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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