Catching Up After Vacation with Outlook + Copilot: Reclaim Your Workday
- Sep 11
- 3 min read
Vacations are great for recharging—but they can leave you dreading the inbox avalanche that’s waiting when you return. For legal professionals, every missed email feels like a missed deadline, and sorting through hundreds of messages can eat up hours you don’t have.
Enter Microsoft Copilot.
With Outlook + Copilot, you can transform your “post-vacation panic” into a streamlined, actionable catch-up session.
What Copilot Can Do
Instead of slogging through your inbox one message at a time, let Copilot:
Summarize your inbox — Capture the highlights from the time you were away.
Identify priority emails — Spot which messages need your response first.
Generate a task list — Turn those flagged items into a prioritized action plan you can actually manage.
Think of it as your personal assistant who already read every email for you and handed you a clean recap.
Real-World Legal Workflow
Imagine you’re a litigation paralegal returning from a week off. Your inbox is stacked with:
Notices from opposing counsel
Court updates
Medical record productions
Client check-ins
Normally, you’d spend hours digging through all of it. With Copilot, you can prompt Outlook to summarize:
“Summarize all unread emails from [Date Range]. Highlight any time-sensitive deadlines, court filings, or messages from [Attorney’s Name]. Provide a bulleted task list with due dates where applicable.”
In minutes, you’ll have a digest and an action list that keeps you on track—without losing half your day.
Ethical Tip: Human Oversight Matters
Copilot is powerful, but it isn’t infallible. Always:
Verify the summary against original emails.
Double-check that no deadlines or client communications slipped through.
Add your professional judgment to prioritize what really matters.
Pro Workflow Insight:
When you flag an email in Outlook, it automatically syncs to Microsoft To Do and Planner, showing up in To Do → Flagged Emails and Planner → My Tasks → Flagged Emails. This is where the human layer comes in: expand the flagged email/task and add critical notes, references, and nuances that Copilot may miss.
The goal isn’t to replace the process with AI—it’s to expedite it so you spend more time practicing law and less time buried in email.
Pro Tips for Input
Narrow the timeframe. Ask Copilot to focus only on the dates you were out of the office.
Filter by sender. Summarize just clients, co-counsel, or court addresses first.
Flag and expand. When you flag an email in Outlook, it syncs to To Do and Planner, which enables you to expand upon the task to add deadlines, context, or references.
Build an action plan. Use your flagged emails in To Do or Planner as the foundation for a prioritized checklist—layering your professional judgment on top of Copilot’s recap.
Final Thoughts
Catching up after vacation doesn’t have to mean sacrificing your first day back. With Outlook + Copilot, combined with the power of To Do and/or Planner, you can get the big picture, surface what matters, and jump straight into action.
Less stress. More focus. And yes—more time to actually practice law.
Stay tuned for Tip #4: Generate Meeting Summaries with Teams + Copilot.
💬 Have you tried using Copilot to manage your inbox yet? Share your experiences—I’d love to hear them.
Misty Murray
Author | Owner | CEO | Paralegal Boss
Arrow Consultants, LLC
At Arrow Consultants, we help legal professionals all over the world create better systems and build sustainable law firms using the full power of Microsoft 365. From case management to training, our mission is to make legal operations smarter, leaner, and built to last.
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