No Plan Survives Contact with Reality: Leading Strategy Beyond the Boardroom

The challenge of executing strategy is neither new nor rare. Despite decades of management theories and methodologies, many organisations still falter when moving from ambition to action.
Research suggests that two-thirds of strategies fail, not because they were poorly conceived, but because execution breaks down (ClearPoint Strategy).

In my experience as an Interim CEO, working closely with leadership teams across sectors, I have seen a common pattern.
Plans are often crafted to look impressive on paper, but they are not designed with execution in mind.
What is frequently missing is a structured, and by structured, I do not mean complicated, way of communicating the plan so that every part of the organisation understands it and sees their part within it.

Much is made of the need for “buy-in,” but too often leaders approach this as something that must be sold to the team.
In practice, I have found that if people know what you are trying to achieve, and if it makes clear sense, they will work towards it willingly.
It is not about selling a vision. It is about creating clarity and trust in the direction, so that execution becomes a natural outcome rather than a forced one.

Another challenge is the way we talk about strategy itself.
Many management consultants use the word “strategy” as a catch-all for the entire plan. In my view, this blurs an important distinction.
Strategy is not the whole plan. It is how you might move from point A to point B. The emphasis is on might because the journey is never guaranteed to follow a neat path.

As Field Marshal Helmuth von Moltke famously observed:

“No plan survives contact with the enemy.”

And this is often where it all falls apart.
The strategy sounds convincing in theory, but if the entire plan relies upon the original strategy holding firm, and it fails under real conditions, then the whole plan unravels.
Without a clearly understood point A, a compelling point B, and an organisation equipped to adapt intelligently when conditions change, success becomes a matter of luck rather than design.

This is also where trust becomes critical.
If you do not trust your people to understand the situation, to make good decisions, and to adapt intelligently, then no strategy, however well written, will succeed for long.
And if trust is missing, it is not a problem of execution, it is a problem of leadership.

The fact is, I have used this approach first-hand.
As an Interim CEO, I have often stepped into businesses led by individuals who, on paper, were highly impressive. Yet what I have consistently found is that success does not come from grand strategies or complex leadership frameworks.
It comes from very quickly getting the existing team aligned, ensuring everyone understands the real goals, and trusting them to get on with it.
People respond remarkably well when leadership does its job properly, setting the direction clearly, providing genuine context, and enabling them to act intelligently.

In real organisations, the ability to adapt matters far more than rigidly following an initial strategy.
If your team does not clearly understand where you are starting from, where you are trying to go, and feel trusted to respond to what they encounter along the way, then even the best-crafted strategy becomes irrelevant the moment it meets reality.

What is more striking is how little this fundamental challenge has changed.
Walk into any boardroom today and you will hear much the same conversations about execution as you would have twenty years ago.
Management theories have evolved, yet the difficulty of bridging strategy and execution remains stubbornly familiar.

A problem that persists across generations points to deeper causes. The solution, therefore, must also be fundamental.
Surprisingly, it is. It has existed for more than a century. It is straightforward, rooted in common sense. Yet, common sense rarely becomes common practice.

This raises a sharper question:
If the solution has been understood for so long, why have so few organisations embraced it?

In my opinion, the reasons are twofold:

The Legacy of Outdated Management Thinking

Much of twentieth-century management theory was shaped by lecturers rather than operational leaders. It succeeded in the classroom but struggled in the real world of dynamic, human-centred organisations.
These theories built formidable structures around control, predictability, and hierarchy. Even where leaders recognise the limitations of such models today, their legacy remains deeply embedded.

The Lack of a Widely Adopted Alternative

While frameworks such as Agile, Lean, and OKRs have offered partial solutions, no single approach has fully displaced traditional management thinking. Many leaders understand that the old ways no longer fit, yet few have completely reimagined how their organisations should operate.

The Legacy of Scientific Management

The roots of the problem lie in the industrial age. Businesses were designed to function like machines. Workers were treated as interchangeable parts. Management’s role was to plan and control.

Frederick Winslow Taylor formalised this thinking in 1911 with The Principles of Scientific Management. His approach rested on three core assumptions:

• That effective planning requires full knowledge in advance

• That planners and doers should be separate

• That there is one correct way to perform a task

Taylor’s methods revolutionised productivity in mechanical, repetitive work. His analysis of tasks such as moving pig iron onto railcars brought measurable gains in efficiency.
Today, however, many of those tasks are automated or embedded within software.

Modern businesses face different demands. They require judgement, creativity, adaptability, and the ability to make rapid decisions in uncertain environments.
In such contexts, rigid top-down control quickly becomes a liability.

Taylorism has rightly faced substantial criticism. It dehumanises workers, reduces initiative, and stifles innovation (Runn.io). Yet although few would openly champion Taylor’s ideas today, their influence persists. Hierarchical structures, rigid KPIs, and compliance-driven performance management systems still reflect Taylorist assumptions.

As an operational advisor, I often see businesses inadvertently reinforcing the very models that slow them down.
The language may have changed, but the mindset lingers.

Leading Beyond the Plan: Alignment and Autonomy

There is, however, a better way. A leadership model better suited to complexity and uncertainty existed long before Taylor’s theories were published.

In the 19th century, Field Marshal Helmuth von Moltke faced a leadership challenge familiar to modern executives: how to execute strategy in unpredictable, fast-moving environments.

Von Moltke understood what many leaders still struggle to grasp today.
Rigid plans cannot account for everything.
Instead of seeking total control, he built his leadership philosophy on alignment and autonomy.
The principle was simple:
The more alignment you create, the more autonomy you can grant.

This is not about adopting military command structures. Quite the opposite.
It is about trusting your people to do a good job, as long as you have done yours: setting clear intent, providing real context, and building a team that can think and act independently when it matters most.

By ensuring that individuals understood the broader intent, von Moltke enabled adaptive decision-making at every level.
Leadership became less about issuing orders and more about equipping teams to think and act intelligently.

Many modern frameworks, from Agile to decentralised decision-making models, echo this philosophy.
The most effective organisations today behave less like machines and more like living systems.
They empower people with context, intent, and authority, trusting them to make decisions when conditions change.

Von Moltke’s approach was not a management fad. It was, and remains, a disciplined way of leading adaptive organisations.
It demands clarity, trust, and the courage to release unnecessary control.
It also demands a deep understanding that execution is not a linear process, but a dynamic, human one.

The solution to the execution gap has always been available.
The real challenge is not understanding it.
It is having the courage to lead differently.