Content Chaos, AI Dreams, and Exec Deadlines: The Truth About “Readiness”

Published: 4/15/2025

I want to share an anecdote — especially after working closely with teams to wrangle a massive website and prepare its content (think articles, research, reports, and more) for very eager stakeholders and execs.

The pressure was real: a global website migration in motion, involving nearly six figures’ worth of localized pages, all while fielding urgent questions about how to make that content "AI-ready."

And here’s the kicker — for years, we were encouraged to use our own internal tools wherever possible. Tools that, frankly, weren’t always built for this level of complexity or scale. A classic case of “drink your own champagne.”
Plenty of wins, yes. But also plenty of challenges. And even more hard-earned lessons.

The Layer No One Sees

Beyond what’s visible on the page — the polished visuals, the crafted copy — there’s a quieter, more foundational layer of work that determines whether content actually performs after it’s published.

That layer includes questions like:

👉 Is it tagged correctly to show up where you want it to?
👉 Can internal systems locate, recommend, and reuse it?
👉 Can those systems talk to each other at all?
👉 Has the content been updated — or is that outdated report from 2019 still live and indexed?

These are the kinds of questions that keep teams up at night — and ones that don’t get much airtime in flashy project decks. But they matter. A lot.

The Cost of Ignoring Content Health

If you’ve ever had to:

• Manually update a spreadsheet just to track which pages were published
• Discover filtering or personalization tools breaking because taxonomy tags were missing
• Deal with stakeholders finding old content resurfacing in critical places

Then you know this pain. It’s not glamorous. But it’s foundational.

And the truth is: content needs recurring health checks — not just before it goes live, but as it ages.

This is how we ensure content is:

• Discoverable through search and filters
• Accurate and aligned with the brand
• Scalable across systems and channels

We Can’t Fix What We Can’t See

When we talk about digital transformation, we often focus on new tools and splashy interfaces. But one of the most impactful changes we can make is behind the scenes — automating metadata, aligning taxonomy, tracking decay, and making sure content is truly ready before (and after) it ships.

That’s what I’ll be sharing more of in the coming weeks.

Because there’s no easy way to explain to execs that the volume of content we’ve all created has simply outgrown the systems we built to manage it. But there are smarter ways forward.

What About You?

If you're deep in a content migration, metadata overhaul, or AI-readiness initiative — I'd love to hear how you're approaching it.

What’s working?
Where are you stuck?
Is it still mostly manual? Or are parts automated?

Let’s swap notes.