Why Good Plans Don’t Survive Contact With Reality​​​

​

Most project failures don’t begin with bad plans.

They begin with good ones.

​

Well-structured.
Carefully sequenced.
Reviewed and approved.

​

The plan made sense — at the time.

This field guide is about why plans break anyway — not because planning is useless, but because reality refuses to stay still long enough to respect it.

​

Planning Assumes a Stable World

Plans are built on assumptions.

That:

• Requirements will remain coherent

• Stakeholders will stay aligned

• Priorities will hold

• Decisions will be timely

At the moment a plan is approved, these assumptions feel reasonable.

Reality’s first move is to invalidate at least one of them.

​

The Plan Is a Snapshot, Not a Contract

A plan captures understanding at a point in time.

It does not:

• Predict behavior

• Control power

• Freeze incentives

• Prevent change

Treating a plan as a promise creates fragility.

Treating it as a hypothesis creates resilience.

​

Why Detailed Plans Fail Faster

The more detailed a plan becomes, the more brittle it is.

Detail assumes:

• Certainty

• Continuity

• Agreement

When any of those shift, detail turns into rework.

Teams don’t abandon the plan because they’re careless.
They abandon it because following it would now be irrational.

​

Plans Fail Quietly Before They Fail Publicly

Plans rarely collapse dramatically.

They erode.

They show up as:

• “Temporary” workarounds

• Minor resequencing

• Small scope accommodations

• Deferred risks

The plan remains on paper.
Delivery moves elsewhere.

By the time the deviation is visible, the plan no longer describes reality.

​

Why Plans Are Defended Long After They’re Broken

Plans provide safety.

They:

• Anchor accountability

• Justify decisions

• Protect reputations

Admitting the plan no longer fits feels like admitting failure.

So teams defend it.

They update status.
They reinterpret milestones.

Reality keeps changing anyway.

​

The Plan Was Never the Problem

When plans fail, the blame usually follows:

• “We didn’t plan enough”

• “The plan wasn’t detailed”

• “We should have anticipated this”

But most failures don’t come from missing foresight.

​

They come from:

• Delayed decisions

• Unowned change

• Power shifts

• Human behavior

No plan survives those intact.

​

What Good Planning Is Actually For

Good planning does not prevent change.

It:

• Creates shared understanding

• Surfaces assumptions early

• Reveals dependencies and risk

• Provides a starting point for adaptation

A good plan doesn’t survive reality.
It teaches the team how to respond when it doesn’t.

​

Plans Fail When They’re Treated as Control Mechanisms

Plans become dangerous when they’re used to:

• Enforce compliance

• Resist new information

• Silence escalation

At that point, the plan is no longer a guide.

It’s a constraint reality will eventually break — violently.

​

Reality Is Not the Enemy of Planning

Reality doesn’t invalidate planning.

It completes it.

The value of a plan is not in its endurance —
but in how quickly and honestly it can be revised when the world changes.

​

“Plans collapse fastest when decision-making is delayed or avoided.”

Link “decision-making is delayed or avoided” to:
➡ Decision-Making Failures in Projects
 

➡ Project Planning Myths (And Why Plans Still Matter)