The Tech Savvy Lawyer

Michael D.J. Eisenberg
  • 5.0 (15)
  • TECHNOLOGY
  • UPDATED BIWEEKLY

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!

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

    5D AGO

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

    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 ABA Model Rules of Professional Conduct (Rules 1.1, 1.4, 1.6, 5.1, 5.3) Software & Cloud Services mentioned in the conversation Lexis (Lexis+ AI category mentioned) — https://www.lexisnexis.com/ Microsoft Word — https://www.microsoft.com/microsoft-365/word Public generative AI "chatbot" tools (general category) — https://en.wikipedia.org/wiki/Chatbot Westlaw (Westlaw AI category mentioned) — https://legal.thomsonreuters.com/en/products/westlaw

    19 min
  2. TSL.P Labs 🧪: Lawyers and AI Oversight: What the VA's Patient Safety Warning Teaches About Ethical Law Firm Technology Use! ⚖️🤖

    FEB 20

    TSL.P Labs 🧪: Lawyers and AI Oversight: What the VA's Patient Safety Warning Teaches About Ethical Law Firm Technology Use! ⚖️🤖

    Join us for an AI-powered deep dive into the ethical challenges facing legal professionals in the age of generative AI. 🤖 In this episode, we discuss our February 16, 2026, editorial, "Lawyers and AI Oversight: What the VA's Patient Safety Warning Teaches About Ethical Law Firm Technology Use! ⚖️🤖" and explore why treating AI-generated drafts as hypotheses—not answers—is quickly becoming a survival skill for law firms of every size. We connect a real-world AI failure risk at the Department of Veterans Affairs to the everyday ways lawyers are using tools like chatbots, and we translate ABA Model Rules into practical oversight steps any practitioner can implement without becoming a programmer. In our conversation, we cover the following: 00:00:00 – Why conversations about the future of law default to Silicon Valley, and why that's a problem ⚖️ 00:01:00 – How a crisis at the U.S. Department of Veterans Affairs became a "mirror" for the legal profession 🩺➡️⚖️ 00:03:00 – "Speed without governance": what the VA Inspector General actually warned about, and why it matters to your practice 00:04:00 – From patient safety risk to client safety and justice risk: the shared AI failure pattern in healthcare and law 00:06:00 – Shadow AI in law firms: staff "just trying out" public chatbots on live matters and the unseen risk this creates 00:07:00 – Why not tracking hallucinations, data leakage, or bias turns risk management into wishful thinking 00:08:00 – Applying existing ABA Model Rules (1.1, 1.6, 5.1, 5.2, and 5.3) directly to AI use in legal practice 00:09:00 – Competence in the age of AI: why "I'm not a tech person" is no longer a safe answer 🧠 00:09:30 – Confidentiality and public chatbots: how you can silently lose privilege by pasting client data into a text box 00:10:30 – Supervision duties: why partners cannot safely claim ignorance of how their teams use AI 00:11:00 – Candor to tribunals: the real ethics problem behind AI-generated fake cases and citations 00:12:00 – From slogan to system: why "meaningful human engagement" must be operationalized, not just admired  00:12:30 – The key mindset shift: treating AI-assisted drafts as hypotheses, not answers 🧪 00:13:00 – What reasonable human oversight looks like in practice: citations, quotes, and legal conclusions under stress test 00:14:00 – You don't need to be a computer scientist: the essential due diligence questions every lawyer can ask about AI  00:15:00 – Risk mapping: distinguishing administrative AI use from "safety-critical" lawyering tasks 00:16:00 – High-stakes matters (freedom, immigration, finances, benefits, licenses) and heightened AI safeguards 00:16:45 – Practical guardrails: access controls, narrow scoping, and periodic quality audits for AI use 00:17:00 – Why governance is not "just for BigLaw" and how solos can implement checklists and simple documentation 📋 00:17:45 – Updating engagement letters and talking to clients about AI use in their matters 00:18:00 – Redefining the "human touch" as the safety mechanism that makes AI ethically usable at all 🤝 00:19:00 – AI as power tool: why lawyers must remain the "captain of the ship" even when AI drafts at lightning speed 🚢 00:20:00 – Rethinking value: if AI creates the first draft, what exactly are clients paying lawyers for? 00:20:30 – Are we ready to bill for judgment, oversight, and safety instead of pure production time? 00:21:00 – Final takeaways: building a practice where human judgment still has the final word over AI RESOURCES Mentioned in the episode American Bar Association Model Rules of Professional Conduct Interview by Terry Gerton of the Federal News Network of Charyl Mason, Inspector General of the Department of Veterans Affairs, "VA rolled out new AI tools quickly, but without a system to catch mistakes, patient safety is on the line".  Software & Cloud Services mentioned in the conversation ChatGPT — https://chat.openai.com/ Lexis - https://www.lexisnexis.com  Westlaw - https://legal.thomsonreuters.com

    23 min

  3. FEB 17

    🎙️ Ep. #131, Supercharging Litigation With AI: How StrongSuit Helps Lawyers Transform Research, Doc Review, and Drafting 💼⚖️

    My next guest is Justin McCallan, founder of StrongSuit, an AI-powered litigation platform built to transform how litigators handle legal research, document review, and drafting while keeping lawyers firmly in control. In this episode, Justin and I dig into practical, real-world workflows that solos, small firms, and big-firm litigators can use today and over the next few years to change the economics, pace, and strategy of litigation—without sacrificing accuracy, ethics, or the quality of advocacy. Join Justin and me as we discuss the following three questions and more! What are the top three ways litigators should be using AI tools like StrongSuit right now to change the economics and pace of litigation without sacrificing accuracy, ethics, or quality of advocacy? What are the top three mistakes lawyers make when adopting AI for litigation, and what practical workflows help lawyers stay in the loop and use AI as a force multiplier instead of a risk? Looking ahead to 2026 and beyond, what are the top three AI-driven workflows every litigator should master to stay competitive, and how can platforms like StrongSuit help build those capabilities into day-to-day practice? In our conversation, we cover the following 00:00 – Welcome and guest introduction Justin joins the show and shares his current tech setup at his desk. 00:00–01:00 – Justin's current tech stack Lenovo laptop, ultra-wide monitor, and regular use of StrongSuit, ChatGPT, and Gemini for different AI tasks. Everyday tools: Microsoft Word and Power BI for analytics and fast decision-making. 01:00–02:00 – Android vs. iPhone for AI use Why Justin has been on Android for 17 years and how UI/UX familiarity often drives device choice more than AI capability. 02:00–05:30 – Q1: Top three ways litigators should be using AI right now Using AI for end-to-end legal research across 11 million precedential U.S. cases to build litigation outlines and identify key authorities. Scaling document review so AI surfaces relevant documents and synthesizes insights while lawyers focus on strategy and judgment. Leveraging AI for drafting and editing—improving style, clarity, and consistency beyond traditional spelling and grammar checks. 05:30–07:30 – StrongSuit vs. basic tools like Word grammar check How StrongSuit aims to "up-level" a lawyer's writing, not just catch typos. Stylistic improvements, clarity enhancements, and catching subtle inconsistencies in legal documents. 06:00–08:00 – AI context limits and scaling doc review Constraints of large models' context windows (around ~1M tokens ≈ ~750 pages). How StrongSuit runs multiple AI agents in parallel, each handling small page sets with heuristics to maintain cohesion and share insights. 08:00–09:00 – Handling tens of thousands of documents How StrongSuit can handle between roughly 10,000–50,000 pages at a time, with the ability to scale further for enterprise matters. 09:00–11:30 – Origin story of StrongSuit Why Justin saw a once-in-a-generation opportunity when large language models emerged and how law, with its precedent and text-heavy nature, is especially suited to AI. StrongSuit's focus on litigators: supporting lawyers from intake through trial while keeping them in the loop at every step. 11:30–13:30 – From intake to brief drafting in minutes Generating full litigation outlines, research, and analysis in about ten minutes, then moving directly into drafting memos, briefs, complaints, and motions. StrongSuit's long-term goal: automating 50–99% of major litigation workflows by the end of 2026 while preserving lawyer control and judgment. 12:00–14:30 – How StrongSuit tackles hallucinations Building a full database of all precedential U.S. cases enriched with metadata: parties, summaries, holdings, and more. Validating citations by checking whether the Bluebook citation actually exists in StrongSuit's case database before surfacing it to the user. Why lawyers should still review cases on-platform before filing, even when AI has filtered out hallucinations. 14:30–16:30 – Coverage and jurisdictions Coverage of all U.S. jurisdictions, federal and state, focused on precedential cases. Handling most regulations from administrative agencies, and limits around local ordinances. Uploading your own case files and using complaints and prior research as inputs into StrongSuit workflows. 15:00–17:00 – Security and confidentiality for litigators SOC 2 compliance and industry-standard encryption at rest and in transit. No model training on user data. Optional end-to-end encryption that can even prevent developers from accessing case content, using local encryption keys. 16:30–20:30 – Q2: Top mistakes lawyers make when adopting AI for litigation Mistake #1: Talking about AI instead of diving in with structured experiments and sanitized documents. Using a framework to identify high-impact tasks: high volume, repetitive work, and heavy data/analysis (e.g., doc review, research, contract drafting). How to shortlist tools: look for SOC 2, real product depth, awards, and a focus on your specific workflows. Mistake #2: Expecting immediate mastery instead of moving through predictable adoption stages—from learning the tool, to daily use, to stringing workflows together. 20:30–22:30 – Building firm-wide AI workflows over time Moving from isolated experiments to integrated, low-friction workflows, such as automatic intake-to-research pipelines. Using client intake audio or transcripts to automatically extract facts, issues, and research paths. 22:30–24:30 – Time constraints and "no-time" lawyers Why lawyers don't need to be "technical" to use StrongSuit. Reframing AI as text-based tools where lawyers' writing skills and analytical thinking are assets, not obstacles. 24:00–26:00 – Practical workflows beyond intake Using AI to prepare for expert depositions, including reviewing valuation analyses, flagging departures from market consensus, and generating targeted questions. Reinforcing the value of AI-enhanced legal research and drafting as core litigation workflows. 26:00–29:30 – Q3: 2026 and beyond – AI-driven workflows every litigator should master Rapid improvement of baseline models (e.g., jumping from single-digit to high double-digit performance on difficult benchmarks year over year). The idea of "tipping points," where small performance gains turn AI from marginally useful to essential in specific tasks. Why legal research is a great training ground for understanding where AI excels, where it falls short, and how to divide labor between human and machine. The value of learning basic prompting skills to get more from AI systems, even when platforms offer visual workflows. 29:30–32:30 – Will workflows actually change—or just get better? Why Justin expects familiar litigation workflows (doc review, research, drafting) to remain structurally similar, but become far faster and more sophisticated. AI agents handling the grind work while lawyers focus on synthesis, judgment, and strategy. A future where "AI + lawyer vs. AI + lawyer" resembles high-level chess: same rules, but much deeper thinking on both sides. 32:30–End – Where to find Justin and StrongSuit How to connect with Justin and learn more about StrongSuit's litigation tools. Resources Connect with Justin Justin McCallan on LinkedIn – https://www.linkedin.com/in/justin-mccallon/ StrongSuit website – https://www.strongsuit.com Hardware mentioned in the conversation Android smartphone – https://www.android.com Lenovo laptop – https://www.lenovo.com Software & Cloud Services mentioned in the conversation ChatGPT – https://chat.openai.com Gemini – https://gemini.google.com Microsoft Power BI – https://powerbi.microsoft.com Microsoft Word – https://www.microsoft.com/microsoft-365/word StrongSuit AI litigation platform – https://www.strongsuit.com 🤖

    35 min

  4. FEB 13

    TSL.P Labs 🧪: Courts Are Punishing Fake AI Evidence: How to Protect Your Cases, Clients, and License ⚖️🤖

    Everyday devices can capture extraordinary evidence, but the same tools can also manufacture convincing fakes. 🎥⚖️ In this episode, we unpack our February 9, 2026, editorial on how courts are punishing fake digital and AI-generated evidence, then translate the risk into practical guidance for lawyers and legal teams. You'll hear why judges are treating authenticity as a frontline issue, what ethical duties get triggered when AI touches evidence or briefing, and how a simple "authenticity playbook" can help you avoid career-ending mistakes. ✅ In our conversation, we cover the following 00:00:00 – Preview: From digital discovery to digital deception, and the question of what happens when your "star witness" is actually a hallucination or deepfake 🚨 00:00:20 – Introducing the editorial "Everyday Tech, Extraordinary Evidence Again: How Courts Are Punishing Fake Digital and AI Data." 📄 00:00:40 – Welcome to the Tech-Savvy Lawyer.Page Labs Initiative and this AI Deep Dive Roundtable 🎙️ 00:01:00 – Framing the episode: flipping last month's optimism about smartphones, dash cams, and wearables as case-winning "silent witnesses" to their dark mirror—AI-fabricated evidence 🌗 00:01:30 – How everyday devices and AI tools can both supercharge litigation strategy and become ethical landmines under the ABA Model Rules ⚖️ 00:02:00 – Panel discussion opens: revisiting last month's "Everyday Tech, Extraordinary Evidence" AI bonus and the optimism around smartphone, smartwatch, and dash cam data as unbiased proof 📱⌚🚗 00:02:30 – Remembering cases like the Minnesota shooting and why these devices were framed as "ultimate witnesses" if the data is preserved quickly enough 🕒 00:03:00 – The pivot: same tools, new threats—moving from digital discovery to digital deception as deepfakes and hallucinations enter the evidentiary record 🤖 00:03:30 – Setting the "mission" for the episode: examining how courts are reacting to AI-generated "slop" and deepfakes, with an increasingly aggressive posture toward sanctions 💣 00:04:00 – Why courts are on high alert: the "democratization of deception," falling costs of convincing video fakes, and the collapse of the old presumption that "pictures don't lie" 🎬 00:04:30 – Everyday scrutiny: judges now start with "Where did this come from?" and demand details on who created the file, how it was handled, and what the metadata shows 🔍 00:05:00 – Metadata explained as the "data about the data"—timestamps, software history, edit traces—and how it reveals possible AI manipulation 🧬 00:06:00 – Entering the "sanction phase": why we are beyond warnings and into real penalties for mishandling or fabricating digital and AI evidence 🚫 00:06:30 – Horror Story #1 (Mendon v. Cushman & Wakefield, Cal. Super. Ct. 2025): plaintiffs submit videos, photos, and screenshots later determined to be deepfakes created or altered with generative AI 🧨 00:07:00 – Judge Victoria Kakowski's response: finding that the deepfakes undermined the integrity of judicial proceedings and imposing terminating sanctions—"death penalty" for the lawsuit ⚖️ 00:07:30 – How a single deepfake "poisons the well," destroying the court's trust in all of a party's submissions and forfeiting their right to the court's time 💥 00:08:00 – Horror Story #2 (S.D.N.Y. 2023): the New York "hallucinating lawyer" case where six imaginary cases generated by ChatGPT were filed without verification 📚 00:08:30 – Rule 11 sanctions and humiliation: Judge Castel's order, monetary penalty, and the requirement to send apology letters to real judges whose names were misused ✉️ 00:09:00 – California follow-on: appellate lawyer Amir Mustaf files an appeal brief with 21 fake citations, triggering a 10,000-dollar sanction and a finding that he did not read or verify his own filing 💸 00:09:30 – Courts' reasoning: outsourcing your job to an AI tool is not just being wrong—it is wasting judicial resources and taxpayer money 🧾 00:10:00 – Do we need new laws? Why Michael argues that existing ABA Model Rules already provide the safety rails; the task is to apply them to AI and digital evidence, not to reinvent them 🧩 00:10:20 – Rule 1.1 (competence): why "I'm not a tech person" is no longer a viable excuse if you use AI to enhance video or draft briefs without understanding or verifying the output 🧠 00:11:00 – Rule 1.6 (confidentiality): the ethical minefield of uploading client dash cam video or wearable medical data to consumer-grade AI tools and risking privilege leakage ☁️ 00:11:30 – Training risk: how client data can end up in model training sets and why "quick AI summaries" can inadvertently expose secrets 🔐 00:12:00 – Rules 3.3 and 4.1 (candor and truthfulness): presenting AI-altered media as original or failing to verify AI output can now be treated as misrepresentation 🤥 00:12:30 – Rules 5.1–5.3 (supervision): why partners and supervising lawyers remain on the hook for juniors, staff, and vendors who misuse AI—even if they didn't personally type the prompts 🧑‍💼 00:13:00 – Authenticity Playbook, Step 1: mindset shift—never treat AI as a "silent co-counsel"; instead, treat it like a very eager, very inexperienced, slightly drunk intern who always needs checking 🍷🤖 00:13:30 – Authenticity Playbook, Step 2: preserve the original and disclose any AI enhancement; build a clean chain of custody while staying transparent about edits 🎞️ 00:14:00 – Authenticity Playbook, Step 3: using forensic vendors as authenticity firewalls—experts who can certify that metadata and visual cues show no AI manipulation 🛡️ 00:14:30 – Authenticity Playbook, Step 4: "train with fear" by showing your team real orders, sanctions, and public shaming rather than relying on abstract ethics lectures ⚠️ 00:15:00 – Authenticity Playbook, Step 5: documenting verification steps—logging files, tools, and checks so you can demonstrate good faith if a judge questions your evidence 📝 00:16:00 – Bigger picture: the era of easy, unchallenged digital evidence is over; mishandled tech can now produce "extraordinary sanctions" instead of extraordinary evidence 🧭 00:16:30 – Authenticity as "the moral center of digital advocacy": if you cannot vouch for your digital evidence, you are failing in your role as an advocate 🏛️ 00:17:00 – Future risk: as deepfakes become perfect and nearly impossible to detect with the naked eye, forensic expertise may become a prerequisite for trusting any digital evidence 🔬 00:17:30 – "Does truth get a price tag?"—whether justice becomes a luxury product if only wealthy parties can afford authenticity firewalls and expert validation 💼 00:18:00 – Closing reflections: fake evidence, real consequences, and the call to verify sources and check metadata before you file ✅ 00:18:30 – Closing: invitation to visit Tech-Savvy Lawyer.Page for the full editorial, resources, and to like, subscribe, and share with colleagues who need to stay ahead of legal tech innovation 🌐 Resources Cases In Mendones v. Cushman & Wakefield, Inc. (Cal. Super. Ct. Alameda County, 2025), plaintiffs submitted multiple videos, photos, and screenshots that the court determined were deepfakes or altered with generative AI.📹 Judge Victoria Kolakowski found intentional submission of false testimony and imposed terminating sanctions, dismissing the case outright and emphasizing that deepfake evidence "fundamentally undermines the integrity of judicial proceedings."⚖️ In New York, two lawyers became infamous in 2023 after filing a brief containing six imaginary cases generated by ChatGPT; Judge P. Kevin Castel sanctioned them under Rule 11 for abandoning their responsibilities and failing to verify the authorities they cited.📑 They were ordered to pay a monetary penalty and to notify the real judges whose names had been falsely invoked, a reputational hit that far exceeded the dollar amount.💸 A California appellate lawyer, Amir Mostafavi, was later fined $10,000 for filing an appeal with twenty‑one fake case citations generated by ChatGPT.💻 The court stressed that he had not read or verified the AI‑generated text, and treated that omission as a violation of court rules and a waste of judicial resources and taxpayer money.⚠️  ABA Model Rules Rule 1.1 (Competence): You must understand the benefits and risks of relevant technology, which now clearly includes generative AI and deepfake tools.⚖️ Using AI to draft or "enhance" without checking the output is not a harmless shortcut—it is a competence problem. Comment 8's duty of technological competence; the new sanctions landscape simply clarifies the stakes.📚 Rule 1.6 (Confidentiality): Uploading client videos, wearable logs, or sensitive communications to consumer‑grade AI sites can expose them to unknown retention and training practices, risking confidentiality violations.🔐 Rule 3.3 (Candor to the Tribunal) and Rule 4.1 (Truthfulness): Presenting AI‑altered video or fake citations as if they were genuine is the very definition of misrepresentation, as the New York and California sanction orders make clear.⚠️ Even negligent failure to verify can be treated harshly once the court's patience for AI excuses runs out. Rules 5.1–5.3 (Supervision): Supervising lawyers must ensure that associates, law clerks, and vendors understand that AI outputs are starting points, not trustworthy final products, and that fake or manipulated digital evidence will not be tolerated.👥

    19 min

  5. FEB 6

    TSL.P Labs 🧪: Legal Tech Wars, Client Data, and Your Law License: An AI-Powered Ethics Deep Dive ⚖️🤖

    📌 To Busy to Read This Week's Editorial? Join us for an AI-powered deep dive into the ethical challenges facing legal professionals in the age of generative AI. 🤖 In this Tech-Savvy Lawyer Page Labs Initiative episode, AI co-hosts walk through how high‑profile "legal tech wars" between practice‑management vendors and AI research startups can push your client data into the litigation spotlight and create real ethics exposure under ABA Model Rules 1.1, 1.6, and 5.3. We'll explore what happens when core platforms face federal lawsuits, why discovery and forensic audits can put confidential matters in front of third parties, and how API lockdowns, stalled product roadmaps, and forced sales can grind your practice operations to a halt. More importantly, you'll get a clear five‑step action plan—inventorying your tech stack, confirming data‑export rights, mapping backup providers, documenting diligence, and communicating with clients—that works even if you consider yourself "moderately tech‑savvy" at best. Whether you're a solo, a small‑firm practitioner, in‑house, or simply AI‑curious, this conversation will help you evaluate whether you are the supervisor of your legal tech—or its hostage. 🔐 In our conversation, we cover the following 00:00:00 – Setting the stage: Legal tech wars, "Godzilla vs. Kong," and why vendor lawsuits are not just Silicon Valley drama for spectators. 00:01:00 – Introducing the Tech-Savvy Lawyer Page Labs Initiative and the use of AI-generated discussions to stress-test legal tech ethics in real-world scenarios. 00:02:00 – Who's fighting and why it matters: Clio as the "nervous system" of many firms versus Alexi as the "brainy intern" of AI legal research. 00:03:00 – The client data crossfire: How disputes over data access and training AI tools turn your routine practice data into high-stakes litigation evidence. 00:04:00 – Allegations in the Clio–Alexi dispute, from improper data access to claims of anti-competitive gatekeeping of legal industry data. 00:05:00 – Visualizing risk: Client files as sandcastles on a shelled beach and why this reframes vendor fights as ethics issues, not IT gossip. 00:06:00 – ABA Model Rule 1.1 (Competence): What "technology competence" really entails and why ignorance of vendor instability is no longer defensible. 00:07:00 – Continuity planning as competence: Injunctions, frozen servers, vendor shutdowns, and how missed deadlines can become malpractice. 00:08:00 – ABA Model Rule 1.6 (Confidentiality): The "danger zone" of treating the cloud like a bank vault and misunderstanding who really holds the key. 00:09:00 – Discovery risk explained: Forensic audits, third‑party access, protective orders that fail, and the cascading impact on client secrets. 00:10:00 – Data‑export rights as your "escape hatch": Why "usable formats" (CSV, PDF) matter more than bare contractual promises. 00:11:00 – Practical homework: Testing whether you can actually export your case list today, not during a crisis. 00:12:00 – ABA Model Rule 5.3 (Supervision): Treating software vendors like non‑lawyer assistants you actively supervise rather than passive utilities. 00:13:00 – Asking better questions: Uptime, security posture, and whether your vendor is using your data in its own defense. 00:14:00 – Operational friction: Rising subscription costs, API lockdowns, broken integrations, and the return of manual copy‑pasting. 00:15:00 – Vaporware and stalled product roadmaps: How litigation diverts engineering resources away from features you are counting on. 00:16:00 – Forced sales and 30‑day shutdown notices: Data‑migration nightmares under pressure and why waiting is the riskiest strategy. 00:17:00 – The five‑step moderate‑tech action plan: Inventory dependencies, review contracts, map contingencies, document diligence, and communicate with nuance. 00:18:00 – Turning risk management into a client‑facing strength and part of your value story in pitches and ongoing relationships. 00:19:00 – Reframing legal tech tools as members of your legal team rather than invisible utilities. 00:20:00 – "Supervisor or hostage?": The closing challenge to check your contracts, your data‑export rights, and your practical ability to "fire" a vendor. Resources Mentioned in the episode ABA Model Rule 1.1 – Competence (Technology Competence Comment) – https://www.americanbar.org/groups/professional_responsibility/publications/model_rules_of_professional_conduct/rule_1_1_competence/ ABA Model Rule 1.6 – Confidentiality of Information – https://www.americanbar.org/groups/professional_responsibility/publications/model_rules_of_professional_conduct/rule_1_6_confidentiality_of_information/ ABA Model Rule 5.3 – Responsibilities Regarding Nonlawyer Assistance – https://www.americanbar.org/groups/professional_responsibility/publications/model_rules_of_professional_conduct/rule_5_3_responsibilities_regarding_nonlawyer_assistance/ Tech-Savvy Lawyer Page (February 2, 2026, Editorial & Show Notes Hub) – https://www.thetechsavvylawyer.page/blog/2026/2/2/mtc-clioalexi-legal-tech-fight-what-crm-vendor-litigation-means-for-your-law-firm-client-data-and-aba-model-rule-compliance- Software & Cloud Services mentioned in the conversation Clio – Cloud-based legal practice management platform – https://www.clio.com Alexi – AI‑driven legal research platform – https://www.alexi.com AWS (Amazon Web Services) – Cloud infrastructure provider – https://aws.amazon.com Google Cloud – Cloud infrastructure provider – https://cloud.google.com

    21 min

  6. FEB 3

    🎙️ Ep. #130: Taming Client Data Security – Nick Martin's Proven Tech Strategies for Law Firms 🚀

    Our next guest is Nick Martin, CEO of FileScience. He shares expert insights on stabilizing law firm operations with smart backups and automation. Join us to discover practical, easy-to-implement ways to protect your data from outages and errors, so your clients' information stays safe, secure, and accessible when you need it most. Listen in with Nick Martin and me as we discuss the following three questions and more! 💡 When a firm is drowning in document chaos, what are the first three specific workflows to digitize or automate to stabilize operations? Beyond just losing documents, what are the three specific silent killers of document hygiene that lawyers ignore? How do lawyers solve the top three friction points of digital collaboration: version conflicts, insecure sharing methods, and the loss of institutional knowledge buried inside files? In our conversation, we cover the following 📊 00:00 – Guest intro and Nick's tech setup (MacBook Pro, iPad, iPhone 15, Bang & Olufsen speaker) 🔊 00:30 – Q1: Digitizing workflows – unification of memory, forever undo button, retention 🛡️ 04:00 – Backups for iManage, NetDocuments, Clio, FileVine; air-gapped copies 📁 06:00 – Microsoft 365 outage resilience with FileScience ☁️ 08:00 – Retention periods (5-7 years by state/practice); NY lawful order policy ⚖️ 10:00 – Q2: Silent killers – file degradation, wrong versions, insider threats 🕵️ 13:00 – Q3: Solving friction – immutable timelines, encryption (Purview, CBC), institutional knowledge preservation 🔒 15:00 – End-to-end encryption details; where to find Nick Resources 🔗 Connect with Nick Martin 🤝 FileScience website: https://filescience.io Nick Martin LinkedIn: https://www.linkedin.com/in/nicholasmmartin FileScience LinkedIn: https://www.linkedin.com/company/filescience FileScience Instagram: https://www.instagram.com/filescience Mentioned in the episode 📚 Microsoft 365 outage (recent North America impact): https://www.usatoday.com/story/tech/2026/01/22/microsoft-outage-service-down/88305485007/ Hardware mentioned in the conversation 💻 Bang & Olufsen Beosound Balance (360° omnidirectional speaker): https://www.bang-olufsen.com/en/us/speakers/beosound-balance iPad: https://www.apple.com/ipad iPhone 15: https://www.apple.com/iphone MacBook Pro 16-inch: https://www.apple.com/macbook-pro Software & Cloud Services mentioned in the conversation ☁️ AWS, Azure, Google Cloud (underlying providers): https://aws.amazon.com, https://azure.microsoft.com, https://cloud.google.com Clio: https://www.clio.com FileVine: https://www.filevine.com Google Workspace: https://workspace.google.com iManage: https://www.imanage.com Microsoft 365 (Outlook, Purview encryption, CBC): https://www.microsoft.com/en-us/microsoft-365 NetDocuments: https://www.netdocuments.com[filescience] Parallels (VMs): https://www.parallels.com

    17 min

  7. JAN 30

    🎙️ TSL.P Labs Bonus: Google AI Discussion: Everyday Tech, Extraordinary Evidence: Smartphones, Dash Cams, and Wearables as Silent Witnesses in Your Cases ⚖️📱

    Join us for an AI-powered deep dive into the ethical challenges facing legal professionals in the age of generative AI. 🤖 In this Tech-Savvy Lawyer.Page Labs episode, our Google AI hosts unpack our January 26, 2026, editorial and discuss how everyday devices—smartphones, dash cams, wearables, and connected cars—are becoming "silent witnesses" that can make or break your next case, while walking carefully through ABA Model Rules on competence, candor, privacy, and preservation of digital evidence. In our conversation, we cover the following: 00:00 – Welcome to The Tech-Savvy Lawyer.Page Labs Initiative and this week's "Everyday Tech, Extraordinary Evidence" AI roundtable 🧪 00:30 – Why classic "surprise witness" courtroom drama is giving way to always-on digital witnesses 🎭 01:15 – Introducing the concept of smartphones, dash cams, and wearables as objective "silent witnesses" in litigation 📱 02:00 – Overview of Michael D.J. Eisenberg's editorial "Everyday Tech, Extraordinary Evidence" and his mission to bridge tech and courtroom practice 📰[ 03:00 – Case study setup: the Alex Preddy shooting in Minneapolis and the clash between official reports and digital evidence ⚖️ 04:00 – How bystander smartphone video reframed the legal narrative in the Preddy matter and dismantled "brandished a weapon" claims 🎥 05:00 – From "pressing play" to full video synchronization: building a unified timeline from multiple cameras to audit police reports 🧩06:00 – Using frame-by-frame analysis to test loaded terms like "lunging," "aggressive resistance," and "brandishing" against what the pixels actually show 🔍 07:00 – Moving beyond what we see: introducing "quiet evidence" such as GPS logs, telemetry, and sensor data as litigation tools 📡 08:00 – GPS data for location, duration, and speed: turning "he was charging" into a measurable movement profile in protest and road-rage cases 🚶‍♂️🚗 09:00 – Layering GPS from phones with vehicle telematics to create a multi-source reconstruction that is hard to impeach in court 📊 10:00 – Dash cams as 360-degree witnesses: solving blind spots of human perception and single-angle video 🛞 11:00 – Why exterior audio from dash cams—shouts, commands, crowd noise—can be crucial to proving state of mind and mens rea 🔊 12:00 – Wearables as a body-wide sensor network: heart rate, sleep, and step count as quantitative proof of pain, fear, and trauma ⌚ 13:00 – Using longitudinal wearable data to support claims of emotional distress or sleep disruption in personal injury and civil-rights litigation 😴 14:00 – Heart-rate spikes and movement logs at the moment of an encounter as corroboration of fear or immobility in use-of-force matters 15:00 – Why none of this evidence exists in your case file unless you know to ask for it at intake 🗂️ 16:00 – Updating intake: adding questions about smartwatches, location services, doorbell cameras, dash cams, and connected cars to your client questionnaires 📝 17:00 – Data preservation as an emergency task: deletion cycles, cloud overwrites, and using TROs to stop digital spoliation 🚨 18:00 – Turning raw logs into compelling visuals: maps, synced clips, and timelines that juries can understand without sacrificing accuracy 🗺️ 19:00 – Ethics spotlight: ABA Model Rule 1.1 competence and Comment 8—why "I'm not a tech person" is now an ethical problem, not an excuse 📚 20:00 – Candor to the tribunal and the line between strong advocacy and fraud when editing or excerpting digital evidence ⚠️ 21:00 – Respecting third-party privacy under Rule 4.4: when you must blur faces, redact audio, or limit collateral exposure of bystanders 🧩 22:00 – Advising clients not to delete texts, videos, or logs and explaining spoliation risks under Rule 3.4 ⚖️ 23:00 – The uranium analogy: digital tools as powerful but dangerous if used without adequate ethical "containment" ☢️ 24:00 – Philosophical closing: will juries someday trust heart-rate logs more than tears on the witness stand, and what does that mean for human testimony? 🤔 25:00 – Closing remarks and invitation to explore the full editorial, show notes, and resources on The Tech-Savvy Lawyer.Page 🌐 If you enjoyed this episode, please like, comment, subscribe, and share!

    18 min
  8. 🎙️ Ep. #129, Why Lawyers Should Podcast in the Age of AI: Live Roundtable from Podfest 2026 🎙️⚖️

    JAN 20

    🎙️ Ep. #129, Why Lawyers Should Podcast in the Age of AI: Live Roundtable from Podfest 2026 🎙️⚖️

    In this special episode, recorded live from Podfest 2026 in Orlando, FL at the Renaissance Marriott Hotel near SeaWorld, I was able to gather several attendees who are in the legal world—lawyers and legal industry marketers—to talk about why lawyers should podcast and more! 🎙️ Our roundtable features Dennis "DM" Meador (Legal Podcast Network), Louis Goodman (Love Thy Lawyer), Robert Ingalls (Lawpods), Wendi Wittner (The Writing Guru), and Elizabeth Gearhart (Passage to Profit / Gearhart Law), each bringing deep experience in podcasting, legal marketing, and personal branding for lawyers. We discuss practical, no-fluff insights about how lawyers can use podcasting to build authority, strengthen SEO, show up in large language models (LLMs) like ChatGPT, and connect more authentically with clients and referral sources. Whether you are tech-curious, tech-comfortable, or completely new to podcasting, this episode will help you decide if starting a podcast makes strategic sense for your practice or business. QUESTIONS WE DISCUSS 🎯 Join Dennis, Louis, Robert, Wendi, Elizabeth, and me as we discuss the following three questions and more! Why should lawyers be podcasting in 2026 and beyond, especially with Gen Z and Gen Alpha getting so much of their trusted information from podcasts and social platforms? What is one of the first concrete steps a lawyer should take if they are seriously considering launching a podcast of their own? What is one of the biggest mistakes lawyers should watch out for when launching a podcast, and how can they avoid becoming a "zombie podcast" that dies after a few episodes? 🧟‍♂️ Additional themes we explore include: How podcasting acts as an "electronic resume" and trust-building tool for lawyers. How podcasts can drive SEO, get you discovered in LLMs like ChatGPT, Google Gemini, Perplexity, and Claude, and generate traffic to your law firm website. Why your podcast does not always need to be "about the law" to be effective for your legal brand. How to balance authenticity (including salty language) with your professional brand and ethics rules. TIME-STAMPED EPISODE GUIDE ⏱️ In our conversation, we cover the following: 00:00 – Welcome & guest introductions Live from Podfest 2026: intros from Dennis "DM" Meador (Legal Podcast Network), Louis Goodman (Love Thy Lawyer), Robert Ingalls (Lawpods), Wendi Wittner (The Writing Guru), and Elizabeth Gearhart (Passage to Profit / Gearhart Law). 02:00 – Why should lawyers be podcasting? Gen Z and Gen Alpha treat podcasts as a top trusted media source. 📲 Podcasting vs TikTok for lawyers who don't want to dance but still want reach. Podcast as "electronic resume" and branding vehicle for lawyers and judges. 04:30 – Is podcasting right for every lawyer? Robert on why not every lawyer should podcast, and why goals matter. How a podcast helps potential clients decide if you are "their" lawyer—or not. 06:30 – Personality, language, and fit The Tampa PI lawyer who refuses to bleep swear words to attract the right clients and repel the wrong ones. 🤬 Why authenticity can be a powerful qualification tool, not a liability. 08:00 – Podcasting as a marketing engine Turning a 30–60 minute recording into video clips, written content, and evergreen assets. How podcast content keeps working for you long after the recording session. 09:30 – Personal branding and storytelling for lawyers Wendi on using podcasts to develop a personal brand, tell your story, and highlight your "superpower" as a lawyer. Why sharing your career pivots and non-traditional path resonates deeply with listeners. 12:00 – Getting discovered in ChatGPT and other LLMs Elizabeth on using a podcast and transcripts to improve visibility in ChatGPT, Google Gemini, Perplexity, and Claude. 🤖 How regular podcasting and transcript optimization sustained and improved hits from LLMs to Gearhart Law's website. 15:30 – Future-proofing and "language-based internet" DM explains why we're moving from a page-based to a language-based internet and why early podcast adopters will win—similar to early website and SEO adopters. Podcasting as both "future-proofing" and "present-proofing" your practice. 18:00 – Hobby vs business podcast Louis on starting his podcast as a social hobby and discovering the SEO and networking upside. How a niche local legal podcast can drive referrals and reputation even without direct monetization. 21:00 – How personal is too personal? Robert's own experience evolving his podcast from estate planning to broader personal topics. Balancing sharing about yourself with focusing on the listener's problem (StoryBrand "guide vs hero" concept). 25:00 – Beyond law: topic flexibility Why your legal podcast can focus on tech, politics, entrepreneurship, or hobbies while still supporting your legal brand. Examples of lawyers podcasting about politics and broader societal issues to grow recognition. 28:30 – Helping lawyers find their story Wendi's process: asking about upbringing, first-generation experiences, career pivots, athletic feats, and long-term goals to unlock unique stories. How those stories fuel compelling podcast episodes and stronger interviews. 34:00 – Thinking beyond your current role Using podcasting and personal branding to position yourself for boards, politics, and second careers outside traditional law practice. 37:00 – AI hallucinations & validating LLM output Elizabeth's workflow for cross-checking answers across ChatGPT, Gemini, Perplexity, Claude, and Grok. Why LLMs "love" natural, conversational podcast transcripts as training material. 40:00 – Networking power of "you should be on my podcast" How inviting people as guests changes the dynamic at networking events. 🤝 Using podcast guest outreach on LinkedIn and pod-match style platforms. 43:00 – Content, authority, and algorithm signals DM on why consistent, custom content will always outperform gimmicks in SEO and algorithm changes. How podcasts support authority, trust, and long-term discoverability in search and LLMs. 48:00 – Question #2: First steps for lawyers considering a podcast Robert and DM: "Know your why" and who your ideal listener/client really is. Are you using the show for lead nurturing, referral education, or brand visibility? 52:00 – Political/legal shows and indirect monetization Discussion of political/legal commentary podcasts that soft-sell the firm. Why they can work—but why expectations and time horizon matter. 56:00 – Brand consistency before you launch Wendi on auditing your website, LinkedIn, business page, and social handles for consistent branding (e.g., "The Writing Guru"). Using CTAs and data capture to turn podcast listeners into contacts. 59:00 – Knowing your deeper "why" Elizabeth's "peel the onion" exercise: repeatedly asking why until you reach the core motivation, often helping people out of "impossible situations." 1:03:00 – Solo vs agency vs studio Pros and cons of DIY gear and production vs working with podcast agencies or studios. Why time value, ethics, and avoiding scams all matter for lawyers. 1:08:00 – Ethics, multi-jurisdiction practice, and global reach How legal ethics, multistate audiences, and global distribution impact what lawyers can say on their podcasts. 1:12:00 – Question #3: Biggest mistakes lawyers make launching a podcast Elizabeth: ethics, off-the-cuff comments, and aligning tone (including swearing) with your brand and practice area. Wendi: perfectionism vs progress—accepting that early episodes will be imperfect but valuable. Robert: no long-term plan and no content strategy, leading to inconsistency and podfade. Louis: underestimating time; a solid 30 minutes of content may require several hours early on. DM: expecting immediate impact and treating podcasting like a short-term campaign instead of a long-term asset. 1:22:00 – Test-driving podcasting as a guest first Why appearing as a guest on other shows (via Podmatch and similar platforms) is a smart "trial run" before launching your own. 1:25:00 – Where to find today's guests & closing Each guest shares their preferred platforms, emails, and websites so you can connect and learn more. RESOURCES 📚 Connect with our Guests Louis Goodman ⚖️ Podcast: Love Thy Lawyer ("Love v. Lawyer") https://www.lovethylawyer.com LinkedIn Profile https://www.linkedin.com/in/louis-goodman-3b359/ Elizabeth Gearhart 📻 Gearhart Law (Chief Marketing Officer) https://www.gearhartlaw.com[ Passage to Profit Show (syndicated radio show & podcast) https://podcasts.apple.com/us/podcast/passage-to-profit-show-road-to-entrepreneurship/id1481650359 Email elizabeth@gearhartlaw.com LinkedIn (active profile) https://www.linkedin.com/in/elizabeth-gearhart-ph-d-97ba0b51/ Robert Ingalls 🎧 Lawpods (Founder & CEO – podcast agency for law firms) https://www.lawpods.com LinkedIn https://www.linkedin.com/in/robertingalls/ Dennis "DM" Meador 💼 LinkedIn: Dennis Meador – "Dennis Meta like a meadow, but with an R and no W" 🌱 https://www.linkedin.com/in/dennismeador/ Legal Podcast Network (Founder & CEO) https://thelegalpodcastnetwork.com Wendi Wittner ✍️ The Writing Guru – Legal Executive Branding & Career Strategy https://www.thewritingguru.net LinkedIn: Wendi Weiner / "The Writing Guru" https://www.linkedin.com/in/thewritingguru/ Above the Law (Wendi's column) https://abovethelaw.com/author/wendiweiner/ HuffPost article – "How I Used My Law Degree to Get Out of Law" (Wendi) https://www.huffpost.com/entry/how-i-used-my-law-degree-to-get-out-of-law_b_57bef010e4b0b01630ddd15c Mentioned in the episode Non‑Hardware/Software 🔍 Attorney Tom (PI lawyer & content creator) https://www.youtube.com/@AttorneyTom Podfest 2026 (Orlando, FL) https://podfestexpo.com Hardware mentioned 🧰 (Exact models are discus

    1h 10m
See All (151)

5
out of 5
15 Ratings

About

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!

Information

  • Creator
    Michael D.J. Eisenberg
  • Years Active
    2020 - 2026
  • Episodes
    151
  • Rating
    Explicit
  • Copyright
    © ℗ 2020 Michael D.J. Eisenberg
  • Show Website
    The Tech Savvy Lawyer

You Might Also Like