🎙️ Ep. #134 — AI-Powered Legal Writing: How BriefCatch Helps Lawyers Write Smarter, Not Harder with Ross Guberman.

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My next guest is Ross Guberman — founder of BriefCatch, nationally recognized legal writing trainer, and author of several acclaimed books on persuasive legal writing. Ross has trained thousands of lawyers and judges across the country. After years of teaching the craft of legal writing, he channeled that expertise into building BriefCatch — a purpose-built AI writing tool that lives right inside Microsoft Word and Outlook, scanning your legal documents using roughly 17,000 rules to help you write cleaner, sharper, and more persuasive work product. Whether you're a solo practitioner or part of a large firm, Ross brings insights that are immediately practical — no matter your tech comfort level. 🚀

Join Ross Guberman and me as we discuss the following three questions and more!

  1. 🏆 From your vantage point — having trained thousands of lawyers and judges and now running BriefCatch — what are the top three ways lawyers can leverage AI-driven writing tools like BriefCatch inside Word and Outlook to measurably improve the quality and persuasiveness of their briefs without sacrificing their own voice or judgment?

  2. ⚖️ For a tech-curious but time-strapped practitioner, what are the top three everyday workflows beyond traditional brief writing where lawyers are leaving the most value on the table by not using tools like BriefCatch and other legal tech?

  3. 🔮 Looking ahead five years, what are the top three technology competencies every lawyer must develop — not just "nice to have" skills — to collaborate effectively with AI, stay ethically compliant, and turn technology into a genuine competitive advantage rather than a source of risk?

In our conversation, we cover the following:

  • [00:30] 💻 Ross's current tech setup — MacBook Pro M4 Max, macOS, and iPhone 16

  • [01:30] 🔄 Why keeping your OS updated matters — security and performance

  • [03:00] 🖥️ External monitors, portable screens, and traveling with tech

  • [07:00] 📱 Using your iPad as an external monitor via Apple Sidecar

  • [08:30] 🎪 Bonus Question #1 - Ross’s experience in the ABA TECHSHOW Startup Alley

  • [11:00] ✍️ Question #1 — Top 3 ways to use AI writing tools to improve briefs without losing your voice

  • [12:00] 🧑‍⚖️ Using AI to role-play as a skeptical judge or opposing counsel to pressure-test your brief

  • [13:00] 📊 Transforming fact sections into timelines and case law into comparison charts

  • [14:00] 📝 Using AI as a self-check for hyperbole, redundancy, and tone

  • [15:30] 📲 How judges now read briefs on iPads — and what that means for your writing style

  • [17:00] 📂 Using Text Expander to store and deploy your best prompts

  • [18:30] 🎙️ Google Notebook LLM as a learning and podcast creation tool

  • [20:00] 🧩 Bonus Question #2 — What is BriefCatch and why use purpose-built legal AI over general tools?

  • [21:00] 🚀 The origin story of BriefCatch — from side hustle in 2018 to funded legal tech startup

  • [22:30] ⚙️ Workflow, ethics rules, and attorney-specific conventions — why legal-specific AI wins

  • [24:30] 📋 Question #2 — Top 3 underused everyday workflows for lawyers using AI

  • [25:00] 📧 Using AI with your email to surface unanswered messages and unresolved threads

  • [25:45] 📁 Mining your past work product for patterns, style, and reusable language

  • [26:30] 📅 Having AI review your calendar and correspondence for efficiency insights

  • [27:00] 🔒 Data privacy, security settings, and the risks of default AI configurations

  • [28:30] 🏛️ New York State's data protection approach and what more states should do

  • [29:30] 🤖 Question #3 — Top 3 technology competencies every lawyer must master in the next five years

  • [30:00] 🧠 Understanding how LLMs actually "think" — reading the AI's reasoning chain

  • [30:45] 🖊️ Making AI output sound like you — the human voice in an AI-generated world

  • [31:30] 🔧 Integrating AI into your daily workflow while preserving human judgment

  • [32:00] 👏 Closing thoughts and where to find Ross and BriefCatch

RESOURCES

🔗 Connect with Ross Guberman

  • 📧 Email: ross@briefcatch.com

  • 🌐 Website: https://www.briefcatch.com

  • 💼 LinkedIn: Search "Ross Guberman" on LinkedIn at https://www.linkedin.com

📌 Mentioned in the Episode

🖥️ Hardware Mentioned in the Conversation

☁️ Software & Cloud Services Mentioned in the Conversation

📖 Word of the Week: RAG (Retrieval-Augmented Generation) - The Legal AI Breakthrough Eliminating Hallucinations. 📚⚖️

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What is RAG?

USEd responsibly, rag can be a great tool for lawyers!

Retrieval-Augmented Generation (RAG) is a groundbreaking artificial intelligence technique that combines information retrieval with text generation. Unlike traditional AI systems that rely solely on pre-trained data, RAG dynamically retrieves relevant information from external legal databases before generating responses.

Why RAG Matters for Legal Practice

RAG addresses the most significant concern with legal AI: fabricated citations and "hallucinations." By grounding AI responses in verified legal sources, RAG systems dramatically reduce the risk of generating fictional case law. Recent studies show RAG-powered legal tools produce hallucination rates comparable to human-only work.

Key Benefits

RAG technology offers several advantages for legal professionals:

Enhanced Accuracy: RAG systems pull from authoritative legal databases, ensuring responses are based on actual statutes, cases, and regulations rather than statistical patterns.

Real-Time Updates: Unlike static AI models, RAG can access current legal information, making it valuable for rapidly evolving areas of law.

Source Attribution: RAG provides clear citations and references, enabling attorneys to verify and build upon AI-generated research.

Practical Applications

lawyers who don’t use ai technology like rag will be replaced those who do!

Law firms are implementing RAG for case law research, contract analysis, and legal memo drafting. The technology excels at tasks requiring specific legal authorities and performs best when presented with clearly defined legal issues.

Professional Responsibility Under ABA Model Rules

ABA Model Rule 1.1 (Competence): Comment 8 requires lawyers to "keep abreast of changes in the law and its practice, including the benefits and risks associated with relevant technology." This mandates understanding RAG capabilities and limitations before use.

ABA Model Rule 1.6 (Confidentiality): Lawyers must "make reasonable efforts to prevent the inadvertent or unauthorized disclosure of, or unauthorized access to, information relating to the representation of a client." When using RAG systems, attorneys must verify data security measures and understand how client information is processed and stored.

ABA Model Rule 5.3 (Supervision of Nonlawyer Assistants): ABA Formal Opinion 512 clarifies that AI tools may be considered "nonlawyer assistants" requiring supervision. Lawyers must establish clear policies for RAG usage and ensure proper training on ethical obligations.

ABA Formal Opinion 512: This 2024 guidance emphasizes that lawyers cannot abdicate professional judgment to AI systems. While RAG systems offer improved reliability over general AI tools, attorneys remain responsible for verifying outputs and maintaining competent oversight.

Final Thoughts: Implementation Considerations

lawyers must consider their ethical responsibilities when using generative ai, large language models, and rag.

While RAG significantly improves AI reliability, attorneys must still verify outputs and exercise professional judgment. The technology enhances rather than replaces legal expertise. Lawyers should understand terms of service, consult technical experts when needed, and maintain "human-in-the-loop" oversight consistent with professional responsibility requirements.

RAG represents a crucial step toward trustworthy legal AI, offering attorneys powerful research capabilities while maintaining the accuracy standards essential to legal practice and compliance with ABA Model Rules. Just make sure you use it correctly and check your work!

🎙️ Ep. 117: Legal Tech Revolution,  How Dorna Moini Built Gavel.ai to Transform the Practice of Law with AI and Automation.

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Dorna Moini, CEO and Founder of Gavel, discusses how generative AI is transforming the way legal professionals work. She explains how Gavel helps lawyers automate their work, save time, and reach more clients without needing to know how to code. In the conversation, she shares the top three ways AI has improved Gavel's tools and operations. She also highlights the most significant security risks that lawyers should be aware of when using AI tools. Lastly, she provides simple tips to ensure AI-generated results are accurate and reliable, as well as how to avoid false or misleading information.

Join Dorna and me as we discuss the following three questions and more!

  1. What are the top three ways generative AI has transferred Gavel's offerings and operations?

  2. What are the top three most critical security concerns legal professionals should be aware of when using AI-integrated products like Gavel?

  3. What are the top three ways to ensure the accuracy and reliability of AI-generated results, including measures to prevent false or misleading information or hallucinations?

In our conversation, we cover the following:

[01:16] Dorna's Tech Setup and Upgrades

[03:56] Discussion on Computer and Smartphone Upgrades

[08:31] Exploring Additional Tech and Sleeping Technology

[09:32] Generative AI's Impact on Gavel's Operations

[13:13] Critical Security Concerns in AI-Integrated Products

[16:44] Playbooks and Redline Capabilities in Gavel Exec

[20:45] Contact Information

Resources: 

Connect with Dorna:

Websites & SaaS Products:

  • Apple Podcasts — Podcast platform (for reviews)

  • Apple Podcasts — Podcast platform (for reviews)

  • ChatGPT — AI conversational assistant by OpenAI

  • ChatGPT — AI conversational assistant by OpenAI

  • Gavel — AI-powered legal automation platform (formerly Documate)

  • Gavel Exec — AI assistant for legal document review and redlining (part of Gavel)

  • MacRumors — Apple news and product cycle information

  • MacRumors — Apple news and product cycle information

  • Notion — Workspace for notes, databases, and project management

  • Notion — Workspace for notes, databases, and project management

  • Slack — Team communication and collaboration platform 

Hardware:

Other: