From AI Personas to Rogue Agents: Rethinking Legal Training, Security, and Value

Fresh from AALL in Cleveland, Greg reflects on a conference filled with legal information professionals who understand how technology performs under real working conditions. These librarians purchase products, train users, support law schools and courts, and often serve as internal advocates for legal technology. Their expertise makes vendor engagement especially valuable, yet major product announcements were scarce. Marlene balances Greg’s conference report with stories from her hiking trip through Zion and Bryce Canyon, plus a brief comparison of Ohio and Utah karaoke culture.The conversation turns to the rapid growth of innovation attorney positions across law firms and legal organizations. Greg and Marlene describe these professionals as translators who connect legal practice, technology, workflow design, and organizational change. Firms are searching beyond traditional legal career paths for people who combine technical fluency with strong interpersonal skills. For law students and junior lawyers facing uncertainty around AI, these emerging roles offer broader career options beyond the familiar associate track.Marlene explores the growing use of AI personas and simulations for professional development. Deposition witnesses, opposing counsel, negotiation partners, and drafting reviewers now appear as interactive characters with distinct goals and behaviors. Lawyers receive a place to practice, make decisions, and receive feedback before working with clients or appearing in court. Greg connects simulation-based learning with legal fiction, including his Beyond the Model series, which uses a fictional law firm to explain AI systems, business pressures, and changes in legal work.The discussion takes a serious turn with a reported AI benchmarking incident involving an agentic model, a breached sandbox, and unauthorized access to Hugging Face resources in search of an answer key. Greg and Marlene examine the episode as a warning about containment, accountability, and excessive faith in technical guardrails. From there, they consider the renewed importance of knowledge management and security as AI systems gain access to documents, financial information, client data, and institutional expertise. Greg predicts growing attention around AI harnesses, structured software layers designed to guide model behavior and produce predictable outputs.Marlene closes with examples of AI moving into client intake, business qualification, and workflow decisions, including an AI legal receptionist designed for smaller firms. The larger shift involves moving beyond simple tool adoption toward redesigned workflows, staffing models, pricing structures, and client service. Token costs are creating immediate budget pressure, while clients are questioning which AI expenses belong on their bills. Greg and Marlene argue firms must connect AI spending with legal judgment, measurable value, and responsible delivery, rather than treating consumption as a proxy for progress.Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠Substack⁠[Special Thanks to ⁠⁠Legal Technology Hub⁠⁠ for their sponsoring this episode.] Email: [email protected]: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠Transcript: