Every strategy conversation eventually collapses into the same shape: pick the objective, chart the steps, execute. It’s the version of strategy most of us were trained on, and it’s the version most leaders — myself included, plenty of times — default to when a team starts drifting.
It feels true because, in the right conditions, it is. In a stable, predictable environment, converging fast on a single plan is genuinely efficient. There’s no point manufacturing ambiguity where none exists. The problem isn’t the instinct itself. It’s that we keep reaching for it in conditions where it was never going to hold.
Markets aren’t stable. They’re full of other people — competitors, customers, regulators — making their own independent moves, none of whom agreed to stay still while you execute your plan.
Game theory has a blunt way of putting this: nothing is fixed, and your strategy has to adapt to the independent will of everyone else playing the same game. A rigid plan doesn’t account for that. It just assumes the board won’t move.
Reality keeps proving that assumption wrong, expensively.
J.P. Morgan lost roughly two billion dollars in a single trading blowup, in part because leadership trusted a static risk model and had little tolerance for anyone arguing the model might be missing something. Volkswagen and Wells Fargo both stuck rigidly to top-down strategies long after clear signs those strategies weren’t working, refusing to deviate even as the evidence piled up.
Henry Mintzberg, writing decades ago, put it about as sharply as it’s ever been put: charting a fixed course through unknown waters is a remarkably efficient way to sail straight into an iceberg.
Here’s what’s uncomfortable to admit: most leaders already sense this. They know, somewhere, that a linear plan won’t survive contact with a market that’s actively adapting around them. They keep making the plan anyway, because the alternative — sitting in the mess of not knowing exactly what the path forward is — is genuinely stressful, and corporate life rewards the appearance of a clear answer over the discomfort of an honest one.
Which leaves an open, harder question than “should you plan less.” How much psychological discomfort should a leader actually be willing to absorb before falling back on a fast, convergent plan becomes the responsible choice again, rather than just the easy one? And how do you tell, in the moment, whether you’re finally being disciplined — or just quitting on the harder work too soon?