Automatic Timekeeping With Clevermore in Outlook

·Clevermore Team·Time & Billing, iManage

What It Does

End-of-day billing shouldn't mean staring at your calendar trying to remember what you actually did. Clevermore now generates time entries automatically — with narratives, timestamps, and client matter assignments — then syncs them directly to your calendar for a complete visual record of your billable day.

Auto-Generated Narratives — Click "Generate Time Entries" and Clevermore analyzes your Outlook activity — emails sent and received, calendar meetings, and task completions — to produce detailed narratives that describe the work you actually performed. No more vague entries like "email correspondence" or "client call."

iManage Matter Matching — Every time entry is automatically tied to the correct client matter, pulled from your iManage workspace. When you categorize an email or work on a task, Clevermore already knows which matter it belongs to — so your time entries inherit that context without any extra clicks.

Visualize Your Billable Day — Each time entry appears as a calendar event at the exact time it occurred. See your day as a series of blocks — meetings, emails, research, calls — color-coded by client matter.

Spot the Gaps — The empty spaces on your calendar are billable hours you forgot to record. With time entries synced visually, those 15-minute blocks between meetings become impossible to miss.

Edit, Refine, Submit — Generated entries are a starting point, not a finished product. Adjust times, refine narratives, or split entries as needed. The AI gives you an 80% head start; you provide the final 20% of judgment.

The Problem We're Solving

Ask any associate what they dread most, and "timesheets" is near the top. The workflow hasn't changed in decades:

  • Reconstructing the day — Scrolling through your sent folder at 9 PM trying to piece together what happened at 2 PM
  • Generic narratives — "Reviewed documents and provided comments" when the billing partner wants specifics
  • Matter confusion — Which of the three Johnson matters was that call for again?
  • Lost time — The 15 minutes here and there that never make it to a timesheet

Partners have heard the same excuse for decades: "I know I worked more hours than that." And associates have felt the same frustration — you billed 9.5 hours but you were in the office for 12.

The problem isn't laziness. It's that timekeeping tools and calendars have always been separate systems. You remember the day in meetings, but you bill in six-minute increments. Clevermore captures your work as it happens and makes it visible where you already plan your day.

Key Features

  • One-click generation — Analyze your day's activity and produce time entries instantly
  • Smart narratives — Detailed descriptions based on actual email content and calendar context
  • iManage integration — Matters flow directly from your firm's document management system
  • Calendar sync — Time entries appear as events in Outlook for visual review
  • Citation links — Click to open the source email for any entry
  • Inline editing — Adjust times and narratives without leaving the interface
  • 6-minute rounding — Hours calculated to standard billing increments

How to Use It

  1. Open Clevermore in your Outlook sidebar
  2. Navigate to the Time Entries tab
  3. Click Generate Time Entries
  4. Review and edit your entries
  5. Click Sync to Calendar to visualize your billable day
  6. Export your entries to your billing system

Have feedback or ideas? Email us at support@clevermore.ai — we'd love to hear from you.