Buying Legal Tech Starts With Needs, Not Features

For legal ops professionals, buying legal tech starts with needs, not features. A practical approach to legal technology procurement involves 20 questions emphasizing business needs, integration, vendor due diligence, and long-term value, writes Gio DiLuca of Checkbox. Successful software purchasing requires a disciplined process that extends from identifying operational problems to measuring adoption and planning for eventual exit.

Before evaluating vendors, legal ops should define the business problem, improve existing workflows, and prioritize investments based on their potential impact. Teams should consider whether building internally or using existing enterprise platforms will solve their problems.  Avoid disconnected point solutions by leveraging established vendor relationships and evaluating how solutions will serve finance, HR, procurement, and other business departments. Integration with core systems should be a major selection criterion from the outset.

When evaluating vendors, legal ops needs to ask for demonstrations using real-world scenarios and workflows; distinguish available functionality from future promises; and investigate how AI tools handle, retain, and share data. Teams must also make sure vendor due diligence extends beyond product capabilities to financial stability, ownership, leadership, and acquisition risk. Before committing, they should also establish measurable success criteria. Independent customer references can provide additional insight into implementation costs and vendor performance.

After purchase, legal ops should track active users, workflow completion, time savings, cycle-time reductions, and other relevant outcomes. Change management must be included in implementation planning, since technically successful deployments can still fail when users do not adopt the technology. 

Establishing an exit strategy before signing helps legal teams anticipate switching costs and maintain negotiating leverage at renewal. Although buying legal tech starts with needs, these 20 questions position legal tech procurement as a long-term operational investment rather than a standalone software purchase.