Strategy, Risk, and the Missing Map

Lately, I’ve been diving into Wardley Mapping, Simon Wardley’s now-classic work on strategy—and I’ve got to say, it’s some of the best writing on strategy I’ve ever encountered. If you’re curious about the inner workings of competitive positioning, innovation, and situational awareness, I highly recommend giving it a read.

Wardley is famously unsparing in his critique of traditional strategy tools—especially the ones consultants like me have relied on for years. Think 2×2 matrices, SWOT analysis, generic mission statements. He doesn’t just poke holes; he tears down the whole scaffolding.

His central argument? Most strategic thinking today completely ignores the actual landscape, the climate, and the doctrines that shape our ability to act effectively. Instead of situational awareness, we too often rely on gut instinct—usually backed by the loudest or most expensive voice in the room. It’s a damning critique. And honestly? He’s not wrong.

Where Risk Meets Strategy

Reading Wardley’s work got me thinking about risk—and specifically, how it’s treated in most strategic conversations. Tools like SWOT claim to factor in risk (usually tucked into the “threats” quadrant), but they rarely go beyond vague guesses or hand-waving generalities. In reality, risk is a far more dynamic and nuanced element of strategy.

Sometimes risk is something we run from, trying to insulate ourselves with contingency plans and insurance. Other times, risk is exactly what we run toward—to gain a competitive edge, capitalize on change, or bet on a bold idea. Either way, strategy that doesn’t account for risk—explicitly, honestly, and in context—is dangerously incomplete.

A Simple Model of Risk Evolution

To make sense of how risk plays out inside organizations, I use a simple model:

Risks → Impediments → Lessons Learned

Here’s the idea:

• Risks are potential impediments—threats or unknowns that haven’t materialized (yet).

• Impediments are risks realized—problems we’re actively dealing with.

• Lessons learned are what we (hopefully) walk away with after addressing those impediments.

If you’ve spent time with agile teams, you’ll recognize this pattern. What’s exciting is that risks, if we pay close enough attention, can act as early warning signals for upcoming impediments. They’re like strategic radar blips—clues about what may be lurking just out of sight.

Bringing Strategy Back to the Terrain

All of this brings me back to Wardley’s core message: strategy without context is just theater. If we don’t understand the terrain we’re operating in—our markets, ecosystems, competitors, and technological evolution—then our strategy is built on sand. And if we’re blind to the terrain, we’re blind to the real risks too.

So here’s a thought: maybe we should be using Wardley Maps not just for strategy, but for risk analysis as well. Maybe mapping the landscape should become a routine part of identifying and responding to the risks that shape our organizations. After all, you can’t manage what you can’t see.

It’s early days for this line of thinking, but I think it’s worth exploring. And if nothing else, it’s a reminder that better strategy begins with better maps.