The 80/20 Principle

Carolyn Elefant has been practicing law for thirty-five years and writing about solo practice for almost as long. In this episode she and Ernie get into how AI is changing litigation — not in theory, but in the cases she's handling right now. Carolyn walks through experiments she's run and posted publicly, including having AI draft the judge's opinion from both briefs before she wrote her reply, and hiding instructions inside a brief to see which AI tools would follow them. One tool refused. One followed them. The third declined the part it considered unethical and went along with the part it considered harmless — which is the interesting one, because it looks a lot like judgment. They also cover which tools she reaches for and when, why she pays for the business version instead of the free one, where a lawyer should start if all of this feels overwhelming, and her upcoming 'Bellwether AI Litigator' conference on September 17 and 18. Chapters 0:05 Episode Overview 1:45 Smith.ai Sponsor 2:30 A Small Firm That Fights Big Energy 7:09 Her First AI Experiments 10:46 Making AI Write the Judge's Opinion 12:59 The Prompt Injection Test 14:44 When AI Starts to Look Like Judgment 17:38 Connecting Claude to Email, Files, and Court Listener 25:02 Where a Lawyer Should Start 27:02 Free vs. Paid, and What Happens in Discovery 28:35 The Bellwether Litigator Conference Resource Links The Bellweather AI Litigator Conference info Early Bird Registration (special price) Carolyn's LinkedIn profile (follow her from here) The 80/20 Principle (my techlaw newsletter) The Inner Circle (my online community for lawyers) Follow and Review: I'd appreciate if you could drop a review over on Apple Podcasts. It only takes a few seconds and helps spread the word about the podcast. Thanks to the sponsor: Smith.ai Smith.ai is an amazing virtual receptionist service that specializes in working with solo and small law firms. When you hire Smith.ai, you're hiring well-trained, friendly receptionists who can respond to callers in English or Spanish. And they have a special offer for podcast listeners where you can get an extra $100 discount with promo code ERNIE100. Sign up for a risk-free start with a 14-day money-back guarantee now (and learn more) at smith.ai.

In this episode, Ernie Svenson talks with Docket Drafter co-founder Tommy Eberle about what lawyers need to understand to use AI tools like Claude more effectively. They unpack why Word documents consume so many tokens, why AI performance can decline during long chats, how context windows and compaction affect results, and when to use different Claude models and thinking levels. Tommy also explains how lawyers can use AI to organize files, automate repetitive document work, and build more efficient workflows—without needing to become programmers themselves. Chapters 0:05 Why AI Frustrations Make Sense 3:03 From Coding To Legal AI 8:05 Making Word Agent-Friendly 16:20 Why Claude Gets Dumber 26:21 Models, Thinking, And Compaction 34:33 Files, Folders, And Better Prompting Show Notes The 80/20 Principle (my techlaw newsletter) The Inner Circle (my online community for lawyers) Tommy Eberle's LinkedIn page Tommy's Email Address: [email protected] Docket Drafter https://www.youtube.com/@DocketDrafter Follow and Review I'd appreciate it if you could drop a review over on Apple Podcasts. It only takes a few seconds and helps spread the word about the podcast. Thanks to the sponsor: Smith.ai Smith.ai is an amazing virtual receptionist service that specializes in working with solo and small law firms. When you hire Smith.ai, you're hiring well-trained, friendly receptionists who can respond to callers in English or Spanish. And they have a special offer for podcast listeners where you can get an extra $100 discount with promo code ERNIE100. Sign up for a risk-free start with a 14-day money-back guarantee now (and learn more) at smith.ai.

Most lawyers using Claude are only scratching the surface of what it can do. In this episode, Ernie Svenson talks with former litigator and software founder Nick Chapleau about using Claude as more than a chatbot—as a chief of staff that can help run a modern law firm. They explore email triage, workflow automation, firm knowledge bases, custom dashboards, security, and what it takes to build a truly Claude-native practice. Chapters 0:05 Using Claude as Chief of Staff 2:34 Nick's Legal and Software Background 8:07 Building a Claude-Native Law Firm 14:55 Automating Email and Firm Workflows 19:54 Creating a Central Firm Wiki 31:06 Hosting, Security, and Implementation Resource Links The 80/20 Principle (my techlaw newsletter) The Inner Circle (my online community for lawyers) Follow and Review I'd appreciate it if you could drop a review over on Apple Podcasts. It only takes a few seconds and helps spread the word about the podcast. Thanks to the sponsor: Smith.ai Smith.ai is an amazing virtual receptionist service that specializes in working with solo and small law firms. When you hire Smith.ai, you're hiring well-trained, friendly receptionists who can respond to callers in English or Spanish. And they have a special offer for podcast listeners where you can get an extra $100 discount with promo code ERNIE100. Sign up for a risk-free start with a 14-day money-back guarantee now (and learn more) at smith.ai.

Most AI training for lawyers is shiny-object stuff — nine prompts, the "ultimate playbook" — and that's exactly why none of it sticks. My old golf instructor figured this out decades ago, and he taught me the fix before AI even existed. In this episode I tell that story and show you the one approach that actually works when you're learning to use AI in your practice. It's slower than chasing the next shiny thing, but it's the only thing that's ever worked. Resource Links The 80/20 Principle (my techlaw newsletter) The Inner Circle (my online community for lawyers) Follow and Review: I'd appreciate if you could drop a review over on Apple Podcasts. It only takes a few seconds and helps spread the word about the podcast. Thanks to the sponsor: Smith.ai Smith.ai is an amazing virtual receptionist service that specializes in working with solo and small law firms. When you hire Smith.ai, you're hiring well-trained, friendly receptionists who can respond to callers in English or Spanish. And they have a special offer for podcast listeners where you can get an extra $100 discount with promo code ERNIE100. Sign up for a risk-free start with a 14-day money-back guarantee now (and learn more) at smith.ai.

*]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" data-turn-id= "request-WEB:413b47b1-131b-4956-ab51-0904d0f6049f-1" data-turn-id-container= "request-WEB:413b47b1-131b-4956-ab51-0904d0f6049f-1" data-testid= "conversation-turn-4" data-scroll-anchor="false" data-turn= "assistant"> Ernie Svenson sits down with complex litigation attorney Richard Serpe to explore how he went from struggling with AI basics to becoming an advanced user in just 18 months. Richard shares how he uses tools like Claude, Perplexity Computer, NotebookLM, and AI skills to manage complex cases, organize research, prepare witnesses, and build better legal workflows. They also discuss the real costs of agentic AI, why file structure matters, how lawyers can avoid getting locked into one platform, and why curiosity may be the most important skill for adopting AI in legal practice. Chapters *]:pointer-events-auto scroll-mt-(--header-height)" dir="auto" tabindex="-1" data-turn-id= "c9c2e10c-c222-4dda-96fc-a25e253f5f32" data-testid= "conversation-turn-1" data-scroll-anchor="false" data-turn="user"> *]:pointer-events-auto scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" tabindex="-1" data-turn-id= "request-WEB:b3210431-d026-4045-b30d-b7c09679a93c-2" data-testid= "conversation-turn-2" data-scroll-anchor="false" data-turn= "assistant"> 0:07 Richard's AI Journey 4:26 Early AI Friction 9:25 File Structure And Memory 15:34 Perplexity Computer Costs 26:17 Skills In Claude 35:57 Final AI Adoption Advice Resource Links AI Lab (a weekly AI workshop for lawyers) LinkedIn post by attorney offering AI chatbot that protects privilege The Inner Circle (my online community for lawyers) The 80/20 Principle (my techlaw newsletter) Follow and Review: I'd love for you to follow me if you haven't yet. Click that purple '+' in the top right corner of your Apple Podcasts app. I'd love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select "Ratings and Reviews" and "Write a Review" then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast. Thanks to the sponsor: Smith.ai Smith.ai is an amazing virtual receptionist service that specializes in working with solo and small law firms. When you hire Smith.ai, you're hiring well-trained, friendly receptionists who can respond to callers in English or Spanish. And they have a special offer for podcast listeners where you can get an extra $100 discount with promo code ERNIE100. Sign up for a risk-free start with a 14-day money-back guarantee now (and learn more) at smith.ai.