motivation. However, there’s a tendency for a disconnect to occur with employees at lower levels, which can lead to a perception of a gap.

However, some CEOs have realised that they share the same desire for making a difference as their employees. When people at all levels feel frustrated due to thwarted aspirations, it leads to inaction. By contrast, rallying the organisation around Big Hairy Audacious Goals (BHAGs) is a powerful way to ignite engagement at every level. Without such ambitious goals, you risk settling for a business-as-usual approach.

However, not just any BHAG will do. Goals like “double profits at all costs” may meet the criteria but lack deep meaning to most. In fact, the world now demands holistic collections of BHAGs.

Case in point: the United Nations’ 17 Sustainable Development Goals (SDGs). These multi-pronged commitments address the interests of multiple stakeholders simultaneously.

This approach works even when individual goals are average. They only achieve BHAG status in unison, making them more attractive, but also more difficult.

2. Embrace Credible BHAGs

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Thankfully, these goal collections tend to be more sustainable as they take into account multiple perspectives. This boosts their credibility a little.

But, this is only the beginning. The SDGs are currently facing the type of problem that arises when goals are combined. They consist of 17 goals and 169 targets and were established in 2015. People doubt the feasibility of their overly ambitious vision for 2030.

It’s unsurprising that they are completely off-course. They resemble more of a wish-list rather than a serious commitment. Countries have converted the project into a perfunctory “check-the-box” exercise in response.

Yet, this did not happen in the past. In 2006, Collins and Porras introduced the term “BHAG” and people were inspired by the announcement of one audacious goal.

Regrettably, that is no longer the case. Today, the overall aspiration must be credible in order to have significance. This is the elevated standard you must achieve as an executive.

And now, we face another hurdle in our journey.

3. Integrate Strategy and BHAGs

In organizations that embrace BHAGs, it’s essential to ensure there’s a concrete strategic plan that accompanies these goals. The SDGs face a similar challenge. Employees and stakeholders now demand a clear, detailed pathway to achieve these significant goals.

In summary, take your collective BHAGs, make them both meaningful and credible, and use them as a catalyst to kick-start your strategic planning process. This approach will bring your ambitions down to a realistic level, even for the skeptics.

In today’s world, where millennials are actively seeking purpose in their work, failing to provide a sense of meaningful action can be a disservice. If you’re not prepared to embrace these new approaches and provide a sense of purpose, it might be time to consider a transformation or find a new path in leadership.

This article was inspired by a prior column in the Jamaica Gleaner.

The Problem with the Sustainable Development Goals (SDGs) – A preview

Why they lack rigorous strategic thinking but can still be rescued.

You are someone who is aware of the 17 Sustainable Development Goals (SDGs) announced in 2015 by the United Nations. Their value is not in question – they are objectives the entire world hopes to realize.

But recently, Secretary General Antonio Guterres declared that the SDGs are on the path to failure.

Launching a special edition of the Sustainable Development Goals (SDGs) progress report, he warned that their collective promise made in 2015 of a more green, just and equitable global future, is in peril. 

“Unless we act now, the 2030 Agenda will become an epitaph for a world that might have been,” he said

Like others, he offered a number of prescriptions. However, they aren’t likely to move the needle on disappointment looming on December 31st, 2030, the date on which they are supposed to be achieved.

Those of us who know about long-term strategic planning are horrified by the lack of progress, similar to everyone else. But for us, there’s more. This failure was inevitable due to fatal design flaws. By violating the fundamental principles of our narrow discipline, the UN cannot avoid the unfortunate situation it finds itself in.

Despite the tireless work by thousands of well-meaning people, a slow-moving disaster is taking place in real time.

However, with six years to go between 2023 and 2030, there is a vanishing opportunity to declare victory at the end of the decade. How? Continue reading to understand why a “hard reset” could save the world from disillusionment.

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Unlocking the Power of Irresistible Offers

Many companies lack a formal product development unit. Instead, ideas are casually pitched to the CEO, and the next steps depend on their mood at the moment. This approach often falls short in delivering consistent innovation, resulting in products and services that closely resemble competitors’ offerings. If you’re a monopoly, your products might become stale over time. To stand out, you need innovative ideas that provide real value to your customers.

The challenge? You may not have the resources to hire a full-time R&D team, and even if you could, you might not trust newcomers to handle the job effectively. So, how can you consistently set your offerings apart from the rest?

Recently, I experimented with an approach outlined by Alex Hormozi in his book, “$100m Offers.” This approach revolves around the customer experience and has yielded promising results. I highly recommend this method, as it takes an inside-out perspective. Let me walk you through the steps I followed, using a local example.

Step 1 – Envision Dream Outcomes

Start by listing the experiences you want your ideal customers to have. Even if some of these experiences seem unattainable, record them. The goal is to capture what your customers truly desire.

Step 2 – Identify Customer Pain Points

Think about the moment a customer considers your offering. What are the hurdles and obstacles preventing them from achieving their desired outcomes? Consider issues that arise during and after using your product or service. For instance, let’s imagine you own the Krispy Kreme franchise in Jamaica. If someone has never tried your donuts, what challenges might they face?

  • Traffic around the store’s location is congested.
  • There are long lines inside.
  • The customer is on a diet.
  • They don’t like overly sweet food.
  • They had a bad experience with a competitor’s product.

This is just a starting point. Keep going until you’ve identified at least a hundred pain points for your offering. The more you list, the deeper you’ll delve into the customer experience, leading to more valuable insights than traditional surveys.

Step 3 – Propose Solutions for Each Problem

Address each pain point with a solution, expressed in the form of a “How to…” statement. For example, “I am on a diet” could be solved with “How to enjoy our product while sticking to your diet.”

But don’t stop there. Be thorough.

Step 4 – Design Strategies to Implement Solutions

Let your imagination run free in this step. Create offers, or “vehicles,” that correspond to each “How to…” solution from the previous step. Give these vehicles catchy, descriptive names that would grab your customer’s attention. Be comprehensive and include even those you may not intend to provide.

For example, considering the solution “How to enjoy our product while on a diet,” what could you name the corresponding vehicles to attract customers?

  • The 47-Calorie Donut Hole
  • The Perfect Donut for a Dieter’s Cheat Day (Help dieters plan effective cheat days with this brand.)
  • Free Traffic Morsels (Offer complimentary pastries for people stuck in traffic.)
  • Our Lowest-Ever Calorie/Fat Gram Donut (Give diet-conscious customers a guilt-free treat.)
  • The Unsweet Spicy Donut (Appealing to dieters who prefer savory over sweet.)

This list took me just 10 minutes to create. You don’t need to be exceptionally creative; following this structured process can help you brainstorm at an impressive pace.

Step 5 – Evaluate and Prioritize Solutions

Assign two measures to each vehicle: its value to the customer and the cost to your business to offer it. Use these measures to rank your offers and establish a timeline for implementation.

In conclusion, these lists can jumpstart your innovation. Thanks to Alex Hormozi, these lightweight forms of R&D leverage the everyday experiences you’re already gathering.

This article appeared in an earlier form as a Jamaica Gleaner column.

Transforming Frustrating Board Meetings into Strategic Sessions

As a dedicated board member, you actively contribute to meetings and aim to make a meaningful impact. However, there are moments when you find yourself quietly frustrated, wondering if the discussion has veered into the minutiae, and then even further into micro-details. Why does this happen?

While the topics at hand may be interesting, you understand that such operational details are better left to middle managers who specialize in these functions. The board’s role should be holding these managers accountable, not getting lost in the weeds.

After an hour or two of discussion, you may find that little progress has been made. This can leave you shaking your head in disbelief, thinking that there are more productive uses of your time.

So, how can you address this issue before your frustration reaches a breaking point?

  1. Focus on What Truly Matters

Board members have limited time, often juggling other important responsibilities. Therefore, it’s crucial to engage in high-leverage discussions. Your participation should be reserved for tackling the most challenging and intractable problems. If discussions jump around with random advice, it’s a sign that something needs to change.

It’s important to note that your fellow board members are well-intentioned, smart, and experienced. They can provide valuable insights on various topics. However, the aim should be to make significant decisions during board meetings, not to offer scattered tips.

  1. Encourage Decisive Actions

Some board members believe that major decisions only come into play during unexpected emergencies. While these situations demand immediate attention, boards can also proactively influence decision-making.

One effective approach is to require your executives to develop long-term plans. Short-term plans tend to be incremental, as discussed in my May 2022 column, “Five-Year Plans Aren’t Strategic. They’re Dangerous.”

For inspiration, consider Kennedy’s lunar challenge in 1961. This ambitious goal led to the creation of the Apollo program and spurred innovations in various fields. To foster big decisions, challenge your CEO or MD to articulate a bold, long-term vision for the organization.

Few top executives have been trained in this kind of thinking. Some offer vague visions with no concrete plans, while others attempt to rebrand five-year plans as “long-term.” As a discerning board member, you should seek game-changing commitments that transform industries and elevate your company’s performance.

  1. Engage the Best Minds

While board members may be eager to make significant decisions, many C-Suite executives might not be ready for such audacious goals. They are often promoted based on their ability to deliver short-term results.

You can encourage a shift in mindset by introducing the concept of “big, hairy, audacious goals” (BHAGs) with long-term horizons. While this may seem unconventional and risky to some, it’s the right approach. As a board member, your role is to challenge assumptions, ensure the credibility of plans, and evaluate end-game scenarios.

Your collective expertise can add rigor to the management team’s plans and elevate the quality of discussions. Over time, this focused process can lead to game-changing outcomes, making board meetings inspiring and far less frustrating.

This article was inspired by an earlier version published as a column in the Jamaica Gleaner.

How Board Members Turn Frustrations into Strategy


As a dedicated board member, you actively contribute to meetings and aim to make a meaningful impact. However, there are moments when you find yourself quietly frustrated, wondering if the discussion has veered into the minutiae, and then even further into micro-details. Why does this happen?

While the topics at hand may be interesting, you understand that such operational details are better left to middle managers who specialize in these functions. The board’s role should be holding these managers accountable, not getting lost in the weeds.

After an hour or two of discussion, you may find that little progress has been made. This can leave you shaking your head in disbelief, thinking that there are more productive uses of your time.

So, how can you address this issue before your frustration reaches a breaking point?

  1. Focus on What Truly Matters

Board members have limited time, often juggling other important responsibilities. Therefore, it’s crucial to engage in high-leverage discussions. Your participation should be reserved for tackling the most challenging and intractable problems. If discussions jump around with random advice, it’s a sign that something needs to change.

It’s important to note that your fellow board members are well-intentioned, smart, and experienced. They can provide valuable insights on various topics. However, the aim should be to make significant decisions during board meetings, not to offer scattered tips.

  1. Encourage Decisive Actions

Some board members believe that major decisions only come into play during unexpected emergencies. While these situations demand immediate attention, boards can also proactively influence decision-making.

One effective approach is to require your executives to develop long-term plans. Short-term plans tend to be incremental, as discussed in my May 2022 column, “Five-Year Plans Aren’t Strategic. They’re Dangerous.”

For inspiration, consider Kennedy’s lunar challenge in 1961. This ambitious goal led to the creation of the Apollo program and spurred innovations in various fields. To foster big decisions, challenge your CEO or MD to articulate a bold, long-term vision for the organization.

Few top executives have been trained in this kind of thinking. Some offer vague visions with no concrete plans, while others attempt to rebrand five-year plans as “long-term.” As a discerning board member, you should seek game-changing commitments that transform industries and elevate your company’s performance.

  1. Engage the Best Minds

While board members may be eager to make significant decisions, many C-Suite executives might not be ready for such audacious goals. They are often promoted based on their ability to deliver short-term results.

You can encourage a shift in mindset by introducing the concept of “big, hairy, audacious goals” (BHAGs) with long-term horizons. While this may seem unconventional and risky to some, it’s the right approach. As a board member, your role is to challenge assumptions, ensure the credibility of plans, and evaluate end-game scenarios.

Your collective expertise can add rigor to the management team’s plans and elevate the quality of discussions. Over time, this focused process can lead to game-changing outcomes, making board meetings inspiring and far less frustrating.