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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 instruction How to explain complex legal issues without relying on legalese Why complexity doesn't always equal business value What lawyers should understand about a business before advising it How to communicate uncertainty and confidence levels How to evaluate AI-generated answers, prompts, facts, and assumptions Why critical thinking and meaningful review remain essential in the age of AI How clear communication builds trust with business stakeholders Timestamps:00:00 Introduction01:37 Matthew Lowe's career journey05:00 Law, technology, and in-house practice07:00 Why legal advice gets lost in translation09:00 Making legal advice accessible12:00 Complexity versus business value13:00 Collaboration and stakeholder context15:00 Communicating with different audiences19:00 Making legal advice actionable22:00 Confirming facts and understanding the real question23:00 Understanding the business before advising27:00 Communicating confidence and uncertainty30:00 Simplifying technical information31:00 ChatGPT, prompts, and context33:00 Curiosity, humility, and asking questions35:00 Human skills in the age of AI37:00 AI hallucinations and critical thinking38:00 Building analytical skills before delegating to AI40:00 Why meaningful review matters41:00 Matthew's key advice43:00 Final reflections Matthew'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.com INTERSECTION 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 transformation How to move from AI experimentation to responsible, meaningful adoption Why understanding real workflows is essential to implementing legal technology How psychological safety helps legal teams adapt to change Why AI fluency doesn't necessarily mean competence or accuracy How to influence stakeholders without formal authority Why understanding people's incentives can improve collaboration How legal operations leaders can bridge the gap between legal, technology, and business teams Why in-house counsel should build relationships with business partners before legal issues arise How to identify practical opportunities to improve repetitive legal workflows Timestamps: ⁠00:00⁠ Introduction to Notes to My Legal Self ⁠00:43⁠ Whitney Stefko on law, AI, and organizational transformation ⁠01:37⁠ Whitney's career journey: From litigation to legal operations ⁠04:16⁠ Why technology initiatives fail to create change ⁠06:17⁠ The human side of change management ⁠09:28⁠ Diagnosing why transformation efforts stall ⁠11:30⁠ What organizations misunderstand about technology adoption ⁠13:26⁠ Moving from AI experimentation to meaningful adoption ⁠16:25⁠ What it means to be an AI realist ⁠17:31⁠ AI fluency vs. accuracy and competence ⁠20:34⁠ Influencing people without formal authority ⁠22:21⁠ Understanding incentives and motivating stakeholders ⁠23:41⁠ Building influence through communication and connection ⁠28:33⁠ Aligning legal, technology, and business stakeholders ⁠33:11⁠ The role of in-house counsel in business strategy ⁠35:26⁠ Where in-house lawyers should begin ⁠37:08⁠ Whitney's key takeaway: People are the strategy Whitney'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.com⁠ INTERSECTION 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 matters Timestamps: 00:00 Introduction 03:00 Legal operations becomes essential 05:00 AI and the second stage of legal ops maturity 08:00 From systems to AI advisors 10:00 The evolution of the Core 1213:00 Knowledge management and AI 15:00 AI adoption vs. AI-native legal teams 19:00 What makes a strong legal ops leader 23:00 Building trust with lawyers 27:00 Taking initiative with AI 31:00 Where legal teams should start 35:00 Mistakes legal departments are making with AI 38:00 One action legal ops leaders should take Adam'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.com INTERSECTION 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 judgment Timestamps: 00:00 Introduction 04:33 Leaving litigation to go in-house 07:10 Becoming a business partner in financial services 12:41 Why technical excellence is not enough 16:35 Creating confidence with executives 20:13 How legal departments create possibility 27:24 Legal judgment in the age of AI 32:15 How to build good judgment 38:00 Final advice for future in-house lawyers Carly'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.com INTERSECTION OF LAW AND FUN® #NotesToMyLegalSelf #InHouseCounsel #GeneralCounsel #LegalLeadership #LegalJudgment #LawyerPodcast

Welcome to Season 15, Episode 4 of Notes to My Legal Self, the in-house counsel podcast for lawyers who want to lead. Bradley Bald, In-House Counsel at Lifestyle Communities, joins Olga V. Mack to talk about burnout, taking a sabbatical, and why the power of the pause is an underrated legal leadership skill. Bradley shares his path from private practice to in-house counsel at a vertically integrated real estate developer. He opens up about what a career pause really feels like, how to answer interview questions about a resume gap, and how cognitive empathy helps lawyers resolve conflict without absorbing other people's emotions. In this episode, you'll learn: - How to know when a sabbatical is the right move for your legal career - Why most lasting regret comes from inaction, not action - How to handle interview questions about a resume gap - How the power of the pause improves negotiations and conflict resolution - What cognitive empathy is and how it differs from sympathy - How in-house lawyers add value beyond contracts as proactive business partners Timestamps: 0:00 Introduction 0:35 Meet Bradley and Lifestyle Communities 2:10 From real estate to in-house counsel 3:53 Taking a sabbatical to prevent burnout 6:43 Returning to work after a career gap 11:12 The ""gray place"" during a career pause 13:09 Building visibility as an in-house lawyer 15:54 Handling interview questions about a resume gap 19:25 The power of the pause 25:51 Cognitive empathy vs sympathy 28:01 What executives expect from legal leaders 31:50 The decision that shaped his legal career 33:47 Final takeaway: life is long Key takeaways: - Career success comes in stages. Life is long, not short. - A strategic pause can prevent burnout and create clarity. - Listening and cognitive empathy often create more impact than a quick, witty answer. Enjoyed this episode? Rate and review Notes to My Legal Self on Apple Podcasts or Spotify. It helps more in-house lawyers find the show. Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage. Like, comment, subscribe, and hit the bell so you never miss an episode. Subscribe: @NotesToMyLegalSelf INTERSECTION OF LAW AND FUN® #InHouseCounsel #LawyerPodcast #LegalLeadership #LawyerWellBeing #BurnoutPrevention

Welcome to Season 15, Episode 3 of Notes to My Legal Self, the in-house counsel podcast for lawyers who want to lead. Kemi Ijitimehin, an Atlanta-based advertising and ad tech attorney, joins Olga V. Mack to talk about the power of the pivot, building trust as product counsel, and growing from first-gen lawyer to trusted business partner. Kemi shares her path from public policy in Washington, D.C., to the federal government during COVID, to in-house work at a tech company. She explains how her family's history shaped her comfort with change, how to turn rejection into redirection, and why authenticity is what turns lawyers into trusted strategic advisors. In this episode, you'll learn: - How to know when it's time to pivot your legal career - How to turn rejection into redirection - Why product counsel work is one of the most creative roles in law - The difference between advising a business and helping build one - What ""learning the business"" really means for in-house lawyers - How authenticity builds trust and buy-in with stakeholders - The first step to take after a layoff or career transition Timestamps: 0:00 Introduction 1:03 Becoming an advertising and ad tech lawyer 3:08 Family roots and the power of the pivot 7:16 How to know when it's time to pivot 10:51 Can lawyers trust their gut? 12:03 Turning rejection into redirection 13:55 Creativity in product counsel work 15:43 What surprised her most about going in-house 17:33 Advising a business vs helping build one 20:26 How to build trust and buy-in 22:42 AI and the human side of lawyering 24:19 Thinking like a business leader 26:44 What ""learning the business"" really means 29:17 Becoming a trusted strategic advisor 31:34 First steps after a layoff or career transition 33:06 Final takeaway: be brave Key takeaways: - Pivoting starts with a feeling, but your ""why"" decides the right move. - Relationships and authenticity matter as much as knowing the law. - Learn the business by sitting in on engineering, product, and marketing meetings. Enjoyed this episode? Rate and review Notes to My Legal Self on Apple Podcasts or Spotify. It helps more in-house lawyers find the show. Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage. Like, comment, subscribe, and hit the bell so you never miss an episode. Subscribe: @NotesToMyLegalSelf INTERSECTION OF LAW AND FUN® #InHouseCounsel #ProductCounsel #LawyerPodcast #LegalCareers #LegalLeadership

Welcome to Season 15, Episode 2 of Notes to My Legal Self, the in-house counsel podcast for lawyers who want to lead. Elizabeth Colombo, Associate General Counsel at Vendavo, returns to talk with Olga V. Mack about red lines, relationships, and real leadership. Elizabeth shares how 14 years in-house taught her the psychology of contract negotiation, how to get comfortable with acceptable risk, and why embedded humanity makes in-house lawyers indispensable. In this episode, you'll learn: - Why negotiation is about people, not just the paper - How to separate material risk from theoretical risk - How to make the business want legal involved early - How to resolve stakeholder conflict without being the bad guy - The soft skills lawyers most often underestimate Timestamps: 00:00 Introduction 03:04 Negotiation lessons: people, psychology, and risk 07:05 How to make the business want legal involved 10:59 Why in-house lawyers should assume they belong 14:32 What ""embedded humanity"" means 20:23 Handling stakeholder conflict 23:41 From referee to decision architect 29:07 Soft skills lawyers underestimate 34:37 Final takeaway: be human Elizabeth's advice: in the age of AI, your human judgment is what sets you apart. Is your legal team seen as the referee or the partner who helps make the call? 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.com INTERSECTION OF LAW AND FUN® #NotesToMyLegalSelf #InHouseCounsel #GeneralCounsel #LegalLeadership #ContractNegotiation #LawyerPodcast

Welcome to Season 15, Episode 1 of Notes to My Legal Self, the in-house counsel podcast for lawyers who want to lead. Alexandra Sepulveda, Associate General Counsel at Trust & Will, joins Olga V. Mack to explore how lawyers build legal judgment when AI does more of the thinking. Alexandra shares her path from patent litigator to in-house counsel at General Mills, Kabam, and fast-growing startups. She explains what junior lawyers miss when AI drafts first, why judgment is different from benchmarking, and the simple habits she uses to keep her own "lawyer gut" sharp. In this episode, you'll learn: - What junior lawyers lose when they skip the early reps - The human-AI-human "Oreo cookie" method for using AI well - Why the purposeful pause is a negotiation tool AI can't replace - The difference between legal judgment and knowing what's market - How to spot and close judgment gaps on your legal team Timestamps: 00:00 Introduction 03:34 Meet Alexandra and Trust & Will 05:11 From patent litigator to in-house counsel 09:23 The early work that teaches judgment 13:30 The power of the purposeful pause 16:02 How AI is changing legal team capacity 21:48 The human-AI-human method 24:53 Judgment vs. benchmarking 28:26 Why junior lawyers need informal mentors 32:35 Expecting senior judgment without junior reps 36:14 Redesigning law school for AI 39:00 Habits that build legal judgment 44:53 Final takeaway: stay curious Alexandra's advice: stay curious, because no one is going to replace your gut. Do you write your own first draft before asking AI, or let AI go first? 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.com INTERSECTION OF LAW AND FUN® #NotesToMyLegalSelf #InHouseCounsel #LegalJudgment #AIinLaw #LegalLeadership #LawyerPodcast

Welcome to Season 14, Episode 10 of Notes to My (Legal) Self®, the in-house counsel podcast exploring AI, legal judgment, and the future of the legal profession. Host Olga V. Mack talks with Dharshi Harindra, Assistant General Counsel for APAC at FTI Consulting, live from Singapore. Drawing on 20 years across big law, TMT, and data privacy in the UK, Australia, Dubai, and Singapore, Dharshi challenges the popular claim that ""AI won't replace lawyers, but lawyers who use AI will."" Her view: AI is a mirror, and without strong human judgment it only produces confident but risky answers faster. This general counsel podcast conversation is for in-house lawyers, legal leaders, and anyone navigating legal tech and AI adoption. In this episode, you'll learn: - Why human judgment, not technical fluency, will set lawyers apart - Which traditional lawyer labels are weakening and what is replacing them - How AI can amplify bias, and why lawyers are positioned to correct it - A practical framework for legal judgment: what matters, what doesn't, what happens next, and who owns the consequences - How early-career lawyers can build judgment without years of ""learning by osmosis"" - Why legal tech needs subject matter experts at the table Timestamps: 00:00 Introduction 01:06 Meet Dharshi: a global legal career from London to Singapore 03:48 Is ""lawyers who use AI will replace lawyers"" the right framing? 07:10 The lawyer labels that are weakening 11:35 How AI mirrors and amplifies bias 15:21 What legal judgment looks like in practice 21:29 Technically right vs. strategically wise 25:17 Why lawyers should document how they think 31:24 Skills early-career lawyers need now 35:13 Pairing legal tech with subject matter expertise 39:25 Redefining the exceptional lawyer 41:33 The profession five years from now 44:35 Final takeaway If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal leaders find these conversations. S U B S C R I B E! Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage. Engage with us below, like, comment, and subscribe to follow the future of in-house law! Thank you for watching! Like, Comment, Subscribe and hit the bell so you never miss an episode! Subscribe to our channel: @NotesToMyLegalSelf INTERSECTION OF LAW AND FUN® #NotesToMyLegalSelf #LegalInnovation #LegalTech #FutureOfLaw #LegalLeadership

Welcome to Season 14, Episode 9 of Notes to My Legal Self, the in-house counsel podcast on AI, contracting, and the future of legal work. Host Olga V. Mack talks with Cherryn-Paige Bissett, Internal Commercial Counsel at LegalSifter, about what to automate in contracting and what still needs a lawyer's judgment. With over 20 years as a commercial attorney, Cherryn shares her ""automate 80%, own 20%"" approach: use AI and playbooks to cut through contract noise, then focus your time on the risks that matter. This legal tech and legal operations conversation is for in-house lawyers, corporate counsel, and anyone who wants to close deals faster without taking on unnecessary risk. In this episode, you'll learn: - How AI contract playbooks build consistency and reduce contract noise - What separates a useful playbook from one that becomes rigid or ignored - When to step outside the playbook, including new AI provisions in NDAs - Which contracting decisions still require human judgment - How to weigh possibility vs. probability when deciding which risks to push back on - How a one-page contract primer can speed up negotiations Timestamps: 00:00 Introduction 00:44 Meet Cherryn Bissett 01:33 From LegalSifter customer to in-house counsel 02:29 Automate 80%, own 20% 03:50 Cutting through contract noise 05:28 Building playbooks that scale across teams 07:35 When to step outside the playbook 09:46 AI provisions showing up in NDAs 10:31 When playbooks slow the business down 12:07 Where AI creates real value in contracting 14:51 Decisions that still need human judgment 18:02 How to be fast and accurate under pressure 20:12 Safest legal answer vs. best business decision 22:32 Skills that will set in-house lawyers apart 24:17 Final takeaway If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal ops professionals find these conversations. S U B S C R I B E! Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage. Engage with us below, like, comment, and subscribe to follow the future of in-house law! Thank you for watching! Like, Comment, Subscribe and hit the bell so you never miss an episode! Subscribe to our channel: @NotesToMyLegalSelf #NotesToMyLegalSelf #LegalInnovation #ContractManagement #CommercialLaw #LegalOperations

Welcome to Season 14, Episode 9 of Notes to My Legal Self, the in-house counsel podcast on AI, contracting, and the future of legal work. Host Olga V. Mack talks with Cherryn-Paige Bissett, Internal Commercial Counsel at LegalSifter, about what to automate in contracting and what still needs a lawyer's judgment. With over 20 years as a commercial attorney, Cherryn shares her ""automate 80%, own 20%"" approach: use AI and playbooks to cut through contract noise, then focus your time on the risks that matter. This legal tech and legal operations conversation is for in-house lawyers, corporate counsel, and anyone who wants to close deals faster without taking on unnecessary risk. In this episode, you'll learn: - How AI contract playbooks build consistency and reduce contract noise - What separates a useful playbook from one that becomes rigid or ignored - When to step outside the playbook, including new AI provisions in NDAs - Which contracting decisions still require human judgment - How to weigh possibility vs. probability when deciding which risks to push back on - How a one-page contract primer can speed up negotiations About the guest: Cherryn-Paige Bissett is Internal Commercial Counsel at LegalSifter, which offers AI contract review and a CLM platform. She has practiced commercial law for over 20 years, including at a London-based law firm, and joined LegalSifter after starting as a customer. Timestamps: 00:00 Introduction 00:44 Meet Sharon Bissett 01:33 From LegalSifter customer to in-house counsel 02:29 Automate 80%, own 20% 03:50 Cutting through contract noise 05:28 Building playbooks that scale across teams 07:35 When to step outside the playbook 09:46 AI provisions showing up in NDAs 10:31 When playbooks slow the business down 12:07 Where AI creates real value in contracting 14:51 Decisions that still need human judgment 18:02 How to be fast and accurate under pressure 20:12 Safest legal answer vs. best business decision 22:32 Skills that will set in-house lawyers apart 24:17 Final takeaway If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal ops professionals find these conversations. S U B S C R I B E! Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage. Engage with us below, like, comment, and subscribe to follow the future of in-house law! Thank you for watching! Like, Comment, Subscribe and hit the bell so you never miss an episode! Subscribe to our channel: @NotesToMyLegalSelf #NotesToMyLegalSelf #LegalInnovation #ContractManagement #CommercialLaw #LegalOperations

Welcome to Season 14, Episode 7 of Notes to My Legal Self, the in-house counsel podcast on legal design, legal operations, and serving clients better. Host Olga V. Mack talks with Marco Imperiale, founder of Better Hub and author of Practicing Legal Design, about a basic question lawyers often skip: do we actually know our clients? Marco explains why legal design is much more than icons and colors. It is a new way to build contracts, policies, and legal processes around the people who use them. This legal tech and legal innovation conversation is for in-house lawyers, legal ops professionals, and anyone who wants legal work that people can actually understand and use. In this episode, you'll learn: - What legal design is, and what it is not - Why clearer contracts and policies can save money, not just improve the experience - The biggest sources of resistance to clearer legal communication - How to run a "listening dinner" and truly hear your clients - How to balance clarity and accessibility with legal precision - Why visuals, white space, and typography matter more than lawyers think - Why curiosity matters more than specialized knowledge in the age of AI About the guest: Marco Imperiale is a former copyright and entertainment lawyer, the first head of innovation at a law firm in Italy, and founder of Better Hub, a benefit corporation focused on legal operations, legal innovation, and AI. He has taught legal design at Harvard Graduate School of Design and is the author of Practicing Legal Design (Globe Law and Business). Timestamps: 00:00 Introduction 00:41 Meet Marco Imperiale 01:25 His book, Practicing Legal Design 02:03 Why he wrote a practical guide to legal design 03:57 Why legal design matters 07:36 Lawyers, visuals, and "just send the picture" 09:23 Why legal design matters right now 13:30 Where the resistance comes from 18:38 Common misconceptions about legal design 21:20 How to really listen to your clients 24:02 Balancing clarity with legal precision 26:34 Testing and validating your assumptions 29:41 The role of visuals and typography 32:31 Why curiosity beats specialization in the age of AI 36:40 Where curious but skeptical lawyers should start 38:45 Final takeaway: less ego, more humility When was the last time you asked a client how they actually experience your work? Share your answer with us in the comments. If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal ops professionals 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.com #NotesToMyLegalSelf #InHouseCounsel #LegalDesign #LegalOps #LegalInnovation #LegalTech

Welcome to Season 14, Episode 6 of Notes to My Legal Self, the in-house counsel podcast on compliance, AI, and leading with empathy. Host Olga V. Mack talks with Angela Madathil, technology attorney at Werner Enterprises, about compliance and storytelling. In an industry where trucks are becoming computers on wheels, Angela shares how getting to know end users, like the professional drivers who rely on in-cab technology every day, helps her tell stories that move leaders to make the right compliance decisions. This legal tech and legal leadership conversation is for in-house lawyers, product counsel, and anyone who wants to make compliance part of how the business works. In this episode, you'll learn: - Why being in the room makes in-house counsel more valuable than outside counsel - How to understand end users and their real pain points - How to bake compliance into every process, not just contracts - How Angela uses AI tools like Gemini to review, negotiate, and draft faster - Where AI output is reliable for contracts and where it falls short - How storytelling helped leaders commit to clear AI disclosure - How self-awareness tools like Gallup CliftonStrengths can guide your legal career Timestamps: 00:00 Introduction 00:47 Meet Angela 01:00 How trucks became computers on wheels 02:13 From oil and gas contracts to in-house technology law 03:20 Why in-house work appeals to her 05:51 Getting to know end users and their pain points 07:41 The hard parts of in-house work 09:11 How compliance became part of her role 11:37 Baking compliance into every process 12:43 How AI changed her legal work 14:41 How reliable is AI for contract negotiation? 17:50 Using storytelling in compliance conversations 20:06 Balancing AI efficiency with the human touch 21:42 Building trust with stakeholders 23:07 Skills she is still sharpening 24:41 Advice to her younger self 26:23 Why being ""high in harmony"" helps in-house 29:26 Final takeaway When was the last time you talked to the people who actually use your company's products? Share your answer with us in the comments. If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal leaders 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.com #NotesToMyLegalSelf #InHouseCounsel #LegalLeadership #Compliance #Storytelling #LegalTech #LegalInnovation

Welcome to Season 14, Episode 5 of Notes to My Legal Self, the in-house counsel podcast on technology transactions, career transitions, and lawyering where no precedent exists. Host Olga V. Mack talks with Geoffrey Brow, Assistant General Counsel at Roku, about nearly 30 years of practice, from corporate M&A in New York and London to in-house technology transactions at Dell, Google, AT&T, and Virgin Hyperloop One. Geoffrey shares what it takes to draft deals for technologies that have never existed before and why great in-house lawyers learn to land the plane even when parts are falling off. This general counsel and legal tech conversation is for in-house lawyers, technology transactions attorneys, and anyone thinking about moving from Big Law to in-house. In this episode, you'll learn: - Why technology transactions leave more room for creativity in legal practice - How to structure deals for new technologies like Hyperloop and drone delivery when there is no precedent - How to work with engineers to understand and reduce risk - Why drafting is a skill worth loving, not just a task to finish - What Big Law lawyers need to unlearn to succeed in-house - How to decide what is "good enough" legally and why B2B and B2C deals need different levels of care - What skills lawyers need to keep up with AI and future technologies Timestamps: 00:00 Introduction 00:37 Meet Geoffrey Brow 01:49 Why he moved from corporate law to technology transactions 04:16 Creativity in legal practice 04:44 Lawyering for Hyperloop with no precedent 06:20 How to be the first, not the follower 07:45 Why he loves drafting 09:21 Negotiating drone delivery deals with regulators 11:11 From international relations to law school 14:50 Training in Big Law in New York and London 16:16 Moving from Big Law to in-house at Dell 19:02 How to unlearn perfectionism 21:53 The airplane analogy: just land the plane 23:37 How his background shaped his comfort with uncertainty 25:38 Deciding what is "good enough" legally 28:03 Skills lawyers need in the age of AI 31:15 Final takeaway: keep an open mind If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more in-house counsel and legal leaders find these conversations. Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage. Engage with us below, like, comment, and subscribe to follow the future of in-house law! Thank you for watching! Like, Comment, Subscribe and hit the bell so you never miss an episode! Subscribe to our channel: @NotesToMyLegalSelf

Welcome to Season 14, Episode 4 of Notes to My Legal Self, the general counsel podcast where legal leaders share what really works inside the company. How do you stay optimistic when AI, geopolitics, and constant change keep shaking the ground under your team? Carolyn Herzog, Chief Legal Officer at Elastic, has led legal teams through COVID, cybersecurity crises, and now the generative AI wave. In this conversation with host Olga V. Mack, she explains why the horse has already left the barn on AI, why legal's job is now to guide rather than block, and why the strongest teams are built on trust and accountability. She also shares how she sets boundaries on a global team and why legal operations belongs at the center of every modern legal function. Timestamps: 00:00 Introduction 00:34 Meet Carolyn Herzog 01:06 From the World Bank to Chief Legal Officer 02:48 The most memorable changes she has led 04:14 How we came out of COVID 06:24 Why optimism matters as a leader 09:43 Leading teams through the AI transition 12:31 The pillars of responsible AI 14:30 The risks legal teams now accept 18:07 Assistive AI vs. decision-making AI 20:36 What breaks when AI adoption outpaces governance 23:08 How geopolitics is reshaping contracts 26:14 Building trust in uncertain times 28:05 Helping teams manage turbulence and well-being 31:21 What a resilient legal team looks like 34:20 Where legal teams over- and under-index on risk 35:41 How she would design a legal team today 37:46 Final takeaway: be curious and ask for feedback What is one thing your team could do differently this quarter? Listen, reflect, and tell us in the comments. If you enjoy this lawyer podcast, follow the show and leave a rating. It helps more general counsel and legal leaders find these conversations. Explore more episodes at https://www.notestomylegalself.com