Contractor offboarding

This playbook manages the structured offboarding of an external contractor or freelancer whose engagement is concluding under approved terms. One run covers one departing contractor engagement from the initial offboarding notice through deliverable reconciliation, knowledge and file transfer, system access deprovisioning, and final billing status verification. The access and fallback boundary ensures that the agent audits external systems and prepares concrete proposals, but never autonomously deletes assets, revokes administrative privileges without approval, or executes financial disbursements. If connected APIs for Asana, Google Drive, or Notion are unavailable, the agent generates actionable, explicit manual checklists for designated human administrators to execute and verify.

• Extract the offboarding scope from the contractor agreement or Statement of Work, identifying the contract end date, agreed deliverables, internal project sponsor, and invoicing terms. Cross-reference these parameters against active project workspaces to establish the baseline reconciliation requirements for work, assets, access, and finance.
• Audit active task management boards in Asana to identify all open, in-progress, and overdue tasks assigned to the contractor. Group open work items by project milestone and priority, and prepare a preliminary task reassignment proposal mapping unfinished deliverables to internal project owners based on role and project context.
• Scan Google Drive project repositories and shared folders to inventory deliverables, technical documentation, and design assets produced during the contract. Where files are owned by the contractor's external personal account or cross-domain permissions prevent direct ownership transfer under Google Workspace rules, compile an asset custody manifest specifying required contractor export, approved internal copy, or handover into internal shared drives before access is modified.
• Reconcile workspace seats, directory accounts, and tool permissions across Notion, Asana, Google Workspace, and company single sign-on groups. Because public workspace directory listings exclude guest accounts and individual page permissions in Notion, combine connected integration data with administrator-supplied guest rosters to catalog active access, using automated SCIM deprovisioning only where configured on eligible Enterprise plans and manual administrator checklists elsewhere.
• Reconcile contractor billing records by comparing submitted, approved, and paid invoices against the agreed contract budget cap and completed milestones. Identify whether a final invoice has been submitted, is pending delivery sign-off, or remains unsubmitted, and draft a final billing reconciliation status memo for accounts payable.
• Information request. Request deliverable sign-off and task reassignment approval from the internal hiring manager or project lead. Provide the complete inventory of completed milestones, open Asana tasks, proposed internal assignees, and file custody transfer items. If the hiring manager approves the reassignments, proceed to apply the updates and secure file custody; if adjustments to assignees or deliverable scope are requested, update the reassignment schedule accordingly; if the hiring manager is unavailable, hold open task reassignments at the decision boundary and notify the operations coordinator.
• Apply approved task reassignments in Asana by updating task assignees and due dates to designated internal owners. Confirm the updates by reading back task records from the Asana API or recording verified confirmation from the project administrator.
• Secure internal custody of contractor-created assets by transferring ownership within the company Google Workspace domain where permitted, or by ingesting approved copies into designated company shared drives. Verify that internal owners possess full administrative control and that external sharing links or external edit privileges are revoked.
• Approval. Request system access revocation sign-off from the workspace administrator or IT security owner. Present the verified access inventory covering Asana, Notion member and guest access, Google Workspace, and single sign-on accounts, alongside confirmation that internal file custody is verified and active deliverables have been reassigned. If approved, execute automated deprovisioning where supported and issue manual revocation instructions for remaining tools; if deferred or rejected, retain active access for specified tools and record the administrator's operational justification; if the administrator is unresponsive, maintain current access and escalate to the operations security lead.
• Execute deprovisioning across Asana, Notion, and Google Workspace accounts as approved by the IT administrator. Read back directory and member rosters to verify that seats have been deactivated, licenses released, and sharing permissions removed, using manual administrator confirmation for Notion guest access and unintegrated systems. For manual revocations, obtain explicit written or ticket confirmation from the administrator before logging deprovisioning as complete.
• In a representative offboarding case, a freelance frontend engineer's contract ended with two Asana code review tasks still assigned and a core architecture document in Google Drive stored under the contractor's personal email. Because cross-domain Google Workspace ownership transfer was restricted, the agent prepared a handoff proposal reassigning the review tasks to the engineering lead and routing the document for approved copy and ingestion into the internal engineering shared drive. The engineering lead approved the task transfers, IT verified internal file custody and revokes Notion guest access and Asana seats, and finance received a billing reconciliation memo confirming the final milestone invoice matched the remaining contract balance.
• Compile the final Contractor Offboarding Record summarizing deliverable disposition, verified file transfer locations, access deprovisioning receipts, and final invoice status. Transmit the billing reconciliation memo to the finance administrator for standard accounts payable processing.
• Exception. If an unresolved dispute arises regarding unfinished deliverables, unauthorized contract budget overruns, or uncooperative handover of critical business assets, immediately halt automated offboarding workflows. Compile an offboarding dispute brief detailing contract requirements, current evidence, and conflicting claims, and route the case to the operations director and legal counsel for executive resolution.
• Conclude the offboarding run when all deliverables have been accepted or reassigned, file custody is transferred, system access revocation is verified by directory read-back or administrator sign-off, and the final billing status has been delivered to finance. If access revocation or invoice disputes remain unresolved, transition the case to the declined or unresolved terminal state with an explicit operational summary and designated human follow-up owner.