Evaluating Legal Technology – a Checklist

After successfully putting it off for a decade after every other industry, it seems like the legal world is finally – FINALLY – poised on the edge of a technology revolution. Walk the exhibit halls of any legal conference nowadays and you’ll see dozens of companies ready to sell you all sorts of solutions that will make your practice life easier and save you money. But will they? How can you tell?

To that end, I developed a check list to go through whenever you are thinking of adopting or purchasing a technology product or service.

  1. Know thyself. Before you even begin to consider purchasing a technology tool or service, you need a basic understanding of your operational costs (both time and actual monetary costs) of your activities. For example, if you don’t have a receptionist, how many hours a week do you spend answering the phone? Could you be spending that time doing something more profitable? If you’re spending 10 hours a week doing something that that could cost you $10/hour instead of doing something that could earn you $20/hr, then it may be time to find a cheaper solution for that. But you may find that a new and shiny solution is just that – new and shiny but doesn’t really save you any money.
  2. Beyond the ROI. There are many ways to classify technology, but a simple way of looking at them is to divide them into two types. The first type is those that do Old Things in New Ways. As in the above example, an outsourced receptionist service that saves you time and money by answering your phones, allowing you to pick up messages anywhere, and saving the costs of a physical receptionist hire. Other examples are video conferencing instead of face to face meetings or even typing in a word processor software on your computer instead of on paper. The great majority of technology solutions for legal are of this variety. The second type are products and services that do New Things in New Ways. For these, a straight ROI analysis is not always going to be sufficient, because you’ve never had the ability to do these things before. The use of Artificial Intelligence, Big Data Analytics and, I would argue, the newer aspects of Technology Assisted Review in eDiscovery fall into this category. Think about if these “new things” are something that you actually need to do.
  3. How Much Will It Cost? Technology is like puppies – no matter if you get it for free or if you buy it, you’re looking at a lifetime of costs associated with upkeep. Ask yourself and the company representatives the following questions: Is it a one-time fee or a monthly/yearly license? Are there costs per user or is it a site license? Will I have to upgrade my current hardware in order to use it? How long will it take for me to get trained on this and begin using it efficiently? Will I have to pay for upgrades? Will I have to hire someone (or assign a current IT employee) to manage it?
  4. Dig into the Company. The legal market is worth hundreds of billions of dollars and until recently, it has been an untapped market as far as technology goes. The tech industry is behaving like sharks when they smell blood in the water. It’s a feeding frenzy and companies are appearing and disappearing yearly. This means you have to do a little due diligence on the company trying to sell you something before you get to the product itself. Ask them about their company history – is the founder a former lawyer that wanted to do something better, a do-gooder type that wants to make law cheaper and thus more accessible, or a straight technology company that thinks law is an emerging market? Ask about their funding models – are they supported by investor capital only or are they surviving on customer fees? Ask if they hope to be acquired by someone. Yes, this is uncomfortable as heck to ask, but you’re a lawyer. You can do it. Plus, this is about saving you time and money. There’s nothing inherently wrong with investor capital or being acquired, but you do want to get a sense if the company is it in for the long haul or if you’re going to invest you time and energy using a product that will disappear in the next year.
  5. What are the Problems? Salespersons are just that – sales persons. Their job is to sell you the product and tell you everything good that it can do. Your job, as a customer, is to find out what it can’t do. So you have to ask. Get specific! “What’s the number one problem that your customers have had?” “After the beta test, what did you have to fix?” Ask to speak to an existing customer. Actually, this is probably my number one tip: NEVER BUY A TECHNOLOGY TOOL OR SERVICE WITHOUT SPEAKING TO SOMEONE WHO CURRENTLY USES IT. If you have to, put feelers out on social media or email listservs to find one.
  6. What Does Support Look Like? Once you go home with your new product, are you alone with it? Do they have trainings? User groups? A phone number hotline? Good documentation? Just remember any time you spend trying to figure out how to use a tool is money that you may never get back, so you want to make sure you have the ability to do so as quickly as possible.
  7. Know the Rules and Make Sure They Do Too. Using a technological tool to do something doesn’t erase your lawyerly duties. Sometimes this adds news ones. What are your obligations towards, for example, client confidentiality? For storing client information in “the cloud”? Ask about these things and make sure that this product or service is either built for the practice of law or that you can use them in your practice and still maintain your ethical duties.

Listen folks, we’re in the Wild West period of technology in law. Don’t go into it blind and don’t think you have to purchase everything that comes down the block in order to succeed. Technological tools aren’t a panacea, but if you pick the right ones, you can greatly improve your practice. The trick is to pick the right ones. I hope the above list will get you closer to that.


  1. Hi Sarah. Thanks for the excellent list.
    I would add something to the list – A key question to ask is “how will I/we make this work”.

    For law firms, this is a big question. Is the new tech a bucket that everyone will fill with content? Is the new tech enabling a process change (old thing in new way) that will require training? Is the new tech like a database that a person will keep current/relevant or is it people who will manage it? Does adoption mean adding people? Do we have the capacity to roll this out now/when? What does implementation depend on? Ownership of the tech should make sure these questions are answered.

    Without this aspect of the ‘beyond ROI’ question being addressed, new tech can take an unexpectedly long time to actually happen or never get past the pilot stage.

  2. Number 5+1. Can also add:

    *Do we really need this add-on module for extra dollars? What is the ROI?
    *Can we export our data cleanly in a common format that’s importable to other software, if the firm goes belly-up? We have to be able to search and view the original data and its documents.
    *If there is workflow automation built-in, can we customize parts of it with compromising on usability or does it require design from ground level?

  3. “can we customize parts of it with compromising on usability or does it require design from ground level?” I meant “without” compromising usability .