Notes to My Legal Self®

Are 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-enabled

Follow Notes to My (Legal) Self® for more conversations on the future of in-house law.

Are 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

Are 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

In 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 upside

This 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.

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In 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 governance

If 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.

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