Your Server Map
What you've got, how old it is, what's dead, what's duplicated. Nobody has ever seen this picture of your own firm. Read-only, so it's safe today.
Filing Convention
One page of rules: how folders and documents get named. Yours if you have one, ours if you don't. It's what stops the mess growing back.
A Change Log
Every change in plain English you can hand to anyone: what it was, what it is now, when, who approved it. Undos logged too.
Do you use FYI, SuiteFiles, Karbon or Virtual Cabinet?
Then Document Assistant maps your server but never changes a file. It checks on the first run and locks itself read-only.
That's protecting you. Your system uses file names and paths as its index, like a library catalogue. Rename underneath it and it doesn't lose the link, it loses the record. You still get the map, which is the part nobody has seen anyway.
1.Pick one folder
One messy folder you know well. The scans that never got filed, one client's folder, the templates folder everyone moans about. A few hundred files.
You want to look at the result and know instantly whether it did a good job.
Decide this first2.Install the plugin
Download it. In Cowork: Customize → Plugins → Add → Upload Plugin.
Nothing to connect. No logins, no keys, no third-party service. Your files are never uploaded anywhere.
Get the plugin → Claude's plugin help →3.Point Cowork at your folder
The step people miss. Your other co-workers read your Brain. This one needs to see the actual folder.
New task, Opus 4.8 on High. Hit Add folder, pick the one from Step 1. Your Brain is optional.
Files in Dropbox, Drive, OneDrive or SharePoint? Fine, as long as the desktop app is on so they show up in Finder. Cloud-only will not work.
Do not skip this4.Run the audit
Part 1, the map. What's there, how old, the dead folders, the true duplicates, and how many naming habits are secretly in play. Minutes on a big folder. Changes nothing.
Part 2, the plan. A folder structure and a naming convention, on paper. Half-following a convention already? It finishes yours. Haven't got one? It writes you one.
Expect a surprise. Usually: "34 versions of the engagement letter, across 11 folders, three of them different."
Type it, do not paste. Type /, start typing document-auditor, pick it from the list.
This might be all you need. Plenty of firms read the plan, shift one dead folder, and stop there. Nothing below is compulsory.
5.Folder names, or document names?
Two different jobs. Most firms only have one.
Three folders for the same client? Acme Pty Ltd, ACME, acme pty ltd - OLD. One rename fixes every path underneath and touches no files at all. The safest thing here, and usually the biggest win.
Document names a mess? Sick of "Engagement Letter FINAL v2 (1).docx". Names most of them from the file name alone, tells you which ones it can't work out, and asks before opening a single one.
Both? Do the folders first, it is the safer one. Either way you approve every change before anything happens.
6.Prove the undo works
Rename something small, then undo it and watch it come back. Two minutes, and it changes how you feel about the whole tool. Or just say "undo that".
Separate records for each. Liked the new names, hated where things moved? Undo just the move.
A co-worker who does five jobs.
This is the bit that lasts. Not a one-off clean-up: a co-worker you point at any folder, any time. Ask in plain English or type /. Auditing goes first. After that, folders and documents are independent jobs.
What your AI actually sees.
Fair question. Ask it of every AI tool. No third-party service, nothing uploaded, no copy of your server anywhere. But your own AI has to see something. Here's exactly what.
The audit never opens a document. Your AI sees the list: file names, folders, sizes, dates. Worth knowing a file name is itself sensitive. "Smith v Jones settlement.pdf" says a lot.
Renaming folders never opens a document either. Folder names only.
The renamer reads only the ones you approve. It names most from the file name, tells you how many it can't, and asks. Those it opens go to your AI exactly as if you dragged the file into a chat. Nowhere new, but not nowhere.
Can't put client documents through AI at all? Run the audit and the folder renaming and stop. Neither opens a document, and you still get the map, the duplicates and the folder clean-up.
Tell your team before a big tidy.
Renaming re-syncs everything that changed, and breaks share links that point at a file by name, including anything a colleague has starred. Nothing gets lost, and Document Assistant warns you before every run. But a heads-up saves a phone call.
The account owner enables it once for everyone.
On a personal plan you can install it yourself. On Team or Enterprise, members cannot. The owner enables the plugin for the organisation first, then members refresh. A greyed-out install button is almost always this. Claude's help docs have the steps →
What to expect.
- ·Regular renames. VIP moves. Renaming leaves every document in its folder. Moving is the VIP job and it's off until you switch it on.
- ·It never deletes. There is no delete button in it. It'll tell you about the six copies. Removing five is your call, in Finder.
- ·It never overwrites. Two documents heading for the same name stops the whole run.
- ·It admits what it can't read and leaves those alone. A wrong rename looks tidy and is lying.
- ·Your archive folders are safe. It knows your backups from your mess.
- ·No third-party service, ever. No connectors, no logins, no keys. What your own AI sees is set out above.
- ·One folder at a time. Ask for the whole server and it will push back.