Designing for Uncertainty
Most strategy playbooks were built for a predictable world but today’s volatility is constant. The winners will be best at adapting not forecasting. Keep reading to learn how to design for uncertainty
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A few weeks ago, I found myself on the 66th floor of The Spiral building in New York, in front of a room full of executives at LHH, a global human talent firm. Outside the floor-to-ceiling windows: nothing but clouds. No skyline. No streets. Just white.
Normally, from that height, you can see for miles with Manhattan laid out like a blueprint of ambition and motion. But that morning, the city had vanished into fog. I knew it was all still there with all its sirens, scaffolding, and traffic, but none of it was visible.
And that disorienting view, or lack of one, was the perfect metaphor for what I was there to talk about: uncertainty.
There’s no better place to talk about unpredictability than New York. It’s a city that reinvents itself daily, that lives in flux and somehow thrives in it. And while New York can be seen as a microcosm of today's ever-shifting world, most companies are still operating on the assumption that the world should behave predictably. That strategy is something you can lock in each January, cascade through the org chart by March, and measure by December.
But that’s a fantasy. And it’s time we let it go. The cycle has shortened dramatically.
The Illusion of Stability
Much of what we think of as "strategy" was forged in a moment of artificial calm. From 1979 to 1999, the U.S. and much of the developed world experienced an era of relative macroeconomic and geopolitical stability. Inflation was subdued. Globalization smoothed supply lines. The Cold War wound down without a shot fired. The rules of the game felt clear and unchanging.
It was during this period that the dominant tools of modern management were born. The annual budgeting cycle. The BCG growth share matrix. Porter’s Five Forces. We still teach them in business schools and paste them into boardroom decks. But here’s the hard truth: every one of those frameworks assumes a relatively stable playing field.
They were built for a world that doesn’t exist anymore.
Today, the playing field shifts beneath our feet. Prices jump not annually, but overnight. Political lines blur and redraw. Customers behave irrationally, influenced by social movements or viral videos instead of rational models. War, climate, and pandemics disrupt what once felt like fixed variables.
The volatility is no longer episodic: it’s ambient.
Preparing for What You Can’t Predict
The flaw in traditional strategic thinking is that it tries to predict. It assumes that the role of leadership is to get the future “right,” to model the next 12 to 18 months as if they’re waiting for us like a straight stretch of road. But in environments of discontinuity, the road bends faster than we can steer.
Peter Compo, in The Emergent Approach to Strategy, argues that most businesses are optimized for consistency, not adaptation. They have procedures, not instincts. Guardrails, not options. The result is an organization that knows what to do when things go according to plan but freezes when they don’t. What’s needed isn’t clairvoyance. It’s optionality. The capacity to move quickly in uncertain terrain. And that starts with designing for unpredictability, not in spite of it.
Outthinker members will soon have a unique chance to explore these ideas further, as Peter will be leading a roundtable on Integrating Scenarios into Strategy on September 18, 2025. It’s a valuable opportunity to dive deeper into designing strategy for the unpredictable world ahead. An uncertain world that, as we’re learning, often resembles the realities faced by those who have never known stability.
Click here to register for the "Integrating Scenarios into Strategy" roundtable.
Strategy Lessons from People Living with Instability
If you want to understand what it means to operate in uncertainty, don’t look to Silicon Valley. Look to people and places that have never had the luxury of predictability.
In many underdeveloped regions, supermarket inflation is not a policy debate. It’s a survival pattern. When word spreads that the price of eggs or rice will go up tomorrow, there’s a mad rush today. Not because people panic, but because they’ve learned to anticipate instability. There’s no illusion of control. Only the constant muscle of adaptation.
On small islands, shipping delays and sudden cost spikes aren’t anomalies. They’re built into daily life. So people stockpile. They share resources. They collaborate, not for efficiency, but for resilience.
These are not third-world problems. They are first-world previews. When supply chains are disrupted by tariffs or war, when weather closes ports and policy closes borders, then suddenly every business operates like a Caribbean grocer.
When the World Is Unstable, the Advantage Goes to the Prepared
Scenario planning isn’t a novel idea. Shell used it to great effect in the 1970s to weather the oil shocks. They didn’t guess the right future. They prepared for several. That preparation let them act faster, more coherently, and more confidently than competitors.
We’re seeing this mindset resurface among companies that don’t just want to withstand change but capitalize on it.
Maersk, during the pandemic, didn’t just react to shipping chaos. It reconfigured inland logistics and diversified container pathways before others even acknowledged the crisis.
Nestlé has quietly restructured procurement to operate through decentralized sourcing nodes so that no single political border can shut down their supply lines. Tesla, anticipating tariff unpredictability, now builds final-stage assembly capabilities on multiple continents.
They’re not gambling on predictions. They’re investing in agility.
The New Strategy Playbook
So where does that leave the rest of us? What does it mean to lead a company, or a team, when the future refuses to hold still?
It means flipping the strategic playbook. Here are three shifts I believe every organization must embrace:
1. Replace Annual Plans with Strategic Repositioning.
The idea that January sets the tone for the year is obsolete. Market trends don’t care about your planning calendar. July should be a second January. Maybe October should be a third. You need checkpoints that don’t just review performance, but question relevance. Are you still playing the right game?
2. Invest in Slack, Not Just Efficiency.
For decades, we’ve idolized lean operations. But lean isn’t always nimble. At our Outthinker Chief Strategy Officer Summit in New York on June 25, Eddie Fishman, author of Chokepoints, pointed out that resilience is by definition inefficient. Today’s advantage lies in strategic slack, backup suppliers, financial buffers, and the freedom to delay or double down. Slack isn’t waste when it’s seen as insurance against the unknown.
3. Measure Optionality, Not Just Outcomes.
How fast can you reroute supply? Launch a new offer? Reposition a team? The best KPI in uncertain times isn’t quarterly growth but how many paths forward you have when the ground shifts.
Thriving in the Flux
As I looked out at that executive crowd in New York, I told them this: You don’t need to predict the next crisis; you need to become the kind of company that can handle the turbulence. Better yet, be the kind of business that gets stronger because of it.
We’ve built decades of infrastructure, culture, and tools for managing certainty. Now we have to rewire for ambiguity. We have to trade some clarity for resilience. Some precision for range. Because the winners of the next decade won’t be the ones with the best forecasts. They’ll be the ones with the fewest assumptions, and therefore, the most options.
It’s like looking out those windows toward the horizon on that foggy morning in New York. The sharp details dissolve into white, leaving only vague outlines. We can’t make the fog lift, but we can build the instincts, structures, and strategic slack to keep moving forward even when the view ahead is obscured.
For more about short-term strategic planning, business agility, supply chain disruptions and maximizing uncertainty, visit Outthinker.com.