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In-house at home: Easy Automation Tricks to Use when Working from Home

“In-house at Home” is a new column about working from home, inspired by the coronavirus lockdowns and work from home orders. Greg Stern, author of ACC Docket’s Tech Toolbox in the print magazine, has been working from home for five years steadily and three years intermittently before that. In this column, he offers insights on how to make teleworking work for you and your company.

Now that you have developed a WFH routine, spent some time improving a few of your processes, and become more accustomed to participating in videoconferencing, you may be ready to try more creative and effective ways to work and help your clients. 

In particular, you may be able to automate some of the work you do to save yourself time and frustration. Below are some suggestions. 

Automate and use your own “snippet” library 

Most lawyers stash boilerplate legal forms or phrases or other precedents that they repeatedly use. From now on, whenever you draft something you could use again, don’t just save a copy to your precedent folder. Instead, set it up as a “snippet” that you can trigger using a keyboard shortcut. 

You can do this in AutoText or AutoCorrect in Word, in Text Replacement in iOS (Settings → General → Keyboard → Text Replacement) or MacOS (System Preferences → Keyboard → Text). Or in specialized apps like TextExpander or Breevy, which allow you to create more complex snippets that include embedded snippets, fillable fields, and other neat tricks. The really good ones let you create them on the fly.

On my Mac, I use an app called PopClip that lets me turn any language selected from any app into a TextExpander snippet with one click. As illustrated by the following screenshot, it also lets me search the selection in Amazon or Google, or create calendar entries, task reminders, or a host of other things. 

Mac toolbar

Automate file management

Most of us spend too much time on our digital file management. To simplify your organization workflow, try File Juggler for Windows or Hazel for Mac. These apps monitor designated folders while looking for particular characteristics, then automatically perform user-specified acts on those documents. 

For example, suppose you want to automatically clear your Downloads or Trash folders if files have been sitting in there for several weeks or months. Or you might want to take any documents that contain a particular client name anywhere in the document, then move it to that client’s folder. Or you might want to rename any files with a particular name format and give them a colored tag. These apps can do all that for you without your being involved (other than to set up the rules). 

[Related: 3 Easy Wins to Elevate Your Tech Competence with Contract Management Software]

As the monthly Tech Toolbox columnist for ACC Docket, I research and collect a lot of reference materials for each article. I keep the materials and columns in a TechTool folder in my Dropbox account (mostly out of habit). But on my Mac and iOS devices, I use the Devonthink Pro app that swiftly searches and organizes my research. One Hazel rule I’ve set automatically searches through all my Tech Toolbox folders and adds all new materials into Devonthink. 


I also use ScanSnap, an intuitive scanner by Fujitsu, to scan all the paper bills and other important documents I still receive every month. Then, I have Hazel sort them into various categories (e.g., water bills, electric bills, medical bills, etc.), by assigning Hazel to “watch” for particular keywords in the PDFs. You could also use this approach to sort work items into appropriate folders. 

Automate opening computer workspaces for various types of work 

We often use specific apps on our computers to do certain types of work. For example, when I am writing one of these columns, I usually keep Safari, Devonthink, Notes, and Word open at the same time. Or, if I am on a Zoom call, I might keep Notes and Messages open. 

You can arrange those sets of apps to open automatically when you trigger keyboard shortcuts in MacOS, iOS, and Windows operating systems. I use the Keyboard Maestro app for my Mac, and the fantastic app Shortcuts to do this in iOS. You could also use Launchy or similar app launcher on Windows. 

Automate your proofreading 

I have been writing for many years, and while I think I am fairly proficient, nobody is so good that they can’t benefit from having someone else’s proofreading. And face it, Word’s spell and grammar check just doesn’t cut it for these purposes. 

If you are lucky you can have a colleague check your work (like Karmen and Joshua do for me for these columns — thanks!), but this obviously isn’t as easy when you are working from home. However, there are a few good online and other automated services that can help. One app I’ve tried and like is Grammarly; I don’t always agree with its suggestions, but at least they make me consider what I have written in a way that I wouldn’t otherwise.

[Related: Make It Work: Finding Normalcy in Uncertain Times]

Automate your work breaks 

Studies have shown that you cannot be truly productive for long periods of time unless you take periodic breaks. One approach to systematizing breaks is to use Francesco Cirillo’s Pomodoro Technique, which advises breaking each work period into 25-minute chunks, followed by five minutes of rest or distraction. You then rinse and repeat three more times, taking a longer half-hour break before you start the cycle anew. 

I can’t speak for everybody, but I generally can stay in a creative flow much better if I follow that method. There are many free online apps that will track the time for you, but you can just as easily ask Siri to do it for you, or set up a Siri Shortcut to do it. 


Automation is based on the idea that if there are tasks you do repeatedly, automating those tasks will save you a great deal of time and frustration in the long term. These are just some of the ways you could automate the work you do at home (or in the office). Pay attention to the things you do; if some of them are repetitive, you can almost certainly find some ways to automate them. 

For more advice on the coronavirus pandemic, visit ACC's Coronavirus Response Resource Page.

About the Author

Gregory SternGreg Stern is formerly global integration counsel at Chubb Group of Insurance Companies, and is presently ACC Docket’s Tech Toolbox columnist. [email protected]

The information in any resource collected in this virtual library should not be construed as legal advice or legal opinion on specific facts and should not be considered representative of the views of its authors, its sponsors, and/or ACC. These resources are not intended as a definitive statement on the subject addressed. Rather, they are intended to serve as a tool providing practical advice and references for the busy in-house practitioner and other readers.