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Automatically Creating a Digital Filing System for your Paperless Office

By January 20, 2016No Comments

Note: While this post will completely automate the setup of a digital filing system, it’s written specifically for those of you on Macs. You’ll need to use Dropbox or Google Drive (I haven’t tested it with, Clio, and Hazel. That’s sounds intense, but it’s easy, and the automation is worth it.


The first step in operating a paperless office is creating a paperless filing system. After all, if you’re going to replace all that paper with digital copies, you need to replace all those manilla folders, bankers boxes, and metal clasps with the digital equivalent. recommends a system of numbered folders within a matter folder, like the screen shot below.

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The numbers ensure that the folders are in a logical order when they are sorted by name.

In a paper office, the filing system is manually created by a secretary or paralegal. Manually creating the digital folders is not only tedious, but unnecessary. Why? Because we can create them automatically. And, at a software cost of $25 (for Hazel), and a bit of time for setup, it’s a significant cost savings over hiring an assistant.

Before we get started, you should download this zip file. It contains the Hazel rules and the Automator script you’ll need to complete this workflow.

Step One: Link Clio with Dropbox

The first step in this automation is the Clio-Dropbox integration. Within Clio, look for Settings, then Dropbox. Follow the prompts to link your accounts. Set Dropbox to sync “Open and Pending” matters, as demonstrated in the screen shot below. Now, whenever you add a “pending” or “open” matter in Clio, Clio will create the client folder and the matter subfolder within Dropbox (and, if you already have an open matter for that client, Clio is smart enough to create a second matter folder). Dropbox will sync those folders to the hard drives of every computer in your office. But we still don’t have subfolders.

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Make sure the setting for “Synchronize Matters with a Status of” is set to “Open and Pending”

Step Two: Creating Subfolders with Hazel

I use Hazel by Noodlesoft to create my subfolders. It costs $25, which is a bargain for the time it’ll save on this task alone. Hazel works by assigning rules to a folder. When a folder or file matches the given rules, Hazel will perform a task. The file I linked to above contains the rules for Hazel that will read your Clio folder and create subfolders for new matters. You can skip to Step 3 at this point, but if you want to learn the guts of what’s going on, keep reading.

We need to tell Hazel to watch matter folders, the subfolders within each client’s folder, and create the matter-level subfolders when necessary. This is done with the two Hazel rules below.

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Watch client folders for new matter folders

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Now look for an empty matter folder.


The first tells Hazel that we’re looking at subfolders (the matter folders), not the top-level (client) folders within Clio. The second rule tells Hazel to look for empty matter folders. That’s where we need to create our numbered subfolders (The last rule, which searches the folder name for a “-“, is a personal preference. I have a “General” folder within some client folders that I want excluded, and all my Clio matter folders contain a dash).

So now that we’ve told Hazel what to look for, we need to tell it what to do when it finds it. Hazel cannot create the numbered folders itself, so we need to use some AppleScript.

Step Three: Setting up Automator and AppleScript

Automator does the actual grunt work of creating the file-level subfolders. Simply install the “Create Client File Folders” service included in the package, and tell Hazel to run the service when it finds a match. Once you install the service, you can also run it fro the context menu. If you want to setup the Automator Action yourself, just follow the screen shot below.

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This does not show the full automator action, but should give you the basic idea.

Step Four: Sip Coffee. Enjoy Automation.

Now you should be set. Generally, I can create a new or pending matter within Clio, and by the time I need to save a file within the matter, my folder system is setup on my local hard drive. I cannot ask for much more, but someone can probably figure out a way to advance this. A draft engagement letter within the Word Processing folder would be neat. If you’re able to expand on this workflow, let us know in the comments.

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