About the Author
Every SharePoint environment I walk into tells the same story. Years ago, someone sat down and built a folder structure with real care. Contracts by year, by client, by status. HR policies by department, by category, by effective date. Projects by name, by phase, by deliverable. It was thoughtful work, and at the time, it solved a real problem: where do we put things so we can find them later?
It worked — for a while. Longtime employees learned the paths by heart. They could click their way to any document without thinking. New hires struggled, but they eventually caught on too. And then Microsoft 365 Copilot showed up, and suddenly the cracks in that carefully built hierarchy started to show.
Here’s the uncomfortable truth: folders organize content for humans. Metadata organizes content for AI. And if your SharePoint environment is built around folders, Copilot is going to disappoint you.
Why Folders Fail Copilot
When Copilot looks at a folder path like /Contracts/2024/Acme Corp/Signed/, it sees a string of characters. That’s it. The path doesn’t tell Copilot that “Acme Corp” is a client, that “2024” is a fiscal year, or that “Signed” is a contract status. Those relationships are obvious to you and me because we bring context to the reading. Copilot has no such context.
The magic of Copilot — the reasoning, the summarization, the ability to pull together information from across dozens of documents to answer a natural-language question — depends on structured signals. Content types tell Copilot what a file is. Site columns tell it what attributes matter. Managed metadata term sets tell it how values relate across the organization. Together, these feed the Microsoft 365 Semantic Index, which is the engine behind everything Copilot does.
Without that structure, Copilot is guessing. It can read the contents of your files, but it can’t reliably tell which documents belong to the same process, the same client, or the same project. The result: weaker grounding, less accurate answers, and a frustrating user experience that makes leadership wonder why they bought Copilot licenses in the first place.
The Transition Is Worth It
I’ll be honest — when I start explaining content types, site columns, and managed metadata to a client, I can see the energy drain from the room. It sounds bureaucratic. It sounds like more work for users. It sounds like a project that could drag on for months. And the resistance is real: change in SharePoint touches every part of how people work.
But helping organizations make this shift is one of the most impactful things I do. Here’s why:
- Content management gets simpler. Once metadata is in place, content owners stop worrying about where to file things. They tag, save, and move on. Views and filters do the organizing.
- Findability goes up dramatically. Users who’ve never seen the site before can filter by what they actually care about — document type, year, client, status — instead of guessing at a folder path somebody else designed.
- Self-service becomes real. Users can build their own views, their own dashboards, their own Power Apps on top of structured content. You stop being the bottleneck.
- AI adoption takes off. This is the big one. Copilot’s accuracy, grounding quality, and ability to synthesize across documents all improve dramatically. The difference between a well-structured site and a folder-heavy site is the difference between “Copilot is kind of useful” and “we can’t imagine working without it.”
A Practical Path Forward
The good news is that you don’t have to rebuild everything from scratch. Here’s the phased approach I use with clients:
- Analyze the existing hierarchy. Your folder paths are actually implicit metadata — each level usually encodes a business attribute. Document these patterns across a representative sample of libraries. Clients often realize, “We’ve been doing metadata all along, just in the most fragile way possible.”
- Define content types and site columns. Translate the attributes you discovered into formal content types (Contract, Invoice, Policy, Project Deliverable) and reusable site columns (FiscalYear, Department, Client, Status). Managed metadata term sets handle values that need organizational consistency.
- Map folders to metadata. Build a table showing how each folder path translates. For example, /Contracts/2024/Acme Corp/Signed/MSA.docx becomes a Contract with DocumentType = Master Service Agreement, Client = Acme Corp, FiscalYear = 2024, Status = Signed.
- Migrate in place. Use Power Automate, PnP PowerShell, or tools like ShareGate or Syntex to apply metadata to existing files automatically. Most files tag themselves from the mapping table.
- Replace folder navigation with views. Create library views that group and filter by metadata — “Active Contracts by Client,” “Policies by Department.” Users get the familiar navigation experience. The underlying structure is fully machine-readable.
- Govern forward. Set default content types, require key metadata fields, and train content owners. New documents inherit the structure automatically.
The Payoff
When you’re done, you have a SharePoint environment that looks familiar to users but speaks fluently to Copilot. A natural-language question like “Show me all signed contracts with Acme Corp from fiscal year 2024” returns a precise, grounded answer — not a list of folder paths to sift through.
If your team is looking at Copilot and wondering why the results feel underwhelming, this is almost certainly the reason. And if you’re preparing to roll Copilot out, doing this work first is the single highest-leverage investment you can make.
It’s not glamorous work. It won’t end in a ribbon-cutting. But it’s the foundation everything else rests on — and in my experience, it’s the difference between AI that disappoints and AI that transforms how your organization operates.
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Gunars Foldats leads SharePoint and AI consulting at Weidenhammer. If you’d like to talk through what this transition might look like for your organization, reach out — every environment is different, and the right path depends on where you are today, where you want to go, and how much change your team can absorb.
