Dipping Your Toes in the Automation Pool: 3 Dead Simple Tech Tools for Lawyers to Try

You can’t swing a dead cat around practice management and legal tech circles without hitting somebody talking about ChatGPT. And I know a lot of lawyers have developed a bone-deep fatigue of hearing about all things AI over the past few weeks.

I’ll admit, I am really interested in (and a bit worried about) what feels like the beginning of a sharp upward trajectory of AI’s presence in the professional lives of lawyers. Growing up watching sci fi movies in the 80s left me with a healthy concern of what will happen eventually with AI, but I also don’t think there’s any putting this genie back in the bottle. And, who knows, maybe the positives will outweigh the negatives. (But only If every sci fi movie ever turns out to be wrong.)

I spend a lot of time working with lawyers in small firms who are interested in tools and strategies to improve their practices, but don’t have a lot of time to invest in overheated rhetoric and empty promises of transformative technologies that don’t deliver. That said, I worry that the native skepticism some of these folks have toward tech and AI is going to cause them to miss out on the career-enhancing tools that are rolling rapidly toward us.

Lawyers who have spent a career doing things manually and minimizing the role of tech in their practices are not going to be able to pivot seamlessly to use the AI tools the minute they arrive. Understanding and incorporating these tools into your workflow, to say nothing of learning to trust them, will be like any developing any other skill: it will take some time and it’s best to start with some easy steps in the beginning

To that end, here are three of my favorite, basic tech tools that a lawyer – even one deeply skeptical of the role AI and automation will play in their practice – can take advantage of to improve their practice immediately today, while spending very little money.

Scheduled Send

I think the simplest place to start learning that technology can solve problems for lawyers is with scheduled send in email. All the major email programs have this feature, which in short, allows you to write an email at whatever time is convenient for you and then instead of pressing send to deliver it immediately, it allows you to program the time you would like it to be sent. So, if you’d rather an email that you wrote at 11pm go out at 9am the next morning, it’s super easy to do in Gmail, Outlook, iCloud, etc.


Once you have mastered scheduled send, I am big fan of text shortcuts for quickly producing documents where you have a lot of repeated text. For example, signature blocks, directions to your office, canned responses to vendor emails or blind job applications… any time you use a go-by to copy and send some text is an opportunity to use a text shortcut.

My favorite of the shortcut apps is TextExpander, which is cross platform and available on mobile, and allows you to create all kind of automation around blocks of texts. I get repeated emails for some orthopedic surgeon in Italy whose email was once wrong on a conference email list. And while it is tempting for me to render my opinion on the revised upper limb module for pediatric cases around the world, I feel like it is better karma for everybody if I connect the person who needs help with the doctor who is an actual expert in it.

Email Rules

After figuring out text shortcuts, the next place to experiment with automation is in setting up some email rules. Auto-forwarding emails based on sender or subject line or keyword into certain folders can be a great time-saver but it takes a certain degree of faith that your filter is not going to cause you to miss something critical. Again, this is a space where all of the major email programs have this functionality built in. My advice: go slow. Start with one filter and live with it for a while. Double check it to make sure it is not filtering too much or too little. When you’re satisfied that it is working properly, then move on to your next filter.

Okay, are these three tools going to radically transform your practice and make you a productivity deity? No, probably not. But if you give them a try, I hope you will find that they do make life a tiny bit easier. And just as importantly, you will have taken some proactive steps to begin learning and using the next generation of tech tools that are going to change how we practice.

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