For over 20 years, we’ve been asking the same question: What’s the best way to organize content in Microsoft 365?
In our latest Microsoft 365 Showdown webinar, hosted by Orchestry in collaboration with our friends at Sympraxis Consulting, we took this age-old debate to the (virtual) battlefield.
We dug into the classic folders vs. metadata discussion, weighing the pros and cons of each approach for organizing content in SharePoint. By the end, we shared our expert recommendations on which method delivers the most value and why.
And a lurking challenger: Team AI, demanding structure and surfacing the impact of our IA choices.
Moderated by Orchestry’s own Michal Pisarek (CEO and janitor), the debate featured a head-to-head between:
💥 Marc D. Anderson and Michal for Team Folders
🧠 Julie Turner and yours truly (Joy Apple) for Team Metadata
Let’s recap the rounds - and the reasons metadata might just have won more than a few hearts.
Team Folders argued for the power of what’s familiar. After all, most users know folders from shared drives and creating them feels natural. Folders also play nicely with OneDrive sync and support per-folder permissions (which, granted, can become more curse than blessing).
Team Metadata countered with the scalability and cross-site findability of metadata. Folders reflect one person’s mental model. Metadata unlocks everyone’s ability to slice and dice content across libraries, teams, and time zones. It supports better security design, prevents accidental silos, and it doesn’t collapse under deep nesting when Copilot and Search come knocking.
🎤 My take: “The deeper your folders go; the less effective Copilot becomes. The Microsoft Graph doesn’t spelunk 20 folders deep.” (And honestly, people don’t really like it either!)
Winner: Team Metadata (backed by the chat)
Ah yes, the eternal excuse: “But folders are easy!”
Sure, they are. But that doesn’t mean they’re effective.
We flipped the script by showing that metadata-based views can mimic folder structures - drag-and-drop included. Users still get a familiar UI while benefiting from flat architecture, better search, and AI readiness. The key? Show users what’s in it for them.
📸 We even shared a screenshot showing grouped views organized by metadata, busting the myth that metadata means an unfamiliar mess. Boom💥
Team Folders stuck with the “change is hard” line. Metadata, they claimed, is too much work. But as Julie rightly said, “If users don’t fill out a field, maybe it’s not providing value. That’s not a user issue - it’s an information architecture or a culture issue.”
Winner: Metadata again. Even some grumpy old men began to waver.
This round called for honesty. So we took turns revealing our tools’ kryptonite.
Still, when used intentionally, metadata scales better, supports security-first design, and unlocks the power of Copilot and Microsoft Search.
A powerful quote from Julie: “If you need 5000 items in one view, you probably need to rethink your IA.”
Honest truth: Neither side is perfect. But metadata enables long-term findability, automation, and AI - while folders trap content in someone else’s headspace.
We wrapped with a lighthearted crowd favorite: favorite metadata types.
Highlights:
And yes, we all agreed: “I never met-a-data I didn’t like.” 🥁😉
While Team Folders brought humor and nostalgia, Team Metadata proved its mettle - especially in a world shaped by AI, governance, and search.
But the real lesson? You don’t have to pick just one. The smart move is to blend familiar interfaces with smart architecture: metadata behind the scenes, intuitive views up front.
🥊 Jab: Folders Might Win Rounds
🧠 Hook: But Metadata Wins Championships
In the content ring of Microsoft 365, folders swing fast with familiarity—but metadata hits with strategy, stamina, and serious footwork. One might win a round, but the other’s built for a full twelve.
As Rocky said, “It’s not about how hard you hit. It’s about how hard you can get hit and keep moving forward.”
And nothing keeps your content moving forward - securely and intelligently - like well-structured metadata and flat information architecture.
So, whether you're Team Folder, Team Metadata, or secretly Team “It Depends,” remember this:
"With great metadata comes great findability."
And here's the serious hook:
📉 Deep folder structures weaken Copilot’s context.
🕵️ Granular permissions inside folders create more confusion than control.
🔐 Flat IA isn’t just smarter for search—it’s stronger for security.
Train your users. Build purposeful architecture. And when AI steps into the ring?
Struggling to flatten your IA, set up metadata, and prepare for Copilot? Reach out! Orchestry can help! Put your flat information architecture and custom metadata on repeat with robust templated provisioning engine. Get rid of ROT and ensure you have correct group membership with our archival and workspace review policies. Remember, if your governance isn’t automated, it’s probably not successful.