Alice asks the Cheshire Cat which way she ought to go. He asks where she wants to end up. She doesn’t know. He tells her, then, it hardly matters which road she takes.
That exchange gets treated like gospel in most strategy rooms. Know your destination, chart the road, don’t wander. The alternative — not knowing exactly where you’re headed — sounds like a recipe for chaos, especially for any organization with something real at stake.
So capable executives commit to a direction and hold it, even when things start going sideways. They optimize. They push harder. Revisiting the strategy itself feels like the failure, not the fix. That instinct toward control and order runs deep — deep enough that even the most celebrated leaders default to it without noticing.
It feels right because it’s what’s always been done, and because the track record of history’s most admired companies backs it up, at least on the surface. What gets left out of that story is the environment those companies actually operated in, and how much of it has changed since.
Here’s what the data actually says: Henry Mintzberg’s research found that only 10 to 30 percent of a company’s intended strategy ever gets realized as planned. The rest emerges — adjusted, improvised, discovered along the way, in response to a market that never agreed to hold still.
Companies that ignore this tend to find out the hard way. Nokia kept its strategic plan intact well past the point where smartphones made it obsolete. Volkswagen falsified data rather than confront a strategy that wasn’t holding up, and burned decades of earned trust doing it. And Wells Fargo, under CEO John Stumpf, pushed an aggressive cross-selling target — eight products per customer — even as regional leaders on the ground warned, repeatedly, that the goal was unreasonable and driving exactly the kind of behavior that would eventually blow up the bank.
A rigid five-year plan isn’t a strategy for a complex, dynamic market. It’s a bet that the market will stay still long enough to let the plan catch up. It rarely does.
Even Taylor’s scientific management, the whole tradition modern strategic planning grew out of, leans hard on this same instinct — break the problem into manageable, convergent pieces, execute in order. That works beautifully on a factory floor. It works far less well anywhere the ground keeps shifting under you.
Underneath all of it sits a divide that rarely gets named directly: the people setting strategy and the people executing it are often two entirely different groups. The ones closest to daily reality — customers, front-line staff, the actual texture of what’s working and what isn’t — usually understand the shifting landscape better than the leadership making the call. And they’re rarely consulted before the plan gets locked in.
What genuinely puzzles me is why. It’s not that leaders can’t see the market moving. Most of them can. Something else stops them from acting on it — from admitting the sunk cost, walking away from what isn’t working, and adjusting course before the damage compounds. I don’t have a clean answer for what that something is yet.