From the Desk of Chad Enterprise, CTO of MegaCorp
Developers keep telling me we’re ‘Agile.’ Meanwhile, I’ve got Gantt charts stretching to 2029. Let’s discuss how to ship WordPress features in two-week sprints… after our 18-month ‘Discovery Phase.’
chad
Greetings, digital artisans. Chad Enterprise here, CTO of MegaCorp—where dreams are big, systems are bigger, and our documentation is big enough to require its own cloud storage tier.
Today, I bring you a tender tale of romance, heartbreak, and ultimate corporate reconciliation. It’s the story of Agile—our plucky, fast-moving hero—and the towering, immovable object known as our 3-Year Waterfall Roadmap.
Grab your coffee, friends. It’s about to get emotional.
Act I: The Meet-Cute
Once upon a fiscal quarter, our VP of Digital Transformation announced, with breathless enthusiasm, that “We are going Agile.”
This proclamation arrived in an email titled “Agile Revolution,” complete with fireworks gifs and bullet points about synergy.
Suddenly, we were told to do standups, burn-down charts, and user stories. I even had to memorize what “INVEST” stands for. (Still working on the S.)
Meanwhile, lurking in our SharePoint server was our sacred 3-Year Waterfall Roadmap—a Gantt chart stretching from today until the sun burns out.
This roadmap contains every milestone, dependency, budget forecast, and resource allocation ever devised. It’s been presented to the Board. It’s written into vendor contracts. It’s tattooed on my soul.
Act II: The Courtship
Despite their differences, Agile and the Roadmap tried to date.
Our Agile coach introduced sprint ceremonies. Meanwhile, PMO insisted on updating the entire Gantt chart after every sprint review—because “we need visibility.”
Product Owners began writing user stories like:
“As a stakeholder, I want the entire multi-site migration complete by Q3 2026 so that our stock price goes up.”
We attempted to reconcile the irreconcilable:
- Sprints vs. Annual Budget Cycles
- Continuous delivery vs. Procurement approvals that take 14 weeks
- MVP releases vs. the 600 requirements written in the Roadmap
Act III: The Drama
Conflict reached its peak during our quarterly planning meeting.
Agile’s champions proposed the daring idea of releasing small increments of value.
Meanwhile, a senior stakeholder clutched the printed roadmap and shrieked:
“But where is the PowerPoint deck that guarantees delivery on September 12, 2027, at precisely 10:14 AM?”
Tears were shed. Voices were raised. Someone suggested a hybrid model. Someone else threatened to start writing everything in Jira and MS Project simultaneously.
Act IV: The Reconciliation
Eventually, we settled on a compromise—a grand corporate tradition:
- We run two-week sprints…
- …but still update our 3-Year Roadmap every month.
- We write user stories…
- …but still deliver a giant Requirements Traceability Matrix.
- We talk about MVPs…
- …but no one’s allowed to launch anything without 12 signoffs and a marketing plan.
In essence, we’re Agile… inside the Waterfall.
Like peanut butter and jelly. Or a speedboat carrying a concrete anchor.
Lessons for Aspiring Enterprise Developers
So, my fellow WordPress developers plotting a future in enterprise, remember this:
- Agile and Waterfall are not mortal enemies. They’re star-crossed lovers in a corporate soap opera.
- You’ll often be asked to “be Agile” while adhering to rigid schedules written years in advance.
- Communication—and a sense of humor—is your best survival tool.
- When in doubt, nod sagely and say, “It depends.”
Agile is a mindset. The Roadmap is a reality. And in enterprise, we dance between them every day.
Until next time, keep your sprint boards tidy, your Gantt charts updated, and your stakeholder expectations delicately managed.
Yours in incremental synergy,
Chad Enterprise, CTO of MegaCorp
