Beginner Prompting Tips for Lawyers: Ready, Set, Prompt

In this practical session, Ali Chaudhry, Senior Legal Engineer at Simmons & Simmons, demonstrates how legal professionals can move beyond basic AI literacy to reflexive AI fluency using structured prompt engineering. It covers how to adopt the mental model of AI as an always-on junior colleague and sparring partner, structure prompts using a four-part framework (Context, Goal, Expectations, and Grounding), deploy chain-of-thought prompting for complex contract reviews, and apply "negative summaries" to diagnose hallucinations and surface omitted information. Inside: 00:00 - Moving from AI Literacy to Daily AI Fluency in Legal Work 03:40 - Mental Model: Treating Generative AI as an Always-On Junior Colleague 05:23 - How LLMs Work: Statistical Prediction & Subtractive Prompting 06:55 - The AI Bridge: Time Reallocation and Scaling Legal Judgment 10:57 - Prompt Types: Zero-Shot, Few-Shot & Chain-of-Thought Workflows 15:48 - The 4-Part Framework: Context, Goal, Expectations, and Source Grounding 21:06 - Live Walkthrough: Engineering a Supplier Governance Review Prompt 23:24 - Demystifying Hallucinations, Model Sycophancy, and Risk Mitigation 27:39 - Diagnosing Poor Outputs & Using "Negative Summaries" to Surface Omissions 30:17 - From Prompting to Practice: The 5-Point Legal Prompt Checklist 33:05 - Q&A: Handling AI Self-Contradictions and Anchoring Perspective 34:30 - Q&A: Navigating ESG, Compute Power, and Prompt Length 36:38 - Q&A: Risk of Influencing AI vs. Using It as a Sparring Partner 38:40 - Q&A: Prompt Libraries and Using AI to Generate Bespoke Personas At Friday AI Advisory, we audit your team’s day-to-day workflows, identify where AI can save time and improve efficiency, and show your team how to use it in practice through hands-on training and workshops. 📧 Contact team@fridayaiadvisory.com