What happens if your client asks ChatGPT for advice about their case? Is that discoverable? Is it your fault if you didn't warn them it might be? Leslie Bender and Craig Linton join the show to unpack two cases: Heppner and Warner v Gilbarco, that seem to reach opposite conclusions as judges try to draw lines around privilege, work product, and AI in an area where the rules haven't caught up to the tools.

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝘀𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗔𝗜 𝗶𝗻 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲:

Spotify: https://open.spotify.com/show/1RqIrtqTgbng2BGuzr4aAq

Apple: https://podcasts.apple.com/us/podcast/ai-in-practice/id1846506529

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁𝘀:

https://www.linkedin.com/in/lescbender/

https://www.linkedin.com/in/craigalinton/

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox.

➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster

➞ try it free: https://www.spellbook.legal

https://www.linkedin.com/company/spellbookai/posts/?feedView=all

https://www.linkedin.com/in/mikewhelanjr/

https://www.linkedin.com/in/scottas/

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction

1:49 - Meet Leslie Bender 2:31 - Meet Craig Linton

3:31 - Attorney-client privilege and work product 101

5:54 - Clients have always gone rogue with case info

8:00 - The Heppner case: a CEO, AI, and a 31-point memo

11:21 - Does it matter if the lawyer directed it?

13:00 - Warner v Gilbarco: the pro se counterpoint

16:08 - What discoverability means for pro se litigants

19:21 - Assume your AI self-help is discoverable

21:37 - The engagement letter hack

23:19 - Should we encourage or discourage client AI use?

25:06 - Lawyers as AI consumers: is Claude enough?

28:10 - Reasonable privacy expectations vs. the fine print

30:49 - Three predictions for the next 10 years

33:06 - Connect with Leslie and Craig

Kyle Westaway has run his firm for 17 years without ever tracking a billable hour. In this conversation, he breaks down why he believes 75% of a lawyer's value has nothing to do with documents—and why that makes AI a tailwind, not a threat, for firms built around outcomes instead of time. He also shares how he prices work without defaulting to hourly estimates, why clarity with clients takes courage, and what it means to design a law firm from first principles.

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal

https://ca.linkedin.com/company/spellbookai https://www.linkedin.com/in/mikewhelanjr https://ca.linkedin.com/in/scottas

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction 1:14 - Meet Kyle Westaway 2:30 - Starting a firm fresh out of law school 4:00 - Designing a firm for startups from first principles 5:00 - What do lawyers actually sell? 7:00 - Why the billable hour persists 10:45 - Flat fees only: How Kyle prices work 13:00 - Why clarity with clients takes courage 15:00 - Why they've never tracked a single hour 17:00 - The "market for lemons" problem in legal 19:30 - Why AI helps flat-fee firms (and hurts hourly ones) 22:00 - Purpose and the future of law practice 23:30 - Connect with Kyle

Ryan Juliano runs Darwin Legal, a subscription-based fractional general counsel practice serving early-stage tech startups. After 15 years moving down the legal food chain from IPOs to pre-seed companies, he's built a model that replaces the crushing wave of hourly billing with committed capacity—and he's using AI across every part of his practice. In this conversation, he shares what it means to use tools "promiscuously," why lawyers need to get comfortable chopping with blunt axes, and how AI helps him think through not just legal problems but business model design.

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁:

https://www.linkedin.com/in/ryan-juliano-b3833124 https://darwinlegal.com/

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction

1:12 - Meet Ryan Juliano

2:15 - From IPOs to early-stage startups

5:34 - The subscription fractional GC model

8:34 - Who manages legal before you arrive

11:01 - Running everything through AI

16:19 - Good enough vs. perfect

17:55 - Will tools consolidate or stay fragmented?

20:29 - How Ryan spends his time now

24:37 - Shifting from inputs to outputs

27:23 - Capturing knowledge to repurpose

32:57 - Defining "good enough" in legal services

34:04 - Connect with Ryan

Colin Lachance helps law firms implement AI without the paralysis. As founder of LawQi and former Innovator in Residence at the Ontario Bar Association, he's developed a practical framework: start with tasks, not processes. In this conversation, he explains why most firms aren't ready for full process redesigns, what infrastructure you actually need before experimenting, and how to build the skills that prevent expensive mistakes.

📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿:

Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 

𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁:

https://www.linkedin.com/in/colinlachance https://lawqi.com/

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction 1:30 - Meet Colin Lachance 4:15 - Working inside a real law firm 6:00 - The messy garage problem 11:30 - Tasks vs. processes: which comes first 14:00 - What infrastructure you actually need 17:30 - Why start with tasks, not whole processes 21:30 - How lawyers should learn AI 24:15 - Connect with Colin

Washington, DC attorney Shavon J. Smith runs a small firm that serves growing businesses as their fractional general counsel. In this episode, she explains how AI helps her compete with larger firms – from mapping workflows to drafting contract checklists, improving client alerts, pressure-testing assumptions, and crafting clearer redline comments during negotiations. She also shares where AI meaningfully improves efficiency, where it simply improves quality, and where human judgment still matters most, especially in negotiation and client counseling. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction 2:15 - Meet Shavon J. Smith 3:32 - What is fractional general counsel? 4:00 - AI for process mapping and improvement 6:03 - Using AI as a brainstorming partner 7:46 - Marketing and client communication 8:25 - How clients find the firm (including through AI) 10:06 - Email overwhelm and client management 13:12 - AI for contract drafting and review 16:06 - Being a better strategic advisor 18:00 - Understanding clients' businesses 19:48 - Managing people and processes 22:35 - Where AI can't help: settlement psychology 24:17 - Learning from other lawyers 24:35 - Connect with Shavon

Olivia Anderson helps law firms build the IT infrastructure they need before adopting AI. As Principal at Framework IT, a managed service provider working with legal practices of all sizes, she's seen what happens when firms rush into AI without the cybersecurity foundations in place. In this conversation, she walks through shadow AI, the $5.5 million problem most firms don't know they have, and why managing partners need to own AI governance whether they like it or not. 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:21 - Meet Olivia Anderson 2:11 - Shadow AI and the $5.5M problem 6:09 - IT readiness for solo lawyers 10:16 - Consumer AI vs. legal-specific tools 13:15 - Creating a responsible AI policy 17:22 - Who owns AI governance at your firm 21:45 - Risk tolerance culture in law 28:56 - Quantifying your firm's risk profile 31:00 - Connect with Olivia

Todd Smith is a board-certified appellate lawyer in Texas who consults with trial teams and handles appeals. In this conversation, he explains how AI tools are changing his work—and where they hit their limits.

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸:

Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:42 - Todd's appellate practice model 6:10 - AI collaboration challenges 9:15 - Analyzing trial transcripts with AI 14:57 - Finding arguments vs. knowing what to do with them 19:03 - Small data sets and judgment calls 24:50 - Why hourly billing is breaking down 28:04 - Flat fee experiments 31:23 - Marketing as an AI quick win 34:19 - Connect with Todd

Before "AI automation" was a buzzword, Joey Vitale built Indie Law to operate without him. That experience—paired with years helping lawyers scale through virtual assistants—turned him into a quiet expert on systems, delegation, and identity. In this episode, he and host Mike Whelan dig into what happens when the work that once defined you starts running itself, and why the real value of a lawyer might have less to do with tasks and more to do with trust.

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal/

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction

2:15 - Why Joey left litigation

5:34 - The crisis that forced systematization

8:27 - Four stages: doer to strategist

14:44 - Managing VAs prepares you for AI

19:42 - Prompting AI effectively

24:15 - 80% right is 100% awesome

32:51 - Redefining lawyer identity

36:20 - Why clients still need attorneys

Alessandra Colaci helps in-house legal teams figure out how to actually use AI—not just talk about it. As the founder of Legal Plus AI and former founding marketer at Harvey, she's spent years teaching lawyers to prompt, experiment, and integrate AI into their daily work. In this conversation, she breaks down the quick wins that build momentum, the security concerns that keep lawyers up at night, and why most teams need to start smaller than they think. 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:10 - Meet Alessandra Colaci 2:34 - The adoption gap: Strategy vs. reality 3:42 - Micro-learning and experimentation 6:04 - Quick wins 6:54 - Using AI as a thought partner 11:32 - The "prompt library" approach 13:48 - What to try on your own vs. with the team 17:18 - What's real vs. what's fear 22:53 - When courts will catch up to AI as standard practice 24:27 - Learning what works for you 27:34 - Connect with Alessandra

Beau Atkins runs Evolve Family Law in Saskatchewan, Canada, where he's using AI to reach the 79% of people with legal problems who never hire a lawyer. In this conversation, he shares how he built an AI-assisted tool that guides self-represented clients through court processes — and how he's testing an AI agent to handle intake calls. His end goal? Serve with three lawyers what would normally take 300.

𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀:

0:00 - Introduction 1:14 - Meet Beau Atkins 2:15 - The journey from frustrated lawyer to entrepreneur 5:34 - AI experiments in family law practice 8:27 - Solving the 79% problem 14:44 - Ethics, disclaimers, and hallucinations 19:42 - What clients really want (and don't get) 27:58 - Product design: Flat fees and AI tools 30:25 - Learning from COVID experiments 32:51 - How Beau uses AI today 33:33 - Connect with Beau

💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.com