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.

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.

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.

In the rapidly shifting terrain of organisational management, debates around structure have become increasingly prominent. On one side, there are proponents of trendy frameworks like Holacracy, which advocate for flat, self-organising teams with distributed authority.

On the other hand, traditional hierarchical structures still hold sway, promising clarity and stability in decision-making. Yet, the real challenge facing organisations today isn't about choosing between hierarchy and flat structures.

I propose a holistic approach to enabling organisations to operate in increasing complexity and uncertainty, allowing them to be self-organising, self-regulating, and adaptable. This holistic approach looks to develop a synergy between the Viable Systems Model (VSM), the principles of Misson Command and a culture of decentralised decision-making.

How can organisations effectively balance the needs of the present with preparing for the future?

The Viability Challenge: Balancing Present and Future, Inside and Outside. For any organisation to be viable over the long term, it must strike a careful balance. It needs to meet the demands and realities of the present while also adapting and evolving for the future. It must optimise internal operations while responding to the external environment. Stafford Beer, a pioneer in management cybernetics, emphasised that for systems to be viable, they must be "self-organising, self-regulating, and capable of adapting to ensure long-term sustainability and effectiveness."