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The Tech Savvy Lawyer

The Tech Savvy Lawyer

By: Michael D.J. Eisenberg
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The Tech Savvy Lawyer interviews Judges, Lawyers, and other professionals discussing utilizing technology in the practice of law. It may springboard an idea and help you in your own pursuit of the business we call "practicing law". Please join us for interesting conversations enjoyable at any tech skill level!© ℗ 2020 Michael D.J. Eisenberg Politics & Government
Episodes
  • TSL.P Labs 🧪 Initiative: Why 96% AI Accuracy Still Fails Lawyers: Ethics, Hallucinations, and the Future of the Billable Hour ⚖️🤖

    TSL.P Labs 🧪 Initiative: Why 96% AI Accuracy Still Fails Lawyers: Ethics, Hallucinations, and the Future of the Billable Hour ⚖️🤖
    Mar 6 2026
    📌 To Busy to Read This Week's Editorial? Welcome to the TSL Lab's Initiative. 🤖 This weeks episode builds on my March 3rd, 2026, editorial "Even Though AI Hallucinations Are Down: Lawyers STILL MUST Verify AI, Guard PII, and Follow ABA Ethics Rules ⚖️🤖" is a misleading comfort blanket for lawyers, and how ABA Model Rules on confidentiality, competence, diligence, candor, supervision, and client communication must govern every AI prompt you run. Our Google LLM Notebook hosts translate the theory into practical workflows you can implement today—from document grounding and tokenization to vendor due diligence and line‑by‑line verification—so you can leverage AI confidently without sacrificing ethics, privilege, or your professional license. You will hear how document grounding changes what LLMs actually do, why uploading active case files to cloud AI tools can quietly trigger Rule 1.6 problems, and how cross‑border data flows, vendor training rights, and retention policies can erode privilege if you do not negotiate them carefully. 🔐 We also unpack practical safeguards like tokenization, internal sandbox testing, and bright‑line "danger zones" where AI must never operate unsupervised—especially on open‑ended research, choice of law, and any task that turns statistical text into real‑world legal risk. Finally, we confront the economic paradox: when AI can compress 100 hours of document review into seconds, but partners must still verify every line to protect their licenses, what exactly are clients paying for—and how does the billable hour survive? 💼 👉 Tune in now to learn how to stay tech‑forward without becoming the next ethics cautionary tale, and start designing AI policies that actually protect your clients, your firm, and your bar license. In our conversation, we cover the following 00:00 – Why "96% fewer hallucinations" is still not good enough in law ⚖️01:00 – How the remaining 4% error rate can trigger malpractice, sanctions, and ethics violations02:00 – From IT issue to ethics issue: ABA Model Rules as the real constraint on AI adoption03:00 – Document grounding 101: turning a free‑floating LLM into a reading‑comprehension engine04:00 – The hidden danger of "just upload the file": how Rule 1.6 confidentiality is instantly implicated05:00 – Cloud AI architecture, cross‑border data transfers, GDPR, and privilege risk 🌐06:00 – Model training nightmares: when your client's trade secrets leak back out through someone else's prompt07:00 – Negotiating no‑training clauses and ring‑fencing vendor data use (before you upload anything)08:00 – Tokenization explained: turning John Doe into "Plaintiff 01" without losing legal meaning 🔐09:00 – What AI does well today: grounded summarization, clause extraction, and playbook‑based redlines10:00 – The "danger zone" of tasks: open‑ended research, choice of law, and abstract legal reasoning11:00 – Phantom case law: how LLMs manufacture perfect‑looking but fake citations (and Rule 3.3 candor)12:00 – Sandboxing AI tools internally and measuring real‑world failure rates against known outcomes 🧪13:00 – Building bright‑line firm policies around forbidden AI use cases14:00 – Verification as a workflow, not a suggestion: what Model Rules 5.1 and 5.3 demand from supervisors15:00 – The efficiency paradox: when partner‑level verification erases associate‑level time savings ⏱️16:00 – Making AI verification as routine as a conflict check in your practice17:00 – Falling hallucination rates, rising risk: why better AI can still make lawyers more vulnerable18:00 – Client communication under Rule 1.4: when and why clients may be entitled to know you used AI19:00 – "You can delegate the task, not the liability": Rule 1.2 and ultimate responsibility for AI‑assisted work20:00 – Treating every AI prompt and ToS as a potential ethics document 📝21:00 – The existential question: if AI drafts in seconds, what exactly are clients paying lawyers for?
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    24 mins
  • 🎙️ Ep. #133 | AI Search, GEO & Legal Marketing Tech: How Small Law Firms Win Cases — Not Just Clicks!

    🎙️ Ep. #133 | AI Search, GEO & Legal Marketing Tech: How Small Law Firms Win Cases — Not Just Clicks!
    Mar 17 2026
    My next guest is Nick Cohen, Chief Operating Officer of Matador Solutions — a legal marketing think tank and agency — and a newly minted partner at Cohen Injury Law Group. Nick brings a rare dual perspective: he lives the daily grind of running a law firm AND helps over 170 firms across the country use technology and marketing strategy to grow their practice. With more than $1 billion in case value generated for clients, Nick knows what separates the law firms that thrive from the ones that spin their wheels. 🚀 Whether you are just hanging out your shingle or you have been practicing for years and feel overwhelmed by the alphabet soup of SEO, GEO, PPC, and AI, this episode breaks it all down in plain language. Nick shares actionable steps — some of which cost nothing — to help your firm show up where your next great client is already looking. ⚖️ Join Nick Cohen and me as we discuss the following three questions and more! 🤔 What are the top three ways a small or mid-size law firm can leverage AI-driven search — like Google AI Overviews and ChatGPT — to reliably generate better cases, not just more clicks?💡 For firms that feel overwhelmed by SEO, paid search, and social media, what are the top three pieces of marketing technology or automations they should implement first to turn their website into a true new case acquisition system?🏆 Looking across $1 billion+ in case value generated for over 170 law firms, what are the top three technology habits the most successful firms share — and what are their less successful peers simply not doing? In our conversation, we cover the following: [0:00] 🎤 Introduction & five-star review shoutout[0:45] 👨‍💼 Nick's background: Matador Solutions, Cohen Injury Law Group, and tech stack overview (Jira, Google Suite, Claude, ChatGPT, WordPress, Slack)[1:30] 💻 Hardware setup: MacBook Pro M4, desktop, HDMI monitor — what Nick runs on daily[3:00] 📱 iPhone, planned obsolescence, and the Apple ecosystem slowdown conversation[4:00] ❓ Question 1: Leveraging AI-driven search (Google AI Overviews, ChatGPT) to get better cases — not just traffic[5:00] 🔍 GEO vs. SEO explained — what is Generative Engine Optimization and why it matters for your law firm right now[6:30] 📖 The difference: SEO = Google ranking; GEO = getting cited by ChatGPT, Claude, Perplexity, and Grok[8:00] 🤖 Schema markup, robots.txt, and opening your website to LLM crawlers — practical steps any firm can take[9:00] 📋 Attorney directory listings (Avvo, Super Lawyers, FindLaw) — are they worth the money in 2026?[10:30] ✍️ Tip #2: High-quality thought leadership content as a GEO and SEO powerhouse[11:30] ⭐ Tip #3: Reviews, reviews, reviews — the single highest-ROI, zero-cost activity for any law firm[12:00] 📲 The "one-click review link" strategy: why text beats email every time[13:00] 😬 How to handle negative reviews — call first, respond professionally, and why a 4.9 rating beats a perfect 5.0[15:00] ❓ Question 2: Top three marketing tech tools/automations for overwhelmed firms — CallRail, case management software, and understanding your channels[17:30] ❓ Question 3: The technology habits that separate high-growth firms from stagnant ones — intake systems, engagement, and growth mindset[19:30] 🗺️ How Matador Solutions walks a brand-new firm from zero to a steady stream of cases — step by step[22:00] 📬 Where to find Nick Cohen Resources 🔗 Connect with Nick Cohen 📧 Email: nick@matadorsolutions.net💼 LinkedIn: https://www.linkedin.com/in/nickecohen/🌐 Website: matadorsolutions.net 📚 Mentioned in the Episode (Non-Hardware / Non-Software) 🎙️ Apple Podcasts — podcasts.apple.com ⚖️ Matador Solutions — Legal marketing agency — matadorsolutions.net📋 Avvo — Attorney directory — avvo.com⚖️ Cohen Injury Law Group — Nick's law firm — https://cohenandcohen.net/⭐ Facebook Reviews — facebook.com📊 GEO (Generative Engine Optimization) — The emerging discipline of optimizing for AI-driven search engines⭐ Google Reviews — google.com/business📋 FindLaw — Attorney directory — findlaw.com📋 Super Lawyers — Attorney directory — superlawyers.com⭐ Yelp — yelp.com 💻 Hardware Mentioned in the Conversation 📱 Apple iPhone 15 — Nick's smartphone (approximate model) — apple.com/iphone📱 Apple iPhone (latest, annual upgrade) — Michael's smartphone — apple.com/iphone🖥️ Apple Mac Studio (M3 chip) — Michael's desktop — apple.com/mac🖥️ Apple MacBook Pro (M4 chip) — Nick's primary laptop — apple.com/macbook-pro ☁️ Software & Cloud Services Mentioned in the Conversation 📞 CallRail — Call tracking & marketing ROI — callrail.com🤖 ChatGPT (OpenAI) — AI assistant & AI search — chatgpt.com🤖 Claude (Anthropic) — AI assistant — claude.ai🤖 ...
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    24 mins
  • 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 🎙️⚖️

    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 🎙️⚖️
    Mar 3 2026
    In this special episode, I join Professor Wondracek virtually to guest-host Capital's very first Podcast Club session for a live conversation about AI, legal ethics, deepfakes, and metadata. We talk candidly with law students about how AI-generated evidence, consumer AI tools, and digital footprints are already impacting sanctions, privilege, and professional responsibility, then translate those issues into practical safeguards for everyday practice. Whether you are in law school, running a small firm, or managing litigation for a larger organization, this inaugural Podcast Club episode shows how to stay competent, secure, and credible when AI and technology are part of your case strategy. Questions section Join Professor Jennifer Wondracek and me as we discuss the following three questions and more! How do deepfakes and manipulated digital evidence challenge a lawyer's ethical duties under core rules on competence, candor to the tribunal, and honesty?What can we learn from recent cases involving deepfake videos, privilege risks in consumer AI tools, and sanctions for hallucinated citations when designing our own AI workflows?How can lawyers and law students build realistic, sustainable practices for reviewing metadata, using VPNs and secure Wi‑Fi, and choosing secure legal AI and eDiscovery tools? Timestamps In our conversation, we covered the following: 00:00 – Welcome to Capital University Law School's first Podcast Club: live recording and today's focus on AI and ethics 🎓01:00 – Introducing Michael D.J. Eisenberg as guest host and his work with veterans, and The Tech-Savvy Lawyer.Page blog and podcasting 📚02:30 – What is a deepfake, and how a staged "Bethesda incident" highlights the real-world risk of fake video evidence 🚨04:00 – Applying competence rules to technology: why "I didn't know" is not a sustainable defense for lawyers05:00 – Everyday tech risks: public Wi‑Fi, airports, coffee shops, and why lawyers must use VPNs when client information is involved 🌐06:30 – Discussing NordVPN, ExpressVPN, and how unsecured sessions can compromise client portals, trust accounts, and email 🔐07:30 – First steps in vetting digital evidence: what to look for in image files and when to call in a forensic expert08:30 – Lessons from deepfake litigation and obviously altered video: shadows, color-in-black-and-white, and credibility with the court 🎥10:00 – Candor to the tribunal and rules against dishonesty, fraud, and misrepresentation in the AI era11:00 – Student question: can you rely on built-in operating system tools to review metadata, or do you need specialist software? 🖼️13:30 – Live demo: opening file properties, reading timestamps, device info, and geotags to validate or challenge evidence16:00 – When scrubbed metadata makes sense, when it doesn't, and how to request original metadata in discovery18:00 – Five practical safeguards for new and experienced lawyers: education, protocols, client transparency, updated letters, and constant monitoring of AI changes ✅20:00 – Why refusing to learn AI and tech is itself a risk to your bar license and your clients' interests21:00 – Student Q&A: low-resource firms, large volumes of data, and using sampling plus AI to stretch limited budgets22:30 – Using legal AI to surface anomalies in documents and metadata while still protecting privilege23:00 – How consumer AI terms and conditions can put privilege and work product at risk, and what to look for in safer options ⚠️24:00 – Free vs paid AI accounts: retention, training, and why personally identifiable information doesn't belong in general chatbots25:00 – Evaluating legal AI vendors: zero retention, encryption, prompt confidentiality, and subpoena requirements26:00 – Using tightly controlled legal research platforms and "vault" environments to access models like GPT or Claude securely 🧠27:00 – Documenting prompts and AI use so that, if questioned by a court or bar, you can show reasonable diligence28:30 – Reasonable metadata review in practice: random sampling, documenting your process, and knowing when to bring in eDiscovery tools30:00 – How modern eDiscovery platforms surface metadata and support deeper analysis at scale 📂31:00 – Staying current on AI and tech: newsletters, bar alerts, court updates, and following The Tech-Savvy Lawyer32:30 – AI hallucinated citations and sanctions: how one New York matter became a warning to the entire profession 💸34:30 – Firm-wide consequences when AI misuse becomes a pattern: reputational damage, client impact, and even firm dissolution36:00 – Owning mistakes, repairing trust with judges, and why transparency matters more than perfection37:00 – Live giveaway of The Lawyer's Guide to Podcasting during the first Podcast Club session 🎲38:00 – Inviting students to Capital's upcoming summit/bootcamp and to dinner at the Red Door Tavern, plus closing thoughts on the future of tech ...
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    40 mins
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