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January/February 2020

The Digital Toolkit

Building Your Digital Toolkit 2020

Tom Mighell

Back in 2016, I introduced the newly renamed “Digital Toolkit” column (previously called “Web 2.0”) by discussing the best ways to utilize web-based and mobile tools in your practice, and how to put together a collection of those tools that makes sense for you. Four years later, I’ve decided you have probably heard enough from me, and it’s time to turn this column over to another voice, one who will no doubt provide a different perspective on the tools and strategies lawyers should be using these days.

So for my final entry, I decided to revisit my 2016 column and see how well it holds up today. Interestingly, while a lot has changed, a lot has stayed the same. Hopefully, many of you already have a solid digital toolkit in place. If not—or even if you do—here are some of the lessons I’ve learned over the past few years.

Jobs To Be Done

One thing that certainly has not changed over the years is that each of you has different criteria, goals and objectives for the apps, services and tools you want to use. A feature that is critical to one lawyer may be trivial or of lessor priority to another lawyer. That’s why it’s hard for me to answer when I am asked “what’s the best tool for doing [X]”—with the wide variety of tools available in every category, it’s impossible to make a pronouncement that something is “best” because that judgment will vary from one lawyer to the next.

That’s where the theory of “jobs to be done” comes in. My good friend and podcast partner Dennis Kennedy frequently mentions this theory when we discuss tools, web-based or otherwise. It was coined by Clayton Christiansen, a professor at Harvard Business School and leading management and innovation expert. Simply put, it means “what am I hiring this app (or device, or tool or service) to do for my practice?”

Let’s say you’re looking for something as basic as a good note-taking app—when each of you asks “what am I hiring this note-taking app to do?,” the answers that each of you comes up with are likely to be different. When looking at adding a tool to your digital toolkit, ask this question first. The answers will help to point you in the right direction.

Failure Is Ok

J.K. Rowling said, “It is impossible to live without failing at something unless you live so cautiously that you might as well not have lived at all—in which case, you fail by default.” Maybe that’s a bit of a dramatic statement when it comes to selecting digital tools for your law practice, but there are two grains of truth there. First, lawyers by nature are cautious when trying out new things, particularly technology. Second, when you select a technology tool for your practice, there’s no rule that says the first tool you try should be the one you select. There’s nothing wrong with caution, but there’s also nothing wrong with trying out a lot of tools; by experiencing the failure of using one tool, it will help you make better decisions about the tool that will work best for you.

Even if a tool does work for you, don’t settle for it until you know it works better than the rest. Most of the tools I have mentioned over the years in this column are either free, offer free trials or have subscription pricing that you can walk away from at any time. Be prepared to spend time and effort trying out the different tech options in a particular space, but most of the time you won’t have to spend a lot of money.

Here’s another interesting result of trying out multiple tools: You might find that the one you are using now is still the best one for the job. This is actually a valuable exercise—even though you may stick with your current technology, by trying out the new tools you are helping to improve your level of technological competence, which can only be a positive development. You have a better idea of what’s possible out in the market, so the next time you have to choose a tool you will be a more educated consumer.

Legal Tools vs. General Tools

In this column I have spent most of my time discussing general technologies that lawyers can put to work in their practices. But there are dozens of legal apps and tools that aim to address specific problems you might be having relating to the practice of law. If you’re heading to ABA TECHSHOW 2020 (or reading this while you’re there), make the most of your time in the EXPO Hall; you’ll find some great new technologies on display, with vendors who are eager to let you try them out.

General Considerations

There are several general criteria to consider when evaluating a new tool; perhaps not surprisingly, these criteria haven’t changed much since 2016. These are some of the features I consider important when evaluating web-based tools, apps or programs:


Will the tool work in a Windows, Mac, iOS or Android environment? This is important to me because I work on multiple platforms, but it may matter less to you if you live exclusively in the world of Windows or Mac. Consider, however, whether you’ll be using the tool to work with others; will they need to access it on another platform? The best collaboration tools offer access for multiple platforms because not everyone is a Windows or a Mac.

Collaboration Features.

While we’re on the subject, do you plan to use the tool to work with others? If not, check the box and skip ahead to the next criteria. But if you are looking for a tool you will use to share work product or communicate with others, the tool should allow team members to collaborate in a synchronous (at the same time) or asynchronous (not at the same time) manner.


Is it important that the tool be able to “share” information with other apps or services? On a phone or tablet, it’s extremely useful to move a document to a file-sharing service when you’re done working on it. Likewise, many people enjoy sharing information from their tools with their friends on relevant social media platforms.

Synchronization Features.

If you plan to use the tool on your phone, then on your laptop, then on your tablet, it’s important to have good synchronization capabilities to ensure your content is the same no matter what device you use. If security is a bigger issue for you, you may only want to keep data on one device, making this feature less significant (as well as potentially making you less productive).

Mobile or Desktop?

Some tools are built solely as a web-based app with associated mobile apps for your phone or tablet. On the other hand, some tools also offer a standalone desktop app for Windows or Mac, often with more (or different) functionality than the web-based version.

Easy-to-Use Interface and Customization.

If the tool isn’t easy to use, chances are you won’t use it. Customization of the tool should also be a consideration; some tools are great out of the box with their basic functionality, but others really shine when you apply advanced customizations that give you even more power within the application.


A lot of tools are simple efforts from individual developers who offer little to no technical support if the tool doesn’t work. If the ability to get help when you need it is important, select a tool with good customer support, or find a user community that can help when you’re in a bind.


Even though this consideration is last, it’s really the most important. Because you are likely entrusting this new tool with sensitive or sometimes even confidential information, appropriate security is a must. Ask (at a minimum) whether the tool:

  • Offers encryption of data, whether in transit or at rest?
  • Provides a method to back up your data, so it’s not lost in the event your device crashes or is lost?
  • Provides two-factor authentication as an added layer of security?

By keeping these criteria in mind, finding the right tools will be much easier—or at least, not so overwhelming. And although you won’t find me writing this column any longer, I’m not going away—please feel free to reach out to me on Twitter (@TomMighell), LinkedIn or at my blog ( Thanks for allowing me to share my technology passions with you over the years—and good luck in building your digital toolkit!

Tom Mighell

Tom Mighell is vice president of Delivery Services at Contoural, Inc. and has served as chair of both the ABA Law Practice Division and ABA TECHSHOW.