Trisha’s Beginner’s Guide to Selecting New Legal Tech

Leveraging technology and AI is not going to be optional in 2026 for all legal teams. Selecting a new addition to your organization’s tech stack is a sizable portion of your budget. If you have not made one of these purchases before yourself or you have not been out on the marketplace recently, the diversity and richness of the legal technology marketplace can be overwhelming. You have likely already had several pitches made to you to demonstrate their newest tool that they guarantee can revolutionize your law practice, automate your in-house team, or practically draft your documents for you. Even the most stalwart of skeptics can be enchanted by the slickness of a good demo; after all, so much of what you are hearing aligns with the current atmosphere in the legal industry – that heady mix of excitement at the prospect of doing less of the work you don’t like while doing more of the work you do with notes of ambient anxiety of the robots coming for all of our jobs. Maybe you have even received an edict from your senior leadership that you need to do something with AI – even if they cannot give you direction of what that is or even the outcome they want.

With these competing pressures, the stakes (and likelihood) for the worst outcomes – implementing a legal tech solution that is not a good fit or taking too long to reach operational goals – are greater than in years past. To ensure that you are directing your limited time and budgetary resources to your advantage, there are some preparations you can make that will not require a heavy lift on your part and still give you confidence in your selection.

1. Collect technical requirements

Reach out to a trusted IT professional in your orbit if you do not have someone in your organization. What you are going to collect from them will be deductive or exclusionary factors in your decision matrix. Getting these together first will save you time on the vendor onboarding process, too. Some of the most common requirements will include the following:

• Multifactor authentication (MFA): This one should be a low hurdle and the lowest security bar to pass. This is similar to but not the same thing as SSO (single-sign-on), but your IT may require this ability, too.
• Data center locations: For the cloud servers that retain, transmit and otherwise access your data, the vendor must be able to impose geographical restrictions (e., all data stays within the United States).
• List of current software systems and packages: This will be critical for integrations; adding a new system that does not integrate into your existing systems is an utter waste of time. You can opt to request this from the vendor of what software and systems they have pre-built integrations for and match them to your post-demo, too.
• Compliance checklist requirements: You will be listening for “SOC II, type II” compliance, but this is not the end-all-be-all. Like others on this list, you will have to rely on the expertise of your team.

2. Assess maturity

This is a judgement call that depends on your and/or your organization’s risk tolerance. Greater maturity tends to signal stability and adequate support. For those in highly regulated industries – healthcare and finance, as top examples – will want to opt for more mature solutions with a strong concentration in cybersecurity measures. Maturity does not mean that the vendor or solution must be widespread, have tremendous market presence, or be a market leader to be adequately mature. You are looking for (a) the vendor’s age, (b) the relative age of the product in relation to both the vendor and the market, (c) multiple versions or rebrands of the product, and (d) the frequency and impact of improvements or upgrades. You are striking the balance between reliability and innovation. Be on the lookout for community resources as an indicator of maturity: things like rich engagement on user boards, walkthroughs, and trainings will be very helpful during implementation and for off-loading a portion of the burden of you personally training others to use the system.

This is not meant to steer you away from startups or newer technology solutions. There may be incredibly vigorous, battle-tested vendors with a competitive edge that have the perfect fit for your use case. There are some advantages that you can look for if you want to take a more innovative approach:

• Narrow scope: If you are not looking for a comprehensive system but are instead looking to fill a specific gap between your existing systems or to add an element that enhances an existing system, a newer tool can meet your needs with a lower effort to implement and lower impact on other systems.
• Customization: Startups and newer solutions are often created to deliver on niche needs. These vendors are more likely to be able to deliver on customizable options or at least not be stuck in the same rigid structure as legacy systems.
• More support: There is a certain value in not having to compete with a large, pre-existing client base for attention. This may mean that you get faster responses, or willingness to walk/talk through issues. Depending on what you experience and the mutual interest, your feedback could influence upcoming features to be developed. If you are looking for collaboration and deep dives, these newer solutions may be a better fit for you.

3. “Vibe-check” the user interface

In change management, you can either go the path of choosing something that “feels” familiar or you can go the path of choosing something that is starkly new. Each have their benefits and disadvantages, but what you do not want to have to compromise on are the terminology used and an organic process. Subtleties, such as component labels, can be a boon or a barrier when it comes time to implement. If you have ever tried to assemble furniture using instructions that were very clearly not written in your native language or for which the translation was poor, this frustration will be exponentially increased when you are trying to learn, implement, and train when the software developers do not speak your language. Remember: what you see in the demo is performed by someone who has intimate knowledge of the product; if you will be processing everything you are learning through your own internal translator, it will take you longer to develop those reflexes and easy of navigation.

From the simplest terminology, how early that struggle triggers can be a red flag or indicate that a death by a thousand cuts may be in your future. A recent example I had to contend with was regarding how dates are labeled in a CLM (contract lifecycle management) implementation: a Service Start Date could be very different from something such as a Commencement Date in your understanding, or a Termination Date versus an Expiration Date may trip your team up later. If you have multiple systems to integrate, you will have to be ready not only to match those fields for data handoff, but have clear instructions for the state change of the same data as it passes through the new system. Unless your particular brand of savviness is database architecture, tech savviness alone does not bridge as much as this gap as you would think. So much of how operations can be completed in any given system depends on how that system identifies, categorizes, prioritizes, and retrieves incoming data. This ultimately determines how that data can be manipulated.

4. Be realistic about your timeline

You may get a pitch that a product could be stood up and functional within a single quarter. Understand that these timelines from the vendor’s perspective could be realistic, but they are the best-case scenario. This is the perfect world in which your data sources and documents have already been identified and isolated, there has been work done to perform quality control or enhancements on these items, or that you are not incorporating much in the way of expired or archival documents.

In timeline or roadmap discussions, be prepared to get very honest about the state of your current data, resources, and expectations. Have the vendor explain how they get to that estimate and what are the common circumstances for how those estimates get blown. It is not unusual that the drive to onboard a legal tech solution is the first time this type of work has been really done; as such, the time required to do this work is underestimated. Small teams with hard deadlines – even when there is no scope creep – will have to shell out extra money for implementation, often incurring more charges to the vendor than originally budgeted for to having them step in and perform more of this type of work.

5. Don’t be dazzled by AI

When it comes to “out of the box” features, AI capabilities are likely at the top of your list. Determining consistency and reliability of a vendor’s AI tools is a challenge. Benchmarking in an apples-to-apples comparison is limited. Without performing your own tests, gathering the information you would want regarding this element will likely be limited to how the AI is structured, what data it can access versus what it excludes, and what measurements the vendor has been tracking as to actual time savings by using these features. AI should be a feature that can grow as it develops; it does not supplant the infrastructure of the core functionality the solution is meant to perform. Ask this: if the AI breaks down, does the core functionality remain intact? Think of this like the back-up camera in your car; it is a bummer, but you can still turn your head and use your mirrors to back up.

Bonus round: Request off-boarding details. I equate this to having a “pre-nup” discussion: how someone ends a relationship, I have found, is more indicative of the vendor’s values and operational philosophy. That may not sound important…until you come up against a conflict. Vendors with the ability to explain their off-boarding process, how they release or export your data back to you, whether they facilitate data transfer to a third party or replacement vendor, the format of that data, what costs are there for exporting or porting data, and how long they retain compliance documentation like access logs are all better to know up front rather than as sour surprises at the end of the relationship.