A Guide to Buying Legal AI
Legal teams have more AI options than ever. That means buying it has become harder than ever. New AI-native vendors show up every week, established legal tech companies keep bolting on new AI features, and the underlying models keep changing, so the product you evaluate in March isn’t quite the one you’d be using in September.
In our recent webinar, Preston Clark, CEO and co-founder of SimpleDocs and Law Insider, and a former in-house lawyer who later spent nearly a decade leading revenue at venture-backed software companies, together with Jordan Trevino, CTO of SimpleDocs, who ran vendor evaluations in management consulting at Novartis before building software across fintech, healthcare, and legal tech, walked through the framework they use with buyers every day. We’re a vendor, so read this with that in mind - but our goal is to show you a repeatable process for finding the right product for you.
1. Name your friction before you look at a single product
Don’t start with features. Start with where work is actually slower than it should be: incoming third-party paper you have to review and negotiate (know your monthly volume), your own paper coming back with redlines, drafting from templates, tracking pre-signature contracts, internal collaboration, or just finding information buried in agreements you already signed. Rank your top two or three honestly. Lawyers tend to absorb bottlenecks by working longer hours instead of naming them—but a credible business case starts with a friction point you’re willing to admit to.
2. Run a premortem before you evaluate anything
Assume the purchase disappoints, and ask why. Six failure modes recur: a product that demos beautifully and underdelivers in your hands; buying too much and drowning in a nine-month implementation; not being ready, because templates and playbooks were never cleaned up, so the work lands on you anyway; buying too little, so a narrow tool does less than the approval process cost you; integration breakdown, sometimes because a legacy vendor charges five figures to connect to a competitor; and failed adoption, where nothing is technically broken and your team simply doesn’t use it. Naming these upfront turns each into something you test for, rather than discover at renewal.
3. Translate friction into capabilities, not vendor logos
Resist “Vendor X has a vault product, so we need a vault.” Start from the capability: storage and retrieval, review and drafting, workflow and approvals, or self-serve access for the business. Then go a level deeper than the category - a law firm and an in-house team can want very different things from the same product, and your industry niche may be served better by a vendor you haven’t heard of than by the market leader. Independent studies (our own market report lives on the SimpleDocs homepage) can narrow twenty vendors to three or four. Put your criteria and shortlist in a plain spreadsheet, so the evaluation is yours, not assembled from three competing vendor pitches.
4. Match the evaluation mechanism to the product
Individual, user-driven tools - contract review, contract drafting - suit a free trial: turn it on, run it against real work, and ask whether you’d use it daily. Configuration-heavy, multiplayer products like repository or workflow tools usually need a paid pilot with IT and the business involved from day one.
Two practices make any pilot better: a sandbox that mirrors your work without exposing your data (in one enterprise evaluation, we built a 700-document sample repository across three agreement types, using test scenarios drawn from the customer’s own requirements), and a feedback survey agreed on before the pilot starts, covering frequency of use, features tested, and whether each participant would keep the tool. That data is what turns a couple of enthusiastic advocates into a recommendation your CFO can actually act on.
5. Build the business case capability by capability, then prove it
Never build the case at the vendor level (“we’re spending a million dollars with Vendor X to get faster and smarter”). Build it per capability: the friction on one side (manual intake, approval delays, status chasing), the features that address it in the middle, and outcomes that read as the literal opposite of the bottleneck on the other side - self-serve intake at 2am on a Sunday, escalation points so one person’s vacation doesn’t stall a deal.
Then show how you’ll prove it afterward, using the reporting and adoption data the product itself generates. That protects you at renewal, and it’s your answer when someone asks how the AI plan is going. While you’re at it, prepare for the predictable objections: Is this redundant with something we already own? Is the vendor training on our data? Will it integrate? Could IT just build this themselves?
6. Ask every vendor these twelve questions
A plausible-sounding clause isn’t the same as one grounded in your precedent and playbook, and that gap is what separates real diligence from a nice demo:
- Which models touch our content, under what contracts?
- Is our data ever used for training? (The answer should be an unqualified no.)
- Where do our documents live during review, and after?
- When is our data deleted?
- Which humans can see our content, and when?
- Where is it hosted, and can we choose the region?
- Does SSO work with what we already run?
- How do we test accuracy on our own documents?
- How does the system stay accurate as the underlying models drift?
- If we leave, what do we take with us?
- Do new uses of our data arrive switched on, or off, by default?
- Who like us runs this in production today?
Question nine is the hardest and the most revealing. Every vendor wants access to the most capable models, and every model swap changes the engine underneath what you bought. A vendor who can explain how those changes get verified before they reach you is describing a product built to stay ahead of the curve.
7. You have more leverage than you think
Most legal AI vendors won’t give you real pricing until midway through the evaluation, mostly because they don’t yet know what you’re buying. Once pricing lands, treat everything after as negotiable. Ten to thirty percent off list is a reasonable assumption, and fifty isn’t unheard of. The levers are simple: signing faster is worth money, a longer commitment is worth money (weigh the lock-in), and a case study on successful implementation is a legitimate thing to trade for a further discount.
Lawyers negotiate legal positions ruthlessly, then routinely skip the commercial negotiation because it isn’t their remit. Even with nothing to trade, ask. In this market, you’ll very likely get something.
The work that makes a purchase succeed happens almost entirely before signature: naming the friction honestly, designing a test you control, agreeing in advance how success will be measured. Vendors and models will keep changing. The discipline is what transfers.
Want the full recording, the slides, or the editable business case templates from the webinar? Get in touch - whether or not you end up buying from us, we hope this is the framework you run your evaluation with.
