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

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

• 🎤 ABA TECHSHOW — Annual legal technology conference hosted by the American Bar Association: https://www.techshow.com/
• 🎤 ABA TECHSHOW Startup Alley — Competition for early-stage legal tech startups at ABA TECHSHOW: https://www.techshow.com/sessions/startup-alley/
• ⚖️ Anthropic / Defense Department data privacy discussion — https://time.com/article/2026/03/16/your-data-pentagon-battle-with-anthropic/
• 🗒️ Google Notebook LLM — AI-powered note-taking and audio podcast generation tool: https://notebooklm.google.com
• 📰 Legal Week New York — Premier legal industry conference: https://www.event.law.com/legalweek
• 🎙️ Mac Geek Gab Podcast (Dave Hamilton, Pilot Pete & Adam Christiansons): https://www.macgeekgab.com
• 🎙️ Mac Power Users Podcast (David Sparks): https://www.relay.fm/mpu
• 🌐 MacRumors.com Buyer's Guide — Track Apple product release cycles before you buy: https://buyersguide.macrumors.com
• 📝 Text Expander — Text snippet and macro expansion tool for power users: https://textexpander.com

🖥️ Hardware Mentioned in the Conversation

• 📟 Apple iPad — https://www.apple.com/ipad/
• 📱 Apple iPhone 16 — https://www.apple.com/iphone-16/
• 💻 Apple MacBook Pro 16" (2024, M4 Max chip) — https://www.apple.com/macbook-pro/
• ⌚ Apple Watch — mentioned (Ross humorously declines to use one): https://www.apple.com/apple-watch/

☁️ Software & Cloud Services Mentioned in the Conversation

• 🍎 Apple macOS Tahoe (latest OS at time of recording): https://www.apple.com/macos/
• 🪟 Apple Sidecar — Built-in macOS feature for using iPad as external display: https://support.apple.com/en-us/HT210380
• ✍️ BriefCatch — AI-powered legal writing tool for Word and Outlook: https://www.briefcatch.com
• 🤖 ChatGPT (OpenAI) — https://chat.openai.com
• 🤖 Claude (Anthropic) — https://claude.ai
• 🎧 Descript — Audio/Video editing tool used by the host for podcast production: https://www.descript.com
• 📧 Gmail — https://mail.google.com
• 📓 Google NotebookLM — https://notebooklm.google.com
• 🛠️ GitHub — Code repository mentioned as part of BriefCatch's tech stack: https://github.com
• 📨 Microsoft Outlook — https://www.microsoft.com/en-us/microsoft-365/outlook/email-and-calendar-software-microsoft-outlook
• 🪟 Microsoft Word — https://www.microsoft.com/en-us/microsoft-365/word
• 🐍 Python — Programming language referenced by Ross in context of BriefCatch's development — https://www.python.org/
• 🗒️ Text Expander — https://textexpander.com