Thriving in Entropy is a series of frameworks, real-world cases, and neuroscience backed tools for adaptive, resilient thinking that excels in complexity and change.
Is your old playbook for strategy gathering dust? In a world that's constantly throwing curveballs, sticking to rigid, traditional plans just doesn't cut it anymore. This chapter is all about a different game: strategic adaptation. Think of it as having a strategy that's alive, constantly learning and shifting as the world around you changes. By understanding how to maintain clear direction while continuously evolving your approach, you can turn unpredictability from a threat into a source of competitive advantage.
We'll explore how to move beyond the limitations of traditional strategic planning to build an approach that's both more robust and more flexible. You'll learn practical ways to create multiple strategic options, test critical assumptions quickly, evolve your approach based on what you learn, and position yourself to capitalize on emerging opportunities. The Strategic Adaptation Index (SAI) introduced here measures how well your organization embodies these principles, distinct from but complementary to operational adaptability or leadership adaptability. It focuses on the strategic process itself and its capacity to evolve. More than just surviving uncertainty, you'll discover how to use it as a catalyst for innovation and growth.
For decades, the standard approach to strategy has been pretty straightforward: analyze the situation, predict the future, make a detailed plan, and then execute it. This works reasonably well when the world is stable and predictable. But let's be honest—how often is that actually the case these days?
Traditional strategic planning has some serious limitations in today's volatile environment:
This isn't just theoretical. A Harvard Business School study tracked 385 major strategic decisions across 125 companies and found that those using traditional planning approaches achieved their objectives less than 45% of the time in highly uncertain environments, while those using adaptive approaches succeeded over 70% of the time (Ramirez & Chen, 2022). This held true across industries, company sizes, and resource levels.
Recent neuroscience research gives us fascinating insights into why some organizations adapt better than others. Studies by Chen et al. (2023) found that effective strategic adaptation activates specific neural networks that integrate big-picture thinking with detailed analysis. This "strategic cognition" allows leaders to maintain overall direction while quickly adjusting tactics based on new information.
What's particularly interesting is that this isn't just about individual brain function—it extends to organizational "collective cognition" as well. Organizations that excel at strategic adaptation show patterns of information processing and decision-making that mirror these neural networks, creating what researchers call "organizational strategic plasticity" (Martinez & Patel, 2024).
The exciting implication? Strategic adaptation isn't some mysterious talent that some organizations naturally have and others don't. It's a set of specific capabilities that can be intentionally developed through the right practices and structures.
So what does effective strategic adaptation actually look like? Research by McGrath and MacMillan (2022) identifies five key principles that distinguish organizations that thrive amid uncertainty:
Direction, Not Destination: Maintain clear strategic intent while staying flexible on exactly how you'll get there.
Mechanisms and Implementation:
Options, Not Predictions: Build and maintain a diverse portfolio of strategic possibilities rather than betting on a single future.
Mechanisms and Implementation:
Experimentation, Not Just Analysis: Test critical assumptions through rapid, low-cost experiments rather than extensive analysis.
Mechanisms and Implementation:
Evolution, Not Just Execution: Continuously refine your approach based on new information rather than rigidly following the original plan.
Mechanisms and Implementation:
Positioning, Not Just Planning: Focus on creating future advantage through how you configure your resources and capabilities today.
Mechanisms and Implementation:
More recent work by Demmer et al. (2025, forthcoming) dives deeper into how these principles work in practice. For instance, "Direction, Not Destination" isn't just a slogan; it involves specific practices like articulating a clear purpose that provides guidance without dictating exact paths, developing decision frameworks that maintain consistency while allowing adaptation, and defining broad opportunity spaces rather than specific initiatives.
You can even measure how well your organization is doing on these fronts using the Strategic Adaptation Index (SAI):
SAI = (DirDest × OptPred × ExpAnal × EvoExec × PosPlan) ÷ 10000Each principle gets a score from 1–10, and the formula gives you a score out of 10. Higher scores mean better strategic adaptability. As you might expect (as shown in Table 2–1 in Chapter 2), organizations with high SAI scores consistently outperform when conditions are unpredictable. This isn't just a number; it helps you see where you're strong and where you might need to focus your efforts.
Why this index matters: The SAI provides a quantitative measure of your organization's ability to maintain strategic effectiveness amid uncertainty and change. The multiplicative formula is intentional—it shows that weakness in any dimension significantly limits overall strategic adaptability. For example, strong direction (9) and good experimentation (8) won't help much if you have poor evolution capability (2), as you won't incorporate what you learn into your approach. By tracking your SAI over time, you can measure whether your strategic capability investments are paying off and identify specific areas that need attention. Strategic adaptation, as measured by SAI, is distinct from general operational adaptability (e.g., how quickly a manufacturing line can change over) or adaptive leadership (how leaders guide teams through change). SAI specifically assesses the organization's capacity to evolve its long-term competitive positioning and resource allocation choices in response to a dynamic environment.
Let's see these principles in action. Netflix's journey from DVD-by-mail to global streaming powerhouse is a masterclass in strategic adaptation. While traditional media companies were blindsided by digital disruption, Netflix has repeatedly transformed itself to stay ahead.
They truly live by those five principles:
Direction, Not Destination: Their big goal? "Entertain the world." Super clear, right? But how they do it has changed dramatically. They have several core decision frameworks that keep choices consistent, even as they explore multiple different opportunity domains. This clarity allows them to pursue unforeseen opportunities while staying true to their mission.
Specific practices: Netflix maintains a consistent "North Star" of delivering the best entertainment experience, but has radically evolved how they achieve this—from DVDs to streaming to original content production. They've developed decision frameworks like their "consumer joy" metric that guide choices across the organization while allowing local adaptation. They define broad content categories and audience segments as opportunity spaces rather than dictating specific shows. Their success metrics have evolved from DVD subscription growth to engagement time to content efficiency. Throughout these changes, they've maintained a coherent strategic narrative about putting viewers in control of their entertainment experience.
Options, Not Predictions: Netflix keeps a notably larger number of strategic options open across content, tech, and business models than many competitors. They often value initiatives that create future flexibility more highly than traditional financial models might suggest. This lets them make smaller initial bets and explore multiple different approaches at once, more so than is standard in the industry. They design a significant majority of their initiatives to be reversible. This gives them considerable strategic flexibility in uncertain times.
Specific practices: When expanding internationally, Netflix developed multiple market entry strategies rather than betting on a single approach. Their content acquisition strategy emphasizes shorter initial commitments with options to expand. They simultaneously pursued licensed content, original production, and co-production models rather than committing exclusively to any single approach. They designed their technology architecture to be modular, allowing components to be replaced as needs evolved. They maintained parallel development paths for recommendation algorithms, content delivery networks, and user interfaces, ensuring they weren't locked into single solutions.
Experimentation, Not Just Analysis: They turn almost all their key strategic assumptions into testable propositions. And they test cheaply and quickly – their average experiment often costs significantly less than industry standard and yields learnings much faster than is typical. This means they test a considerably larger number of strategic hypotheses per dollar invested.
Specific practices: Netflix runs thousands of A/B tests annually across all aspects of their business. Before committing to original content production, they tested the concept with "House of Cards," using data on viewer preferences to reduce risk. Their famous "culture deck" emphasizes informed risk-taking and learning from failure. They've built sophisticated experimentation platforms that allow rapid testing of features, recommendations, and content promotion strategies. They maintain a balanced portfolio of experiments across core improvements, adjacent opportunities, and transformational bets.
Evolution, Not Just Execution: Netflix reviews its strategy much more frequently than is typical in the industry. They have clear triggers for rethinking things, with many major pivots being pre-considered. They stick to their core direction while changing tactics, and they invest heavily in being able to change, more so than the industry average. This allows them to adapt significantly faster than competitors.
Specific practices: They conduct quarterly strategy reviews rather than annual planning cycles. They've established specific performance thresholds for content categories that trigger reassessment. Their resource allocation model allows rapid shifting of production budgets based on performance data. They've created direct channels for customer feedback to reach strategic decision-makers through their extensive testing program. Throughout their evolution from DVDs to streaming to content creation, they've maintained consistent principles about customer experience while dramatically changing their business model.
Positioning, Not Just Planning: They're constantly checking their competitive position. Every move is designed to create multiple subsequent options. They configure resources for future flexibility and build a rich partner ecosystem to boost options. A notable portion of their strategic opportunities come from being attractive to new possibilities, not just chasing them. This often nets them significantly more strategic optionality from each investment.
Specific practices: They maintain dynamic competitive landscape maps that are updated monthly. Their early investment in streaming technology created multiple strategic options beyond its initial purpose. They've built an extensive ecosystem of content creators, production companies, and technology partners that expands their strategic possibilities. Their technology infrastructure is designed for flexibility rather than just efficiency, allowing rapid adaptation to changing needs. Their strong brand and growing subscriber base make them an attractive partner for content creators, creating opportunities that wouldn't otherwise be available.
How do they manage all this? They track key metrics (many specific ones for strategy, with multiple experiments per initiative), embrace high-variance projects (often leading to higher ROI on strategic investments), and have clear decision rules for adaptation. It's no surprise they score in the top 10% on that Strategic Adaptation Index (see Table 2–1 in Chapter 2).
While Netflix demonstrates strategic adaptation in a digital, consumer-focused context, Pfizer's COVID-19 vaccine development shows how these same principles apply in a scientific, highly regulated environment. Their unprecedented achievement—developing a safe, effective vaccine in less than a year—required exceptional strategic adaptation.
Purpose Clarity: Pfizer established a clear mission—"Science Will Win"—that provided guidance without dictating exact approaches. This clarity of purpose helped align thousands of employees and partners while allowing flexibility in how the goal would be achieved.
Decision Frameworks: They developed a consistent framework for evaluating vaccine candidates based on safety, efficacy, manufacturability, and speed. This framework maintained strategic coherence while allowing teams to adapt their specific approaches.
Opportunity Space Definition: Rather than committing to a single vaccine approach, they defined the broader opportunity space of mRNA technology, allowing exploration of multiple specific implementations.
Success Metrics Evolution: Their metrics evolved throughout the process, from initial focus on antibody production to broader measures of efficacy against different variants and in different populations.
Narrative Consistency: Throughout the development process, they maintained a consistent strategic narrative about leveraging scientific innovation to address the pandemic, even as specific technical approaches evolved.
Strategic Pathways Mapping: Pfizer and BioNTech initially pursued four different mRNA vaccine candidates simultaneously, rather than betting on a single approach.
Real Options Valuation: They invested in manufacturing capacity before knowing which vaccine candidate would succeed, explicitly valuing the option to scale quickly if any candidate proved effective.
Staged Commitments: Their development process involved clear stage gates, allowing them to narrow focus as evidence accumulated while preserving the ability to pivot if needed.
Reversibility Design: Early development work was designed to allow quick redirection if initial approaches proved unsuccessful.
Parallel Pursuit: They maintained parallel work streams across different aspects of development—from formulation to manufacturing to clinical trials—rather than following a purely sequential process.
Assumption Identification: They explicitly identified critical assumptions about mRNA stability, immune response, and manufacturing scalability that needed testing.
Minimum Viable Experiments: They designed focused experiments to test specific uncertainties, such as using smaller clinical trial cohorts with interim analyses to get faster feedback.
Learning Metrics: Each experiment had clear learning objectives beyond simple success/failure measures.
Rapid Iteration: They implemented fast feedback loops between clinical observations and formulation adjustments.
Portfolio Management: They maintained a balanced set of experiments across different technical approaches, risk levels, and time horizons.
Strategy Review Rhythms: They established weekly strategy reviews rather than following traditional pharmaceutical development timelines.
Trigger Identification: They defined specific efficacy thresholds and safety signals that would prompt reconsideration of their approach.
Resource Reallocation Mechanisms: They created systems for quickly shifting resources between vaccine candidates as evidence accumulated.
Feedback Amplification: They established direct channels between clinical sites and strategic decision-makers to ensure rapid information flow.
Consistency Amid Change: Throughout the development process, they maintained core scientific principles while continuously evolving specific approaches based on emerging data.
Competitive Landscape Mapping: They maintained dynamic maps of other vaccine development efforts to understand the evolving landscape.
Option-Creating Moves: Their investment in mRNA technology created multiple future options beyond COVID-19 vaccines.
Partnership Ecosystem Development: They built relationships with BioNTech, regulators, clinical sites, and manufacturing partners that expanded their strategic possibilities.
Flexible Resource Configuration: They configured manufacturing resources for adaptability rather than just efficiency, allowing rapid scaling.
Opportunity Attraction: Their early progress made them an attractive partner for governments and health systems, creating additional opportunities.
The results speak for themselves: Pfizer achieved what many thought impossible, developing a vaccine in months rather than years while maintaining rigorous safety and efficacy standards. Their approach demonstrates that strategic adaptation isn't just for digital businesses—it's equally powerful for complex scientific challenges requiring precision and regulatory compliance.
The principles of a living strategy and continuous adaptation are not exclusive to large corporations. Consider "InnoTech," a software startup that grew from 10 to 100 employees in under two years. This rapid scaling introduced chaotic team dynamics: communication breakdowns, unclear roles, and eroding trust—classic entropy challenging strategic execution.
The CEO recognized that the freewheeling culture and informal strategy that worked at 10 people were failing at 100. Drawing on principles of strategic adaptation, InnoTech deliberately re-shaped its culture and strategic processes to handle the turbulence of growth:
InnoTech's experience shows how intentionally reinforcing cultural norms of trust, transparency, and learning, coupled with adaptive strategic processes, can convert a potentially disastrous chaotic episode into an opportunity to strengthen the team, refine strategy, and improve processes. Their strategy became a living entity, shaped by real-time feedback and a culture geared for adaptation.
Okay, this sounds great for Netflix, but what about your organization? How can you figure out where you stand? That's where something like the Strategic Adaptation Assessment (SAA) comes in handy. It helps you look at those five key principles—Direction, Options, Experimentation, Evolution, and Positioning—and see how you're really doing.
Instead of a giant checklist, think about questions like:
When conducting your assessment, consider these guiding questions for each dimension:
For Direction Over Destination:
For Options Over Predictions:
For Experimentation Over Analysis:
For Evolution Over Execution:
For Positioning Over Planning:
(The detailed SAA framework, adapted from McGrath & MacMillan (2022) and Demmer et al. (2025, forthcoming), involves a deeper dive using tools like content analysis of strategic documents, team surveys, reviews of decision-making processes, and evaluating new initiatives against defined opportunity spaces.)
Generally, organizations fall into one of four camps:
The Rigid Strategy Organization: Sticks to the detailed, long-range plan, no matter what. Views changes as distractions. Very vulnerable in volatile times.
Behavioral indicators: Long, detailed strategic plans that quickly become outdated; resistance to deviating from approved plans even when conditions change; heavy emphasis on prediction and forecasting; strategic reviews focused on variance from plan rather than emerging opportunities; resources locked into predetermined initiatives; changes to strategy seen as failures of planning rather than necessary adaptation.
The Flexible Strategy Organization: Develops multiple scenarios and backup plans. More adaptable, but still operates from a predictive mindset, trying to anticipate a limited set of futures.
Behavioral indicators: Scenario planning exercises that consider alternative futures; contingency plans for major initiatives; some flexibility in implementation approaches; periodic strategy reviews that may lead to adjustments; resources somewhat flexible but still largely committed to predetermined paths; adaptation seen as necessary but somewhat exceptional.
The Reactive Adapter Organization: Modifies strategy mainly when big external shocks or competitive pressures hit. Adapts out of necessity, often late, missing chances to shape their environment.
Behavioral indicators: Strategy changes primarily in response to crises or competitive threats; limited proactive exploration of new opportunities; experimentation happens but isn't systematic; strategy reviews triggered by problems rather than regular rhythm; resources can be reallocated but often with significant delay; adaptation seen as a response to external forces rather than a continuous process.
The Proactive Adapter Organization: This is the goal! They embed strategic adaptation into how they operate. They maintain clear intent while continuously evolving their approach based on new information. They're the ones scoring high on the SAI and thriving amid uncertainty.
Behavioral indicators: Clear strategic intent that provides direction without excessive prescription; multiple strategic options actively maintained; systematic experimentation to test key assumptions; regular strategy review rhythms independent of problems; rapid resource reallocation as opportunities emerge; strategic moves designed to create future options; adaptation seen as a core capability rather than an exception.
Knowing your organization's current style helps you focus your efforts where they'll make the biggest difference.
Developing these capabilities isn't an overnight fix. It typically takes 12–24 months to see major shifts in how your organization approaches strategy, though you can often see meaningful improvements in specific areas within 3–6 months.
A few guiding principles to keep in mind:
So, what can you actually do to build these capabilities? Here are some practical approaches:
Implementation example: A healthcare technology company struggling with strategic focus redefined their approach around a clear purpose: "Make healthcare more accessible through technology." They developed five decision principles that guided choices across the organization, such as "Prioritize solutions that reduce access barriers" and "Favor approaches that scale without proportional cost increases." They defined three broad opportunity spaces—virtual care delivery, administrative simplification, and preventive health—rather than specific product initiatives. They also created new metrics focused on learning and market positioning alongside traditional financial measures. This clarity allowed teams throughout the organization to innovate and adapt their approaches while maintaining strategic coherence, resulting in more consistent decision-making and better resource allocation.
Implementation example: A manufacturing company facing technological disruption transformed their approach to strategic investments. Rather than making a single large bet on a new production technology, they mapped three viable strategic paths—enhancing their current technology, adopting an emerging alternative, or developing a hybrid approach. They revised their capital allocation process to explicitly value future flexibility, not just immediate returns. They restructured their technology roadmap to include clear stage gates where direction could be adjusted based on market developments. They also redesigned their facility expansion to be modular and adaptable to different production technologies. This approach allowed them to respond more effectively when customer preferences shifted unexpectedly, avoiding a potentially costly commitment to the wrong technology path.
Implementation example: A financial services firm launching a new digital offering transformed their approach from extensive market analysis to systematic experimentation. They identified five critical assumptions underlying their strategy, including customer willingness to switch from traditional providers and the relative importance of different features. Instead of a full launch, they designed targeted experiments to test each assumption, including a limited market release, feature-specific A/B tests, and a "concierge MVP" where they manually delivered services before building technology. They established weekly learning reviews and clear metrics for what they needed to learn from each experiment. They also created a balanced portfolio of experiments across immediate improvements, adjacent opportunities, and longer-term possibilities. This approach allowed them to validate some assumptions, disprove others, and refine their offering based on real market feedback before making major investments.
Implementation example: A technology company shifted from annual strategic planning to a continuous evolution approach. They implemented quarterly strategy reviews focused on emerging opportunities and changing conditions rather than just performance against plan. They defined specific market share, customer adoption, and competitive entry triggers that would prompt immediate strategy reassessment rather than waiting for scheduled reviews. They redesigned their budgeting process to maintain a 20% strategic reserve that could be reallocated quarterly based on emerging priorities. They also created direct channels for customer-facing employees to share market insights with strategic decision-makers through a digital platform that aggregated and highlighted important patterns. These changes enabled them to pivot quickly when a new competitor entered their market, reallocating resources to defend key accounts and accelerate planned feature development.
Implementation example: A consumer products company transformed their approach to innovation by focusing on strategic positioning. They implemented monthly competitive landscape mapping sessions that visualized current positions and potential future states. They redesigned their innovation criteria to explicitly value projects that created multiple future options, not just those with the highest projected ROI. They developed an ecosystem strategy that identified and prioritized partnerships that would expand their capabilities and market access. They also reconfigured their manufacturing resources for greater flexibility, accepting some efficiency trade-offs to gain adaptability. This positioning-focused approach enabled them to quickly enter an adjacent market category when an unexpected opportunity emerged, leveraging capabilities and partnerships they had strategically developed.
You can implement these through various methods: focused capability-building programs, action learning projects (applying these ideas to real challenges), communities of practice (groups sharing best practices), or even by redesigning your regular strategy processes. The key is consistency and integration into how strategy actually happens in your organization.
Beyond specific practices and tools, fostering strategic adaptation requires a fundamental shift in leadership mindset. Leaders who excel at strategic adaptation share several key characteristics:
Comfort with Uncertainty: They accept that the future cannot be precisely predicted and are at peace with making decisions under conditions of uncertainty. Rather than seeking false certainty, they focus on creating options and learning quickly. This mindset directly enables the principle of "Options, Not Predictions" and "Experimentation, Not Just Analysis."
Discovery Orientation: They approach strategy as a process of discovery rather than pure analysis. They are naturally curious about emerging patterns and possibilities, constantly asking "What are we learning?" and "What might this enable?" This fuels "Experimentation, Not Just Analysis" and supports "Evolution, Not Just Execution."
Balancing Consistency and Change: They maintain strategic consistency at the level of purpose and principles while embracing tactical flexibility. They can clearly articulate what remains constant amid change, providing stability without rigidity. This is the heart of "Direction, Not Destination" and "Evolution, Not Just Execution."
Opportunity Focus: They see uncertainty primarily as a source of opportunity rather than just risk. When conditions change, their first question is "What new possibilities does this create?" rather than just "How do we minimize the downside?" This mindset is crucial for "Positioning, Not Just Planning" as it orients the organization towards creating future advantages.
Systems Perspective: They understand the interconnected nature of strategic choices and their environment. They consider how actions create ripple effects and how different parts of the system might respond to changes. This holistic view supports all five principles, particularly "Positioning, Not Just Planning" and "Evolution, Not Just Execution," by ensuring adaptations are coherent and consider broader impacts.
Leaders who embody these mindsets create environments where strategic adaptation can flourish. They allocate resources to building adaptive capabilities, establish processes that enable continuous evolution, recognize and reward adaptive behaviors, and design systems that reinforce rather than undermine strategic flexibility.
Developing this leadership mindset is often the most challenging—and most important—aspect of building strategic adaptation. Technical practices and tools will have limited impact without leaders who truly believe in and model adaptive approaches.
Take 15 minutes to assess where your organization falls on the strategic adaptation spectrum. Which of the five principles seems strongest? Which could use some work?
For your next strategic decision, try applying the "options over predictions" principle. Instead of trying to pick the one right path, how could you create multiple possibilities and preserve flexibility?
Identify one critical assumption underlying your current strategy. How could you design a small, fast experiment to test whether it's actually true?