Don’t Go Chasing Waterfalls 🌊

Agile Without Courage Is Just Control

This post didn’t come out of theory.
It came out of fatigue. 😮‍💨

My company is redesigning quarterly planning. What started as an internal practice in my department is now being rolled out across all of engineering. Along with it comes Big Day Planning 💒. An event that was once one day long… then two… then three. 📅 📅 📅

Not because it worked.
Because it didn’t.

And instead of questioning the premise, the response was predictable: add more time, more structure, more ceremony. As if the problem was insufficient planning hours, not the fact that the entire idea is fundamentally misaligned with how work actually happens.

That escalation pattern should feel familiar.

When a system fails, we don’t ask whether the system is wrong 🤔
We assume it needs more enforcement 🔒

More slides 📊
More spreadsheets 📈
More alignment about alignment 🧠➡️🧠

The irony is hard to miss. A process meant to make us faster keeps getting longer. A model meant to improve flow keeps adding weight. A planning system meant to reduce friction keeps pushing us closer to the edge.

We all agree waterfall is broken.

We mock it. We warn against it. We train entire generations of engineers to avoid it. And yet somehow, we keep rebuilding it. Not all at once anymore. We’ve learned better than that.

Now we do it every 90 days ⏱️

We don’t call it waterfall. That would be uncomfortable. We call it quarterly planning. We dress it up with better language, more collaboration, and a lot of ceremony 🎭 But underneath the rebrand is the same instinct that drove waterfall in the first place: the belief that complex, uncertain work can be controlled by pinning it to a calendar.

We say we want agility 🏃‍♂️
Then we organize everything around a quarter 📆

We say we want flow 🌊
Then we try to dam it 🧱

Waterfall isn’t showing up because leadership forgot the lesson.
It’s showing up because they’re not strong enough to fight the gravity of past decisions made in the name of control ⬇️

1. What Leadership Wants (And Why It Sounds Sensible 🧠)

Leadership isn’t inventing problems. They’re reacting to real ones.

The org is bigger 🏢
Work is more cross-functional 🔀
Dependencies are everywhere 🕸️
Capacity is tight 🧃
Misses are expensive 💸
Confidence in “the plan” is low 😬

So the instinct is structure.

Quarterly planning promises order:

• Strategic alignment instead of chaos 🎯
• Forced prioritization instead of “yes to everything” 🚦
• Capacity awareness instead of silent burnout 🔋
• Dependency visibility instead of late surprises 👀
• Clear OKRs tied to commitments 📌
• Ongoing updates instead of end-of-quarter panic 📣
• Explicit change management instead of thrash 🔁

This is leadership saying, “We need control.”

The problem isn’t wanting control.
The problem is mistaking control for progress 🚨

2. Where the System Breaks (We Rebuilt the Dam 🧱)

We’re trying to run a portfolio-level planning system using tools and rituals that only work if humans constantly compensate for them.

Every quarter, the whole thing has to be rebuilt by hand ✋

Spreadsheets become the source of truth 📊
Meetings become the glue 🪢
Slides become the story we tell ourselves after the fact 🎬

The system doesn’t enforce the model.
People do.

Guardrails Enforced by Memory 🧠

Capacity limits.
Dependency validation.
Explicit tradeoffs.
Escalation paths.

None of these are embedded in the system. They’re enforced socially, inconsistently, and often too late ⏰

So what happens?

• Rules are applied unevenly ⚖️
• Overcommitment sneaks in quietly 🕵️‍♂️
• Dependencies surface mid-stream 🌊
• Escalations feel like failure instead of signal 🚨

That’s not rigor.
That’s fragility 🧊

Fragmented Artifacts, Fuzzy Accountability 🧩

OKRs live over here.
Capacity plans live over there.
Dependencies live in a doc.
Context lives in people’s heads.

Every quarter becomes a soft reset 🔄

Planning Eats the Capacity It Claims to Protect 🍽️

Eventually, a meaningful chunk of engineering time is spent maintaining the plan instead of delivering value.

At that point, the dam isn’t protecting the river.
It’s choking it.

The Quarter Becomes the Cliff 🪂

We don’t follow value.
We follow the edge and hope the fall is survivable.

That’s waterfall with better optics.
A better view on your way down 😶‍🌫️

3. The Actual Fix (Stop Trying to Control the Current 🌊)

This doesn’t get fixed by refining quarterly planning.

More templates won’t help 📄
More rigor won’t help 📐
More enforcement won’t help 🚓

Quarters are the wrong unit for delivering value.

Trying to be agile inside a quarterly cage creates performance theater 🎭
Lots of motion. Lots of agitation. Very little flow.

Agile without courage is just control with better branding 🏷️

Final Chorus (Gravity Still Wins ⬇️)

Big Day Planning expanded 📈
Quarterly planning redesigned 🧩
Ceremony stretched to compensate for a system that can’t carry its own weight 🏋️‍♂️

Marshmallows ready 🍡, sitting in front of this dumpster fire of a week 🔥.

When this fails, the answer won’t be “the model was wrong.”
It’ll be “we didn’t execute it rigorously enough.”

So we’ll add another artifact 📄
Another meeting 📞
Another day of planning 🗓️
Another layer of enforcement 🧱

And gravity will keep winning ⬇️

You swim a lot better when you don’t fight the water 🏊‍♂️🌊