Mary O'Carroll isn't experimenting for fun, she's trying to solve one of legal's biggest scaling problems: the fact that the profession's best judgment and hard-earned experience still lives in people's heads, buried in laptops, or scattered across years of emails. So in this episode of Pearls On Gloves Off, Mary runs a real test: she trains a digital twin on essentially all of her content (podcasts, talks, blogs, speeches), and then sits down for a conversation with "Digital Mary" to find out whether a digital mentor can actually deliver useful guidance.

In this episode:

Digital Mentors, Tested: Why Mary built a digital twin trained on decades of her content - and whether AI can realistically scale mentorship and judgment in legal.
Legal Ops, Rewritten: How the function has evolved from managing outside counsel spend to driving technology, data, and GenAI-enabled transformation.
The Lawyer Skillset Is Shifting: Why trust, judgment, and relationship-building matter more than ever, even as training models struggle to keep up.
Tech Hype vs. Real Impact: How to think "problem first, tool second," and why foundational legal tech still delivers massive value alongside AI.
Pressure on the Billable Hour: What AI exposes about law firm economics, pricing, and the growing need for right sourcing and true partnership.

If you're thinking about training, legal ops scale, AI disruption, or the future of law firm economics, this episode is a rare, real-time look at how the profession might start "bottling" expertise, and what it will take to do it well.

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