Notes to My Legal Self®

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.

Notes to My Legal Self® is a business podcast hosted by Olga V. Mack, with 205 episodes on record and a Required Pod Score of 80.

Olga V. Mack hosts Notes to My Legal Self®, a business show with 205 episodes published.

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  Episode #6

  Legal Ops Is No Longer Optional (Adam Becker) Notes To My Legal Self S15E6

  Oct 5, 202641 minS15

  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

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  Episode #5

  From Practicing Law to Practicing Leadership (Carly Mcallister) NTMLS S15E5

  Jul 26, 202640 minS15

  Welcome to Season 15, Episode 4 of Notes to My (Legal) Self, where Olga V. Mack sits down with Carly Mcallister to explore what it means to move from practicing law to practicing leadership. Together, they discuss why the best in-house lawyers do more than manage risk, they build trust, empower business partners, and create possibilities. Carly shares how her transition from litigation to financial services taught her that technical legal excellence is only the beginning of becoming an effective in-house leader. Drawing from her experience in litigation, judicial work, and financial services, Carly explains why understanding the business, investing in yourself, and developing sound judgment are essential to legal leadership. She also explores why, in an AI-driven world, human judgment, communication, and connection will remain among a lawyer’s greatest competitive advantages. You'll discover: • Why moving in-house requires shifting from legal expert to business partner • How legal teams can create possibilities instead of simply managing risk • Why great in-house lawyers look for responsible ways to get to “yes” • How understanding the business builds trust and strategic influence • Why listening, humility, mentorship, and continuous learning strengthen judgment • How personal development can make you a better lawyer and leader • Why collaboration across teams creates better business outcomes • How legal departments can empower people through thoughtful governance • Why AI can amplify legal work but cannot replace human judgment • How lawyers can evolve from risk managers into leaders who create possibilities Whether you're considering an in-house career, growing as legal counsel, or leading within an organization, this conversation offers practical insights on business partnership, judgment, personal development, and creating value beyond traditional legal advice. If you've ever wondered how to become a more trusted, strategic, and human-centered legal leader, this episode is for you. Takeaways: • Technical legal excellence is the foundation, not the finish line. • Great in-house lawyers create confidence and possibility. • Understanding the business is essential to becoming a trusted partner. • Judgment grows through experience, humility, listening, and continuous learning. • AI will transform legal work, but leadership and human judgment remain essential. 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® #LegalLeadership #InHouseCounsel #Leadership #CareerDevelopment #GeneralCounsel

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  Episode #4

  The Art of the Pause and Cognitive Empathy as a Legal Superpower (Bradley Bald) Notes To My Legal Self S15E4

  Jul 20, 202636 minS15

  Welcome to Season 15, Episode 4 of Notes to My (Legal) Self. In this thought-provoking conversation, host Olga Mack sits down with Bradley Bald, In-House Counsel at Lifestyle Communities, to explore how taking a pause can become one of the most powerful leadership tools in a lawyer’s toolkit. Together, they discuss the realities of burnout, the courage required to take a sabbatical, and why cognitive empathy may be one of the most underrated superpowers for modern legal professionals. Bradley shares his personal journey from private practice to in-house counsel, the lessons learned during a career pause, and how listening, reflection, and emotional intelligence can create stronger relationships, better negotiations, and more impactful leadership. Bradley Bald serves as In-House Counsel for Lifestyle Communities, a nationwide mixed-use multifamily real estate developer focused on creating wellness-centered communities. With experience spanning private practice, real estate, business development, and in-house leadership, Bradley brings a unique perspective on career growth, resilience, and the evolving role of legal professionals. Key insights from this episode: • Why the most enduring regrets often stem from inaction rather than action • How taking a sabbatical can provide clarity, prevent burnout, and create space for personal growth • The importance of embracing discomfort during career transitions • How the “power of the pause” can improve communication, negotiations, and conflict resolution • Why cognitive empathy helps legal leaders understand others without absorbing their emotions • How modern in-house counsel can add value beyond legal advice by becoming proactive business partners • The role of self-awareness, reflection, and emotional intelligence in effective leadership Whether you're navigating burnout, considering a career transition, building your influence as in-house counsel, or looking to become a more effective communicator, this episode offers practical insights and meaningful perspective for legal professionals at every stage of their careers. About the Guest: Bradley Bald is In-House Counsel at Lifestyle Communities, where he supports a vertically integrated real estate development organization spanning development, construction, property management, hospitality, and lifestyle brands. With a background in private practice and over a decade of experience in real estate, Bradley is passionate about leadership, psychology, cognitive empathy, and helping legal professionals build careers that align with both purpose and well-being. Takeaways: • Taking a strategic pause can create opportunities for long-term growth. • Burnout prevention requires intentional reflection and self-awareness.• Cognitive empathy strengthens relationships while preserving objectivity. • Great legal leaders are valued for influence, not just expertise. • Listening often creates more impact than speaking. • Emotional intelligence is becoming a critical leadership skill for modern lawyers. • Career success is not only about advancement, it is also about alignment. 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® #InHouseCounsel #CognitiveEmpathy #LawyerWellBeing #BurnoutPrevention #CareerGrowth

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  Episode #3

  The Power of the Pivot (Kemi Ijitimehin) NTMLS S15E3

  Jul 13, 202635 minS15

  Welcome to Season 15, Episode 3 of Notes to My (Legal) Self, where Olga V. Mack sits down with Kemi Ijitimehin to explore why the most meaningful careers aren't carefully mapped, they're built through courageous pivots. Together, they discuss how trusting your instincts, embracing creativity, and investing in relationships can transform not only your legal career but the businesses and people you serve. Drawing from a career that spans public policy, the federal government, and the technology sector, Kemi shares how every unexpected turn prepared her for the next opportunity. From navigating rejection and career transitions to becoming a trusted business partner, she explains why curiosity, authenticity, and human connection remain every lawyer's greatest competitive advantage in an AI-driven world. You'll discover: • Why "pivoting is a vibe" and how trusting yourself can unlock unexpected opportunities • How family history, resilience, and adaptability shape long-term career success • Why rejection is often redirection toward a better opportunity • How creativity is one of the most underrated skills in modern legal practice • Why product counsel requires lawyers to think beyond legal answers and help build businesses • The importance of curiosity in learning your business and becoming an indispensable legal partner • Why relationships and trust matter more than always having the perfect legal answer • How authenticity helps lawyers build credibility across cross-functional teams • Why AI can improve efficiency, but judgment, empathy, and human connection remain irreplaceable • How today's lawyers can evolve from legal advisors into strategic business leaders Whether you're an aspiring lawyer, an experienced in-house counsel, a legal operations professional, or a business leader navigating constant change, this conversation offers practical insights on career pivots, business partnership, leadership, and the uniquely human skills that define exceptional lawyers. If you've ever wondered how to embrace uncertainty while building a meaningful legal career, this episode is for you. Takeaways: • Career pivots are often driven by purpose, not perfect planning. • Curiosity is one of the most valuable skills an in-house lawyer can develop. • Strong relationships create trust, and trust creates better business outcomes. • Great lawyers don't just solve legal problems—they help build businesses. • AI will continue to transform legal work, but creativity, empathy, and judgment remain a lawyer's greatest strengths. 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® #InHouseCounsel #LegalLeadership #CareerGrowth #BusinessPartner #ProductCounsel

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  Episode #2

  The Soft Skills That Power In‑House Law (Elizabeth A. Colombo) Notes To My Legal Self S15E2

  Jul 6, 202638 minS15

  Welcome to Season 15, Episode 2 of Notes to My (Legal) Self , where host Olga V. Mack sits down with Elizabeth Colombo, Associate General Counsel at Vendavo. Together, they explore why great negotiation is about more than contracts. Beth shares practical lessons on empathy, business judgment, communication, and how in-house lawyers can become trusted business partners in an AI-assisted world. In this episode, you'll learn: Why negotiation is about people, not just paper How empathy leads to better business outcomes Why lawyers must embrace calculated risk The difference between being a referee and a decision architect How "embedded humanity" creates value AI can't replace Practical communication strategies for cross-functional teams Why human judgment remains a lawyer's greatest competitive advantage Whether you're an in-house lawyer, legal leader, or aspiring counsel, this episode offers actionable insights on leading with trust, business acumen, and humanity in the modern legal profession. INTERSECTION OF LAW AND FUN® #InHouseCounsel #LegalLeadership #GeneralCounsel #Negotiation #NotesToMyLegalSelf

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