How to find “it’s a match!” software for your legal team

Anton Vashkevich
8 min readApr 12, 2022


Legal team: “We want to get more done for less.”

Innovation team: “here is a legal tech solution with thousands of features. It’s based on AI, designed like Apple, collaborative, and integrates with the business. Oh, we forgot, it’s the most expensive purchase you’ve ever had.”

Legal team: continues searching through e-mails and tracks changes by red-lining**

It’s classic. Although a lack of adoption turned into a meme with legal tech folks, it’s a true problem for many legal teams.

When buying legal tech products a law firm or legal department focuses too much on features. This happens because software suppliers usually focus lawyers’ attention on product features only and ignore the client’s true pain points.

After attending dozens of product demos the legal team who set out to make life easier feels baffled — every provider assumes their product is the most progressive in the market. Eventually, the legal team selects the one with the largest number of features for the least amount of money.

But it doesn’t work this way.

The truth is that the selection of tech should be the last thing on your to-do list when increasing efficiency. People and their problems come first.

Here is our approach on how to find an “it’s a match!” software for your legal team.

Spoiler: there’s a possibility your legal team doesn’t need software at all.

01 — Make sure legal tech is what you really need

The first task on the to-do list is to find out:

  • true causes for your legal team’s problems;
  • existing ways to solve these problems.

Is legal tech the only option? Are you sure you have explored all the possibilities? This set of questions will be helpful:

  • How are lawyers working and solving issues right now?
  • Why do we want to change it? What is a trigger for lawyers to think about process efficiency?
  • Why do we consider the current process inefficient?
  • Which process stages benefit a client? Is it possible to get rid of less valuable stages? Why not?
  • Is the client satisfied with the current process? Why not?
  • What have we already done to increase efficiency (aside from tech solutions)? If so, why didn’t it help?

Most likely you don’t need any tech at all. Try creating process maps and check all the bottlenecks — in many cases process reengineering and eliminating useless stages bring more benefits than introducing new products or tools.

For legal departments, it’s critical to communicate with other business units before buying legal tech. Legal teams often face problems that finance, sales, etc. have dealt with a long time ago. For example, ERP systems by SAP or Oracle may fit the legal department’s need for contract data capturing and analysis in some cases.

02 — Encourage lawyers to innovate

Legal tech implementation is complicated, time-consuming, and expensive. And let’s be frank, humans are calculating and thrifty creatures. They rarely feel happy to waste their resources on something obscure (as legal tech seems to many lawyers). A question an innovation team should ask: what are true reasons for lawyers to change their typical work approach?

Clear and constant communication is a game-changer. The goal is to find out all the pain points of individual lawyers, clients, and a legal team as a whole. Afterward, this information would help to demonstrate to lawyers the ROI in legal tech.

Jack Shepherd shares some bright ideas on why communication with users is crucial. This is a must-read.

Be ready to meet resistance from users. It’s typical for all innovation projects. So, one more challenge is to provide a mindset change and draw lawyers’ attention to the business experience.

When a business launches change-driving projects, it concentrates more on the resulting profits that new technology brings. A business’ priority is always on an expected efficiency rather than the temporary discomfort change may cause to the employees. The same approach is suitable for legal tech implementation.

How do you drive lawyers’ mindset change?

  • Constantly explain why change is important and share the progress timeline;
  • Make lawyers trust the software. People only trust the things they are familiar with. Organize regular training sessions, prepare guidelines, process all feedback, and provide experience sharing within the team;
  • Demonstrate to lawyers how the software increases their efficiency — legal data and KPIs are helpful (keep reading for more about those items).

03 — Make your legal team data-driven

The right choice of metrics and KPIs enables legal teams to test dozens of legal tech solutions a year and compare them on more objective criteria. For legal departments, metrics and KPIs help demonstrate project results to the business.

On a basic level, metrics and KPIs provide answers to 3 important questions:

  • How did we start?
  • What did we want to achieve?
  • What did we achieve?

Measuring KPIs is a continuous exercise. KPIs are individual for every legal team and depend on its objectives. Don’t be afraid of experimenting with metrics. Over time it becomes clearer whether chosen metrics are informative or not. Here are some possible metrics and KPIs for legal tech projects:

  • Amount of time spent;
  • Legal advice quality (it can be a set of criteria similar to NPS (net promotion score));
  • Correlation of low-value to high-value tasks;
  • Number of documents drafted;
  • Cross-functional integration opportunities;
  • UX-quality;
  • Time of training sessions needed to learn how to use the software;
  • Configurability of the software;
  • File storing and other knowledge management opportunities;
  • Security level.

We recommend the SMART concept for goal setting. It’s 5 simple, accurate, and objective criteria to define your team’s desired result: every project goal should be Specific, Measurable, Attainable, Relevant, and Time-bound. SMART goals can be tracked and modified along the way. So, it can be a great starting point for building a data-driven team.

04 — Pay attention to UI-quality

Design is crucial for legal tech. Often it seems that good design is just like a bonus to good-quality software. In reality, an intelligent interface design is your best friend in change management as it significantly increases users’ liking and hence the adoption of software.

A lack of great design is the number one reason for users to escape and resist new software. Lawyers are allergic to mistakes and do everything to avoid them. When logging into a complicated and unpredictable system, they consider it an unreasonable risk. At this point, inefficient, but predictive and familiar e-mail negotiation seems more rational than any useful collaboration tool.

Good design is inconspicuous and intuitive. Just remember your personal experience with iPhone, Google, or YouTube — you don’t feel confused and always know how to use it, without lengthy instructions. That’s why we all spend hours with these apps. The same goes for legal tech.

05 — Launch a pilot project and test the software

Never implement technology without testing.

The testing stage is imperative and the only way to estimate the system’s value for your legal team. Gut feeling and chasing new shiny things is the main reason why so many legal teams have their own so-called “legal tech graveyard”.

Testing and piloting provide some more advantages:

  • Your decision to use the software or not will be well-informed;
  • The implementation phase can be better mapped — timeline, budget, stakeholders, need for outside services, etc. are much more obvious;
  • Piloting mistakes can be turned into insights and avoided during implementation.

A critical point for software testing is to define the right team to experiment with the tools. It should be a group of 2–7 lawyers interested in technology and client experience. The team leader’s task is to maintain prompt and good communication. It includes:

  • Developing an easy and quick way to get feedback; as well as process feedback, comments, and recommendations;
  • Facilitating team brainstorming sessions to explore and settle on the next steps.

Plan your testing project carefully. Clearly define its goals, duration, timeline, and schedule meetings accordingly. Develop a list of 3–5 basic use-cases for testing — they should be frequent and typical for the entire legal team. You need to set KPIs specifically for the testing phase.

Testing itself is a series of hands-on meetings where lawyers try the software in real-life scenarios. Before every meeting provide a detailed script with a description of roles and a list of features to test. The “How to” format is optimal.

Finalize the project by capturing and documenting all the comments, recommendations and criticism. If the experimenting team is happy with the software, launch a full-scale pilot with the entire legal team (using the testing approach that worked for the experimental team).

Of course, just one piloting project isn’t enough; perform deep testing on several solutions before you decide to implement any software.

A summary

  1. Put users’ problems first. Getting to the bottom of the users’ problems is the starting point. Analyze current processes, ask probing questions, and communicate with users. And yes, communication is mandatory. Not only will you make better decisions, but it will also make it easier to demonstrate value and ROI.
  2. Legal tech is just one of several possible tools, no more. Never limit yourself to technology solutions only. Maybe you don’t need technology at all — a lot of times the real problems are at a process level.
  3. Design matters. Design is no less important than features. An intelligent interface design is a key to a successful software implementation. Always set UI quality as one of the metrics and keep in mind — a good legal tech solution is something lawyers would use every day. That’s why it should be convenient and a joy to use, really.
  4. Make all your decisions data-driven. Establishing metrics and KPIs is the best method for performance assessment. It’s more accurate, transparent, and informative. Furthermore, precise data is like currency in communication with business — it helps the business realize that investments in legal tech improve the legal team’s performance.
  5. Allocate enough time for testing. Before you decide to implement legal tech, be sure you’ve tested all the alternative options. The testing stage also helps to detect possible implementation difficulties and avoid them. It’s a basis for the whole implementation project.

Every business and every team are unique hence the tools they use need the ability for customization and adaptation. That’s why you should always put the users’ experience first, and software features second.

One tool isn’t the end for legal tech implementation. The more you innovate — the more perspectives for improvement you’ll see. So, never stop experimenting and keep testing different solutions in different use-cases.

At we believe, technologies shape the future of collaborative, business-oriented, and data-driven legal teams. All you need is to find the right space for it to add value.



Anton Vashkevich

Law Automation, Legal Tech and Legal Design