I’ve been watching the legal-tech landscape for a long time, and this morning’s announcement from Thomson Reuters’ partnership with DeepJudge marks a moment worth pausing over. (DeepJudge) On October 22, 2025, TR disclosed that DeepJudge’s enterprise-search and AI-knowledge-platform capabilities will be integrated into TR’s CoCounsel Legal offering to bring internal-firm knowledge and
This week, we welcome back Kara Peterson and Rich DiBona of Descrybe to talk about the company’s rapid growth and its expanding role in legal research. Since their last appearance, Descrybe has not only built out new tools but also entered academia by joining the curriculum of more than 350 universities around the world. Kara reflects on her earlier career in legal education and how this new partnership feels like coming full circle. Together, she and Rich share how Descrybe is positioning itself to fill the gap left by other providers while keeping affordability and accessibility at the core of their mission.
A major highlight of the discussion is Descrybe’s unique approach to legal citators. Unlike traditional tools that often provide a blunt “treatment” of a case, Descrybe’s citator allows issue-level analysis and even introduces a “backwards citator.” This means researchers can see not only how later courts interpreted a case but also how the judges who wrote the opinion cited and treated earlier authorities. Rich explains the technical challenges involved in training their system on 30 million citations, while Kara describes how these innovations give researchers new storytelling and analytical power when building arguments.
The conversation also dives into the Legal Research Toolkit, Descrybe’s paid tier that offers a collection of tools designed for professionals who need more advanced case law analysis. While the company continues to provide free access to its core research platform, the toolkit adds features such as issue explorers and advanced citator functions. Kara emphasizes the company’s deliberately simple pricing model, which prioritizes trust and accessibility. At just $10 a month for non-commercial use and $20 for commercial users, the service is priced more like everyday software than the traditional high-cost legal research platforms.
The discussion moves into broader industry trends, including the wave of acquisitions by major players like Thomson Reuters and Clio. Kara and Rich note that while consolidation is reshaping the market, it also leaves space for new entrants to innovate. With data becoming the most valuable commodity in legal tech, Descrybe is building curated and clean datasets across statutes, regulations, state constitutions, and even attorney general opinions. Both guests highlight the importance of accuracy, data hygiene, and minimizing hallucinations, explaining how their closed-system approach helps ensure that results remain grounded in actual legal documents rather than speculative AI outputs.
Finally, the episode touches on ethics, recognition, and the future. Descrybe recently won the Anthem Award for Ethical AI, a nod to its safeguards against hallucinations and commitment to transparent data practices. At ILTACon, the team found themselves impressing not only potential clients but also leaders from larger companies who were curious about how such a lean startup was able to achieve so much. Looking ahead, Kara predicts the pace of change in legal technology will only accelerate, challenging law firms to keep up, while Rich warns of the commoditization of AI capabilities and stresses the importance of staying ahead of the curve. Together, they bring both humor and insight, reminding listeners that the legal research market is shifting quickly and that affordability, accuracy, and ethics will shape its next chapter.
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[Special Thanks to Legal Technology Hub for their sponsoring this episode.]
Blue Sky: @geeklawblog.com @marlgeb
Email: geekinreviewpodcast@gmail.com
Music: Jerry David DeCicca
In this episode of The Geek in Review, we welcome back Pablo Arredondo, VP of CoCounsel at Thomson Reuters, along with Joel Hron, the company’s CTO. The conversation centers on the recent release of ChatGPT-5 and the rise of “reasoning models” that go beyond traditional language models’ limitations. Pablo reflects on his years of tracking neural net progress in the legal field, from escaping “keyword prison” to the current ability of AI to handle complex, multi-step legal reasoning. He describes scenarios where entire litigation records could be processed to map out strategies for summary judgment motions, calling it a transformative step toward what he sees as “celestial legal products.”
Joel brings an engineering perspective, comparing the legal sector’s AI trajectory to the rapid advancements in AI developer tools. He notes that these tools have historically amplified the skills of top performers rather than leveling the playing field. Applied to law, he believes AI will free lawyers from rote work and allow them to focus on higher-value decisions and strategy. The discussion shifts to Deep Research, Thomson Reuters’ latest enhancement for CoCounsel, which leverages reasoning models in combination with domain-specific tools like KeyCite to follow “breadcrumb trails” through case law with greater accuracy and transparency.
The trio explores the growing importance of transparency and verification in AI-driven research. Joel explains how Deep Research provides real-time visibility into an AI’s reasoning path, highlights potentially hallucinated citations, and integrates verification tools to cross-check references against authoritative databases. Pablo adds historical and philosophical perspective, likening hallucinations to a tiger “going tiger,” stressing that while the risk cannot be eliminated, the technology already catches a significant number of human errors. Both agree that AI tools must be accompanied by human oversight and well-designed workflows to build trust in their output.
The conversation also delves into the challenges of guardrails and governance in AI. Joel describes the balance between constraining AI for accuracy and keeping it flexible enough to handle diverse user needs. He introduces the concept of varying the “leash length” on AI agency depending on the task—shorter for structured workflows, longer for open-ended research. Pablo challenges the legal information community to break down silos between disciplines like eDiscovery, research, and litigation, envisioning a unified information ecosystem that AI could navigate seamlessly.
Looking to the future, Joel predicts that the adoption of AI agents will reshape organizational talent strategies, elevating the importance of those who excel at complex decision-making. Pablo proposes “ambient AI” as the next frontier—intelligent systems that unobtrusively monitor legal work, flagging potential issues instantly, much like a spellchecker. Both caution that certain legal tasks, especially in judicial opinion drafting, warrant careful consideration before fully integrating AI. The episode closes with practical insights on staying current, from following AI researchers on social platforms to reading technical blogs and academic papers, underscoring the need for informed engagement in this rapidly evolving space.
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[Special Thanks to Legal Technology Hub for their sponsoring this episode.]
Blue Sky: @geeklawblog.com @marlgeb
Email: geekinreviewpodcast@gmail.com
Music: Jerry David DeCicca
Blue Sky: @geeklawblog.com @marlgeb
Email: geekinreviewpodcast@gmail.com
Music: Jerry David DeCicca
This week we welcome Raghu Ramanathan, President of Legal Professionals at Thomson Reuters, for an insightful discussion on the profound impact of Artificial Intelligence (AI) on the legal industry. Bringing a fresh perspective shaped by his extensive background in technology leadership at companies like SAP and strategy consulting with McKinsey, Raghu shares why he believes the legal sector, alongside healthcare, stands at the forefront of the AI revolution. His journey into the legal tech world, driven by the transformative potential of AI, sets the stage for a deep dive into current trends, future predictions, and the strategic initiatives shaping the future of law.
Central to the conversation is Raghu’s updated perspective on the evolution of law firms, revisiting predictions he first made in 2017. He outlines a compelling framework describing “three waves” of AI adoption currently underway. The first wave, “Optimization,” which many firms are experiencing now, focuses on using AI to enhance existing workflows, making tasks faster and more efficient. The second wave, “Re-engineering,” involves fundamentally rethinking processes, staffing models (including the traditional pyramid structure), pricing strategies, and the very nature of legal work to leverage AI’s capabilities more deeply. Looking further ahead, the third wave anticipates the emergence of entirely “New Business Models,” where law firms might offer tech-based services, explore adjacent business lines, embrace true outcome-based pricing, and potentially even reshape the legal value chain.
The discussion delves into the significant implications these waves have for law firm talent and structure. Raghu predicts a shift in the traditional law firm pyramid, potentially leading to leaner associate ranks but a greater need for experienced partners and, crucially, integrated tech talent. This necessitates not only attracting technologists but also potentially rethinking firm equity structures to retain them. Furthermore, the skill set required for the “lawyer of the future” is evolving; proficiency in delegation to AI tools, broader unstructured problem-solving, and embracing technological integration will become paramount, demanding changes in legal education and professional development.
Thomson Reuters is actively navigating and shaping this transformation, particularly through its AI platform, CoCounsel. Raghu highlights the rapid evolution of CoCounsel, emphasizing the continuous development of new “skills”—capabilities ranging from summarization and research to drafting and complex analysis like the innovative “Claims Explorer.” He explains TR’s strategy involves integrating proprietary data (like Westlaw), client-provided documents, and public information, leveraging advancements in Large Language Models (LLMs) from various providers to deliver comprehensive and powerful AI assistance. Prioritizing new skill development involves balancing significant client value with technical feasibility, constantly informed by close collaboration with innovation-focused customers.
Beyond law firms, the conversation explores the crucial role and adoption of AI within the court system. Raghu notes a surprising enthusiasm among courts, driven by the urgent need to address growing case backlogs and enhance access to justice within tight budgets. He points to Thomson Reuters’ significant partnerships, including a major agreement to deploy AI tools across the US federal courts and ongoing collaboration with the National Center for State Courts (NCSC), which is fostering education and policy discussions among judges and court staff nationwide. Complementing product innovation, TR’s expanded “Customer Success” initiative underscores the importance of user adoption, providing dedicated resources and best practices to help lawyers and legal professionals effectively integrate AI tools into their daily workflows, ensuring technology translates into tangible value.
Concluding with a look ahead, Raghu anticipates that smaller and mid-sized law firms may initially leverage AI more aggressively as a competitive equalizer, pushing larger firms to make bolder, more strategic moves beyond simple optimization. He stresses that the ultimate differentiator for success in the AI era will likely be less about the technology itself and more about effective change management—strategic clarity, operational implementation, and fostering a culture that embraces new ways of working. The rapid pace of AI adoption already witnessed in the legal sector signals that this transformation is not a distant prospect but a present reality reshaping the industry at an unprecedented speed.
Read the Whitepaper: “2025 Generative AI in Professional Services Report“
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[Special Thanks to Legal Technology Hub for their sponsoring this episode.]
Blue Sky: @geeklawblog.com @marlgeb
Email: geekinreviewpodcast@gmail.com
Music: Jerry David DeCicca
This week, we bring back our original TGIR podcast guest, Zena Applebaum. Zena is now the Senior Vice President of Market Development at Harbor, and we discuss the ongoing transformation driven by technological advancements and strategic shifts. Her insights provide a valuable perspective on the challenges and opportunities facing legal professionals as they navigate these changes.
Zena talks about the integration of generative AI (Gen AI) into legal research tools, particularly at Thomson Reuters, where she previously worked. She emphasizes the challenges in managing expectations around AI’s capabilities while ensuring that the products deliver on their promises. The legal industry has high expectations for AI to simplify the time-consuming and complex nature of legal research. However, Applebaum highlights the need for balance, as legal research remains inherently challenging, and overpromising on AI’s potential could lead to dissatisfaction among users.
Zena was one of the first in the legal market to understand the role of competitive intelligence in shaping product development and market strategies. Applebaum reflects on her experience at Thomson Reuters, where she applied competitive intelligence not just to monitor competitors but to anticipate market dynamics and plan for the future. This approach allowed Thomson Reuters to stay ahead by avoiding surprises and making informed decisions that aligned with long-term goals. Her emphasis on listening to customer needs and understanding market trends underscores the importance of strategic foresight in the legal tech industry.
We also talk about Zena’s move over to Harbor, where she now focuses on market development. She explains that her move was motivated by the opportunity to impact a smaller, more agile company and leverage her legal domain expertise in a broader context. At Harbor, Applebaum aims to redefine the company’s value proposition and position it as a holistic service provider for the legal industry. This shift from a product-centric role to a more strategic, client-focused position highlights the evolving nature of legal services and the increasing demand for comprehensive solutions that address various aspects of legal practice.
Furthermore, the podcast explores the potential impact of AI on the legal landscape and Harbor’s role in helping law firms and legal departments adapt to these changes. Applebaum notes that while AI has not yet revolutionized the industry as quickly as some anticipated, it is gradually driving efficiency and reshaping how legal professionals approach their work. Harbor’s technology-agnostic approach allows it to assist firms in optimizing their tech stacks and preparing for the future, whether through AI, cloud migration, or other technological advancements. This adaptability positions Harbor as a key player in guiding firms through the ongoing digital transformation.
Zena shares her outlook on the future of the legal industry, particularly the growing sophistication of in-house legal departments and the increasing competition for legal talent. She predicts that as AI continues to enhance efficiency and drive changes in the industry, the demand for skilled legal professionals will rise. Law firms will need to adapt to these shifts by embracing new technologies and rethinking their strategies to remain competitive in a rapidly evolving market.
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Music: Jerry David DeCicca
Transcript
Continue Reading AI, Market Dynamics, and the Future of Legal Services with Harbor’s Zena Applebaum
Reflections on the Stanford HAI Report on Legal AI Research Tools
The updated paper from the Stanford HAI team presents rigorous and insightful research into the performance of generative AI tools for legal research. The complexity of legal research is well-acknowledged, and this study looks into the capabilities and limitations of AI-driven legal research tools
In this episode of “The Geek in Review,” hosts Greg Lambert and Marlene Gebauer celebrate the one-year anniversary of CoCounsel, the pioneering Generative AI Legal Research Tool launched by CaseText. They are joined by Pablo Arredondo, Vice President of CoCounsel at Thomson Reuters and co-founder of CaseText, to discuss the significant strides and challenges faced in developing and implementing generative AI in legal research. Pablo shares insights into the early days of exploring generative AI and the transformative potential it held for overcoming the limitations of traditional keyword-based search methods in legal research.
The conversation delves into the technical and strategic journey of bringing CoCounsel to market, highlighting the team’s rapid pivot to leverage GPT-4 technology and the collaborative effort that ensured its successful launch. Pablo emphasizes the importance of quality control, trust, and addressing the nuanced requirements of legal research to ensure that CoCounsel met the high expectations of its users, including law librarians and legal professionals.
Pablo also reflects on the broader implications of generative AI for the legal industry, including the rapid adoption by law firms and legal departments seeking to leverage this technology to enhance their research capabilities and workflow efficiencies. The discussion touches on the ongoing challenges and opportunities presented by generative AI, such as regulatory considerations, ethical concerns, and the need for continuous education and adaptation within the legal profession.
The acquisition of CaseText by Thomson Reuters is discussed, with Pablo sharing his perspective on the strategic move and its potential to further expand and enhance CoCounsel’s capabilities and reach. He highlights the synergy between CaseText’s innovative approach and Thomson Reuters’ extensive resources and market presence, which together aim to drive the next wave of advancements in legal technology and research tools.
Finally, the episode explores future directions for generative AI in legal research, including the expansion of CoCounsel’s capabilities to encompass a wider range of legal tasks and its potential to transform the practice of law. Pablo’s enthusiasm for the possibilities ahead underscores the significant impact that generative AI is set to have on the legal industry, promising to revolutionize how legal professionals interact with information and conduct research.
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Music: Jerry David DeCicca and Eve Searls
Transcript
Continue Reading Pablo Arredondo on the One-Year Anniversary of CoCounsel
The Geek in Review podcast welcomed Kriti Sharma, Chief Product Officer of Legal Tech at Thomson Reuters, to discuss AI and ethics in the legal industry. Kriti talks to us about the importance of diversity at Thomson Reuters and how it impacts product development. She explained TR’s approach to developing AI focused on augmenting human skills rather than full automation. Kriti also discusses the need for more regulation around AI and the shift towards human skills as AI takes on more technical work.
A major theme was the responsible development and adoption of AI tools like ChatGPT. She discusses the risks of bias but shared TR’s commitment to building trusted and ethical AI grounded in proven legal content. Through this “grounding” of the information, the AI produces reliable answers lawyers can confidently use and reduce the hallucinations that are prevalent in publicly commercial Gen AI tools.
Kriti shares her passion for ensuring people from diverse backgrounds help advance AI in law. She argues representation is critical in who develops the tech and what data trains it to reduce bias. Kriti explains that diversity of experiences and knowledge amongst AI creators is key to building inclusive products that serve everyone’s needs. She emphasizes Thomsons Reuters’ diversity across leadership, which informs development of thoughtful AI. Kriti states that as AI learns from its creators and data like humans do, we must be intentional about diverse participation. Having broad involvement in shaping AI will lead to technology that is ethical and avoids propagating systemic biases. Kriti makes a compelling case that inclusive AI creation is imperative for both building trust and realizing the full potential of the technology to help underserved communities.
Kriti Sharma highlights the potential for AI to help solve major societal challenges through her non-profit AI for Good. For example, democratizing access to helpful legal and mental health information. She spoke about how big companies like TR can turn this potential into actual services benefiting underserved groups. Kriti advocated for collaboration between industry, government and civil society to develop beneficial applications of AI.
Kriti founded the non-profit AI for Good to harness the power of artificial intelligence to help solve pressing societal challenges. Through AI for Good, Kriti has led the development of AI applications focused on expanding access to justice, mental healthcare, and support services for vulnerable groups. For example, the organization created the chatbot tool rAInbow to provide information and resources to those experiencing domestic violence. By partnering frontline organizations with technologists, AI for Good aims to democratize access to helpful services and trusted information. Kriti sees huge potential for carefully constructed AI to have real positive impact in areas like legal services for underserved communities.
Looking ahead, Kriti says coordinated AI regulations are needed globally. She calls for policymakers, companies and society to work together to establish frameworks that enable adoption while addressing risks. With the right balance, AI can transform legal services for the better.
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Continue Reading Thomson Reuters’ Kriti Sharma on Responsible AI: The Path to Trusted Tech in Law
This week we have Damien Riehl, VP, Litigation Workflow and Analytics Content at FastCase, and one of the drivers behind SALI (Standards Advancement for for the Legal Industry.) Damien is definitely a “big thinker” when it comes to the benefits of creating and using standards for the legal industry. SALI is a system of tagging legal information to allow for better filtering and analysis. It works like Amazon’s product tags, where a user can search for a specific area of law, such as patent law, and then choose between various services such as advice, registration, transactional, dispute, or bankruptcy services. The tags cover everything from the substance of law to the business of law, with over 13,000 tags in the latest version. SALI is being adopted by major legal information providers such as Thomson Reuters, Lexis, Bloomberg, NetDocuments, and iManage, with each provider using the same standardized identifiers for legal work. With this standardization, it will be possible to perform the same API query across different providers and receive consistent results. Imagine the potential of being able to ask one question that is understood by all your database and external systems? 
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This week we talk with Factor’s Ed Sohn and Michael Callier on the consulting for in-house legal teams through what they describe as New Law companies. New Law is who corporate legal counsel reach out to in order to streamline their operations and find ways of integrating themselves into the overall mission of the corporation, rather than just the department which mitigates legal and business risks. Sohn and Callier stress that New Law companies are not a threat to established law firms, but rather a partner who can help firms differentiate themselves from their peers by allowing for the consultation to clients for alternative legal strategies.Process adoption, or its failure oftentimes rests with people. It actually rests with social learning. it actually rests with how do you celebrate and story tell and create a culture that’s conducive to the adoption of technology and innovation.
To be honest, it’s not that people fear change, it’s that people fear the loss associated with change. We change every day. We change clothes. We eat different things. We go to different places that we’ve never been before. So it’s not it’s not fear of change, it’s fear of the loss associated with change. And so in particular, with the legal industry.
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