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How to Evaluate Law Firm Technology

improve your productivity law practice technology legal operations Mar 31, 2021

Note: This is an excerpt from the article I prepared with Kenton Brice for our 2021 ABA Techshow presentation on Slack vs. Teams for law firms. We thought the assigned topic was too simple, so we expanded it into a broader discussion of how to evaluate legal tech. This post is part 2. You can read part 1 here, and part 3 here.

Choosing Legal Tech: Start with Your Problem, not the (Purported) Solutions

The first and biggest mistake people make when selecting software is jumping straight to a comparison of two or more possible tools. When you do this, you’re already playing the game by somebody else’s rules (and that somebody is usually trying to sell you something). It is easy to fall into the false comfort of comparing features and benefits and pricing. This comparison gives you the illusion that you are being analytical, but more likely you are following someone’s carefully crafted marketing funnel.

A better first step is taking the time to think about—and engage with your team around—exactly what problem you are encountering. What is the nature of the problem? In what conditions does it present itself? What is its frequency? Its severity? Is it customer-facing or internal? Does it create external risks? Internal delays?
I like to classify problems into one of four categories:
  1. Delivery problems. These are things that are causing friction along your value delivery path, the combination of information, resources, and know-how that go into the work your clients hire you to accomplish. These most commonly occur when you have plenty of demand for the work you do, but you're having
  2. Operational problems. These are the issues that arise on any of the enabling functions of your practice (sometimes known as back office functions, but I prefer the former term). They include anything that makes it possible for the delivery function to do their job but aren't directly on the customer value path.
  3. Demand problems. These are issues with getting work in the door. They obviously include traditional marketing and sales functions, but also include product development/design, pricing, and branding/positioning.
  4. Executive problems. These are the things that naturally come up within the context of any human endeavor when trying to coordinate work across multiple people or functions. They include purpose, goals, values, strategy, culture, or anything else that, when not in place, leads to a sense of not being able to get everyone's oars in the water at the same time.
As you might imagine, it is a good idea to engage your team around the whole suite of the problems you encounter on a regular basis (assuming, of course, that you have more than one problem). That way you can compare your problem sets against each other and determine which ones you should prioritize solving. You also might be able to knock out more than one problem with a single solution if you're paying attention.

To do this, it helps to have a consistent way of describing the problem (more on ways to do this in Part 3 of this series). Once you have multiple problems defined, you will also want to come up with a way to score or rate the problems to figure out which ones to try to solve first. When you’ve picked a specific problem to tackle, the next step will be to brainstorm a range of possible solutions including training and process improvements that have nothing to do with purchasing additional software.

Here too, you’ll want to compare the potential cost and expected impact of a range of solutions to determine which to implement (more on that in the next section). Finally, before you go to put your solution in place, you need to determine how you’ll measure the success (or lack thereof) of your efforts so that you can either bask in your brilliance or adjust your plans as appropriate.

Comparing Possible Solutions to a Legal Operations Problem

Once you understand more about the specific elements of the problem (or problem set) you are trying to solve, the first question to ask is whether that problem even requires a technology solution. Tech can appear sexy, but it is rarely as magical as the marketing gloss would lead you to believe. True game-changer tools are rare and, as we said above, they can create a host of new problems even as they solve for an old one.

John’s maxim for this situation (echoed by Kenton!), drawn from decades of work in process improvement and change management, is as follows:

The best results come from improving people, processes, and tools; roughly in that order.


Look at it this way: If you drop new tech into your system you’re going to need to train your people and adapt your processes anyway. Your investment for implementing new technology will almost certainly be bigger (and more disruptive) than the one required to train your team and/or improve your processes to make better use of the technology you have.
This idea gets to two other concepts from the Lean philosophies of process improvement. The first is  “Start where you are,” which is both something of a command and a imploration to start your journey at step 1 and not your idealistic future state. Surely you’ve been doing something right to get to this far in your practice or operations; resist the urge to chuck it all in favor of some fancy new tool.

The other is to pursue continuous, incremental improvement. This is an important concept on a couple of levels. With respect to the actual problem you’re trying to solve, adopting a cadence of small but regular improvements helps you validate (or invalidate) the core assumptions you’re making about the problem and your proposed solution. That, in turn, sets you up to make small, inexpensive adjustments to account for what you’ve learned at each iteration. At a larger scale, a commitment to continuous improvement is essential to creating an adaptable, learning organization that will count problem-solving as a core competency. As the pace of change in our industry accelerates, a culture of continuous improvement—one that embraces, but doesn’t rely on, technological advances—will serve your practice well.

Key Considerations for Selecting a Legal Technology Solution

Once you’ve determined that you truly have reached the upper limits of your existing technology, the matrix you’ve created above becomes your best friend in evaluating your various alternatives. Drop those factors in a spreadsheet and allow yourself to score the tech you’re considering against the needs you’ve defined. And be sure to base your scores on your own evaluation, not just the marketing promises of the companies behind the tools. You’ll also want to consider a few other questions as you evaluate your options:

  • How well could this tool integrate with your existing tech stack?

  • Are there native integrations?

  • Can you connect it with API-integrators like Zapier,, or ITTT? If so, can the tools you’re trying to connect pass the data fields you need through the API?

  • Does the tool meet the standards of your security policy? (You do have a security policy, don’t you?) Is account access properly controlled, including with 2-factor authentication if necessary? Can you set appropriate user roles and quickly contain possible breaches? Is sensitive data encrypted in transit and at rest? Is it stored on servers in countries you consider safe for your purposes?

    Note here that the “free” tier of some freemium software products often has fewer security protections than the paid version, even during free trials. If your data is sensitive (which, as a law practice, it almost certainly is), you should understand the company’s security protections for trial accounts consider paying for a month or two while you kick the tires if it buys you the security you need.

  • How stable is the company behind the product? This is an easy one to overlook when you’re gawking at some cool new product, but the last thing you need is to invest a bunch of time, money, and effort on implementing a tool only to have the company behind it go under within a few months.  How long as the company been in business? What do you know about its investment rounds? How about its user growth?

    When you’re researching companies, the Stanford Legal Technology Index and Crunchbase are good resources. This isn’t to say you should never use a newer, smaller company; just make sure you do so with your eyes wide open.

  • How good is the company’s helpdesk & other support? Do they have robust online help articles that are updated regularly? Can you easily connect with support agents via phone, chat, or email?  Beyond the company itself, is there an ecosystem of consultants, technologists, or other professionals who can help you roll out and manage the tool?

  • Does the company provide data migration and implementation assistance? How about training? Here too, determine the extent to which the company itself has options and also whether third parties are available to assist you.

The level of detail you go into for each of the above questions will depend on how mission-critical the tool is and to what extent it will house sensitive data or other information. It is a good idea to get yourself and your organization in the habit of considering these bigger-picture issues. Aside from the obvious reasons to do so, it might help make your existing technology look a little more attractive by comparison!



Want to discuss how to better integrate technology into your law practice workflows? I can help. While I'm a fan of technology, I also am realistic about what it can and can't accomplish. I love helping lawyers and their teams find ways to work better, so don't hesitate to schedule a free 30 minute discovery call to talk about improving the flow of work in your law practice.



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