Simon Hollander on a Legal Career Built on Curiosity and Tips to Tackle AI Tools in the Market

Special guest, Simon Hollander is Senior Corporate Counsel at Amazon Web Services and supports Products and Security Legal across Asia Pacific as AWS's regulatory expert on cloud and AI. Simon shares his interesting career path and the women lawyers who influenced every pivotal career decision he ever made. We hear about the tools coming out of leading AI models, Simon's insights on brain fry, and what lawyers should be working on in this age of AI.If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:How nearly every pivotal legal career decision Simon has ever made was influenced by a woman lawyer. Listen in for some shoutouts to our LOA community!The “uncommon sense” lesson lawyers need to learn that no law school teachesSimon’s experience from the front line of AI development and the “brain fry” phenomenon replacing “brain rot”About SimonSimon is Senior Corporate Counsel at Amazon Web Services and supports Products and Security Legal across Asia Pacific (ex-China but including Japan and New Zealand). Before joining Amazon Web Services in 2016, he was Senior Counsel at Accenture Japan. Before going in house he was in private practice on the corporate legal team at Morrison & Foerster LLP in Tokyo. He is qualified as a barrister in New Zealand and has a BA/LLB from Auckland UniversityBefore life as a lawyer Simon spent seven years working as an IT Consultant for Deloitte Tohmatsu, and later as an environmental policy consultant at Tokio Marine Risk Consulting before deciding to earn his New Zealand bar admission while living and working in Japan and to finally try out becoming a lawyer. Simon grew up - in his own words - an army brat, moving around attending 16 schools. He moved to Japan straight out of uni and has lived here for 27 years now. In his years in Japan he has been a rugby referee, managed the local French rugby club for several years, been a club DJ and his latest passion is running and is hoping he can run the Tokyo Marathon once again with the current lottery. In his free time he also has a video blog about weekly news and culture topics in Japan he has been doing for more than 15 years now.Like everyone else Simon is wrapped up in learning AI and feels very lucky to be in a position to get access to the latest models and tools, and is a trainer of how to use this tech inside Amazon Legal globally, and has given seminars for regulators inside and outside of Japan on the technology. Connect with SimonLinkedIn https://www.linkedin.com/in/simon-hollander-9b5a3a5/  LinksPunk Doily: https://www.instagram.com/punkdoily Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair

What do you do when a global financial crisis derails your carefully planned legal career before it even begins? Rather than hold out for the law firm role she wanted, Nancy Miyaji threw herself into the deep end and built her career anyway. With a superpower of bridging perspectives, Nancy's story is one of resilience, clarity of purpose that shows another successful pathway in law, whatever is happening around you. If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:How arriving in Japan at age 11 without a word of Japanese forged a resilience that still her todayChoosing a startup role during the global financial crisis when no law firm jobs were availableThe valuable lessons she learned in the deep end working on an IPO and M&A at a start up companyThe reframe she would give her younger self: stop asking "why me?" and start asking this insteadHer favourite beverage and other fun facts About NancyNancy Miyaji is a corporate lawyer whose work focuses on cross-border transactions, compliance, and corporate matters in Japan and internationally.She is a Foreign Lawyer at Iwata Godo and a member of the New York Bar. Her experience spans both private practice and global companies, including Simmons & Simmons and Hitachi, where she has worked on cross-border transactions, compliance, and corporate matters.Rather than following a conventional legal career path, Nancy has built a career across private practice and in-house environments, developing her own perspective on professional growth and success.She holds an LL.B. from Kyushu University and an LL.M. from the University of California, Berkeley School of Law, and works in Japanese, English, and Chinese.Outside of work, Nancy enjoys pushing her limits. She played competitive table tennis in her youth and later led her high school mountaineering club. She has since climbed Mount Fuji and completed the Saitama Marathon. She is also passionate about volunteer work supporting foreign women in Japan to achieve success on their own terms.Connect with NancyWebsite: https://www.iwatagodo.com/english/lawyers/miyaji_nancy.html LinksSeattle’s Best Coffee: https://www.jrff.co.jp/seabest/ Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair

What do you do when your first employer hands you a uniform and tells you to serve tea, despite having a law degree from Tokyo University? For Sachiko Ichikawa, the answer was to quit, pick up law again, and spend the next three decades collecting edges that no one else had. Now a founding member of BDTI (the Board Director Training Institute), a qualified lawyer and CPA, and a Business Lawyers Award winner in governance, Sachiko has trained over 4,000 board directors in Japan and sat in boardrooms where she has seen—up close—what separates the A team from the B team. If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:Sachiko’s first job at a bank that saw her take control of her career and go into lawThe Livedoor securities fraud case that introduced Sachiko to corporate governanceWhat Sachiko observed in her very first boardroom that taught her how to be an excellent board memberHer favourite book and other fun facts About SachikoSachiko Ichikawa a lawyer at Tanabe & Partners, a director at Board Directors Training Institute, an independent director at Azbil, Olympus and Tokyo Electron Connect with Sachiko LinkedIn: https://www.linkedin.com/in/sachiko-ichikawa-203bb621/ LinksEnoura Observatory: https://www.odawara-af.com/ja/enoura/ Boards that lead: https://amzn.asia/d/02LOo8NO Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair

Dajeong Lee is a partner specialising in dispute resolution and insolvency, currently in Japan as a research fellow at Waseda University.  Dajeong's story is about the moments no one plans for. With wisdom drawn from jazz music, long-distance running, and the rhythm of daily life in Japan, Dajeong offers a refreshingly honest perspective on ambition, identity, and what it really means to keep moving forward through career detours and parenthood.If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:How navigating three major life changes at once, tested her in completely different waysWhy Dajeong sees her Waseda research fellowship as an investment in herself, not stepping away from her partner level legal careerHer shift from sprinter mindset to long-distance runner mindset: why endurance now matters more to her than speedHer favourite author and other fun facts About DajeongDajeong Lee is a Korean lawyer and a partner in the Litigation Practice Group at Yulchon LLC, one of Korea’s leading law firms. She majored in Communications at Ewha Womans University and received her J.D. from Yonsei University Law School. Since joining Yulchon in 2018, she has focused primarily on insolvency and restructuring, financial disputes, and corporate litigation, representing clients in a wide range of civil and commercial matters. She is currently a visiting researcher at Waseda University in Japan, where she is conducting comparative research on insolvency law in Korea and Japan. After giving birth to her first child in late 2025, she has been balancing motherhood, legal research, and her career as a lawyer while living in Tokyo. Outside of work, she enjoys reading mystery novels, watching baseball, and traveling. She is also interested in learning and growing through new languages, cultures, and environments. Connect with Dajeong Law firm contact: https://www.yulchon.com/en/professionals/professionals-view/djlee23264/lee-dajeong.do LinksKeigo Higashino novels: https://www.amazon.co.jp/%E6%B4%8B%E6%9B%B8-Keigo-Higashino/s?rh=n%3A52033011%2Cp_27%3AKeigo%2BHigashino Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair

Chie Hashimoto is Senior Legal Manager at Richemont Japan LLC, the luxury group behind Cartier, Montblanc, and more. In this episode full of Easter egg surprises, we hear about Chie's path, which was anything but linear. With reflections from Catherine woven throughout, this episode is as much a meditation on non-linear careers as it is a masterclass in legal leadership, cultural nuance, and the value of saying yes to things. Chie shows us how interests outside of law can help you make those impossible work “missions”possible.If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:Chie’s foray into business before attending law school as a mother of a young childThe transition for “advising” to “leading” the business The interests outside of law that make the impossible, possibleHer favourite book and other fun facts About ChieChie Hashimoto is the Senior Legal Manager at Richemont Japan LLC, where she oversees legal strategy, contract negotiation, and compliance across a portfolio of leading luxury brands including Cartier, Montblanc, and Vacheron Constantin. With over 15 years of multinational legal experience spanning the luxury goods and technology sectors, she has built a name for practical, business-focused legal solutions and a forward-thinking approach to legal operations — including the adoption of AI-driven review platforms.Chie holds a Bachelor of Law from Dokkyo University, a Master of Laws (LL.M.) from the William S. Richardson School of Law, University of Hawaii, and a Graduate Certificate in Asia Pacific Leadership from the East-West Center, established by the U.S. Congress. She is a licensed attorney admitted to the New York Bar, a Certified Internal Auditor, and holds qualifications in wine expertise, including the J.S.A. Wine Expert certification and WSET Level 2.Outside of the office, Chie holds a 4th Dan Black Belt in Wado-kai Karate as well as a NAUI Rescue Diver certification. She is also a passionate wine enthusiast and a keen traveler.Connect with ChieLinkedIn: https://www.linkedin.com/in/chie-hashimoto-8458b3a/ LinksDunhill Bar: https://tabelog.com/tokyo/A1301/A130101/13224293/ Absent in the Spring, Agatha Christie: https://amzn.asia/d/05FzJ8Hz Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair

Part two of the conversation with Natsue Ishida dives into the intricacies of governance in Japan and how you can come across opportunities to do pro bono work that expand your area of expertise. Don’t miss the beautiful reading of a poem that has had a big impact on Natsue at the end of the episode. If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:The difference between Chief Legal Officer (CLO) and General Counsel (GC)Managing what’s best for the company and respecting the founder Finding unique ways to contribute to the governance community in Japan and globallyWhat Natsue would say to her younger self Her favourite book and poemAbout NatsueNatsue is a seasoned General Counsel and senior executive with over 20 years of international experience advising senior management, Boards of Directors, and Audit Committees across Asia, North America, and Europe. She brings extensive expertise in legal strategy, IP, compliance, risk management, corporate governance, global subsidiary management, M&A, and data privacy.Her career spans highly regulated industries—including financial services, medical devices, automotive, and gaming—where she has consistently guided organisations through complex regulatory landscapes while shaping strong cultures of compliance and ethical leadership.Natsue is a widely recognised award winning thought leader, deeply committed to advancing excellence within the legal profession.On the weekends, she enjoys rock climbing (shower climbing in the summer). She would like to do more photography (medium format film photo printing), maybe when she retires, if the technology still exists!Connect with NatsueLinkedIn: https://www.linkedin.com/in/theflyingcat/ LinksPart 1: ⁠https://www.catherineoconnelllaw.com/podcast/season-12-ep2-natsue-ishida⁠  Global Council for Responsible AI https://gcrai.ai/ Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair

Natsue Ishida shares her journey from sociology student to general counsel and executive officer advising boards, across many well known global companies. This is part one of a two part conversation filled with literal lightning moments, unconventional career choices, and profound leadership lessons. You will learn lessons from each stage of Natsue’s career and what it means to be an officer of the law inside an organisation.If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:How Natsue’s personal mission that has guided her careerThe importance of focusing on the experience you'll get from a jobWhy taking on responsibilities outside your normal expertise builds supporters for legal and complianceHow Natsue changed the trajectory of her career in the moment she said "I'll do it" to a role she wasn’t offered! Her favourite movies and other fun facts About NatsueNatsue is a seasoned General Counsel and senior executive with over 20 years of international experience advising senior management, Boards of Directors, and Audit Committees across Asia, North America, and Europe. She brings extensive expertise in legal strategy, IP, compliance, risk management, corporate governance, global subsidiary management, M&A, and data privacy.Her career spans highly regulated industries—including financial services, medical devices, automotive, and gaming—where she has consistently guided organisations through complex regulatory landscapes while shaping strong cultures of compliance and ethical leadership.Natsue is a widely recognised award winning thought leader, deeply committed to advancing excellence within the legal profession.On the weekends, she enjoys rock climbing (shower climbing in the summer). She would like to do more photography (medium format film photo printing), maybe when she retires, if the technology still exists!Connect with NatsueLinkedIn: https://www.linkedin.com/in/theflyingcat/ LinksTender Bar: https://tabelog.com/en/tokyo/A1301/A130101/13259123/ Roger and Me: https://www.imdb.com/title/tt0098213/ In the Name of the Father: https://www.imdb.com/title/tt0107207/  Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair

Welcome to the premier of Season 12! K. Lesli Ligorner is a partner with Morgan Lewis and shares what it takes to build a successful legal career spanning two decades across China and Japan. We hear how Lesli has mastered the art of finding flexibility within rigid statutory frameworks while leading diverse teams across cultures. If you are wondering how you will lead a team in Japan in the future, this is the episode for you.If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:The high school homestay in Japan that sparked a lifelong love for Asia How blind spots others created in their minds became Lesli's competitive advantageThe nuanced dance of giving instructions across China and Japan teamsHer favourite podcast, book and other fun facts About K. Lesli LigornerLesli Ligorner is a partner with Morgan Lewis and is based in Tokyo, but splits her time between Japan and China. She relocated to Tokyo 2 years ago after spending 18 years on the ground in Beijing and Shanghai. She first came to Japan in high school and lived with host families. She then returned for her junior year of university to study at Kansai Gaidai and graduated from McGill University in Montreal, Quebec with a major in East Asian Studies. Lesli went on to work at Japanese banks in New York City before heading to law school at American University, Washington College of Law. She then worked 3 years as a litigator for the Law Department of the City of New York and then moved to private practice. In fall 2005 the opportunity came up to move to China with her law firm at the time, and her husband raised her hand for her. Six months later they were on a plane to Shanghai and never looked back.Lesli has developed a practice representing western companies in Asia in some of their most sensitive employment matters and investigations and Asian companies with employment and compliance issues in the US and Europe.Connect with Lesli LinkedIn: https://www.linkedin.com/in/k-lesli-ligorner-asia-employment-investigations/ LinksMarzac 7: https://www.marzac7-nakameguro.com/ 1dL: https://ordinary-inc.com/1dl/ The Loudest Duck by Laura Liswood https://amzn.asia/d/0dSpo08S How to Fail with Elizabeth Day: https://podcasts.apple.com/gb/podcast/how-to-fail-with-elizabeth-day/id1407451189  Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair

Macaulay (Mac) Curtis, is a New Zealand native who has just qualified as a solicitor in England and Wales through the new SQE pathway. He achieved this while working as a legal translator first for Mori Hamada & Matsumoto, then in his own legal translation company. This episode is full of gems for those who are considering taking another step forwards in their legal career. It’s now entirely possible to use real life legal work experience to help you on your way. Listen to hear more!If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:Why Mac chose legal translation over interpreting and what it’s like to work in a big four firm’s translation departmentThe SQE pathway explained: qualify as a UK solicitor without attending universityWhy firms don't care about your age and what they do care aboutWhat translators must unlearn to become lawyersHis favourite book and other fun facts About MacMacaulay (Mac) is a linguist-turned-lawyer from New Zealand. Highly fluent in Japanese, he qualified as a simultaneous interpreter in Australia before going to work at Mori Hamada & Matsumoto in their in-house translation department. He later started his own legal translation business, working remotely from New Zealand as he lent his expertise to many of Japan's biggest companies and law firms. He recently qualified as a solicitor, and is now back in Japan to open a new chapter of his career as a lawyer in Tokyo.Connect with Mac LinkedIn: https://www.linkedin.com/in/macaulay-curtis/ LinksHow to win friends and influence people: https://amzn.asia/d/0iqkBUut SQE: https://www.law.ac.uk/study/postgraduate/sqe/ Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair

What does it take to transform from a technical legal expert into a strategic conductor of organisational change? Keiko Uchida, Head of Legal and Compliance at Roche Diagnostics Japan, shares her journey to leadership from playing the figurative “violin in an orchestra” to becoming “the conductor.”Discover what it means to move from solving one case with 100 pieces of evidence to solving 100 questions with almost none, and why doubling productivity in Japanese companies has become Keiko Uchida’s driving purpose.If you enjoyed this episode and it inspired you in some way, we’d love to hear about it and know your biggest takeaway. Head over to Apple Podcasts to leave a review and we’d love it if you would leave us a message here!In this episode you’ll hear:The powerful conversation that shifted her entire career trajectoryWhy being a housewife became her greatest strength rather than a setbackHow Keiko is building a regional legal network across APAC Her favourite book and other fun facts About KeikoKeiko Uchida is the Head of Legal & Compliance at Roche Diagnostics K.K., where she sits on the leadership team as a direct report to the CEO and oversees legal affairs, compliance, data privacy, corporate governance, and risk management across the organisation.Since joining Roche in 2022, Keiko has played a pivotal regional leadership role, earning the “Change Maker of the Year 2024” award for APAC in recognition of her impact in building a high-performing, collaborative legal network across the region, as well as driving market-focused partnerships between legal, security, and commercial operations teams. One of her team members was also recognised as VIP of the Year 2024 within Roche Diagnostics Japan — a reflection of her strength as a people leader.Before Roche, Keiko served as Corporate Officer, General Counsel, Chief Compliance Officer, and Data Privacy Officer at AXA General Insurance Co., Ltd., where she led legal and compliance transformation initiatives during a period of organisational change. She previously held senior legal and corporate secretary roles within AXA, and earlier in her career practiced as a lawyer in private practice after completing her legal training in Japan.Keiko’s career is uniquely cross-sector, with earlier professional experience in financial institutions including J.P. Morgan and Shinsei Trust Bank, as well as academic work as an Assistant Professor at a research center of The University of Tokyo. She later returned to the University of Tokyo to complete her J.D., following a Master’s degree in law from Kyoto University.Recognised on the Legal 500 GC Powerlist Japan 2023, a panelist at GC Summit 2024, and co-author of a practical legal handbook on contract law published in 2023, Keiko is known for blending deep legal expertise with organisational leadership and strategic thinking.Her professional passion lies in balancing opportunity and risk while building high-performing organizations, and outside of work she enjoys traveling and exploring new cultures.Connect with KeikoLinkedIn: https://www.linkedin.com/in/keiko-uchida-3bab7a30/ LinksHow to Win Friends and Influence People: https://amzn.asia/d/09azrBtm Connect with Catherine LinkedIn https://www.linkedin.com/in/oconnellcatherine/Instagram: https://www.instagram.com/lawyeronair