Register for a free webinar
How Leading Law Firms Are Building Judgment in the AI Era Through Deliberate Practice and Simulations
Webinar
How Leading Law Firms Are Building Judgment in the AI Era Through Deliberate Practice and Simulations
May 21, 2026 at 11 AM EST

Session time: 1 hour
For decades, junior lawyers developed judgment by doing the early-stage work of practice, including drafting, reviewing, researching, negotiating, and learning through repetition. As AI reshapes those workflows, firms face a more urgent training question: if associates get fewer meaningful reps on real matters, how will they develop the judgment, instincts, and confidence that practice requires?
This panel will focus on practical strategies for solving that problem, including how one of the legal industry’s most innovative firms, Orrick, Herrington & Sutcliffe LLP, is reinventing attorney development through deliberate practice, tech-enabled simulations, and hands-on training. Over the last six years, Orrick has significantly invested in its attorney training program, recently expanding its approach with AI-powered simulations that provide real-time feedback and help attorneys build better judgment skills on real matters. Those efforts include a first-of-a-kind AI training program focused on teaching the judgment skills lawyers need to use AI tools effectively and efficiently, as well as a unique technology transactions training program for all of its attorneys.
Attendees will learn how to design training that gives associates more practice, better feedback, and clearer opportunities to build judgment before client matters put those skills to the test. The session will offer a practical framework for using AI to strengthen lawyer development without weakening the critical thinking, strategic decision-making, adaptability, and communication skills lawyers need in practice.
You’ll learn how to:
- Preserve meaningful skill-building opportunities as routine work becomes automated
- Use simulations to develop judgment in realistic legal scenarios
- Design training that gives associates more deliberate, structured practice
- Leverage AI-enabled feedback to support more targeted coaching and mentoring
- Adopt AI in ways that strengthen, rather than weaken, the next generation of lawyers
Richard Tromans
Founder of Artificial Lawyer
Abdi Shayesteh
CEO and Founder of AltaClaro
Kate Orr
Managing Director of Practice Innovation at Orrick, Herrington & Sutcliffe LLP
Kelly Cullen
Senior Manager Talent Innovation at Orrick, Herrington & Sutcliffe LLP


Traditional deposition training is expensive, infrequent, and rarely repeatable. DepoSim changes that.
Conduct live, realistic oral depositions on-demand—with AI acting as the witness, opposing counsel, and court reporter—then get structured, objective feedback within minutes so you can run the next rep better.
How DepoSim works
DepoSim places attorneys in a live, simulated deposition, complete with AI agents acting as the witness, opposing counsel, and court reporter. Attorneys conduct the deposition in real time, handling objections, managing exhibits, and adapting their questioning strategy on the fly. Within minutes of completing the session, they receive detailed, rubric-based feedback.
