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Claude Cowork1 min read

Drive cleanup playbook — never lose a file again.

Triage 50 files at a time, approve in batches, and let Claude move them where they belong. Done in an afternoon.

Haojun See
Haojun See

Founder & Director, On The Ground

Updated 6 June 2026

Overview

Most working professionals have a Drive root that looks like a dumping ground. The cleanup playbook turns an afternoon's work into an hour, and the maintenance after is a 10-minute weekly habit.

Step 1 — triage

Ask Claude: "Look at the top 50 files in the root of my Drive. For each: one-sentence summary, suggested folder, and whether it looks important, routine, or stale. Don't move anything yet — give me a table." You'll review the table for 10 minutes and approve in batches.

Step 2 — approve and move

"Move the routine ones into the folders you suggested. Skip stale ones — I'll deal with those separately." Repeat in batches of 50 until your root is clean.

Step 3 — weekly maintenance

Add a Friday recurring task: "Look at any files created or moved to root this week. Suggest a folder for each." Five minutes once a week and the root stays clean forever.

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