How strategy execution really fails: Lessons from the CIA's simple sabotage manual.

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.

It didn't call for explosives or espionage. It recommended something far more effective:

• Prolonging meetings unnecessarily

• Referring all matters to committees

• Insisting on perfect adherence to formal processes

• Making speeches

• Advocating caution

• Reopening decisions

• Writing everything in long, convoluted language

These were not acts of active rebellion. They were subtle ways to break orientation, stall decision-making, and erode trust. And they worked because they looked exactly like normal operations.

Eighty years on, many organisations still run on the same dysfunctions. Not because anyone's trying to sabotage strategy. But because they've created environments where this behaviour thrives by default.

Sabotage thrives when planning replaces preparation

In my last article, "The plan is nothing, Planning is everything" I argued that most strategies fail because we treat planning as an attempt to predict and control. We create rigid artefacts. We script behaviour. We eliminate ambiguity.

But then the environment adapts. And the plan, no matter how perfect, is now irrelevant.

The danger is not just that the plan breaks. It's that the organisation lacks the structure and the readiness to adapt. And when that happens, even basic acts of decision-making get stuck.

You start to see the CIA's list in action. Meetings without outcomes. Delays dressed up as governance. Endless requests for details distract from the actual decision. Resistance disguised as process.

Strategy doesn't fail in one big moment. It bleeds out through a thousand small, reasonable-sounding actions that destroy momentum.

Execution fails when orientation breaks

The sabotage manual is, at its core, a guide to breaking shared orientation. Its tactics work because they create uncertainty about what matters, who decides, what action is safe, and when to move.

The same breakdown happens in organisations that confuse planning with control. Without shared orientation, people freeze. They default to risk aversion, overprocessing, and polite avoidance.

You see it in:

• Teams waiting for direction rather than acting on intent

• Leaders escalating decisions rather than enabling discretion

• Functions protecting silos rather than pursuing shared outcomes

• Energy drained by meetings that substitute discussion for movement

None of these are acts of open resistance. But they all grind execution to a halt.

Planning is how you protect execution

You do not stop sabotage by cracking down. You stop it by making adaptation and freedom of action the default mode of work.

That means planning must prepare people to act, rather than instruct them on how to perform tasks. It must build shared orientation. It must clarify outcomes and constraints, rather than dictate a method. It must test for coherence under pressure.

Ask:

• Do people know what to do when conditions shift?

• Can they act on intent without waiting for permission?

• Is the structure reinforcing autonomy with accountability?

• Are your governance routines slowing you down or speeding you up?

The real purpose of planning is not control. It is to defend execution against drift, distraction, and paralysis.

The saboteur doesn't need to destroy the plan. They only need to slow the team.

The genius of the sabotage manual is that it recognises how fragile execution really is. You don't need to collapse the structure. You only need to inject just enough confusion, bureaucracy, or doubt to make the team hesitate.

And in many organisations, this kind of sabotage doesn't come from outside. It is the natural consequence of processes built on prediction rather than readiness.

So if your strategy is starting to stall, don't just look at the plan. Look at the space you've created for action. Look at how decisions get made. Look at how meetings are run. Observe whether people are moving with purpose or merely performing the motions of alignment while nothing actually shifts.

Because strategy rarely fails in theory.

It fails when contact with reality reveals how brittle your execution really is.

And in those moments, planning is not about control.

It is your only defence.

A strategy that survives contact with reality starts by protecting your ability to act.