This week on The Geek in Review, we talk with Abdi Shayesteh, CEO of AltaClaro, and Jeanine Conley Daves, Littler’s New York office managing shareholder, about a different question in the legal AI conversation. Instead of asking whether AI will write the brief, summarize the contract, or replace the junior associate, they focus on whether AI might help lawyers learn how to practice law. Their recent work around AltaClaro’s DepoSim points toward a model of legal training built less on passive observation and more on structured repetition, feedback, and skill development.

Shayesteh traces the origin of AltaClaro back to his own early years at King & Spalding, where he benefited from proximity to a mentor willing to explain the work. That experience also showed him the unevenness of the old apprenticeship model. Access to assignments, feedback, and sponsorship often depended on luck, relationships, and office geography. For Shayesteh, the idea of a “flight simulator for lawyers” grew out of the realization that pilots, athletes, and musicians all practice in structured environments before performance, while lawyers too often learn in front of clients, courts, and opposing counsel.

DepoSim applies this flight simulator concept to one of litigation’s highest-pressure skills: taking and defending depositions. The platform gives attorneys a simulated witness, opposing counsel, court reporter, and feedback system, with options to vary the difficulty and personalities involved. Conley Daves explains why this kind of realism matters. In a real deposition, a lawyer might face an evasive witness, a hostile witness, an aggressive opposing counsel, or a combination of all three. The simulator lets lawyers practice those moments repeatedly, receive targeted feedback, and return to specific skills such as exhibit handling, follow-up questions, or managing objections.

The conversation also connects AI training to equity in professional development. Conley Daves notes that access to high-quality assignments and sponsorship has not always been distributed evenly across firms. A standardized, rubric-based feedback system gives more lawyers a chance to build core skills without waiting to be selected by the right partner or assigned to the right matter. Shayesteh adds that firms seeing the strongest results are not treating training as an after-hours side quest. They are creating protected time for deliberate practice, pairing AI feedback with human mentorship, and using simulation as a bridge rather than a substitute for coaching.

Looking ahead, Shayesteh and Conley Daves see simulation moving well beyond depositions. Oral argument, cross-examination, meet-and-confer sessions, negotiations, client interviews, and even Supreme Court preparation all fit within this training model. The larger shift is not automation for its own sake. It is the use of AI to help lawyers build judgment before the stakes are real. For law firms, that means better preparation, more consistent training, stronger associate development, and a clearer path toward delivering value to clients. For the profession, it suggests a future where competence is practiced deliberately, measured thoughtfully, and taught more fairly.

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[Special Thanks to Legal Technology Hub for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading The Flight Simulator for Lawyers: Abdi Shayesteh and Jeanine Conley Daves on AI, Deliberate Practice, and the Future of Legal Training

We recorded this episode live at the TLTF Summit and the energy in the room made it feel like the perfect place for a conversation about growth, training, and the rapid climb of legal tech. We grabbed our gear, claimed a corner in the podcast room, and pulled in two guests with front row seats to the changes hitting the industry. Joining us were Kyle Poe from Legora and our friend and guest host, Zena Applebaum of Harbor. The Summit attracts a focused group of founders, investors, and leaders, and the four of us jumped straight into what this event represents and what attendees hope to get from it.

Kyle had been on the job for only two months, but Legora moves at a pace that feels closer to dog years. In that short time the team doubled, a new round of funding closed, and the company introduced a major product release. Kyle walked us through Legora’s new Portal experience, which brings clients inside the legal workflow in a controlled, collaborative environment. Instead of long email chains and static work product, the Portal supports shared editing, direct review of diligence work, and a more responsive model for client engagement. In an era when clients expect quick turnarounds, this shift sets up a new dynamic for firms.

Zena added helpful perspective from her prior trips to TLTF. She described the Summit as a place that rewards conversation, curiosity, and hallway exchanges. It is also a place to study the different stages of the legal tech journey, from early ideas on the startup stage to the seasoned players on the scale stage. She also brought timely news of Harbor’s acquisition of Encore Technologies, a move that strengthens Harbor’s ability to support training and adoption workflows across firms and corporate legal teams. Her focus on education paired well with Kyle’s insights on how Legora approaches enablement through its team of legal engineers.

Training became the heart of the conversation. We compared old habits with the expectations of a generation of associates who have been taught to avoid AI until they enter a firm. Kyle stressed the need to anchor attorney training in real use cases and to give them early wins so they build trust in the tools. He described the shift from task-based training to workflow-based thinking. Zena echoed this point and highlighted the growing trend of firms reserving time for associates to explore AI tools as part of their professional development rather than treating experimentation as a side project squeezed between billable work.

We also talked about how AI is influencing both the pace and structure of client service. Kyle shared examples of how Legora uses prior work product to build integrated workflows, such as interrogatory response generators that pull from a full library of past responses. This not only speeds up production but also increases consistency and helps attorneys understand the reasoning behind revisions. Zena pushed the idea even further, noting that these systems give associates a chance to study the rationale behind changes in a way that human reviewers rarely have time to provide. This leads to better training and stronger validation of the final work product.

We closed with our crystal ball question. Kyle sees more adoption on the horizon but also anticipates uneven impacts across different practices as firms figure out how to adjust their business models. Zena pointed to the operational challenges ahead, especially the pressure to invest in data management and cloud infrastructure that supports true AI enablement. Her message was clear. If firms want the benefits later, they need to start organizing the foundations now. This episode blends optimism with realism, and it highlights the practical work ahead for firms, vendors, and everyone in between. Tune in for the full conversation and get ready for a lively discussion recorded right in the middle of the Summit buzz.

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[Special Thanks to Legal Technology Hub for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading AI Dividends and Workflow Training: Live with Legora and Harbor at TLTF