• What should NEVER go in AI-accessible files (passwords, SSNs, regulated data)
• Separating public, internal, and confidential information
• Using local folders for sensitive work
• How to think about "what could leak" if your AI tool gets compromised
• Role-specific compliance concerns:
  • Legal: attorney-client privilege, work product
  • Insurance: PHI, PII under HIPAA
  • Finance: material non-public information
  • All roles: trade secrets, competitive intelligence