The Problem: Copilot is the ultimate "insider threat"—but it’s an invited one. It doesn't hack your data; it simply reads everything you forgot you had access to.
If your data is messy, Copilot will be messy. If your permissions are loose, Copilot will be dangerous.
This guide expands on the Data Readiness pillar of our assessment, providing specific pitfalls and immediate action plans to get your environment "Copilot Ready."
1. The "Security by Obscurity" Failure
The Pitfall: For years, companies relied on the fact that nobody could find the "CEO_Bonus_2019.xlsx" file buried 10 folders deep in a public SharePoint site. Copilot doesn't care about folder depth. If the user has "Read" permission (even by accident via an "Everyone" group), Copilot serves it up instantly in a chat.
The Reality Check:
- Does "Everyone except external" actually mean everyone?
- Are sensitive HR sites truly locked down, or just "unlisted"?
Action Plan: The Permission Purge
- Run the "Sharing Links" Report: audit SharePoint for "Anyone with the link" permissions and revoke them globally or set aggressive expiration policies (e.g., 30 days).
- The "Just Enough Access" Audit: specifically review permissions for the Big Three: Executive Leadership, HR, and R&D.
- Implement Sensitivity Labels: Don't rely on folder permissions. Tag documents as [Confidential]. Configure Copilot to ignore or redact content with this label.
- Quick Win: Set a default label of "Internal" for all new files.
2. The R.O.T. Crisis (Redundant, Obsolete, Trivial)
The Pitfall: Copilot treats a policy document from 2018 with the same authority as one from 2026 if it looks relevant. If you ask, "What is our remote work policy?", and Copilot finds a draft from 2020 that wasn't deleted, it might halluncinate an answer based on old rules.
The Reality Check:
- You are paying specifically for storage you don't need.
- You are feeding the AI "bad memories."
Action Plan: Digital Housekeeping
- The "5-Year" Rule: Use Microsoft 365 Retention Policies to auto-archive (or delete) content untouched in 5+ years.
- Establish "Official" News Sites: designate specific SharePoint sites as "Authoritative Sources" in Microsoft Search. This clues Copilot to prioritize these sites over a random user's OneDrive.
- Archive, Don't Delete (Psychology): Employees hoard data because they "might need it." Create a "Cold Archive" site that Copilot is excluded from, and move old projects there.
3. The "Version Control" Nightmare
The Pitfall: Employee asks: "Summarize the Project Alpha proposal." Copilot finds:
Copilot might blend these sources, creating a frankenstein summary that includes rejected ideas from Jim's comments.
Action Plan: The "One Truth" Policy
- Enforce Versioning Training: Teach teams to use built-in Version History instead of "Save As... v2".
- The "Final" Stamp: When a document is actually done, convert it to PDF or mark it as "Final" using a specific retention label that locks the file.
- Delete Drafts: Encourage a "Drafts" folder for work-in-progress, and delete the folder contents once the project ships.
4. The "Unstructured" Dead Zone
The Pitfall: Your organization runs on PDF scans, images of whiteboards, or audio recordings without transcripts. Copilot is blind to these files unless they are OCR'd (Optical Character Recognition) properly. You have data, but no intelligence.
Action Plan: Modernize the Format
- Turn on Transcription: For all Teams meetings, enable transcription and recording preservation (subject to privacy policies) so Copilot can "remember" decisions.
- OCR Your Scans: Ensure your PDF editor utilizes OCR so text is searchable.
- Wiki -> Page: Move rigid static "Wiki" libraries into modern SharePoint Pages, which Copilot reads much more effectively.
Summary Checklist for IT & Leadership
- Audit: Run the "Data Access Governance" report in SharePoint Admin.
- Label: Roll out specific "Sensitivity Labels" for [Confidential] data.
- Exlude: Explicitly exclude sensitive sites (HR, Legal) from search results if granular permissions aren't ready.
- Purge: Auto-archive R.O.T. data older than 3-5 years.
- Educate: Train staff: "If you can see it, Copilot can see it."
Getting "Data Ready" isn't a one-time project; it's a hygiene habit. Start today.
To learn more about Copilot, why not complete our M365 Copilot Challenge
