The courtroom is a battlefield, and as a trial lawyer, you know that the best-prepared warrior wins. But preparation isn’t just about knowing the law—it’s about leveraging every tool at your disposal to outmaneuver the opposition. In today’s digital world, technology is one of the most powerful weapons there is.
Robert Simon, a trial lawyer who built a powerhouse personal injury firm, The Simon Law Group, knows this firsthand. He’s not just a lawyer—he’s an innovator. As the founder of Justice HQ and Attorney Share, Simon stands at the intersection of law and technology, using cutting-edge tools to give his firm—and others—a significant advantage in the courtroom. He recently spoke during the Peak Practice in 2025 webinar about leveraging technology fully to accelerate personal injury practices.
The Tech-Driven Advantage for Trial Lawyers
Imagine this: You’re knee-deep in trial prep, juggling motions, depositions, and client meetings. The clock is ticking. What if you could free up hours of your time—without sacrificing quality?
That’s exactly what Simon has done by implementing automation and AI in his firm. He has built an infrastructure that doesn’t just assist with case management—it keeps lawyers on his team focused on what matters most: helping the client by winning.
Simon is constantly refining the tools that make trial preparation smarter, faster, and more precise. But he warns: not all AI is created equal.
The AI Trap: Why OpenAI May Be Dangerous for Lawyers
AI is everywhere, but trial lawyers must be cautious. OpenAI’s public models pull data from sources like Reddit and Google—unverified, biased, and potentially disastrous if relied on for legal work. Simon’s golden rule? Never drop confidential client information into an open AI platform.
Instead, invest in closed-data AI models, built on secure, verifiable legal data. This isn’t just about efficiency—it’s about protecting your clients and your reputation.
AI-Driven Tools That Give Trial Lawyers the Edge
Simon has tested and vetted dozens of AI-powered tools that supercharge trial preparation. Here are the ones that stand out:
1. Foundation AI – Say goodbye to endless scanning and document sorting. Foundation AI automatically renames, categorizes, and files documents, saving hours of manual work.
2. AI-Powered Chatbots – Simon built his own chatbot using Personal.ai, trained on his personal trial transcripts, depositions, and case strategies. It serves as an instant resource for his firm and Justice HQ members, offering on-demand legal knowledge.
3. AI-Assisted Discovery (EsquireTek) – Creates instant discovery documents, pulling case details into a ready-to-use format. No more paralegals spending hours on this—just review, refine, and file.
4. Automated Intake and Case Management – Tools like Clio Grow, Lead Docket, and Filevine streamline client intake, ensuring that every lead is tracked, assessed, and processed efficiently.
Revolutionizing Legal Research: Finding the Smoking Gun Faster
Legal research used to be an exhausting grind. Now, AI tools like Lexis+ AI, Westlaw Practical Co-Counsel, and CaseText can sift through thousands of cases in seconds, pinpointing the exact precedent needed to crush an opponent’s argument.
Simon urges trial lawyers to verify AI-generated work but notes that these tools now hyperlink directly to their sources, eliminating the risk of hallucinated citations.
The Art of the Demand Letter
If you handle personal injury cases, EvenUp might be your new best friend. It doesn’t just generate demand letters—it calculates case values, factoring in adjuster trends, injury severity, and jurisdiction. That means stronger demands, bigger settlements, and less time wasted.
Turning Your Marketing into a Case-Generating Machine
For trial lawyers, visibility means victory. AI isn’t just changing how cases are handled—it’s transforming marketing.
Simon uses GetMunch AI to extract the best clips from his long-form content, generating engaging LinkedIn and Twitter posts. The result? More engagement, more referrals, and more high-value cases coming directly into his case management system.
And what happens when those leads convert? AI tools like CaptureNow handle AI-powered intake screening, ensuring that only qualified cases reach his legal team.
The Future: AI-Powered Advocacy
Picture this: An AI-powered intake system that speaks with your voice, screening potential clients in real time. This isn’t science fiction—it’s happening now. Trial lawyers who ignore this shift will get left behind.
Simon’s message is clear: Don’t just practice law—build a system that lets you practice better. Automate the grunt work. Let AI handle the drudgery. Focus on winning cases and dominating your niche.
The firms that embrace technology will thrive. The ones that resist it? They’ll struggle to compete.
Are you ready to transform your firm?
For insights, product recommendations, or a deeper dive into the AI tools shaping the future of trial law, connect with Robert Simon on Instagram (@PlanetFunBob) or here on LinkedIn at https://www.linkedin.com/in/roberttsimon/
But be patient—his AI assistant might screen you first.
https://www.linkedin.com/pulse/robert-simon-leveraging-technology-transform-legal-jason-d–h2wle
