Where my lawyers at?

I’d be interested to hear what my fellow lawyers are using for software and work flows. I’m a lone Mac user at a PC-based firm. It is PAINFUL.

Right now I’m trying to figure out the best work flow for taking client notes/memos in markdown and easily converting to Word docs. I think I figured out how to do this on Drafts for IOS, but not on the desktop. In general I’m switching between Bear, Drafts, and Joplin and trying to figure out which one to commit to.

Meanwhile, I’d also be interested to hear what Hazel rules everyone finds useful in their law practice.

I’m not sure where to start, especially since my pre-pandemic workflows have faded a bit from memory. For many years, I was the sole Mac user in a PC-based firm, but I also kept a Windows machine running in my office. My happiest moment was about four or five years ago, when we switched from document management and case management systems that we hosted in our server room, and required Windows locally, to cloud-based systems. That allowed me to get rid of the Windows machine and go 100% Mac.

Drafts might be my most essential piece of software. In most meetings, I type notes in Drafts on the iPad, which syncs over to Drafts on my iMac. And when I’m at my desk, notes from almost every new phone call or thought goes into Drafts, before getting transferred into our case management system. I have various Keyboard Maestro macros and text expansion snippets to help with this. For example, I have a Typinator snippet that sets up a template if I am talking to a new client, and then I have a Keyboard Maestro macro that converts the Markdown headers to the kind supported by our case management system. I also use the keyboard shortcut to call up a new Drafts note wherever I am on the Mac.

DEVONthink is my repository for items that don’t go into our case management system (common legal research that spans cases, administrative documents for the firm, etc.), but I also mirror select cases locally to DEVONthink for trial, depositions, etc. That gives me quick access to everything, and lets me use the power of DEVONthink’s search, etc.

To answer your question about Hazel, I don’t use it nearly as much as I did in the past. DEVONthink has smart rules that can be applied to imported documents, so I find many of my rules have moved there. I do have a Hazel rule that detects when I’ve downloaded a document from our case management system, and opens it in the default app.

This is getting a bit long, so the final thing I’ll add is that I’ve programmed buttons on the Stream Deck, using Keyboard Maestro macros, to filter notes in our case management system by various tags. This lets me just tap a button to get to desired notes.

On a side note, ironically, at the start of the pandemic, we bought MacBook Airs for our entire staff, and there was some grumbling about learning something new. But as people are returning to the office, I’m hearing grumbling about getting back to Windows now.


I would suggest listening to MPU#571 Catching up with Jeff Richardson.


He is a lawyer in NOLA and discussed some workflows that might help you.


This is the bane of my existence. Our files are on a local server and we use TABS for billing. I am able to remote into my work PC desktop, but it is so painfully slow that I decided early on I would do all my work on my MacBook Pro and only remote in to log my billing. The file management part is hard though. I basically keep all my client folders in Google Drive and at the end of the day remote in to my PC and copy my folders onto the server. It’s a horrible system.

If there’s another “tech influencer” in your firm, drag him/her to the ABA TECHSHOW next time it isn’t virtual. I convinced the other techie in our office to go with me to TECHSHOW in 2016 and visit the vendors, and he also attended the security sessions. That was enough for us to break free from the inertia of sticking with our current systems, and we started the migration shortly thereafter of all our systems (document management, case management, phones, and a move from self-hosted Exchange server to Office 365). He was big on security, and at the time he thought it was important for us to host our own data, but the TECHSHOW security sessions terrified him and convinced him that most firms are not equipped to secure their own data, and should leave it to the pros.