Draft Clio Time Entries from Google Calendar via n8n + Claude

Turn Google Calendar billable events into Clio time-entry drafts—safely—with n8n + Claude

This n8n workflow automatically pulls tagged, timed Google Calendar events from yesterday, generates compliant billing narratives using Anthropic Claude, emails an attorney approval digest, and then creates draft time entries in Clio only after explicit webhook confirmation.

What this workflow does

• Runs daily at 7am to build yesterday’s UTC date range and fetch matching events from Google Calendar.
• Filters to timed events whose titles include a bracketed matter reference (e.g., [2026-CH-042]), then calculates duration and captures relevant metadata for each billable item.
• Matches matters in Clio by searching for the appropriate matter; if the exact display number match isn’t found, the event is flagged for manual handling.
• For matched items, sends event metadata to Anthropic Claude to generate a short billing narrative, then runs multiple safety controls: a self-check, keyword scanning, and a 200-character limit.
• Sends one digest email via SMTP that groups “ready to approve” drafts (with approval links) and items needing attention. It also logs the digest via an external compliance sub-workflow.
• Creates Clio time entries only after approval: clicking an approval link serves a review page via webhook and requires a POST confirmation. On valid confirmation, the workflow creates the time entry in Clio and logs the approval via the compliance sub-workflow.

Use cases

• Law firm billing ops: convert calendar-based time tracking into Clio drafts with attorney-controlled approval.
• Automation engineers: reduce manual entry while keeping narrative generation constrained (safety checks + length limits).
• SaaS operators: standardize billing workflows across teams using n8n, Claude, and Clio.

Technical details

• Integrations/steps: Google Calendar (OAuth2), Clio (search + webhook-confirmed creation), Anthropic Claude (narrative generation), SMTP (digest email), Webhook (approval review + POST confirmation).
• n8n node concepts used: if, code, no op, merge, webhook, email send.
• Setup: add a Google Calendar OAuth2 credential and configure the Clio and Claude components used by the workflow.