How Legal Departments Should Pilot New Legal Tech Before Signing a Long-Term Contract

Legal departments are investing more in technology than ever before.

According to the Thomson Reuters 2024 Legal Department Operations Index, over 60 percent of in-house teams reported increasing their legal technology budgets in the past two years. The pressure to modernise is real. But so is the failure rate.

Research consistently shows that a significant proportion of enterprise software implementations fall short of their intended goals — not because the technology is wrong, but because it was never properly tested in real conditions. For legal teams, the stakes are particularly high: bad tool choices affect matter quality, compliance posture, and attorney time.

The most reliable way to reduce this risk is not a better vendor demo. It is a structured, deliberate pilot program conducted before any long-term commitment is made.

The Problem with Demo-Driven Buying

Most legal tech purchasing decisions begin with vendor-controlled demos: polished, pre-loaded with ideal data, and optimised to highlight features rather than expose limitations. Legal teams then evaluate based on feature lists, peer recommendations, or internal pressure to show modernisation progress.

The result is a growing disconnect between what tools promise and what they deliver. Gartner research indicates that nearly 70 percent of technology implementations fail to meet user adoption targets — a finding that legal tech buyers should treat as a direct warning.

The core issue is that demos do not replicate real workflows. They do not test your matter management system integration, your existing document naming conventions, or how junior attorneys will actually interact with the interface on a deadline.

A vendor demo shows what a tool can do under ideal conditions. A pilot reveals whether it works under yours.

What a Legal Tech Pilot Should Actually Look Like

A pilot is not a free trial. It is not two weeks of informal access handed to one curious associate. A properly designed pilot is:

•      Time-bound — typically 60 to 90 days, long enough to surface real friction

•      Use-case specific — focused on one workflow (e.g., NDA review, matter intake, or billing reconciliation)

•      User-inclusive — involving the lawyers and legal ops staff who will actually use the tool daily

•      Metrics-driven — evaluated against pre-defined success criteria, not gut feel

What to Evaluate During the Pilot

Legal teams should enter the pilot with a structured evaluation framework. The following areas represent the highest-risk dimensions of any legal tech procurement decision:

Vendor responsiveness during the pilot period is often more informative than the tool itself. A vendor that is slow to resolve issues during active evaluation will not improve after a contract is signed.

Common Mistakes Legal Teams Make During Pilots

The CLOC 2024 State of the Industry Report found that user adoption remains the single most cited barrier to legal technology success — ahead of budget, integration, and vendor quality. That finding reinforces why pilots must include real users from day one.

Strategic Takeaway

A structured pilot does not just reduce procurement risk. It creates organisational readiness. Legal teams that run rigorous pilots before committing tend to see faster post-purchase adoption, fewer post-contract surprises, and better vendor relationships — because both sides have shared expectations set from the start.

The market will continue to produce legal technology at pace. The legal teams that invest in proper piloting will not just avoid bad purchases — they will build a procurement discipline that compounds over time.

Evidence-based procurement starts with a pilot. Not a demo, not a reference call — a structured, measurable test of the tool in your environment, with your people, on your real work