Notes to My Legal Self®
by Olga V. Mack
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.
Episodes
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Better by Design (Russ Jacobs) NTMLS Season 15 Episode 9
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...
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Lost in Translation: Why Great Lawyers Explain, Not Impress (Matthew Lowe) NTMLS Season 15 Episode 8
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...
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The Human Side of Legal Transformation (Whitney Stefko) NTMLS S15E7
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…
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Legal Ops Is No Longer Optional (Adam Becker) Notes To My Legal Self S15E6
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...
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From Practicing Law to Practicing Leadership (Carly Mcallister) Notes To My Legal Self S15E5
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...
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The Art of the Pause and Cognitive Empathy as a Legal Superpower (Bradley Bald) Notes To My Legal Self S15E4
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...
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The Power of the Pivot (Kemi Ijitimehin) NTMLS S15E3
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...
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The Soft Skills That Power In‑House Law (Elizabeth A. Colombo) Notes To My Legal Self S15E2
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...
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Raising Lawyers Who Can Think When AI Does the Thinking (Alexandra Sepulveda) Notes To My Legal Self S15E1
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...
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When AI Starts Doing Lawyers Work, What Labels Still Matter? (Dharshi Harindra) Notes To My Legal Self S14E10
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...
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Automate the 80% Own the 20% (Cherryn-Paige Bissett) Notes To My Legal Self, Season 14, Episode 9
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...
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Good Legal Judgment is Built the Hard Way (Matthew Thomas) Notes To My Legal Self Season 14, Episode 8
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...
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Human-Centered Law in Practice: Tools, Tactics, Outcomes (Marco Imperiale) Notes To My Legal Self Season 14, Episode 7
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...
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How Stories Can Help You Reach Compliance Compromises (Angela Madathil) NTMLS Season 14, Episode 6
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...
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Building the Legal Backbone of Breakthrough Tech (Geoffrey G. B. Brow) NTMLS Season 14, Episode 5
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...
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What Matters More: When Everything Is Uncertain, Judgment Matters More (Carolyn Herzog) NTMLS Season 14, Episode 4
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…
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Outsourcing in the Age of AI: When Legal Shapes the Deal (Irina Beschieriu) NTMLS Season 14, Episode 3
Welcome to Season 14, Episode 3 of Notes to My Legal Self, where in-house lawyers share what really works in technology deals. What happens when the vendor uses AI to write its RFP response, and the buyer uses AI to read it? Irina Beschieriu, a deals attorney specializing in outsourcing and...
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The Fourth Closing Argument: What Leaders Need to Know About Depositions (Dean Whalen) NTMLS Season 14, Episode 2
Welcome to Season 14, Episode 2 of Notes to My Legal Self, the legal tech podcast for in-house counsel and litigators. Fewer than 1% of cases go to trial. So where are cases really won? Dean Whalen, Chief Legal Officer at Readback, joins host Olga V. Mack to make the case that the deposition is…
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Beyond the Day Job: How Lawyers Create Leverage (Jessica Nguyen, Nada Alnajafi) NTMLS Season 14, Episode 1
Welcome to Season 14, Episode 1 of Notes to My Legal Self, the in-house counsel podcast on careers, personal branding, and building something of your own. Host Olga V. Mack sits down with Nada Alnajafi, Senior Corporate Counsel and Legal Ops Lead at Franklin Templeton and founder of Contract…
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Season 13, Episode 10: Memory Identity and the Machines We Build (ft. Heath Morgan)
Welcome to Season 13, Episode 10 of Notes to My Legal Self, where in-house lawyers explore the future of law and technology. What if your grandchildren could ask an AI version of you for advice long after you are gone? Heath Morgan, fractional general counsel and author of The Memory Project…
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Season 13, Episode 9: Inside a One-Month Six-Hundred-Million-Dollar Deal (ft. Rina Wang)
Welcome to Season 13, Episode #9 of Notes to My Legal Self, the podcast for lawyers navigating startups, AI, and big career moves. Rina Wang, former Assistant General Counsel at AI public safety startup Prepared, joins host Olga V. Mack to talk about moving from litigation to in-house, choosing...
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Season 13, Episode 8: AI Contracts: What Lawyers Must Know (ft. John Pavolotsky)
Welcome to Season 13, Episode 8 of Notes to My Legal Self, the in-house counsel podcast for lawyers navigating AI, contracts, and fast-changing regulation. John Pavolotsky, co-head of the privacy, cyber, and AI group at Stoel Rives, joins host Olga V. Mack to talk about writing AI agreements that...
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Season 13, Episode 7: How Email Turned Me to Attorney to Founder (ft. Carl Davidson)
Welcome to Season 13, Episode 7 of Notes to My Legal Self, the legal tech podcast for builders, founders, and lawyers rethinking how legal work gets done. Carl Davidson, co-founder of Candle AI, joins host Olga V. Mack to talk about how generative AI made it possible to spin up a prototype in a...
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Season 13, Episode 6: Build, Don't Bill: How Lawyers Can Scale with Automation (ft. Dorna Moini)
Welcome to Season 13, Episode 6 of Notes to My Legal Self, where lawyers learn to build, not just issue spot. In this episode of our podcast for lawyers, Dorna Moini, founder and CEO of Gavel, joins host Olga V. Mack to share how pro bono domestic violence work at Sidley Austin led her to build...
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Season 13, Episode 5: From Courtroom to Code: The Dual Drive of Law and Tech (ft. Karl Seelbach)
In this full episode of Notes to My Legal Self, Karl Seelbach, personal injury defense attorney and co-founder of Skribe.ai, explores how software and AI are changing depositions, courtroom practice, and the way legal testimony is captured. Karl joins host Olga V. Mack to talk about the…
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Season 13, Episode 4: The Roads Less Travelled: Alternative Career Paths in Legal (ft. Senne Mennes)
Welcome to Season 13, Episode 4 of Notes to My Legal Self, where we explore the many ways to build a career in law. In this episode of our podcast for lawyers, Senne Mennes, co-founder of ClauseBase, joins host Olga V. Mack to talk about stepping off the traditional law firm to in-house path, the...
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Season 13, Episode 3: Legal Tech Disruptors, New Minds Innovating for Good (ft. Kara Peterson)
Welcome to Season 13, Episode 3 of Notes to My Legal Self, where we take an honest look at how AI is changing legal practice. In this episode of our podcast for attorneys, Kara Peterson, co-founder of Descrybe.ai, joins host Olga V. Mack to unpack why so many lawyers fear AI, why many...
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Season 13, Episode 2: The Gig Economy for Lawyer is Coming (ft. Otto Hanson)
Welcome to Season 13, Episode 2 of Notes to My Legal Self, where we explore how legal teams can become true partners to the business. In this episode of our in-house counsel podcast, Otto Hanson, co-founder and CEO of TermScout and Screens, joins host Olga V. Mack to share how a 40-day contract...
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Season 13, Episode 1: The Journey to a Transparent Marketplace for Legal Services (with Basha Rubin)
Welcome to Season 13, Episode 1 of Notes to My Legal Self, where we explore how legal teams can run more like a business. Basha Rubin, CEO and co-founder of Priori, joins host Olga V. Mack to discuss why AI will grow the legal services pie rather than end Big Law, why legal operations should…
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Season 12, Episode 9: Get Involved in Pro Bono & Community Service Projects (with Adriana Dulic)
Welcome to Season 12, Episode 9 of Notes to My Legal Self, the podcast for attorneys who want to do well and do good. Adriana Dulic, Chief Compliance Officer at a payments company, joins host Olga V. Mack to explain why volunteering is an underrated way to network, how nonprofit work lets you…
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Season 12, Episode 8: The Law Alone Was Never Going to Be Enough! (with Avril Sisk)
The boundaries of a legal career are wider than you think. In this episode, Avril Sisk—independent corporate director and former judge—joins Olga Mack to explore how legal professionals can lead beyond traditional practice and reshape industries, communities, and boardrooms. With a career…
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Season 12, Episode 7: GenAI Breaking through Technology Resistance in Legal Practice (with Tara Emory)
In the season finale of Notes to My (Legal) Self, Olga Mack is joined by Tara Emory—former big law antitrust attorney, general counsel, and legal tech consultant—for a candid conversation on how legal teams can overcome cultural and organizational resistance to GenAI. With two decades of…
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Season 12, Episode 5: Disruptive GC - Doing More for Less! (with Vinaya Ganesan)
The future of in-house leadership is bold, efficient, and business-driven. In this episode, Vinaya Ganesan, General Counsel for Europe at Firstsource Solutions, joins Olga Mack to share how GCs can do more with less—without compromising impact, innovation, or team morale. Drawing on her…
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Season 12, Episode 4: How To Grow From Stress to Success, and Frustration to Freedom (with Gary Miles)
The path to a fulfilling legal career doesn’t have to be paved with burnout. In this episode, longtime trial lawyer turned coach Gary Miles joins Olga Mack to discuss how lawyers can transform stress into success and frustration into freedom. With over 45 years of legal experience, Gary shares...
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Season 12, Episode 6: DEI Begins with Curiosity (with Niti Nadarajah, co-hosted with Memme Onwudiwe)
The path to truly inclusive legal teams starts with one powerful trait: curiosity. In this episode, Niti Nadarajah—a former in-house lawyer turned leadership coach and DEI advocate—joins Olga Mack and co-host Memme Onwudiwe to unpack what it takes to build equity and belonging in the legal...
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Season 12, Episode 10: In-House Lawyering and Beyond (ft. Shanti Ariker)
In this episode of Notes to My (Legal) Self, Olga Mack sits down with Shanti Ariker , a trailblazing Chief Legal Officer and tech veteran, to explore what it means to be the first lawyer at a fast-moving public company. In “First In-House,” Shanti reflects on her journey from Wall Street law…
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Season 12, Episode 2: Wait, I Have To Know How To Do What Now? (with Minh Merchant)
In this episode of Notes to My (Legal) Self, Olga Mack continues the Legal Operations series with Minh Merchant, a three-time General Counsel and mission-driven legal leader in the healthcare industry. In “Leading with Intent,” Minh joins Olga to unpack what it really takes to become—and remain—a...
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Season 12, Episode 3: Stand Up, Speak Out, & Seek Help (with Tara Trantham)
The legal world can be intense—especially when you're the only lawyer in the room. In this episode, Tara Trantham joins Olga Mack to share her powerful story of navigating legal leadership, federal investigations, and mental health challenges without the safety net of a law firm or legal tech.…
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Season 12, Episode 1: Courting Change - Being the Change You Want to See (with Tyler Quillin)
In this episode, Tyler Quillin, Product and Regulatory Counsel at Xbox, joins Olga Mack to kick off Season 12 of Notes to My (Legal) Self with a powerful conversation on how legal professionals can better align with product teams, regulators, and executives in today’s fast-paced tech world.…
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Season 11, Episode 10: AI, ESG, and Other Acronyms Didn't Expect to in my Legal Career (ft. Christine Uri)
Have you ever wondered how in-house legal teams can navigate the rapidly shifting landscape of AI and ESG? Join us in this episode with Christine Uri, Chief Legal and Sustainability Officer, as she reveals how legal leaders are shaping the future of their departments through innovation…
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Season 11, Episode 9: Training Tomorrow's Lawyers with Emerging Technology (with Linsey Krolik)
The future of legal education is here! In this episode, Linsey Krolik joins Olga Mack to discuss how law schools can adapt to the rapidly changing landscape of legal operations and technology. Together, they explore how GenAI, legal ops, and tech adoption should be integrated into law curricula…
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Season 11, Episode 8: Chatting with Ultron: Empowering In-House Legal Teams with Gen AI Chatbots (ft. Navin Mahavijiyan)
Ready to make AI work for your legal team? In this episode, Navin Mahavijiyan unpacks the magic (and the challenges) of implementing and maintaining legal chatbots that are not just functional—but truly aligned with your team’s culture and tone. Continuing our Legal Operations series, Navin joins...
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Season 11, Episode 7: Data-Powered Belonging: Role of Legal Operations and People Analytics (with Flo Nicolas)
What if data could create a stronger sense of belonging in the legal profession? In this episode, Flo Nicolas shows how people analytics and bold leadership can transform legal teams from the inside out. Continuing our Legal Operations series, Flo joins Olga Mack to share her inspiring journey…
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Season 11, Episode 3: The Business Wants LegalTech They Just Don't Know It Yet (with Chad Aboud)
Think lawyers hate legal tech? They don’t—they just don’t know how much they need it yet. In this episode, Chad Aboud reveals how to sell legal tech into corporate legal departments and drive adoption that actually sticks. Continuing our Legal Operations series, Chad joins Olga Mack for a candid...
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Season 11, Episode: 5 Tech & Law Love (with Colin Levy)
Think AI in legal is all hype? Think again. In this episode, Colin Levy breaks down how generative AI, litigation analytics, and strong communities are already reshaping the future of legal work. Continuing our Legal Operations series, Colin joins Olga Mack to share real-world lessons from years…
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Season 11, Episode 6: Change Agents Assemble the Partnership Between ALSPs and Legal Ops (with Maryam Salehijam)
What if the future of law wasn’t just faster—but happier? In this episode, Maryam Salehijam reveals how ALSPs, legal tech, and a human-centered mindset can transform legal teams for the better. Continuing our Legal Operations series, Maryam joins Olga Mack to break down what alternative legal...
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Season 11, Episode 4: S.E.E. Communications are the Key to Legal Operations Success (ft. Jeffery Kruse)
Think legal ops success is all about tech and processes? Think again. In this episode, Jeffery Kruse reveals why communication is the real game-changer—and how lawyers can ditch complexity for clarity that actually moves people. Continuing our Legal Operations series, Jeffrey joins Olga Mack to...
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Season 11, Episode 2: Ops-Course You Can! (with Tanisha Minev)
Think legal ops is just a buzzword? Think again. In this episode, Tanisha Minev shows how smart legal operations can scale your team without burnout—and why the future of law is lean, tech-savvy, and human-first. Continuing our Legal Operations series, Tanisha joins Olga Mack to break down what...
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Season 11, Episode 1: What Clients Really Should Expect From Their Outside Counsel (with Brent Dyer)
Is guilt running your legal career? In this bold episode, Brent Dyer shares why it’s time for lawyers to drop guilt, perfectionism, and people-pleasing—and lead with emotional intelligence instead. Closing out our Legal Operations series, Brent and Olga Mack dive deep into the emotional traps…
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Season 10, Episode 10: Why Authenticity Matters in Law (with Hannah Beko)
Have you ever wondered how authenticity could transform the legal profession? Discover why being true to yourself is a game-changer for lawyers in this episode with Hannah Beko. As part of the "Legal Operations in the Age of AI and Data" book tour, we invite you to explore how authenticity can...
About this show
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.
Hosted by
Olga V. Mack
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