Sawako Kakutani is Corporate Secretarial Department Manager and Legal Department Manager at ASA Professionals Singapore, working remotely from Japan, and an attorney licensed in Washington State. She previously worked as Legal Department Manager at Hitachi Construction Machinery and does hybrid work between Singapore and Japan.

We hear how Sawako decided that law would be a way she could possibly enjoy working at a “traditional Japanese company”. If you are someone with endless curiosity you will find Catherine’s discussion with Sawako an interesting insight to possibilities in the legal world in Japan.

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 a philosophy book in a friend's library, first sparked Sawako's interest in law

• The paralegal role at AVAYA, with Lawyer on Air guest, Junko Mukoyama, that revealed in-house legal work could be genuinely exciting

• The tips Sawako offers for anyone who wants become a bridge between cultures

About Sawako

Sawako Kakutani is Corporate Secretarial Department Manager and Legal Department Manager at ASA Professionals Singapore, working remotely from Japan, and an attorney licensed in Washington State.

Sawako has built an international in-house legal career spanning Japan and Southeast Asia, with extensive experience in cross-border commercial transactions, corporate governance, compliance, data privacy and legal support for overseas businesses. From 2021 to 2025, Sawako was based in Singapore with Hitachi Construction Machinery Asia & Pacific, where she served as General Manager of Legal and supported the company's businesses and subsidiaries across the region. She returned to Japan in April 2025 and served as Legal Department Manager at Hitachi Construction Machinery Co., Ltd. before transitioning to her current roles at ASA Professionals Singapore on July 1, 2026.

Fluent in Japanese and English, Sawako has lived in the United States for 11 years and Singapore for four years. She holds a Bachelor of Laws from Waseda University, a Juris Doctor from Omiya Law School and an LL.M. from Temple University Beasley School of Law, Japan Campus. She became licensed to practise law in Washington State in January 2026.

Outside work, Sawako is an enthusiastic dragon boat paddler and also enjoys marathons, mountain trekking, cycling, motorcycle touring and travel.

Connect with Sawako

LinkedIn: https://www.linkedin.com/in/sawako-kakutani-8902a9bb/

Connect with Catherine

LinkedIn https://www.linkedin.com/in/oconnellcatherine/

Instagram: https://www.instagram.com/lawyeronair

Yoko Arisaka is General Manager of Sony Group's Legal Department and a key architect of Sony's AI ethics guidelines. Yoko shares her journey from Tokyo to New York, experiencing the World Financial Crisis there, and finding her niche at Sony, forging a deep interest in AI governance. You will be surprised at how Yoko looks to the past and outside of the law for hints on how to bring about the future.

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:

• Yoko’s “small”, consistent networking habit that compounded into creating a valuable network for her

• The moment in 2015 when she was first asked to research the new field of AI ethics

• The technical and soft skills a legal general manager needs right now

• Yoko's biggest concern about AI adoption is not speed but the hidden long-term costs

About Yoko

Yoko Arisaka is General Manager of the Legal Section, Legal Department at Sony Group Corporation. She plays an important role in offering legal guidance and support for the implementation of new technologies and creating new businesses in Sony. She works closely with cross-functional teams to ensure compliance with legal requirements and minimize potential risks.

In addition to her expertise in corporate law, she has made contributions to the field of AI ethics. She was a key member of the team responsible for developing Sony Group AI Ethics Guidelines. She has published multiple articles on the subject in reputable Japanese legal journals. She has a Bachelor of Laws (LL.B.) degree from the University of Tokyo and a Master of Laws (LL.M.) degree from UCLA School of Law, and is licensed to practice law in the State of New York.

In her free time, she enjoys staying active, exploring gut health and inner wellness, and dining out with friends.

Connect with Yoko

Please contact Catherine to be connected with Yoko

Connect with Catherine

LinkedIn https://www.linkedin.com/in/oconnellcatherine/

Instagram: https://www.instagram.com/lawyeronair

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 teaches

• Simon’s experience from the front line of AI development and the “brain fry” phenomenon replacing “brain rot”

About Simon

Simon 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 University

Before 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 Simon

LinkedIn https://www.linkedin.com/in/simon-hollander-9b5a3a5/

Links

Punk Doily: https://www.instagram.com/punkdoily

Connect with Catherine

LinkedIn https://www.linkedin.com/in/oconnellcatherine/

Instagram: https://www.instagram.com/lawyeronair