How to Run a Successful Legal AI Pilot

Rolling out Legal AI isn’t about switching a tool on. It’s about proving value, building confidence, and setting your team up for long-term success.

As Legal AI moves from experimentation to expectation in 2026, legal teams are under pressure to prove value quickly, without taking on unnecessary risk.

Many legal teams run pilots that stall: unclear goals, low adoption, too many use cases, or no clear path to rollout. The pilot delivers “interesting results”, but not enough confidence to make a decision. As a result, Legal AI struggles to move from experimentation into day-to-day legal work.

Led by VP Customer Success, Kristin O’Neill, and Legal Solutions Engineer, Harry Day, this webinar is based on LEGALFLY’s real-world pilot framework, refined through supporting Legal AI pilots across complex, multi-stakeholder in-house legal teams.

You’ll see how to design a pilot that focuses on the right use cases, drives real adoption, and gives decision-makers the evidence they need to move forward with confidence, including a live demo of the most popular use case teams choose when running Legal AI pilots.

You’ll learn how to:
– Define clear goals and success metrics for your Legal AI pilot
– Select 3–5 high-impact legal workflows that demonstrate value quickly
– Set up your Legal AI pilot so it aligns with your legal style, policies, and risk thresholds from day one
– Drive adoption across legal and business users (without constant hand-holding)
– Avoid common pilot pitfalls that prevent teams from moving to full rollout
– Evaluate results and build a clear business case for wider deployment

Plus – receive a downloadable Legal AI pilot framework to help apply these learnings within your own organisation.

Join us live on 28 January, or register to watch on-demand.