Reinvention begins with practice
Most legal teams say they want to get better at using AI. Fewer actually start. The hesitation is understandable. You want to be careful, you want to be right, and you don’t want to put privileged data anywhere near an experimental system. But the truth is that fluency only comes from use. The first AI drill ifor legal teams sn’t about mastery, instead, It’s about learning how to think, experiment, and assess risk together as a team.
Start Small and Reversible
The best place to begin an AI drill for legal teams is with something that matters enough to be real but not so high stakes that you’ll panic. Choose a short, standard document your team knows by heart. An NDA works perfectly. It’s short, structured, and safe to test if you redact names and confidential details.
Give your team a simple brief: “We’re going to see what a general-purpose AI tool can do with this NDA.” Ask one person to act as facilitator. Their job is to keep the exercise on track, not to play tech expert.
Frame the Purpose Clearly
The goal here isn’t automation, it’s learning. Think of this drill as an exercise in judgment. What does the tool handle well? Where does it struggle? And what assumptions does it make about the way your team works? When your team approaches the drill as a collaborative simulation rather than a performance test, the whole experience becomes far more valuable.
Have everyone jot down what they expect before they begin. This step is critical because it surfaces unconscious assumptions. Many lawyers assume the system will hallucinate or rewrite terms aggressively. Others expect perfection. Capturing both extremes helps everyone notice what actually happens during the exercise.
Run the Exercise
Paste the NDA into your chosen AI tool. Then ask a few structured questions:
- “Summarize this NDA for a business audience.”
- “What are the top three negotiation risks?”
- “Identify any missing standard clauses.”
Let everyone read the output quietly first. Then discuss. What did the AI notice that surprised you? What did it ignore that you would never miss? And what kind of errors could create real exposure? The value is in the conversation, not the document.
Someone will inevitably ask, “Can we trust this?” That’s the moment to teach what the drill is really about: critical engagement. The goal isn’t to trust or reject the output. It’s to learn how to interrogate it.
Debrief and Reflect
After the discussion, take ten minutes to capture what the team learned. You’ll want three kinds of insights:
- Technical: What did the AI get right or wrong?
- Process: How did the workflow feel compared to manual review?
- Judgment: Where did human reasoning still add the most value?
This debrief transforms the experiment from curiosity into knowledge. You now have a tangible baseline for future AI use. The next time someone wants to pilot an AI tool, you’ll have a shared language for evaluating accuracy, bias, and trustworthiness.
Turn Insight Into Next Step
The first drill is never about the NDA. It’s about building a muscle: the ability to experiment responsibly. Once your team sees that it can explore AI without risking data or credibility, momentum grows.
The next iteration might test a more complex clause or compare two systems. Or you might create a lightweight internal rubric for scoring AI quality. Either way, the important part is to keep practicing.
Reinvention in legal doesn’t happen in theory. It happens in motion. The first drill gets your team moving, together, curious, and ready to learn what this technology can really do.
