Beyond Artifacts Part II: Strategic Foresight Through Design

The room was silent except for the sound of sketching. Twenty-seven executives from a Fortune 100 company, faced with an industry disruption that would eliminate half their revenue within three years, were drawing their way through a crisis they couldn't analyze their way out of.

No PowerPoints. No SWOT analyses. No McKinsey 2X2 matrices or Gartner reports. Just paper, pens, and the uncomfortable truth that their entire strategic planning apparatus—five-year plans, detailed financial projections, elaborate market analyses—had failed to anticipate the disruption now threatening their existence.

"Stop kibbitzing, start sketching, you have 3 minutes" I reminded them. The CFO, who hadn't drawn anything since grade school, was wireframing a business model that would later generate $400 million in new revenue. The head of strategy, freed from her 200-slide deck, was prototyping customer journeys that revealed opportunity spaces her team's analysis had completely missed.

Six months later, three of those rough sketches had become the foundations for new businesses worth $2.8 billion. Not because the wireframes predicted the future—they didn't. They made thinking about the future possible. They made the inconceivable conceivable, the abstract concrete, the complex comprehensible.

The Failure of Strategic Planning in Complex Systems

There is very little strategy in strategic planning, and that's a problem. Most strategic "planning" is actually budgeting in disguise—an elaborate performative dance in extrapolating the past into the future, focusing on what organizations can control (costs, resources, operations) while ignoring what actually matters (customer choices, competitive dynamics, capabilities, and emergent opportunities).

"Planning has always been about analysis," Mintzberg wrote in his seminal The Fall and Rise of Strategic Planning. But "strategic thinking, in contrast, is about synthesis. It involves intuition and creativity." The outcome isn't a plan—it's what Jim Clark of Silicon Graphics had: a hunch that three-dimensional visual computing would transform how humans interact with computers. You can't analyze your way to that insight. But you might sketch your way to it.

Herbert Simon's concept of bounded rationality (for which he won the Nobel Prize) posits that human decision-making is not perfectly rational due to limitations in information, cognitive abilities, and time: there is a limit to how many variables we can hold in our head. Modern strategic contexts involve hundreds of variables. Climate disruption cascades into supply chain complexity, which compounds with technological disruption, which accelerates social transformation, which impacts labor markets. Our mental models, evolved to find linear causation at all cost, collapse under this complexity.

This is where Karl Weick's sensemaking research becomes crucial. Strategy isn't about predicting the future—it's about making sense of the present in ways that enable productive action today. We don't discover strategy; we enact it through our interpretations and through our actions. The question isn't "What will happen?" but "What stories are we telling ourselves, and how do those stories shape what becomes possible?"

Wicked Problems and the Southwest Napkin

Consider the legendary Southwest Airlines napkin sketch—a triangle connecting Dallas, Houston, and San Antonio. Not a strategic plan. Not a market analysis. Just three dots and three lines that reimagined air travel as bus transport. That simple drawing embodied what Mintzberg calls emergent strategy: a pattern realized despite, not because of, formal planning.

Richard Buchanan's concept of wicked problems in design thinking illuminates why that napkin succeeded where elaborate airline strategic plans failed. Wicked problems—like "how to compete in deregulated air travel"—have no definitive formulation. Every attempt to define them changes them. Solutions aren't true or false, only better or worse. There's no stopping rule, no definitive test of a solution.

Traditional strategic planning assumes well-structured, closed problems with optimal solutions. But as Herb Kelleher sketched on that napkin, he wasn't solving a problem—he was redesigning the game itself. The simplicity of the sketch enabled what elaborate plans couldn't: rapid iteration, clear communication, and most importantly, the ability to hold the entire business model in your mind at once.

This is strategic gameplay, not strategic planning.

Instead of optimizing for a predicted future, it creates what Gary Hamel calls "strategic resilience"—the capacity to morph and adapt as circumstances change. Wireframes and prototypes become the game pieces, allowing organizations to explore multiple futures simultaneously without committing prematurely to any single path.

The Five Strategy Myths and Design Alternatives

Research and experience identifies five myths that trap organizations in failing strategic approaches. Design thinking offers powerful alternatives to each:

Myth 1: Execution Equals Alignment Reality: Research finds only 9% of managers can rely on colleagues in other units, despite 84% vertical alignment. Alignment is insufficient. Design Alternative: Cross-functional prototyping sessions that make interdependencies visible and create shared ownership of outcomes. When people sketch together, they align their mental models, not just their objectives.

Myth 2: Execution Means Sticking to the Plan Reality: "No plan of action survives contact with reality," yet organizations punish deviation from the plan, even when it's clearly not working. Design Alternative: Portfolio of prototypes that enable rapid pivoting, while keeping coherence with the vision. As Mintzberg notes, strategies often emerge from "patterns in streams of actions" rather than deliberate plans.

Myth 3: Communication Equals Understanding Reality: 55% of middle managers can't name even one of their company's top five strategic priorities despite endless communication. Design Alternative: Visual prototypes that make strategy tangible. A sketch communicates strategic intent better than a thousand emails.

Myth 4: "Performance Culture" Drives Execution Reality: Performance metrics often discourage the experimentation needed for adaptation, amplify local optimization, and oftentimes punish collaboration. Design Alternative: "Safe-to-fail" prototypes built by teams that celebrate learning over results. As Gary Hamel argues, strategic resilience requires "a portfolio of experiments."

Myth 5: Execution Should Be Driven from the Top Reality: Effective execution emerges from distributed leadership and frontline innovation. Design Alternative: Bottom-up prototyping that harvests emergent strategies from throughout the organization.

Systems Leverage Through Design

Meadows, Leverage Points: Places to Intervene in a System

Donella Meadows, in Thinking in Systems, identified twelve leverage points for intervening in systems, from parameters (least effective, thrashing at leaves) to paradigms (most effective, hacking at the roots). Traditional strategic planning operates at the parameter level—tweaking numbers, adjusting resource allocations from a fixed pie, optimizing processes without questioning their existence. Strategic design operates at the paradigm level—reimagining fundamental assumptions about value creation.

Consider digital transformation initiatives. Most fail because they target parameters: implementing new technologies, training employees in new practices, measuring adoption rates. The paradigm—how the organization understands and structures its relationship to customers and value creation—remains unchanged. The technology gets absorbed into existing patterns, creating what Martin calls "digital incrementalism" rather than transformation.

Strategic prototyping operates simultaneously across multiple leverage points. At the parameter level, prototypes test specific features. At the structural level, they explore new information flows and feedback loops. At the paradigm level, they make new mental models tangible and shareable. This multi-level intervention creates what Peter Senge calls "profound change"—transformation that persists because it shifts underlying structures and assumptions.

Complexity and Emergent Strategy

Ralph Stacey's complexity matrix reveals why Mintzberg's emergent strategy concept is so powerful. In complex systems:

• Small changes can cascade into large effects (the Southwest napkin)

• Large changes can dissipate into nothing (most strategic plans)

• Causality is circular, not linear

• Outcomes emerge from interactions, not intentions

This complexity makes traditional strategic planning not just ineffective but actively harmful. As Gary Hamel notes, "The goal is not to predict the future but to prepare for multiple futures." Strategic prototyping embraces this uncertainty, creating what Stacey calls "catalytic probes"—safe-to-fail experiments (interventions) that reveal how the system responds.

The key insight from complexity science: you can't control complex systems, but you can influence their evolution through strategic interventions that tip the dispositionality towards favorable futures. Prototypes become these interventions—ways of introducing variations that might propagate through the system in beneficial ways.

Design Intelligence as Strategic Capability

Nigel Cross's research on "designerly ways of knowing" reveals why design thinking provides unique strategic advantages:

1. Solution-Focused: While analysis breaks problems down, design builds solutions up

2. Constructive: Design creates new possibilities rather than choosing among existing options

3. Iterative: Design embraces rapid cycles of creation and modification

4. Concrete: Design makes abstract concepts tangible and testable

When applied to strategy, these designerly ways create what we might call "strategic design intelligence"—the organizational capability to sense emerging patterns, prototype responses, and adapt faster than environmental change.

This differs fundamentally from traditional business intelligence. While BI analyzes what happened, design intelligence explores what could happen. While BI optimizes existing operations, design intelligence discovers new possibilities. While BI requires data, design intelligence works with hunches, weak signals, and informed intuition.

The Resilient Organization

Nassim Taleb's concept of anti-fragility provides a useful framing of strategic design: organizations that don't just survive disruption but get stronger from it. This requires what Hamel calls "strategic variety"—multiple experiments running simultaneously, each teaching something about possible futures.

Strategic prototyping creates anti-fragility through:

• Optionality: Multiple prototypes create real options for different futures

• Fast Failure: Quick, cheap experiments that teach maximum lessons at minimum cost

• Adaptation: Rapid modification based on feedback

• Emergence: Allowing successful patterns to emerge rather than imposing them

This approach transforms Mintzberg's insight about emergent strategy into organizational capability. Instead of hoping good strategies will emerge, organizations create conditions—through systematic prototyping—that make emergence more likely and more powerful.

Measuring What Matters

Traditional strategy metrics focus on execution against plan: variance analysis, milestone tracking, budget compliance. But as Martin points out, these metrics optimize for predictability in an unpredictable world.

Strategic design requires different metrics that reward adaptation:

• Learning Velocity: How quickly do we move from hypothesis to validated learning?

• Option Creation: How many strategic possibilities have we opened?

• Sensing Capability: How early do we detect emerging changes?

• Pivot Speed: How rapidly can we shift resources to new opportunities?

• Pattern Recognition: How well do we spot emergent strategies worth amplifying?

These metrics shift focus from "Are we executing our plan?" to "Are we becoming more adaptive?" They reward what Sull calls strategic agility—the ability to seize opportunities aligned with strategy while maintaining coordination.

Practical Considerations

Organizations developing strategic design capability should consider:

1. Create Prototype Portfolios: Maintain 10-20 strategic experiments across different time horizons and risk levels

2. Establish Innovation Ateliers: Physical and virtual spaces where cross-functional teams can rapidly design, prototype, and test strategic options

3. Develop Visual Fluency: Train leaders in sketching, wireframing, and visual communication of strategic concepts

4. Institute Strategy Sprints: Weekly or monthly sessions where teams prototype responses to emerging challenges

5. Harvest Emergent Patterns: Systematic processes for recognizing and amplifying successful experiments

The Southwest napkin wasn't a fluke—it was what happens when strategic thinking escapes the prison of formal planning. Every organization can create similar breakthroughs by embracing design as a strategic capability.

Conclusion: The Future of Strategic Design Practice

The room is no longer silent. The sketching continues, but now with the electric buzz of twenty conversations happening simultaneously—arguments, epiphanies, and wild hypotheses colliding in productive friction. Those twenty-seven executives have transformed their sterile conference room into what complexity scientists call "the edge of chaos"—that fertile zone between rigid order and complete randomness where innovation thrives.

Six months after that initial session, the walls tell the story of their transformation. Gone are the precisely formatted PowerPoint printouts and Gantt charts. In their place: hundreds of sketches, post-its clustered like storm clouds of possibility, wireframes annotated with questions rather than answers. "What if customers don't want to own anything?" reads one. "Why do we assume geography matters?" challenges another. Each hunch, no matter how heretical, gets wall space. Strategy emerges from the accumulation of small insights, not the revelation of grand plans.

Strategic Planning is or at least should be dead. But from its ashes rises something more vital: organizations that pulse with the energy of continuous creation, where strategy isn't an annual ritual but an daily practice of sensing, sketching, and shaping. These organizations won't just survive disruption—they'll dance with it, finding rhythm in the chaos and opportunity in the uncertainty.

And it all starts with the simple act of picking up a pencil and sketching a different future.