Most strategies fail because people are boxed in, not because they’re unmotivated

We spend too much time assuming strategy fails because of poor thinking, faulty plans, or lack of buy-in. But more often, strategy fails in execution because, when it meets the real world, the organisation is unable to act.

Not unwilling. Unable.

The real enemy of execution isn't resistance. It's subtle sabotage disguised as regular work.

In 1944, the CIA's predecessor, the OSS, published a field guide to help ordinary citizens sabotage enemy operations from within. The now-declassified Simple Sabotage Field Manual is both darkly comic and brutally insightful.

The value isn't in the plan. It's in how you prepare to adapt.

There's a military adage that's made its way into business circles: "No plan survives first contact." Eisenhower sharpened it further: "The plan is nothing; planning is everything."

But most organisations still treat planning as if the goal is to lock everything down. Define every milestone. Predict every variable. Control every outcome.

And then they are surprised when it falls apart.

Too often, purpose is treated as something you declare, design, and disseminate. It's written on the walls, embedded into decks, and broadcast at town halls. But when leaders treat purpose as real simply because it's been said, they mistake narrative for reality, and control for coherence.

Here’s the uncomfortable truth: It doesn’t matter what you say your organisation exists to do. It matters what your organisation actually does.

Why buzzwords don't bring clarity — and what strategy actually demands

When marketing captured strategy, we didn't just reframe the message. We reframed the work.

Strategy became something to be cascaded rather than constructed. It became a narrative exercise. A brand asset. A motivational toolkit for internal engagement.

In that shift, we lost something fundamental: the connection between strategic intent and structural capability.

We were sold the lie that strategy starts with "why." The key to coherence was a compelling narrative.

Rethinking aspirations, planning cycles, and the complexity we're actually in.

We must move on from the idea that strategy is a five—or ten–year plan—a fixed vision we march toward. It's comforting fiction: plot the course, cascade the goals, align the incentives. But strategy doesn't live in Gantt charts or glossy roadmaps. It lives in relationships, tensions, and how we continually navigate change.

We've long been sold an orthodoxy of strategy that treats the organisation as an independent organism, competing in a market arena with fixed boundaries and clear rules. It's the image of chess boards, war games, or analytical grids. It is neat, discrete, and ultimately misleading. But organisations don't operate in arenas. They operate in ecosystems.

One phrase in boardrooms and strategy offsites worldwide still dominates: “We need clarity.” Clarity of vision, purpose, and strategy. And yet, in a complex and shifting world, pursuing absolute clarity can be a trap.

What if strategic ambiguity isn’t a weakness to be fixed but a strength to be wielded?