Hand Off a Whole Job with Cowork · Lesson 5 of 6

Job three: a cleanup or batch job

15 minutes, plus the time Cowork works on its own. Let Cowork rename, sort and organize a pile of files, with a written list of what it may and may not touch.

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Every office has one. A "Scans" folder. A "Downloads" folder that became a filing system. A shared drive where "Final" means nothing. At our fictional Comfort Zone Heating & Cooling, it's 600 scanned warranty cards and permits named things like "scan_0412.pdf." Finding the Hendricks furnace warranty takes ten minutes of opening files.

This is the job Cowork can save you the most time on. It's also the job where a sloppy hand-off can do the most damage. A report with a wrong number gets caught in review. A folder where 600 files got renamed wrong, with no copy, is a very bad afternoon.

So this lesson is mostly about limits.

Before anything else:

• Make a new folder in Cowork jobs called Scans cleanup, working copy.
• Copy the whole folder you want cleaned into it. Copy, not move. Check the file count matches the original.
• Leave the original exactly where it is. Don't touch it until the job is done and reviewed.

When the cleanup is done and you've checked it, *you* decide whether to replace the original. That's a person's job, done by hand, after review.

Anthropic's safety page recommends a dedicated working folder and backups of important files. Cowork also asks before permanently deleting any file, by default, and you must actively choose Allow. Good protections. The copy is still your real safety net, because renaming and moving files don't count as deleting.

Don't use this job on: a live shared drive other people are working in, a folder synced to an accounting or practice-management system, or folders with payroll, bank, health or personnel files. Pick something low-stakes for your first batch job.

Marisol's scans do carry customer names and addresses, so she checked with Ray first that the business was comfortable with Claude reading them on their business plan. If you're not sure about yours, start with a folder that holds no customer details at all, like supplier price sheets or product manuals.

Write this before you write anything else in the brief. Be specific. Here's Marisol's:

> Cowork MAY: > - Read every file in "Scans cleanup, working copy." > - Rename files using the naming rule below. > - Create subfolders by year and document type, and move files into them. > - Create one new file: "Cleanup log.xlsx," listing every file's old name, new name and new folder. > > Cowork MAY NOT: > - Open, change or move anything outside "Scans cleanup, working copy." > - Delete any file, including ones that look like duplicates. Put suspected duplicates in a folder called "Possible duplicates" instead. > - Change what's inside any file. Rename and move only. > - Upload, share or send any file anywhere. > - Guess. If it can't tell what a file is, it goes in a folder called "Couldn't tell," with the old name kept.

The log is the most important line. With a log of every old and new name, you can check the work, and you could undo it if you had to.

Write the rule as a pattern with an example:

> Name each file: YYYY-MM-DD Type Customer-last-name Short-detail.pdf > Example: 2025-03-14 Warranty Hendricks Furnace.pdf > Use the date printed on the document, not the scan date. Types allowed: Warranty, Permit, Inspection, Other.

The "types allowed" line keeps it from inventing twelve categories. The "date printed on the document" line stops it from using the date the file was scanned.

Fill in the remaining parts of the Hand-Off Brief:

• Goal: "Make the scans findable by date, type and customer, without losing or changing anything."
• Inputs: "Only the files in 'Scans cleanup, working copy.' There are 612."
• Format: "Renamed files in year and type subfolders, plus Cleanup log.xlsx."
• Ask me about: "Before you start, rename 10 files as a sample and stop. Show me the 10 old and new names. Wait for my OK before doing the rest."

That last line is the key move for batch jobs. Always test on ten before you run on six hundred.

• In the Claude Desktop app, start a Cowork job.
• Select Work in a folder and choose Scans cleanup, working copy. Only that folder.
• Stay in Manual approval. Anthropic's safety page suggests manual approval when a task touches sensitive files or when mistakes would be hard to undo. A batch rename is exactly that.
• Type: "Read BRIEF.md. Show me your plan, then do the 10-file sample and stop."
• Check the sample. Open three of the ten files and compare the new names to what's printed on them. Is the date right? The customer? The type?
• Fix the rule if needed. Marisol's sample put "Permit" on two inspection reports. She added: "If the document says 'inspection' anywhere in the title, it's Inspection."
• Say "The sample looks right. Do the rest, and write the log." Then go do something else.

Anthropic's safety page also says to watch for unexpected patterns: Claude reaching into files you didn't mention, or a task growing beyond what you asked for. If you see that, stop the job and tighten the brief.

Use the batch section of the Review and Release Checklist:

• Count. Same number of files as you started with? The log should have one row per file. 612 in, 612 in the log, 612 in the folders.
• Nothing deleted. If the count is short, find out why before anything else.
• Spot-check ten. Pick ten random rows from the log. Open each file. Does the new name match what's printed on it?
• Read the "Couldn't tell" and "Possible duplicates" folders. A person decides what happens to those. Marisol found 14 true duplicates and deleted them herself, from the working copy, after checking each pair.
• Search test. Try to find the Hendricks furnace warranty. If it takes ten seconds instead of ten minutes, the job worked.

Then, and only then, a person decides whether to swap the cleaned copy in for the original. Marisol renamed the old folder "Scans, original, keep until December" and moved the cleaned folder into its place. If something's wrong in a month, the original is still there.

The same may-and-may-not list works for:

• Turning a folder of 40 supplier price sheets into one comparison spreadsheet.
• Making a one-paragraph summary file for each of 30 meeting-note documents.
• Producing a document set: one welcome letter per new customer from a template and a spreadsheet, saved as drafts for a person to review and send.

Each one: copies in, a log out, a 10-item sample first, nothing sent.

• Copy a messy folder into a new working-copy folder. Check the counts match.
• Write the may-and-may-not-touch list first, then the naming rule, then the rest of the brief.
• Run a 10-file sample in Manual mode. Fix the rule until the sample is right.
• Let it finish and write the log.
• Run the batch checks. A person handles duplicates, unclear files and the swap.

Check it worked

• The original folder is untouched, and you can still find it.
• File counts match from start to finish, and the log has one row per file.
• Ten random spot-checks match what's printed in the files.
• Nothing was deleted by Cowork. Any deletions were made by a person, after checking.
• Your brief, with its may-and-may-not list, is saved for the next cleanup.

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Next: the last check before anything leaves, and the settings your business owner should look at.

→ Lesson 6: Review before anything leaves, plus team settings

Previous: Job two: a deck or document from notes · Next: Review before anything leaves, plus team settings