A Practical Guide for Running Better Legal Tech Pilots
Technology and process change pilots in law firms are notorious for high failure rates. Lawyers often see an impressive demo followed by disappointing adoption: the new tool launches with fanfare, only to gather dust as attorneys revert to familiar habits. With more Legal Tech than ever before, pilots matter more than ever. They are a way to validate solutions and de-risk innovation before full rollout. When done right, pilots allow firms to test-drive new technology in a controlled setting, gather evidence of value, and work out feasibility issues without disrupting business-as-usual.
This advice is based on the author’s experience running hundreds of legal tech pilots over the past decade, including his work at Lupl, supporting law firms across a wide range of use cases.
In short, a well-run pilot can serve as the bridge from idea to proven practice. This article presents a practical framework for running successful legal tech pilots, from problem definition through vendor selection, pilot execution, and finally transition planning for rollout. The goal is to help law firms and legal teams transform pilot projects into catalysts for lasting improvement, to transition from one-off experiments to embedded, effective practices.
Start with the Problem, Not the Product
Every good pilot starts with a clear problem. Too often, firms begin with a tool in mind and go looking for a reason to use it. That approach rarely works. Instead, focus on areas where the work is slow, manual, or prone to errors. Talk to the people doing the job. Ask what tasks frustrate them or where delays happen. You’ll often find repeated complaints, like spending hours reviewing contracts for standard clauses. That’s the problem to solve.
Write a short problem statement that explains what’s broken and why. For example: “Lawyers spend too much time on X because our process is Y.” This helps the team agree on what success looks like. Only then should you consider tools. When the use case is specific, the pilot has a purpose. Instead of chasing features, you’re testing whether the tech fits the workflow. That’s how you set a pilot up to teach you something useful.
Vendor Selection and Scoping
With a problem in hand, the next step is to pick the right solution and define a smart scope for your pilot. Vendor selection should be driven by your problem definition and firm context, not by vendor hype or generic features. Do your homework to find technologies that specifically address your use case. This often means looking for tools with a narrow, deep focus on the task at hand rather than “all-in-one” platforms.
Firms are often hesitant to share their requirements, but to maximize time with vendors, provide them with a clear picture of your firm’s needs and technical environment. They should enquire how your workflows run today, your current tech stack, and any requirements (e.g., key integrations with document management systems or security standards).
Define a pilot scope that’s small but representative. Limit it to the features that solve your problem. Select a pilot team that includes a mix of users, comprising both skeptics and supporters.
This might be a single practice group, an office, or a specific process within a department, depending on the context. Limit the pilot to the key features or workflows that address your problem; don’t attempt to trial every bell and whistle of the product in a few weeks.
Everyone should know their role – who will liaise with the vendor, who will collect user feedback, and who will analyze results. Establishing these responsibilities and processes before launch prevents confusion later.
Most importantly, set a hypothesis and success criteria for the pilot. Treat it like a mini scientific experiment: “We believe that implementing [Tool] for [Problem] will result in [Outcome]. We will test this by measuring [Metric] over [Time].” Write down your hypothesis and identify how you’ll know if it’s validated. This might include baseline measures to compare against or a qualitative score. Being explicit about your metrics for success and the pilot’s scope (what’s in and out) sets a clear target for everyone. It also guards against scope creep – if an unrelated issue pops up during testing, note it for future phases, but stick to evaluating the defined use case.
Pilots as learning opportunities
A good pilot isn’t about proving a tool works. It’s about learning whether it fits your problem, workflow, and users. That learning depends on structure. Start by writing down the questions you need answered. Will this tool reduce time or cost? Will lawyers use it? Does it fit into existing systems? Each question should tie to something you can measure.
Choose a few metrics linked to your goal. If you’re improving a manual process, track time saved or volume handled. If it’s a new function, focus on accuracy, error rates, or user satisfaction. Avoid vague goals, such as “faster drafting.” The clearer your metric, the easier it is to judge success.
Don’t stop at numbers. Collect feedback from users. Simple rating scales work well. Ask if the tool saved time, whether it was easy to use, and if they’d want to keep using it. Both data and personal experience matter. Keep in mind that early use is often slower. Most tools have a learning curve. First-time users may take longer as they adjust. That doesn’t mean the tool failed. Instead, ask whether the process became faster with use, and whether trained users reached the expected pace. Pilots should reflect what full adoption might look like over time. When evaluating results, consider not just early friction, but how long-term value could grow as users become confident.
Plan the pilot process in advance. Set a clear timeline, usually 2 to 6 weeks. Schedule a midpoint check-in and a final review. Decide if users will test with real work or examples. If using live data is crucial, consider implementing safeguards such as parallel runs (although these should be avoided if possible) or obtaining client approval. Ensure that everyone knows how to report issues and who to contact for assistance.
Keep the scope focused, but realistic. The more the pilot reflects real work, the better your insights. Use actual scenarios if possible, but avoid high-risk matters. If the pilot uses fake data or limited functions, note those constraints when reviewing results. What matters is learning. A tool that fails the test still teaches you something useful. A pilot that gives you clarity, even if the answer is no, is time well spent.
Running Successful Pilots
The pilot phase is where all the planning is put into action. Pilots fail when firms treat them like simple software deployments: train once, then wait for results. That approach rarely works. A pilot needs day-to-day attention. It’s a live project that requires guidance, monitoring, and adjustments as it progresses.
Start with a structured launch. Walk users through how to do their actual work using the tool. Avoid vague product tours. Use simple guides or checklists to support common tasks. Before testing starts, confirm access, logins, and any integrations are fully functional. Set up a shared space for communication, such as a Teams channel (for Lupl pilots, we use Lupl matters for this). Use it to share timelines, materials, and answer questions. This keeps everyone aligned and makes it easy to identify and address issues early.
Once underway, stay close to what’s happening. Monitor usage and adoption. Look at logs or metrics daily or weekly. Low engagement is a warning sign. Follow up directly if needed. People may need help, reminders, or extra guidance. Set regular check-ins, such as weekly meetings or office hours. Use these to gather feedback, resolve blockers, and share small wins. If one person figures out a shortcut or sees a time-saving, spread the word. That builds momentum and trust in the process.
Make sure the vendor or IT support is responsive. Problems will come up. Have a clear path for users to report bugs or confusion, routing them to someone who can follow through quickly.
Stick to the plan. If users test features outside the scope, log the feedback, but don’t let it shift your focus. Adjustments are fine if they help test the use case better, but don’t keep moving the target. You’re trying to evaluate a tool under known conditions, not endlessly tweak it.
Measuring Outcomes and Making Evidence-Based Decisions
When the pilot ends, the key question is simple: did the solution work well enough to justify adoption? Start by revisiting your original hypothesis and success criteria. What did you expect to see, and what actually happened? Compare your results against those benchmarks.
Look at your metrics. If you aimed to reduce time spent on a task by 50%, how close did you get? If your goal was 80% adoption, what was the final number? Go through each data point you tracked: efficiency, accuracy, cost, turnaround time, and user satisfaction. Use both numbers and context to interpret the results.
Consider the user feedback. Numbers matter, but qualitative input often explains what the data can’t. Maybe the tool saved time, but the interface confused users. Maybe adoption lagged because people were swamped, not because the tool lacked value. Look for unintended side effects. Did the tool improve one area but disrupt another? Were there benefits you didn’t expect?
Summarize your findings in a simple report or slide deck. Include charts, quotes, and a summary judgment: did the pilot meet its goals? Calculate the impact in real terms, such as time saved, projected dollars, or future potential scale. For example, “30 hours saved this month on task X could lead to Y annual savings.” Even rough estimates help make the business case.
Don’t ignore less tangible wins. Did the tool boost morale or client service? Does it give the firm new capabilities it didn’t have before? These factors can matter just as much as speed or cost. Use data to ground the discussion, but also apply judgment.
Once you’ve reviewed the evidence, bring your stakeholders together to make a decision. Usually, there are three outcomes: move to full rollout, refine and retest, or stop. If the tool fell short, figure out why. Was it a solvable issue, like training or configuration? Or was it a poor fit?
Too often, firms let opinion override outcomes. Only a small share of firms measure ROI or adoption after a pilot.
Beyond the Pilot
When a pilot succeeds, the next step is scaling that success. Moving from a small group test to a full firm-wide rollout requires structure and planning.
1. Training and Change Management: Pilot users had support, but now you need to reach a larger audience. Develop a comprehensive training plan that incorporates live sessions, self-paced tutorials, and clear instructional guides. Ask your early users to help train others or share success stories. Peer support reduces hesitation and speeds up adoption. Clearly communicate the purpose behind the rollout. Focus on benefits like reduced manual work and increased time for strategic tasks. Address common concerns early, such as fears about complexity or job impact. Adoption rises when people understand both the “what” and the “why.”
2. Technical Integration and Deployment: If the pilot used test data or a simplified setup, now is the time to connect the tool to your live systems. Work with IT to integrate it with relevant tools. Fix any issues that surfaced during the pilot, such as slow performance or login problems. If needed, roll out in phases. Start with one group, check performance, then expand. This allows time to solve problems without disrupting firm-wide operations.
3. Governance and Ownership: Assign someone to manage the tool long-term, often from innovation or IT. This person oversees updates, support, vendor communication, and user feedback. Establish clear policies for utilizing the tool, particularly for AI-based systems. Plan for updates and onboarding of new users so the tool remains useful as the firm evolves.
4. Embedding into Practice: Update checklists, templates, and workflows to reflect the new tool. Align incentives if needed. For example, explain how time-saving tools benefit lawyers who bill hourly. Share success stories internally. Let clients know when new tools help you deliver faster, better work. This builds confidence inside and outside the firm.
A strong rollout takes the pilot’s momentum and scales it with care. With good planning, the solution becomes an integral part of how your firm operates.
Best Practices
Below are condensed, practical takeaways that consistently lead to stronger pilot outcomes:
- Start with a real problem: Anchor every pilot to a clear pain point experienced by lawyers or staff. Understand the root cause before exploring solutions.
- Secure stakeholder support early: Involve practice leaders, IT, risk, and actual users during planning. Early input avoids surprises and builds ownership.
- Define success clearly: Use measurable metrics tied to your goal, such as time saved, accuracy, adoption, or cost impact. Write them down before you start.
- Keep the scope tight: Focus on one workflow or team at a time. Broad pilots stretch resources and dilute insight. Start small, prove value, then expand.
- Support users actively: Assign someone to help with questions, training, and blockers. Keep communication steady through office hours or regular check-ins.
- Anticipate risks: Think through data privacy, client concerns, and operational impacts. Use dummy data or parallel runs when needed. Plan for failure too.
- Encourage honest feedback: Make it easy for users to share what works and what doesn’t. Remind them that the goal is learning.
- Be flexible: If a pilot surfaces issues that can be fixed (training gaps or tweaks) address them. If the tool isn’t the right fit, pivot and try another option.
- Prepare to scale: If the pilot succeeds, be ready to roll out. Understand what full implementation will require in terms of budget, systems, and leadership support.
Firms that follow these practices shift from trial-and-error to structured experimentation. They make better decisions faster and reduce risk with each cycle.
Closing Thoughts
Pilots are a way to test, learn, and decide; they are not endpoints. A well-run pilot provides firms with real data to determine whether a solution is effective and worth scaling. The value lies in the process: starting with a clear problem, setting success criteria, closely managing the pilot, and making evidence-based decisions. Whether the tool is adopted or not, each pilot builds capability.
