Do Not Go Gentle into That Good Night— Why Expectation Failure Often Happens When a Project “Looks Like It’s Going Well”

Many years ago, when I watched Interstellar for the first time, I was deeply struck by its visual portrayal of space and black holes. Even today, it remains one of my favorite science fiction films.

In the movie, humanity is forced to leave Earth—the only home it has ever known—in order to avoid extinction. Facing the unknown universe, searching for a new future, the film quotes a line from Dylan Thomas:

“Do not go gentle into that good night.”

The meaning of this line is far from romantic. It implies that:

• Holding on to the status quo may allow us to survive “gently” for a few more generations, but the ending is inevitably slow and certain extinction.

• Exploring the unknown future, while filled with risk, pain, and sacrifice, is the only path that offers a chance of hope.

Years later, I realized that project management forces us to make very similar choices—every single day.

The Two “Dark Moments” of a Project Manager

As a project manager, you are required to stay clear-minded in two extreme situations:

• When everything is chaotic and the direction is unclear, you must find that small ray of light.

• When everyone is energized, confident, and optimistic, you must be able to see the shadows that may lie ahead.

Ironically, the second situation is often far more dangerous.

A Scene Every Project Manager Knows Too Well

The early phase of a project is almost always difficult:

• The team has not yet fully formed or aligned

• Customer requirements are unclear or evolving

• Resources are limited, and support is incomplete

At this stage, project managers tend to be highly cautious—actively identifying risks, securing resources, and seeking executive support. Although things feel messy, everyone understands: this is the ramp-up phase.

Gradually, the project starts to stabilize:

• Issues are logged, tracked, and closed

• Milestones are met

• Communication with the customer becomes smooth and friendly

Everything starts to look “right.” Some people even begin talking about a celebration.

Then, one day—

An email. Or a phone call.

The customer raises strong dissatisfaction about an issue that seems trivial—something that previously received little or no attention. Senior stakeholders are unhappy with a specific deliverable.

Internal leadership immediately starts asking questions:

• Why was this never reported?

• Where was the risk?

• Wasn’t everything going smoothly before?

The project manager begins to doubt themselves:

How could such a small issue turn into such a major crisis?

The Real Problem Is Never Just That One Issue

In the scramble to respond, a pattern often emerges:

That “simple issue” is merely a symptom of something bigger:

• Process gaps

• Misalignment in scope understanding

• Past deliverables that now require revalidation

Weekly reports turn from all green to full red. Stakeholders flood in, demanding explanations, clarifications, and commitments.

The project does not fail immediately. But bringing it back on track often requires far more time, effort, and cost than originally expected.

Worse still, trust—both internal and external—has already been damaged, sometimes irreversibly.

If you have managed enough projects, you have experienced this moment. More than once.

And no, this is not something to be ashamed of.

The Overlooked Root Cause: Expectation Management

When we look back, we often focus obsessively on the root cause of that specific issue, while ignoring a more abstract—and far more critical—factor:

Failure in expectation management.

Expectation management is part of stakeholder management, yet it is significantly underestimated in PMP and most methodologies.

A project manager does not only manage tasks—they manage people. And managing people is not just about assigning work, but about continuously managing expectations.

As a project runs, stakeholders naturally form a mental “image” of the project. That image is not always aligned with reality.

If the project manager fails to continuously correct this perception, the gap between reality and expectation grows silently—until it explodes.

Projects are judged by perception, not by facts alone. This is uncomfortable, but true—much like life itself.

How to Manage Project Expectations Effectively

In practice, I view expectation management as a continuous loop, not a one-time communication task. Once this loop breaks, expectation gaps accumulate and eventually surface as “sudden crises.”

This loop consists of four steps.

1️⃣ Identify the Gap

The first step is not communication—it is awareness.

A project manager must clearly understand two states at the same time:

• The real state of the project: delivery quality, progress, risks, uncertainties

• The perceived state of the project: what stakeholders believe based on available information

The problem is rarely the project itself—it is the gap between these two states.

Special attention should be paid to issues that:

• Are not explicitly listed as risks

• Are routinely minimized or postponed

• Are “well known” within the team but never clearly explained externally

These issues are most likely to be ignored when a project appears to be running smoothly.

I refer to these as expectation gaps— not because the project has failed, but because perception has begun to drift away from reality.

2️⃣ Assess the Gap

Not every expectation gap requires the same level of intervention.

Once a gap is identified, the project manager must calmly assess two dimensions:

• Impact if exposed Would it require a minor adjustment, or could it affect overall delivery, trust, or even historical results?

• Likelihood of occurrence Is it a low-probability edge case, or something that becomes increasingly inevitable over time?

This step helps determine:

• Which gaps can be observed and monitored

• Which must be addressed early to “reset expectations”

• Which should be escalated immediately as formal risks

Expectation management is not about creating fear—it is about applying pressure precisely.

3️⃣ Proactively Communicate

Once an expectation gap is identified and assessed, waiting is no longer an option.

The project manager must explain the gap to the right stakeholders, at the right time, in the right way.

Communication formats may vary:

• A formal risk or status email

• A clear message in a regular meeting

• An early, informal conversation in a less structured setting

But one rule must never be compromised:

Major expectation gaps must be addressed through formal, direct, and traceable communication.

From experience, no critical understanding is changed through a single conversation. Project managers must deliberately repeat, confirm, and recalibrate— until stakeholder perception gradually aligns with reality.

Expectation management requires patience more than eloquence.

4️⃣ Reconfirm Expectations

Expectation management is never “done.”

After communication, the project manager must actively reconfirm in subsequent phases:

• Have stakeholder expectations truly changed?

• Do they understand the underlying risk, not just the surface issue?

• Are different stakeholders forming inconsistent views of the project?

When necessary, cross-check understanding with multiple key stakeholders to ensure a consistent project “image.”

In terms of frequency:

• General expectation gaps: at least once per week

• Critical or urgent gaps: daily

This loop applies both to prevention and to recovery after a crisis has already occurred.

Closing: Expectation Management Is a Form of Leadership

At its core, expectation management is not a technique—it is a responsibility.

It demands that project managers remain clear-headed in two moments:

• When things are chaotic and the path forward is unclear

• When everything looks smooth and applause has already begun

Do not go gentle into that good night.

In project management, true courage is rarely about saving a project at the edge of failure.

More often, It is about speaking uncomfortable truths before the illusion of success collapses.