Why strategy starts with understanding how you're already being shaped

Leaders like to tell themselves they are shaping the game.

Most of the time, the game has already decided which kinds of moves they will even recognise as “strategic.”

The uncomfortable starting point is this: strategy is never just a set of choices about the external environment. It is always an expression of what the organisation already is, its identity, structure, relationships, and the stories it tells itself about what counts as success.

Why grand strategy is an earned identity, shaped through interaction with reality

Most organisations behave as if grand strategy can be decided in isolation.

A leadership team steps away. The language is careful. Purpose, ambition, values, north star. The organisation returns with a refreshed sense of who it is and where it is going.

Except it does not.

What usually emerges is not identity, but aspiration. A story leaders would like to tell about themselves, rather than something that has been earned through action.

Many organisations start strategy with an inspiring purpose — and then wonder why execution fails. This piece explains how the gap between narrative and behaviour erodes coherence, damages trust, and weakens strategy at its core.

How comfort, control, and performance theatre stripped the movement out of strategy

Strategy was once a living craft. In ancient Greece, strategos described a commander who turned uncertainty, terrain, and limited resources to their advantage. It was not a concept to be discussed; it was a role to be lived. The strategist stood at the edge of the unknown, interpreting shifting conditions and acting through others to shape outcomes

Too often, we talk about strategy as if it were an artefact. Something you produce, publish, and put on a shelf. A plan, a framework, a deck.

But strategy is not a thing. It is not an output.

Strategy is a way of being.

It is lived. It is enacted. It is a way of thinking, a way of behaving, and most of all, the ongoing pursuit of viability.

In a world saturated by noise, narrative spin, and institutional echo chambers, the greatest threat to strategy is not what we don’t know. It’s how tightly we cling to what we think we do.

Most organisations will never notice the moment their strategy disconnects from reality. The numbers still look good. The meetings still run on time. The strategy still reads well on a slide. But somewhere, unnoticed, the feedback loop closes.

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.