The Timeline That Lied (Vol. 1, Issue 8)
- D.B Trench
- Dec 29, 2025
- 3 min read
Excerpt:
This week’s dispatch is about a timeline that smiled politely, promised everything, and then betrayed us all. A short story about optimism, pressure, and the quiet dishonesty baked into project dates.
Full Issue
Every PM in Deliveria eventually encounters The Timeline That Lied.
It looks innocent at first — clean lines, pretty colours, dependencies neatly connected, milestones spaced out like civilized little flags.
A timeline like that whispers:
“We can do this.There’s plenty of time.”
It’s comforting. Reassuring. Almost sweet.
And entirely fictional.
Welcome back to The PMTales Dispatch, where we examine the soft lies that shape our projects long before reality gets a vote.
A Tale from the Trench
This was years ago, but the memory is burnt into my professional soul.
Leadership needed a delivery date for an announcement. Communications needed it for their newsletter. The VP needed it for an executive briefing. And someone in HR needed it for reasons I’m still not sure were real.
So I asked the team:
“What’s a realistic target?”
The architect said, “Depends.”
The developer said, “Not Q2.”
The analyst said, “Honestly, no idea.”
The vendor said, “We’ll try our best.”
The sponsor said, “End of May.”
Guess which date we put on the timeline.
Not because it was accurate, but because it was emotionally convenient.
That’s how false timelines are born: Optimism at the top + uncertainty in the middle + silence at the bottom.
For weeks the timeline looked great. Every update meeting was calm. Executives nodded. Stakeholders smiled. Progress felt steady.
Then the first dependency slipped. Quietly. Barely noticeable.
Then another. And another.
Before long, the timeline began to look… fragile. Like a house built by someone who was sure wind didn’t exist.
The Moment the Timeline Breaks
It always happens the same way.
Someone asks:
“Are we still on track?”
And suddenly the timeline — once sturdy and confident — becomes a diplomatic negotiation.
People avoid eye contact. Tasks get renamed. Definitions of “done” get creative. The colour green becomes heavily overused.
The Timeline That Lied begins to unravel in slow motion, like a polite sweater caught on a nail.
By the time leadership realizes it’s false, the team has known it for weeks.
Sometimes months.
Hidden Reasons Timelines Lie
Timelines lie because people lie.
Not maliciously. Just… humanly.
Fear of disappointing leadership
“It’s easier to ask for forgiveness later.”
Optimism under pressure
“It can’t be that hard.”
Misalignment between roles
“What does ‘complete’ mean again?”
No one wants to be the first to say no
A universal phenomenon.
Timeline created before actual planning
We’ve all been here: Being asked for dates before we’ve even formed the team.
The timeline becomes a prophecy. And everyone quietly hopes no one asks too many questions.
Survival Lesson #8: Ask for the Truth Behind the Date
Whenever someone gives you a delivery date, ask:
“What would have to be true for this timeline to hold?”
This exposes hidden assumptions.
“What would break this timeline first?”
This reveals the real risk.
“Whose confidence is this date based on?”
This clarifies ownership.
“Is this a date you believe… or a date you need?”
This is the question that changes the room.
Stakeholders go quiet. People look up from their laptops. Someone exhales.
Because everyone knows the difference.
A PMTales Insight
Here is the uncomfortable truth:
Most timelines aren’t lies. They’re wishes.
And wishes are fragile.
They’re created by people who want success, under pressure from people who want certainty, while being implemented by people who want the time to do it properly.
A timeline holds only as long as its assumptions do.
From the PMTales Armory
If The Timeline That Lied is haunting your project, reach for your Armory Artifacts
Field Note of the Week
A PM’s job is not to protect the timeline. A PM’s job is to protect the truth.
Once you understand why a date exists, you can guide the team toward a realistic plan instead of a political one.
That shift — from pretending to planning —is where real delivery begins.
Until Next Week
May your timelines be honest, your assumptions explicit, and your risks acknowledged before they explode.
See you in the trench,
D.B. Trench
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