Podcast
Notes to My Legal Self®
Hosted by Olga V. Mack · EN
Notes to My Legal Self® is a podcast for lawyers who want to think better, lead better, and practice with judgment, not just knowledge.
Hosted by Olga V. Mack, the show explores the real decisions lawyers face but rarely talk about openly. The gray areas. The tradeoffs. The moments where legal advice shapes business outcomes and trust.
Each episode blends candid reflection and conversations with experienced legal leaders who share what actually works in practice.
This is not about memorizing rules. It is about developing legal judgment, clarity, and confidence over time.
28episodes
Episodes
Newest firstAll episodes
Automate the 80% Own the 20% (Cherryn-Paige Bissett) Notes To My Legal Self, Season 14, Episode 9
4d ago00:25:45Tap to summarizeWelcome to Season 14, Episode 9 of Notes to My (Legal) Self. In this episode, host Olga Mack sits down with Cherryn-Paige Bissett, commercial attorney and Internal Commercial Counsel at LegalSifter, to explore how legal professionals can leverage AI without sacrificing human judgment. Together, they discuss the practical realities of contract automation, the role of playbooks, and why the most valuable legal skill in the age of AI is knowing when to step beyond the process and make a judgment call.With more than 20 years of experience as a commercial attorney, Cherryn-Paige has spent her career helping businesses navigate legal, operational, and commercial risk. As both a customer and now a leader within LegalSifter, she brings a unique perspective on how AI can help legal teams move faster, reduce contract noise, and focus on the issues that truly matter.Key insights from this episode:• Why lawyers should automate the routine 80% and own the critical 20%• How AI helps eliminate contract noise and improve consistency• The difference between applying a playbook and applying judgment• Why legal teams must balance commercial, operational, and legal risk• How to determine when a contract issue truly deserves escalation• The importance of understanding business objectives before negotiating risk• Why possibility and probability are not the same thing• How AI can accelerate contracting without replacing lawyers• The skills that will define exceptional in-house counsel in the years aheadWhether you're an in-house lawyer, legal operations professional, contract manager, or legal technology enthusiast, this episode offers practical insights into how legal teams can work smarter while delivering greater strategic value to their organizations.Takeaways:• Automate repeatable work so lawyers can focus on strategic decision-making• AI is most effective when guided by clear legal playbooks• Human judgment remains essential in complex negotiations• Strong lawyers prioritize the risks that truly matter• Understanding your business is critical to effective legal advice• The future belongs to lawyers who can combine technology with sound judgment• Possibility alone should not drive legal decision-making, probability mattersS 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
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Good Legal Judgment is Built the Hard Way (Matthew Thomas) Notes To My Legal Self Season 14, Episode 8
2w ago00:41:21Tap to summarizeWelcome to Season 14, Episode 8 of Notes to My (Legal) Self.In this episode, host Olga Mack sits down with Matthew Thomas to explore one of the most valuable, and often misunderstood, skills in legal practice: judgment.Together, they discuss how good judgment is developed through experience, mistakes, mentorship, and perspective. From navigating complex negotiations and managing risk to leading through personal adversity, Matthew shares practical lessons on decision-making, communication, resilience, and the human side of legal practice.Matthew Thomas is Senior Corporate Counsel at Elastic, where he advises on procurement, vendor relationships, commercial transactions, and strategic business initiatives.Having worked across industries including oil and gas, mortgage servicing, fintech, and technology, Matthew brings a uniquely broad perspective on risk, leadership, and legal decision-making. Following a leukemia diagnosis, his perspective on work, life, and leadership has evolved in profound ways, insights he shares candidly throughout this conversation.Key insights from this episode:• Why good judgment is built through experience, not textbooks• How mistakes become the foundation of better decision-making• The importance of understanding risk without overreacting to it• Why communication is often the key to resolving conflict and negotiation breakdowns• How empathy and emotional intelligence improve legal outcomes• The role of mentorship in accelerating professional growth• Why perspective matters when evaluating pressure, risk, and leadership decisions• How personal adversity can reshape professional judgment• The connection between resilience, humility, and effective leadership• Why the human element remains essential in an AI-powered future.This episode is for in-house counsel, legal leaders, law firm attorneys, legal operations professionals, and anyone looking to strengthen their decision-making skills. If you've ever wondered how experienced lawyers develop judgment, or how life experiences shape leadership, this conversation offers practical wisdom and a refreshing perspective.Takeaways:• Good judgment is often the result of learning from mistakes• Experience teaches lawyers which risks truly matter• Strong communication prevents many problems before they escalate• Empathy creates better outcomes in negotiations and relationships• Perspective helps leaders make better decisions under pressure• Resilience and adaptability are critical professional skills• The future of legal practice will require both technology and human judgmentsS 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 #Leadership #ProfessionalDevelopment #DecisionMaking
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Human-Centered Law in Practice: Tools, Tactics, Outcomes (Marco Imperiale) Notes To My Legal Self Season 14, Episode 7
3w ago00:40:51Tap to summarizeWelcome to Season 14, Episode 7 of Notes to My (Legal) Self. In this episode, host Olga Mack sits down with Marco Imperiale to explore a fundamental question: Do lawyers truly understand the people they serve?Together, they examine how legal design, curiosity, communication, and human-centered thinking are reshaping the future of legal practice. From client engagement to innovation, Marco challenges long-held assumptions about how lawyers work and why many legal processes remain disconnected from the people they are meant to help.Marco Imperiale is a legal innovation leader, legal designer, entrepreneur, author, and founder of Better Ipsum. A former lawyer and one of Italy's first Heads of Innovation for a law firm, Marco has spent years helping legal departments, law firms, and institutions rethink legal services through design thinking, legal operations, and human-centered approaches. He is also the author of *Practicing Legal Design*, a practical guide to implementing legal design in real-world legal environments.Key insights from this episode:• Why legal design is about much more than visuals and simplified contracts• The importance of listening before advising• How curiosity creates better outcomes than certainty• Why engagement drives understanding and trust• The role of play, experimentation, and prototyping in innovation• How lawyers can better understand clients, customers, and stakeholders• Why humility may be one of the most important leadership skills in law• The connection between legal communication, accessibility, and inclusionThis episode is for in-house counsel, law firm leaders, legal operations professionals, legal innovators, and anyone interested in creating more effective, human-centered legal experiences.If you've ever wondered how legal services can become more engaging, accessible, and impactful, this conversation offers practical insights and a fresh perspective.Takeaways:• Curiosity is often more valuable than expertise alone• Great legal service starts with understanding the client experience• Legal design challenges assumptions about how legal work should be delivered• Innovation requires experimentation, testing, and feedback• Play can unlock creativity, engagement, and breakthrough thinking• The future of law will be increasingly human-centered• Less ego and more humility can transform professional relationships
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How Stories Can Help You Reach Compliance Compromises (Angela Madathil) NTMLS Season 14, Episode 6
3w ago00:31:10Tap to summarizeWelcome to Season 14, Episode 6 of Notes to My (Legal) Self. In this episode, host Olga Mack sits down with Angela Madathil for a thoughtful conversation on compliance, AI, storytelling, and the future of legal leadership.Angela shares how her experience supporting technology initiatives inside the trucking industry shaped her approach to compliance, product counseling, and responsible innovation. From AI transparency challenges to understanding the daily realities of truck drivers, this episode explores how empathy and storytelling can help legal teams build trust and drive better business decisions.Key insights from this episode:• Why compliance works best when embedded into the business• How storytelling helps legal leaders influence stakeholders• The importance of understanding the end user experience• Responsible AI adoption and transparency considerations• How in-house lawyers can scale trust through principles and alignment• The role of empathy, listening, and harmony in legal leadership• Using AI tools to improve legal efficiency and negotiation outcomesThis episode is for in-house counsel, compliance leaders, legal operations professionals, technology lawyers, and anyone navigating the intersection of AI, business strategy, and legal innovation.Takeaways:• Compliance is most effective when it becomes part of company culture• Legal storytelling creates alignment and trust across organizations• AI should enhance human connection, not replace it• Understanding user pain points leads to better legal and business outcomes• Emotional intelligence is a strategic advantage for modern legal leadersWant 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#LegalInnovation #InHouseCounsel #LegalLeadership #Storytelling
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Building the Legal Backbone of Breakthrough Tech (Geoffrey G. B. Brow) NTMLS Season 14, Episode 5
May 1100:33:25Tap to summarizeIn this episode, host Olga Mack sits down with Geoffrey Brow for a fascinating conversation about building legal infrastructure for breakthrough technologies.Geoffrey shares his journey from international law and corporate practice in New York and London to becoming a technology transactions leader working with companies like Dell, Google, AT&T, Roku, and Virgin Hyperloop. Throughout the conversation, he explains how lawyers help shape innovation when there is no existing precedent, no established regulatory framework, and no playbook to follow.Key insights from this episode:• Why transactional law is fundamentally creative work• What lawyers can learn from working alongside engineers and product teams• The mindset shift required to transition from Big Law to in-house practice• How to evaluate legal risk in emerging technology environments• Why drafting remains one of the most important skills for transactional lawyers• What it means to counsel companies building technologies that have never existed before• How AI and emerging technologies are reshaping legal practice• Why adaptability and intellectual curiosity are essential career skills for lawyersThis episode is especially valuable for in-house counsel, transactional lawyers, law students, legal innovators, and anyone interested in the intersection of law, business, and emerging technology. Geoffrey offers practical wisdom on navigating uncertainty, balancing risk, and developing the judgment needed to support innovation responsibly.Takeaways:• Innovation often requires lawyers to operate without precedent• Strong drafting skills remain foundational for transactional lawyers• Great legal counsel balances precision with business practicality• Curiosity and adaptability create long-term career opportunities• Lawyers play a critical role in enabling responsible technological advancement• In-house legal work requires both strategic judgment and resilienceFollow Notes to My (Legal) Self® for more conversations on the future of in-house law.
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What Matters More: When Everything Is Uncertain, Judgment Matters More (Carolyn Herzog) NTMLS Season 14, Episode 4
Apr 2000:39:37Tap to summarizeAre you relying on certainty… or building better judgment in uncertain times?In this episode of Notes to My (Legal) Self®, Olga Mack speaks with Carolyn Herzog, Chief Legal Officer at Elastic, a global search AI company, about leading through disruption, navigating AI, and redefining resilience in the legal function. As the pace of change accelerates, from AI to geopolitical shifts, legal teams are being challenged to move faster, think differently, and operate with both optimism and discipline.Carolyn shares why judgment matters more than rigid rules, how AI is transforming legal work in real time, and why trust, not control, is becoming the foundation of effective leadership and business relationships.Takeaways:• In uncertainty, judgment matters more than perfect answers• Legal leaders must balance optimism with a healthy sense of risk awareness• AI adoption cannot be stopped, only guided responsibly• Trust is the foundation of both leadership and business success• Legal teams must become faster, more adaptive, and more tech-enabledFollow Notes to My (Legal) Self® for more conversations on the future of in-house law.
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Outsourcing in the Age of AI: When Legal Shapes the Deal (Irina Beschieriu) NTMLS Season 14, Episode 3
Apr 600:37:55Tap to summarizeAre you optimizing your outsourcing deals for price… or for long-term success?In this episode of Notes to My (Legal) Self®, Olga Mack speaks with Irina Beschieriu, an attorney specializing in complex outsourcing and global service delivery models, with deep expertise in cross-border technology transactions, vendor governance, and AI-driven services.As outsourcing evolves beyond cost-cutting into a strategic lever for speed, talent, and innovation, legal teams are being asked to rethink how these deals are structured and managed in practice.Irina shares how AI is reshaping outsourcing relationships, why governance and incentives matter more than lengthy contracts, and how in-house counsel can design vendor ecosystems that are resilient, adaptive, and aligned with business reality.Takeaways:• Outsourcing is no longer about cost, it’s about capability and speed• AI is fundamentally reshaping vendor relationships and service models• Governance and incentives often matter more than contract language• Operational reality must inform legal structure• In-house counsel must evolve into strategic business partners
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The Fourth Closing Argument: What Leaders Need to Know About Depositions (Dean Whalen) NTMLS Season 14, Episode 2
Mar 2300:39:28Tap to summarizeAre depositions now more important than trials in litigation strategy?In this episode of Notes to My (Legal) Self®, Olga Mack speaks with Dean Whalen, Chief Legal Officer at Readback, who brings over two decades of litigation and legal leadership experience at the intersection of law and technology.As trials become increasingly rare, modern litigation is shifting toward discovery, where depositions play a decisive role.Dean introduces the concept of the “Fourth Closing Argument” and explains how real-time transcription, AI, and legal tech are transforming deposition strategy, risk management, and expectations of legal competence.Takeaways:• Depositions are no longer procedural, they are decisive• Discovery is where cases are won or lost• Real-time insight improves precision and litigation strategy• Legal tech is reshaping expectations of competence• Strategic depositions create measurable advantage
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Beyond the Day Job: How Lawyers Create Leverage (Jessica Nguyen, Nada Alnajafi) NTMLS Season 14, Episode 1
Mar 201:04:57Tap to summarizeIn this episode, host Olga Mack sits down with Jessica Nguyen and Nada Alnajafi for an honest and energizing conversation about what happens when in-house lawyers build beyond their day jobs, and how personal brands, communities, and bold decisions create real leverage.Nada Alnajafi is Senior Corporate Counsel and Lead Legal Ops at Franklin Templeton and the founder of Contract Nerds, a community she built from a passion project into a thriving business later acquired by DocuSign.Jessica Nguyen is Deputy General Counsel at DocuSign and Head of Contract Nerds, with a track record of building legal teams and scaling legal technology companies from early-stage startups to successful exits.Key insights from this episode:• How side hustles can evolve into strategic business assets• Why email lists and community ownership matter more than social followers• How to evaluate risk as an in-house lawyer• What founders should consider before selling their business• The emotional realities of acquisitions, and how to navigate them• Why lawyers must rethink risk aversion and embrace upsideThis episode is for in-house lawyers, founders, legal operators, and anyone wondering whether they can build something meaningful beyond their role without walking away from it.Takeaways:• Build with generosity first, monetization follows value• Strategic partnerships matter more than short-term offers• Preparation and organization accelerate opportunity• Lawyers are uniquely equipped to build, if they embrace the upside.• Alignment beats adrenaline in both business and life. 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 to our channel: @NotesToMyLegalSelf#InHouseCounsel #WomenInLaw #LegalLeadership #CareerGrowth #PersonalBrand #EntrepreneurialLawyer #NotesToMyLegalSelf
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Season 13, Episode 10: Memory Identity and the Machines We Build (ft. Heath Morgan)
Feb 1600:39:37Tap to summarizeIn this episode of Notes to My (Legal) Self®, host Olga V. Mack speaks with Heath Morgan, in-house attorney and author of The Memory Project, about memory, identity, and the long-term ethical implications of AI adoption.Drawing from his experience in cybersecurity, compliance, and AI governance, as well as his speculative fiction work. Heath explores what happens when technology allows us to preserve, replicate, and even converse with digital versions of ourselves.Together, they explore:• Why AI forces us to confront legacy in ways social media never did• The concept of “conversational time travel” and digital personas of the past and future• How companies may face a two-market reality: privacy as default vs. privacy as luxury• The hidden risks of unintentional AI adoption inside organizations• Why in-house counsel must move from reactive policy drafting to intentional AI governanceIf you’re an in-house lawyer navigating AI implementation or questioning how emerging technologies will reshape privacy, identity, and ethics, this conversation challenges you to think several steps ahead.Explore more episodes, insights, and reflections at:www.notestomylegalself.com#NotesToMyLegalSelf #AI #LegalInnovation #InHouseCounsel #AIGovernance #DigitalLegacy
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