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

/ The Tech-Savvy Lawyer.Page/

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

Shout Out: Previous Podcast Guest Ruby Powers Invites Your The Tech-Savvy Lawyer.Page Blogger and Podcaster Back on Power Up Your Practice!

/ The Tech-Savvy Lawyer.Page/

I recently had the honor of joining Ruby Powers on her Power Up Your Practice Podcast, and I could not be more excited about what we covered for fellow lawyers. We talked about legal podcasting as a practical, ethical, and highly effective way for attorneys to build visibility, deepen relationships, and modernize their marketing without needing to be “hardcore tech people.”

On Ruby’s show, I shared why I believe that podcasting is becoming the new networking standard for lawyers. When you regularly publish episodes—whether about your day-to-day practice, a niche topic, or even a related interest—you push your name and your ideas into the online world in a consistent way. Search engines and AI systems notice this. Over time, your name and your content start to surface more often when people search for your practice area, your type of work, or your expertise. That is real SEO, and it comes from steady, quality content rather than tricks or gimmicks.

Another reason I encourage lawyers to podcast is simple: your voice makes you more human. Listeners hear how you think and how you explain things. They hear your tone and your values. That goes far beyond a static bio or a profile page. Whether your audience is potential clients, referral sources, peers, or the broader public, a podcast lets them get to know you in a safe and scalable way. This is networking that keeps working for you even when you are in court, in a hearing, or taking a much-needed break. 🌟

I also understand that many lawyers hesitate because they are concerned about ethics. That concern is healthy. As attorneys, we cannot ignore ABA Model Rules and similar state rules when we put content into the world. On the podcast, Ruby and I discussed that while a show can be an excellent educational and marketing tool, we must avoid giving individualized legal advice and avoid accidentally creating an attorney–client relationship. I strongly recommend clear, prominent disclaimers that explain the podcast is for informational purposes only, does not create an attorney–client relationship, and should not be relied on as legal advice for any specific matter.

This aligns with our obligation of competence under Model Rule 1.1, which now includes understanding relevant technology, and with our duties around communications and advertising under Model Rules 7.1 and following. A well-run legal podcast respects those boundaries. It presents general information and insights, and it invites listeners to seek formal counsel if they need advice for their specific situation. When you treat your podcast as education plus relationship-building, not as a substitute for representation, you are already thinking in the right direction.

In our conversation, Ruby and I also addressed a common fear: “I’m not tech-savvy enough to start a podcast.” As someone known as the Tech-Savvy Lawyer, I want to be clear: you do not need to be a full-time tech enthusiast to do this. You likely already have access to most of what you need. A solid microphone, a decent camera, and a platform like Zoom, Riverside, or StreamYard can take you surprisingly far. Many of these tools are user-friendly and continue to improve. You can start with the basics and then layer on more sophistication as you grow more comfortable. 🎧

Ruby shared her own experience of initially overthinking her podcast. She wanted it to be perfect, and that almost stopped her from launching. I hear that from lawyers all the time. My advice is simple: do not wait for perfect. Your early episodes will probably make you cringe later, which means you are improving. That is a good sign. Focus on clear audio, honest content, and consistent scheduling. Over time, you can refine your editing, your format, and even your branding. You can bring in a contractor or a service to help with editing once you know you want to keep going.

We also discussed the flexibility podcasting offers. You can publish weekly, every other week, or monthly. You can create solo episodes where you explain key topics. You can host interviews with colleagues, experts, or community leaders. You can even experiment with live formats, where audience members submit questions in advance, and you answer them at a general, educational level. The format should fit your bandwidth, your goals, and your audience.

One concept I emphasized is the idea of an “ideal listener” or avatar. Before you hit record, think about exactly who you are speaking to. Is it a potential client in a specific practice area? Other lawyers in your niche? Law students or young practitioners? Having that profile in mind will guide your topic choices, your language, and your examples. It also helps you stay focused on value rather than drifting into random conversations that do not support your goals.

From a business perspective, legal podcasting can support your referral network in powerful ways. Colleagues can share your episodes, which subtly introduce you as a trusted resource. Prospective clients may listen to several episodes before they ever contact you, which means they arrive already familiar with your style and approach. That can shorten the trust-building curve and make consultations more productive.

What I appreciate about Ruby’s Power Up Your Practice platform is that it treats podcasting not as a vanity project, but as part of a larger ecosystem of law practice management, technology, and professional development. My appearance on her show gave me a chance to tie together what I see in my own practice, my blog, my podcast, and my book: lawyers do not need to fear technology. We need to engage with it thoughtfully, guided by the same ethics and judgment we apply in every other part of our work.

If you are a lawyer with limited to moderate tech skills and you have been on the fence about starting a podcast, I invite you to listen to my conversation with Ruby and let it serve as a practical, encouraging blueprint. You will hear that you are not alone in your concerns, that there are clear ways to stay compliant with ABA Model Rules, and that the path to becoming a “tech-savvy lawyer” does not require perfection—only willingness, consistency, and a focus on delivering value. 🚀

Enjoy!

TSL.P EP# 132 (Special Episode): AI, Deepfakes, and Metadata: Guest-Hosting Capital University Law School’s First Law Library Podcast Club with Professor Jennifer Wondracek 🎙️⚖️

/ The Tech-Savvy Lawyer.Page/

🎙️ This week, we have something special for you. Your The Tech-Savvy Lawyer.Page blogger and podcaster, Michael D.J. Eisenberg, was invited back to his alma mater, Capital University Law School, to guest host their very first Podcast Club — a live, recorded podcast conversation featuring real law students, real questions, and real talk. Moderated alongside Professor Wondracek, this is an unscripted, in-the-moment discussion — not a produced studio episode, not a rehearsed explainer — just an honest, practitioner-led conversation about the issues shaping the legal profession today. 🎓 We think that's exactly what makes it worth your time. 🛡️⚖️

In our conversation, we cover the following:

  • [00:00] 🎬 Welcome & Introductions — Professor Raik introduces Michael D.J. Eisenberg; Michael shares his background representing veterans before the VA and his work at The Tech-Savvy Lawyer.Page, including his Amazon #1 bestselling book The Lawyer's Guide to Podcasting

  • [01:00] 🕵️ What Is a Deepfake? — Defining deepfakes and the real-world Bethesda incident where a fabricated video triggered a police raid and wasted critical law enforcement resources

  • [02:30] ⚖️ Deepfakes in Legal Practice — The serious professional responsibility consequences when attorneys introduce fake or AI-generated evidence into a trial or negotiation — and why "I didn't know" won't always protect you

  • [03:00] 📋 ABA Model Rule 1.1 — Competence & Comment 8 — Why technology competence is an ethical obligation, not optional — and what "competent use of technology" actually means for your daily practice

  • [05:00] 📶 Public Wi-Fi & VPN Security — The real dangers of using public Wi-Fi at airports, coffee shops, and on planes without a VPN, especially when accessing client portals, trust accounts, or confidential client communications

  • [05:45] 🔐 VPN Recommendations — NordVPN vs. ExpressVPN; why the right VPN matters for protecting your clients and your license

  • [07:00] 🔍 How to Detect Deepfakes in Evidence — Reviewing file metadata, spotting visual anomalies, and the Mendones v. Cushman & Wakefield case (Cal. Super. Ct. 2025) where Judge Victoria Kolakowski spotted deepfake videos — and imposed terminating sanctions

  • [08:30] 📜 ABA Model Rule 3.3 — Candor to the Tribunal — Your duty of honesty to the court and the compounding risks of unknowingly submitting falsified AI-generated evidence

  • [09:30] 🧑‍⚖️ ABA Model Rule 8.4 — Dishonesty, Fraud, Deceit & Misrepresentation — How these rules can stack with Rule 3.3 to multiply your ethical exposure

  • [10:30] 🖼️ Live Demo: Accessing File Metadata — A real-time screen share showing how to right-click and access image properties, including GPS coordinates, camera settings, file timestamps, and modification history — using a photo taken right at Capital University Law School

  • [14:00] 🗂️ Metadata Scrubbing — Why some law firms strip metadata from outgoing emails and documents, and why "scrubbed" evidence should raise red flags during discovery

  • [17:30] 🛡️ Five Basic Safeguards for Legal Professionals in the AI Era:

    • Invest in ongoing education — CLEs, podcasts, blogs

    • Know and follow your office's technology protocols

    • Be transparent with clients about your use of AI — in your engagement letters and contracts

    • Update your engagement letters and retainer agreements now

    • Stay alert to the rapidly changing AI landscape — ignoring it is not an option

  • [20:00] 💬 Student Q&A — George's question: Does the ethical obligation to review metadata create a resource gap between large firms and solo practitioners? What AI tools can help level the playing field?

  • [22:00] ⚠️ United States v. Heppner (S.D.N.Y. 2026) — The landmark federal ruling that AI-generated documents used with consumer AI tools are NOT protected by attorney-client privilege or work product doctrine — and why your choice of AI platform is now an ethics decision

  • [23:30] 🔒 Consumer AI vs. Secure Legal AI Platforms — The critical difference between free and low-cost consumer AI accounts and enterprise-grade legal AI tools with zero-data-retention contracts

  • [25:30] 📚 LexisNexis Protégé & Secure AI — How LexisNexis's zero-retention, end-to-end encrypted AI platform — including access to ChatGPT and Claude — lets attorneys use AI ethically without jeopardizing client data

  • [27:00] 💾 Prompt Discoverability — Why your AI prompts may be subpoenaed in malpractice claims or bar investigations, and why documenting and downloading your AI usage history matters

  • [28:30] 📁 Cassia's Question — Documenting AI research and adopting a random sampling strategy for metadata review: practical approaches to demonstrating "reasonable" due diligence

  • [30:00] 🗃️ eDiscovery Tools for Metadata at Scale — Relativity, Disco, and how these platforms help even resource-limited firms surface metadata anomalies across large document sets

  • [33:00] 📰 Current Awareness Resources — Where to stay current on legal tech: law.com, bar association newsletters, The Tech-Savvy Lawyer.Page blog and podcast, CLEs, and legal listservs

  • [33:30] 🚨 Hallucinated AI Citations & Real Consequences — Mata v. Avianca, Wadsworth v. Walmart (Morgan & Morgan pro hac vice revoked), the Chicago firm dissolution case — and why citation-checking is now a non-negotiable litigation skill

  • [37:00] 🎲 Book Giveaway — Rolling the virtual dice; congratulations to the winner of Michael's book, The Lawyer's Guide to Podcasting!

  • [38:00] 🗓️ Upcoming Events — Michael joins the Capital Law Spring Summit/Bootcamp in April; dinner with students at The Red Door Tavern

Resources

Connect with Professor Jennifer Wondracek:

  • E-Mail: jwondracek@law.capital.edu 

  • LinkedIn: https://www.linkedin.com/in/jennifer-wondracek

📌 Mentioned in the Episode

🏛️ ABA Model Rules

⚖️ Case Law

🤔 Other

💻 Hardware Mentioned in the Conversation

☁️ Software & Cloud Services Mentioned in the Conversation

TSL Labs 🧪 Initiative: Attorney-Client Privilege vs. Public AI: The Hoeppner Decision Lawyers Need to Understand in 2026 ⚖️🤖

/ The Tech-Savvy Lawyer.Page/

Join us for an AI-powered deep dive into the ethical challenges facing legal professionals in the age of generative AI. 🤖 We unpack the February 23, 2026, editorial AI may not be your co‑counsel—and a recent SDNY decision just made that painfully clear. ⚖️🤖.  Our Google Notebook LLM hostsbreaks down why a single click on a public AI tool’s Terms of Use can trigger a privilege waiver, and what “tech competence” really means in 2026—especially after United States v. Hoeppner and Judge Jed Rakoff’s wake-up-call analysis of confidentiality and third-party disclosure risk.

🔗 Read the full editorial on The Tech-Savvy Lawyer.Page and share this episode with a colleague who is experimenting with AI in client matters.

In our conversation, we cover the following

  • 00:00 — The “superhuman assistant” promise, and the procedural nightmare risk. 🧠⚖️

  • 00:01 — The core warning: AI use can “blow a hole” in privilege.

  • 00:02 — Editorial overview: “The AI Privilege Trap” by Michael D.J. Eisenberg.

  • 00:02 — The case: United States v. Hoeppner (SDNY) and why it matters.

  • 00:03 — Why Judge Jed Rakoff’s opinion gets attention (tech-literate, influential).

  • 00:03 — The facts: defendant drafts with a public AI tool, then sends outputs to counsel.

  • 00:04 — The court’s conclusion: no attorney-client privilege, no work product protection.

  • 00:05 — Privilege basics applied to AI: “confidential + lawyer” and why AI fails that test.

  • 00:06 — The Terms-of-Use problem: inputs/outputs may be collected and shared. 🧾

  • 00:07 — The “stranger on the street” analogy: you can’t retroactively make it confidential.

  • 00:08 — PII and client facts: why pasting sensitive data into public AI is high-risk.

  • 00:08 — ABA Model Rule 1.1: competence includes understanding tech risks.

  • 00:09 — ABA Model Rule 1.6: confidentiality and waiver risk with public AI.

  • 00:10 — “Reasonable safeguards”: read policies, adjust settings, and know training/logging.

  • 00:11 — Public vs. enterprise AI: why contracts and “walled gardens” matter.

  • 00:11 — Legal research AI examples discussed: Lexis/Westlaw-style AI offerings.

  • 00:12 — ABA Model Rules 5.1 & 5.3: supervise AI like a nonlawyer assistant/vendor.

  • 00:13 — Redefining “tech-savvy lawyer” in 2026: judgment and restraint. 🧭

  • 00:14 — The “straight-face test”: could you defend confidentiality after a judge reads the policy?

  • 00:15 — Client-side risk: clients can sabotage privilege before contacting counsel.

  • 00:16 — Practical takeaway: check settings, read the fine print, keep true secrets offline (for now). 🔒

RESOURCES

Mentioned in the episode

Software & Cloud Services mentioned in the conversation

Redaction Fails & Ethical Tales: What the Epstein Files Teach Us About Data Security

/ The Tech-Savvy Lawyer.Page/

Join us in this Google Notebook LLM-powered discussion on last week’s How To: Redact PDF Documents Properly and Recover Data from Failed Redactions: A Guide for Lawyers After the DOJ Epstein Files Release “Leak”. Watch this informative presentation: Perfect for those who prefer to watch, listen and learn. In this episode, we dissect the Department of Justice’s recent high-profile failure to properly redact the Epstein files—a blunder that exposed sensitive information through a simple "copy and paste." We explore the critical difference between hiding data and destroying it, the technical steps to ensure your redactions are permanent, and the complex ethical obligations under ABA Model Rule 4.4 for both the sender and the receiver of inadvertently disclosed information.

In our conversation, we cover the following:

  • [00:00:00] – Introduction: Introduction to the tech lessons from the DOJ’s redaction failure.

  • [00:00:30] – The Golden Rule of Data Redaction: Why hiding text isn't the same as destroying it.

  • [00:01:00] – Case Study: The Epstein Files release and the "sophisticated" hack that wasn't (it was just a bad redaction).

  • [00:01:30] – The Sticky Note Analogy: Visualizing the difference between masking data and digitally shredding it.

  • [00:02:00] – The 5-Step Safety Check: How to use dedicated tools to sanitize documents and remove metadata properly.

  • [00:02:40] – The "Select All" Trick: Demonstrating how easily black boxes can be bypassed without hacking skills.

  • [00:03:30] – The Sender’s Liability: Analyzing the Duty of Competence and Duty of Confidentiality in the digital age.

  • [00:04:15] – The Receiver’s Ethical Dilemma: Navigating ABA Rule 4.4 when you receive information you weren't supposed to see.

  • [00:05:00] – Conclusion & Call to Action: Steps to stay ahead in legal tech.

RESOURCES:

Mentioned in the episode:

Software & Cloud Services mentioned in the conversation:

🎙️ Ep. #127: Mastering Legal Storytelling and AI Automation with Joshua Altman 🎙️⚖️

/ The Tech-Savvy Lawyer.Page/

In Episode 127, I sit down with Joshua Altman, Managing Director of Beltway.Media, to decode the intersection of legal expertise and narrative strategy. 🏛️ We dive deep into the tech stack that powers a modern communications firm and explore how lawyers can leverage AI without losing their unique professional voice. Joshua shares actionable insights on using tools like Gumloop and Abacus.AI to automate workflows, the critical mistakes to avoid during high-stakes crisis management, and the real metrics you need to track to prove marketing ROI. 📊 Whether you are a solo practitioner or part of a large firm, this conversation bridges the gap between complex legal work and compelling public communication.

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

  1. What are the top three technology tools or platforms you recommend that would help attorneys transform a single piece of thought leadership into multiple content formats across channels, and how can they use AI to accelerate this process without sacrificing their professional voice?

  2. What are the top three mistakes attorneys and law firms make when communicating during high-stakes situations—whether that’s managing negative publicity, navigating a client crisis, or pitching to potential investors—and how can technology help them avoid these pitfalls while maintaining their ethical obligations?

  3. What are the top three metrics for their online marketing technology investments that attorneys should actually be tracking to demonstrate return on investment, and what affordable technology solutions would you recommend to help them capture and analyze this data?

In our conversation, we cover the following:

  • [00:00] Introduction to Joshua Altman and Beltway.Media.

  • [01:06] Joshua’s current secure tech stack: From Mac setups to encrypted communications.

  • [03:52] Strategic content repurposing: Using AI as a tool, not a replacement for your voice.

  • [05:30] The "Human in the Loop" necessity: Why lawyers must proofread AI content.

  • [10:00] Tech Recommendation #1: using Abacus.AI and Root LLM for model routing.

  • [11:00] Tech Recommendation #2: Automating workflows with Gumloop.

  • [15:43] Tech Recommendation #3: The "Low Tech" solution of human editors.

  • [16:47] Crisis Communications: Navigating the Court of Public Opinion vs. the Court of Law.

  • [20:00] Using social listening tools for litigation support and witness tracking.

  • [24:30] Metric #1: Analyzing Meaningful Engagement (comments vs. likes).

  • [26:40] Metric #2: Understanding Impressions and network reach (1st vs. 2nd degree).

  • [28:40] Metric #3: Tracking Clicks to validate interest and sales funnels.

  • [31:15] How to connect with Joshua.

RESOURCES:

Connect with Joshua Altman

Mentioned in the episode

Hardware mentioned in the conversation

Software & Cloud Services mentioned in the conversation

  • Abacus.AI - AI platform mentioned for its "Root LLM" model routing feature.

  • ChatGPT - AI language model.

  • Claude - AI language model.

  • Constant Contact - Email marketing platform.

  • Gumloop - AI automation platform for newsletters and social listening.

  • LinkedIn - Professional social networking.

  • MailChimp - Email marketing platform.

  • Proton Mail - Encrypted email service.

  • Tresorit - End-to-end encrypted file sharing (secure Dropbox alternative).

MTC: The Hidden Danger in Your Firm: Why We Must Teach the Difference Between “Open” and “Closed” AI!

/ The Tech-Savvy Lawyer.Page/

Does your staff understand the difference between “free” and “paid” aI? Your license could depend on it!

I sit on an advisory board for a school that trains paralegals. We meet to discuss curriculum. We talk about the future of legal support. In a recent meeting, a presentation by a private legal research company caught my attention. It stopped me cold. The topic was Artificial Intelligence. The focus was on use and efficiency. But something critical was missing.

The lesson did not distinguish between public-facing and private tools. It treated AI as a monolith. This is a dangerous oversimplification. It is a liability waiting to happen.

We are in a new era of legal technology. It is exciting. It is also perilous. The peril comes from confusion. Specifically, the confusion between paid, closed-system legal research tools and public-facing generative AI.

Your paralegals, law clerks, and staff use these tools. They use them to draft emails. They use them to summarize depositions. Do they know where that data goes? Do you?

The Two Worlds of AI

There are two distinct worlds of AI in our profession.

First, there is the world of "Closed" AI. These are the tools we pay for - i.e., Lexis+/Protege, Westlaw Precision, Co-Counsel, Harvey, vLex Vincent, etc. These platforms are built for lawyers. They are walled gardens. You pay a premium for them. (Always check the terms and conditions of your providers.) That premium buys you more than just access. It buys you privacy. It buys you security. When you upload a case file to Westlaw, it stays there. The AI analyzes it. It does not learn from it for the public. It does not share your client’s secrets with the world. The data remains yours. The confidentiality is baked in.

Then, there is the world of "Open" or "Public" AI. This is ChatGPT. This is Perplexity. This is Claude. These tools are miraculous. But they are also voracious learners.

When you type a query into the free version of ChatGPT, you are not just asking a question. You are training the model. You are feeding the beast. If a paralegal types, "Draft a motion to dismiss for John Doe, who is accused of embezzlement at [Specific Company]," that information leaves your firm. It enters a public dataset. It is no longer confidential.

This is the distinction that was missing from the lesson plan. It is the distinction that could cost you your license.

The Duty to Supervise

Do you and your staff know when you can and can’t use free AI in your legal work?

You might be thinking, "I don't use ChatGPT for client work, so I'm safe." You are wrong.

You are not the only one doing the work. Your staff is doing the work. Your paralegals are doing the work.

Under the ABA Model Rules of Professional Conduct, you are responsible for them. Look at Rule 5.3. It covers "Responsibilities Regarding Nonlawyer Assistance." It is unambiguous. You must make reasonable efforts to ensure your staff's conduct is compatible with your professional obligations.

If your paralegal breaches confidentiality using AI, it is your breach. If your associate hallucinates a case citation using a public LLM, it is your hallucination.

This connects directly to Rule 1.1, Comment 8. This represents the duty of technology competence. You cannot supervise what you do not understand. You must understand the risks associated with relevant technology. Today, that means understanding how Large Language Models (LLMs) handle data.

The "Hidden AI" Problem

I have discussed this on The Tech-Savvy Lawyer.Page Podcast. We call it the "Hidden AI" crisis. AI is creeping into tools we use every day. It is in Adobe. It is in Zoom. It is in Microsoft 365.

Public-facing AI is useful. I use it. I love it for marketing. I use it for brainstorming generic topics. I use it to clean up non-confidential text. But I never trust it with a client's name. I never trust it with a very specific fact pattern.

A paid legal research tool is different. It is a scalpel. It is precise. It is sterile. A public chatbot is a Swiss Army knife found on the sidewalk. It might work. But you don't know where it's been.

The Training Gap

The advisory board meeting revealed a gap. Schools are teaching students how to use AI. They are teaching prompts. They are teaching speed. They are not emphasizing the where.

The "where" matters. Where does the data go?

We must close this gap in our own firms. You cannot assume your staff knows the difference. To a digital native, a text box is a text box. They see a prompt window in Westlaw. They see a prompt window in ChatGPT. They look the same. They act the same.

They are not the same.

One protects you. The other exposes you.

A Practical Solution

I have written about this in my blog posts regarding AI ethics. The solution is not to ban AI. That is impossible. It is also foolish. AI is a competitive advantage.

* Always check the terms of use in your agreements with private platforms to determine if your client confidential data and PII are protected.

The solution is policies and training.

  1. Audit Your Tools. Know what you have. Do you have an enterprise license for ChatGPT? If so, your data might be private. If not, assume it is public.

  2. Train on the "Why." Don't just say "No." Explain the mechanism. Explain that public AI learns from inputs. Use the analogy of a confidential conversation in a crowded elevator versus a private conference room.

  3. Define "Open" vs. "Closed." Create a visual guide. List your "Green Light" tools (Westlaw, Lexis, etc.). List your "Red Light" tools for client data (Free ChatGPT, personal Gmail, etc.).

  4. Supervise Output. Review the work. AI hallucinates. Even paid tools can make mistakes. Public tools make up cases entirely. We have all seen the headlines. Don't be the next headline.

The Expert Advantage

The line between “free” and “paid” ai could be a matter of keeping your bar license!

On The Tech-Savvy Lawyer.Page, I often say that technology should make us better lawyers, not lazier ones.

Using Lexis+/Protege, Westlaw Precision, Co-Counsel, Harvey, vLex Vincent, etc. is about leveraging a curated, verified database. It is about relying on authority. Using a public LLM for legal research is about rolling the dice.

Your license is hard-earned. Your reputation is priceless. Do not risk them on a free chatbot.

The lesson from the advisory board was clear. The schools are trying to keep up. But the technology moves faster than the curriculum. It is up to us. We are the supervisors. We are the gatekeepers.

Take time this week. Gather your team. Ask them what tools they use. You might be surprised. Then, teach them the difference. Show them the risks.

Be the tech-savvy lawyer your clients deserve. Be the supervisor the Rules require.

The tools are here to stay. Let’s use them effectively. Let’s use them ethically. Let’s use them safely.

MTC

📢 Shout Out! ILTACON 2025 Recap: AI Revolution, Cybersecurity Imperatives, and the Exciting Legal Tech Future!

/ The Tech-Savvy Lawyer.Page/

🎉 Three Game-Changing Highlights from Legal Technology's Premier Event!

Iltacon - The only peer-created and led conference for legal technology professionals.

The corridors of the Gaylord National Resort & Convention Center just outside Washington, DC were buzzing with an energy as one fellow reporter aptly put it was the most excitement he’d seen at ILTACON in years – and the catalyst was undeniably artificial intelligence.

With over 4,000 legal professionals from 30 different countries converging in National Harbor, Maryland, from August 10-14, ILTACON 2025 delivered an unprecedented showcase of innovation. The numbers tell the story: over 225 vendors and over 80 educational sessions created a treasure trove of legal technology advancements that had attorneys and IT professionals equally captivated.

🚀 Highlight #1: AI Takes Center Stage – From Pilots to Production

The shift from AI experimentation to implementation was unmistakable. Harvey, iManage, Thomson Reuters, and Litera weren't just talking about AI anymore – they were demonstrating working solutions and real-world results.

AI agents emerged as the breakout stars. These sophisticated systems move beyond simple chatbots to become "digital colleagues" that can plan, reason, and execute complex legal tasks autonomously. The "Orchestrating Intelligence: AI Agents in the Legal Space" session showcased how these tools amplify human capabilities rather than replace them, with speakers noting that agents will be able to do much more, but with a better quality output.

iltacon was ready for it 4000+ attendees from 30+ countries!

Knowledge Management experienced a renaissance. The "KM Roundtable: Embracing the New Wave of Knowledge Management" revealed that KM professionals have become the unsung heroes of AI implementation. Without proper content governance and data structure, even the most advanced AI tools fall flat. KM teams are shifting from maintaining knowledge bases to orchestrating AI workflows and ensuring data quality.

Interoperability standards like the Model Context Protocol (MCP) are breaking down data silos. These developments signal a future where AI tools can seamlessly integrate across platforms without costly custom development.

Real-world applications dominated discussions. Sessions demonstrated concrete time savings: customers reported 50-70% time savings reaching early drafts with better consistency, while legal research showed 60%+ time savings while discovering new arguments in cross-jurisdictional litigation. The "Charting Your Search Journey in the Age of AI" session emphasized how precedent research has evolved from "finding a needle in a haystack" to having a "haystack full of needles".

🔒 Highlight #2: Cybersecurity Rises to Critical Priority

The cybersecurity focus was evident throughout the conference, with sessions like "Emerging Cybersecurity Threats in Legal Tech" and "The Yin & Yang of Cybersecurity in eDiscovery" drawing significant attendance. These sessions addressed how sophisticated cybersecurity threats present new challenges for legal organizations, from AI-driven attacks to vulnerabilities in emerging technologies.

Reporting on iltacon2025 from Gaylord National Resort & Convention Center just outside Washington, DC!

AI Ethics in Legal Writing emerged as a critical intersection between technology adoption and professional responsibility. Ivy Grey of WordRake, recognized as an Influential Woman in Legal Tech by ILTA, led compelling discussions about the ethical implications of using generative AI in legal writing. Her panel explored how lawyers can maintain ethical obligations while leveraging AI tools for document creation, emphasizing the importance of verification, maintaining independent judgment, and ensuring client confidentiality when using AI-assisted writing tools.

Security-AI integration discussions addressed prompt injection attacks, data leakage prevention, and the challenge of educating clients about AI security measures. The "Getting the Most from M365 Copilot: The Do's & Don'ts" session provided practical frameworks for rolling out AI tools while maintaining security protocols.

Document management security revealed concerning trends. Sessions highlighted how firm knowledge is scattered across OneDrive, SharePoint, Teams, and personal folders, making it difficult to locate and use effectively. Security by obscurity no longer works, as AI tools like Copilot can surface documents that were previously hidden by poor organization rather than true security measures.

🔮 Highlight #3: The Future-Forward Mindset Revolution

Keynote speaker Reena SenGupta challenged the industry with her "seven evolutions" framework, urging legal professionals to think of law firms as living organisms rather than rigid hierarchies. Her fungal network metaphor resonated deeply – emphasizing how technology professionals serve as the connective tissue enabling knowledge flow throughout organizations.

Predictive capabilities are replacing reactive approaches. SenGupta showcased how firms are moving from precedent to prediction, with examples like DLA Piper's "Compliance-as-a-Service" product that uses AI to spot minor compliance issues before they become major problems, and Paul Hastings restructuring their white-collar investigations practice around AI-powered anomaly detection.

ILTACON2025 is celebrating 45 years!

The billable hour debate intensified. The "Bill(AI)ble Hours: The Debate Continues" session explored how AI's efficiency gains might fundamentally alter legal economics, with the audience showing more support for alternative fee arrangements (AFAs) than opposition. The discussion centered on capturing value creation rather than time tracking, though the majority agreed the billable hour wouldn't disappear within the next five years.

Multidisciplinary integration emerged as essential rather than optional. SenGupta described the breakdown of the divide between legal and non-legal roles, citing examples like White & Case's integration of project managers into client teams and DLA Piper's consulting unit working hand-in-glove with lawyers. These cross-functional teams are becoming critical for delivering client value.

🎯 Strategic Takeaways for Legal Professionals

For Solo and Small Firms: While ILTACON traditionally targets larger firms, this year's vendor presentations often included scalable solutions. The key insight? Start with AI tools that integrate with existing workflows rather than requiring complete system overhauls.

For Mid-Size Firms: Investment in knowledge management infrastructure emerged as the critical success factor. The KM Roundtable revealed that firms implementing AI without proper data governance struggle to achieve meaningful results.

For Large Firms: Change management and user adoption dominated discussions. Technical capability matters less than organizational readiness to embrace new workflows. The overview from these sessions is that robust workflows and a positive organizational culture are essential building blocks for effective AI adoption.

🔧 Practical Implementation Insights

The most valuable sessions provided actionable frameworks rather than theoretical discussions. The "Actionable AI Strategy & Policy" session offered specific methodologies for balancing governance with flexibility, with speakers emphasizing the need for a mellable but strong foundational governance policy.

Vendor interactions proved particularly valuable. The exhibit hall's "Pirate's Bounty" theme encouraged exploration, and many attendees reported discovering solutions through peer recommendations rather than vendor pitches.

Technology evaluation challenges were evident. The KM Roundtable revealed "POC fatigue" as teams try to evaluate numerous AI tools while managing regular workloads, with general skepticism about which tools will have longevity.

🚢 Looking Ahead: Charting the Course

It was great catching up with The Tech-Savvy Lawyer.Page Podcast Guest (Ep. 109) Jacqueline Schafer, Founder and CEO of Clearbrief!

ILTACON 2025 demonstrated that legal technology has moved from experimental to operational. The questions are no longer "Can AI help lawyers?" but rather "How do we implement AI responsibly and effectively?"

The excitement was palpable – and justified. For technology professionals in law, this represents a career-defining moment where their expertise directly impacts firm competitiveness and client service quality.

As we navigate these transformative waters, remember that the real treasure isn't the technology itself. It's the enhanced client service, improved efficiency, and competitive advantages these tools provide when properly implemented.

Next year's ILTACON promises to build on this momentum. Mark your calendars now – this is where the legal profession's technological future gets written, one innovation at a time.

Ready to implement what you learned at ILTACON 2025? Subscribe to The Tech-Savvy Lawyer.Page for ongoing insights and practical guidance on legal technology adoption.