Notes to My Legal Self®

Welcome to Season 15, Episode 9 of Notes to My Legal Self, the legal operations podcast on turning legal work into measurable results.Russ Jacobs, who leads the intellectual property and innovation group at Starbucks Coffee Company, joins host Olga V. Mack to explain how data, metrics, and continuous improvement make a legal team a better business partner. He walks through a real IP clearance case study, his approach to stakeholder alignment in large and small organizations, and how he uses AI to analyze legal data.In this episode, you'll learn:- How to measure legal team performance with data- How to run continuous improvement in a legal department- How to build psychological safety on a legal team- How AI can support legal data analysisTimestamps:00:00 Introduction01:45 Meet Russ Jacobs02:15 Career path from litigation to in-house IP04:00 Leading legal at a national child welfare association08:00 Rethinking a mature trademark portfolio10:00 Looking beyond trademarks to other IP tools13:00 Start with governance documents and frameworks14:00 Open source and Starbucks farmer support centers18:00 How to define your goals before changing process19:30 Start with the data you already have22:15 Getting buy-in from VPs and executives26:45 Measuring IP clearance: speed versus risk29:30 Lessons from supporting new nonprofit programs31:30 Team goals, thresholds, and safe experimentation36:00 Buying technology after understanding the problem39:30 Final takeaway: work backward from your impact story.Russ's advice: Pick one to three simple data points that show leadership the impact your team has.How does your team talk about mistakes and what it learned from them? Share your answer in the comments.Follow this in-house counsel podcast and rate it so more legal teams can find these conversations.Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage.Like, comment, and subscribe to @NotesToMyLegalSelf so you never miss an episode.Explore more episodes at https://www.notestomylegalself.comINTERSECTION OF LAW AND FUN®#NotesToMyLegalSelf #LegalOps #LegalLeadership #IntellectualProperty

Welcome to Season 15, Episode 8 of Notes to My Legal Self, the in-house counsel podcast for lawyers navigating legal communication, leadership, AI, and the future of legal work.Matthew Lowe joins host Olga V. Mack for “Lost in Translation: Why Great Lawyers Explain, Not Impress” to explore how lawyers can turn complex legal knowledge into clear, practical advice that helps businesses make better decisions.Drawing on his experience in in-house legal practice, technology, cybersecurity, and regulatory compliance, Matthew explains why great lawyers do more than demonstrate expertise. They listen, understand their audience, ask the right questions, and communicate advice people can act on.In this episode, you'll learn:Why legal advice should be a conversation, not a one-way instructionHow to explain complex legal issues without relying on legaleseWhy complexity doesn't always equal business valueWhat lawyers should understand about a business before advising itHow to communicate uncertainty and confidence levelsHow to evaluate AI-generated answers, prompts, facts, and assumptionsWhy critical thinking and meaningful review remain essential in the age of AIHow clear communication builds trust with business stakeholdersTimestamps:(00:00) Introduction(01:37) Matthew Lowe's career journey(05:00) Law, technology, and in-house practice(07:00) Why legal advice gets lost in translation(09:00) Making legal advice accessible(12:00) Complexity versus business value(13:00) Collaboration and stakeholder context(15:00) Communicating with different audiences(19:00) Making legal advice actionable(22:00) Confirming facts and understanding the real question(23:00) Understanding the business before advising(27:00) Communicating confidence and uncertainty(30:00) Simplifying technical information(31:00) ChatGPT, prompts, and context(33:00) Curiosity, humility, and asking questions(35:00) Human skills in the age of AI(37:00) AI hallucinations and critical thinking(38:00) Building analytical skills before delegating to AI(40:00) Why meaningful review matters(41:00) Matthew's key advice(43:00) Final reflectionsMatthew's key takeaway:If you can't explain something to your partner, someone in college, or someone in high school, you may not understand it as well as you think.AI can support legal work, but lawyers still need sound judgment, critical thinking, and meaningful review.The best lawyers don't just know the answer; they understand the context and explain it clearly.How can lawyers make complex legal advice easier to understand without sacrificing accuracy or credibility?Share your thoughts in the comments.Enjoy this legal leadership podcast and podcast for lawyers? Rate and review Notes to My Legal Self on Apple Podcasts or Spotify.Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage.Like, comment, and subscribe to @NotesToMyLegalSelf for more conversations with in-house counsel and legal professionals.Explore more episodes: https://www.notestomylegalself.comINTERSECTION OF LAW AND FUN®#NotesToMyLegalSelf #InHouseCounsel #PodcastForLawyers #GeneralCounsel #LegalLeadership #LegalCommunication #LegalTech #ArtificialIntelligence #FutureOfLaw

Welcome to Season 15, Episode 7 of Notes to My Legal Self, the in-house counsel podcast for lawyers navigating AI, legal technology, leadership, and the future of legal work.Whitney Stefko joins host Olga V. Mack to explore one of the biggest challenges facing legal departments today: how to turn AI experimentation and technological innovation into meaningful, lasting organizational change.Working at the intersection of law, AI, and organizational transformation, Whitney shares why successful legal transformation starts with people, not technology. From responsible AI adoption to influencing stakeholders without formal authority, this conversation offers practical insights for in-house counsel, legal operations professionals, general counsel, and legal leaders navigating the changing legal landscape.In this episode, you'll learn:Why technology alone isn't enough to drive successful legal transformationHow to move from AI experimentation to responsible, meaningful adoptionWhy understanding real workflows is essential to implementing legal technologyHow psychological safety helps legal teams adapt to changeWhy AI fluency doesn't necessarily mean competence or accuracyHow to influence stakeholders without formal authorityWhy understanding people's incentives can improve collaborationHow legal operations leaders can bridge the gap between legal, technology, and business teamsWhy in-house counsel should build relationships with business partners before legal issues ariseHow to identify practical opportunities to improve repetitive legal workflowsTimestamps:⁠00:00⁠ Introduction to Notes to My Legal Self⁠00:43⁠ Whitney Stefko on law, AI, and organizational transformation⁠01:37⁠ Whitney's career journey: From litigation to legal operations⁠04:16⁠ Why technology initiatives fail to create change⁠06:17⁠ The human side of change management⁠09:28⁠ Diagnosing why transformation efforts stall⁠11:30⁠ What organizations misunderstand about technology adoption⁠13:26⁠ Moving from AI experimentation to meaningful adoption⁠16:25⁠ What it means to be an AI realist⁠17:31⁠ AI fluency vs. accuracy and competence⁠20:34⁠ Influencing people without formal authority⁠22:21⁠ Understanding incentives and motivating stakeholders⁠23:41⁠ Building influence through communication and connection⁠28:33⁠ Aligning legal, technology, and business stakeholders⁠33:11⁠ The role of in-house counsel in business strategy⁠35:26⁠ Where in-house lawyers should begin⁠37:08⁠ Whitney's key takeaway: People are the strategyWhitney's hot take: Technology is not your strategy. Your people are your strategy.AI can transform legal work, but lasting progress requires more than new tools. It takes strong leadership, continuous learning, human connection, and a clear understanding of how people actually work.How can legal leaders make AI adoption more effective while keeping people at the center of transformation?Tell us in the comments.If you enjoy this legal tech podcast and podcast for lawyers, rate and review Notes to My Legal Self on Apple Podcasts or Spotify. It helps more legal professionals discover these conversations.Want to be a guest on NTMLS or know someone who should be?Reach out! Self-nominations are acts of courage.Like, comment, and subscribe to @NotesToMyLegalSelf.Explore more episodes at ⁠https://www.notestomylegalself.com⁠INTERSECTION OF LAW AND FUN®⁠#InHouseCounsel⁠ ⁠#PodcastForLawyers⁠ ⁠#LegalAI⁠ ⁠#LegalOperations⁠ ⁠#LegalTech⁠ ⁠#ChangeManagement⁠ ⁠#FutureOfLaw

Welcome to Season 15, Episode 6 of Notes to My Legal Self, the in-house counsel podcast for lawyers navigating AI, legal technology, leadership, and the future of legal work.Adam Becker, Director of Legal Operations at Cockroach Labs, returns to the podcast to share his perspective on one of the biggest changes facing legal departments today: the shift from using AI as a tool to working with AI as an advisor.For in-house lawyers, legal ops professionals, general counsel, and legal leaders, this conversation explores what it takes to move beyond checking the "AI box" and become more fluent in AI-native ways of working.In this episode, you'll learn:- Why legal operations is becoming essential to modern legal departments- The difference between adopting AI and becoming AI-native- How AI can help legal teams work differently, not just faster- Why legal ops leaders need to understand how lawyers actually work- How knowledge management enables better AI outcomes- How to build trust when introducing AI to legal teams- Why legal leaders should experiment rather than wait for a mandate- How to identify practical workflows where AI can make an immediate difference- Why sharing AI learnings across legal teams mattersTimestamps:00:00 Introduction03:00 Legal operations becomes essential05:00 AI and the second stage of legal ops maturity08:00 From systems to AI advisors10:00 The evolution of the Core 1213:00 Knowledge management and AI15:00 AI adoption vs. AI-native legal teams19:00 What makes a strong legal ops leader23:00 Building trust with lawyers27:00 Taking initiative with AI31:00 Where legal teams should start35:00 Mistakes legal departments are making with AI38:00 One action legal ops leaders should takeAdam's hot take: The biggest opportunity isn't simply saving 10% of your time, it's changing how you work.What would you eliminate or simplify if you had an AI advisor working alongside you?Tell us in the comments.If you enjoy this legal tech podcast and podcast for lawyers, rate and review Notes to My Legal Self on Apple Podcasts or Spotify. It helps more legal professionals discover the conversation.Want to be a guest on NTMLS or know someone who should be?Reach out! Self-nominations are acts of courage.Like, comment, and subscribe to @NotesToMyLegalSelf.Explore more episodes at https://www.notestomylegalself.comINTERSECTION OF LAW AND FUN®#LegalOperations #LegalOps #AIinLegal #LegalTech #InHouseCounsel #PodcastForLawyers #FutureOfLaw

Welcome to Season 15, Episode 5 of Notes to My Legal Self, the in-house counsel podcast on legal judgment, leadership, and getting to yes. Carly McAllister, Associate General Counsel in financial services, joins Olga V. Mack to discuss the move from litigator to trusted business partner.Made for in-house lawyers and general counsel, this conversation explores how legal teams can create confidence and possibility for the business, instead of only managing risk.In this episode, you'll learn:- How to transition from litigation to an in-house legal career- Why in-house lawyers must think like business partners- How to find responsible ways to get to "yes"- How to develop legal judgment, and why there is no cap on it- Why AI can amplify legal work but not replace judgmentTimestamps:00:00 Introduction04:33 Leaving litigation to go in-house07:10 Becoming a business partner in financial services12:41 Why technical excellence is not enough16:35 Creating confidence with executives20:13 How legal departments create possibility27:24 Legal judgment in the age of AI32:15 How to build good judgment38:00 Final advice for future in-house lawyersCarly's advice: technical legal skill is the foundation, not the finish line.When was the last time your "no" came with a path to "yes"? Share your answer with us in the comments.If you enjoy this lawyer podcast, rate and review Notes to My Legal Self on Apple Podcasts or Spotify. It helps more in-house counsel find these conversations.Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage.Like, comment, and subscribe to @NotesToMyLegalSelf so you never miss an episode.Explore more episodes at https://www.notestomylegalself.comINTERSECTION OF LAW AND FUN®#NotesToMyLegalSelf #InHouseCounsel #GeneralCounsel #LegalLeadership #LegalJudgment #LawyerPodcast