Proceedings of the Second International Workshop on AI and Intelligent Assistance for Legal Professionals in the Digital Workspace LegalAIIA 2021 Preface The Second International Workshop on AI and Intelligent Assistance for Legal Professionals in the Digital Workplace (LegalAIIA 2021) will be held online on June 21, 2021, in conjunction with the 18th International Conference on Artificial Intelligence and Law (ICAIL 2021). The workshop will provide a venue for these issues in the form of a number of accepted ideation, application, and research papers, as well as an industry panel, and two keynote speakers (one from the perspective of AI, the other from the perspective of IA (Intelligent Assistance). In addition, following the tradition of the DESI workshop series out of which LegalAIIA grew, working “breakout discussions” will be held, where the workshop attendees interact with each other around subtopics of interest and report their back to the larger group on the outcomes of their discussions. Many of the artifacts of the workshop are contained in this volume. Session 1: Morning Introduction & Keynote Address 11:30 – Welcome and goals: Jack Conrad, Jeremy Pickens With introductions to the other organizers: Jyothi Vinjumur, Dan Linna, Hans Henseler, Jason Baron 11:40 – Opening AI Keynote: Introduction: Jack Conrad Dr. Kris Hammond (Northwestern University) “Humanizing the Machine with Language: Building the Bridge between Data and Information” 12:25 – Q&A Session with Discussant David Lewis (Reveal Data) Session 2: Ideation / Application Paper Talks (Chair: Hans Henseler) 12:45 – Legal AI Systems in the EU's proposed Artificial Intelligence Act, Sebastian Schwemer, Letizia Tomada, Tommaso Pasini 13:10 – Utilizing AI to Improve Efficiency of the Environment and Land Court in the Kenya Judiciary: Leveraging AI Capabilities in Land Dispute Cases in the Kenyan Environmental and Land Court System, Florence Ogonjo, Joseph Theuri Gitonga, Angeline Wairegi, Isaac Rutenberg 13:35 – Break A poll will be taken at the start of this break to help us structure the Breakout sessions to take place following the panel. The Breakout session topics will include: 1. How AI is Changing the Legal Profession 2. AI & Access to Justice 3. The Human Role in AI 4. The Evolving Role of Deep Learning in the Legal Space 5. The Future of E-Discovery Session 3: Industrial Panel (Chairs: Jyothi Vinjumur & Dan Linna) 13:50 – A Panel of International Subject Matter Experts on Legal AI and IA in Practice: Today and in the Future • Pablo Arredondo (Casetext) • David Marcos (Microsoft) • Irina Matveeva (Reveal Data) • Julian Tsisin (Facebook) Session 4: Breakout Discussion - Law Practice 2030 14:50 – Participants to join breakout groups based on a topic of their choice 15:30 – Reports from Breakout Groups 16:00 – Break Session 5: Afternoon Keynote Address 16:15 – Concluding Intelligent Assistance Keynote: Introduction: Jeremy Pickens Michelle Zhou (Juji, Inc.) “Democratizing AI for Legal Professionals: Creating Cognitive AI Legal Assistants with No Coding” 17:00 – Q&A Session with Discussant Bruce Hedin (H5) Session 6: Research Paper Talks (Chair: Jyothi Vinjumur) 17:20 – On the Effectiveness of Portable Models versus Human Expertise under Continuous Active Learning, Jeremy Pickens, Thomas C. Gricks III, Esq. Session 7: Closing Remarks 17:45 – Closing Remarks, Announcements, Action Items 18:00 – END Additional details on the program: Topic of panel session • Hype about data analytics, Artificial Intelligence, and Intelligence Augmentation shows no sign of slowing. Abundant examples illustrate how these technologies are transforming industries. What about the legal industry? While technology assisted review is revolutionizing e-discovery and due diligence, will these technologies transform other aspects of legal services? This panel brings together industry experts to discuss how legal services organizations are making the most of data analytics, Artificial Intelligence, and Intelligence Augmentation. Our panelists will discuss bridging the gap between strategy and implementing these technologies, the need for interdisciplinary teams, high-impact tools today, the challenges, and where they see these technologies having the greatest impact in the next five to ten years. • Session Description: This panel will be 45 minutes long. This panel session begins with the moderator introducing the speakers followed by each of our four speakers giving a 2-minute overview of their current work and engagement in the field of Legal AI and IA (10-12 minutes). Following the introductions, the panel moderator will have 4-6 questions which each of the four speakers will be given the opportunity to answer (30 minutes). We conclude the panel session with questions from audience as time permits. Illustrative Questions • Regarding the intersection and collaboration of Technology (AI/IA) and Legal Professionals, how widespread is the Adoption of AI and Analytics in your organization? Who is involved? How do you get started? • How do you bridge the gap between Strategy and AI/IA techniques? In your professional experience, can you explain where a data-driven decision making did not make sense and why? How do strategic partnerships between Legal, Engineering and Policy teams work in your organization? • Intelligent Automation and AI relies on a strong synergy between human adoption and a robust technology platform. What are the big challenges to watch out for and the key capabilities that enterprises need, to gain an operational edge? Follow-up question: How do you measure success in such systems? • Future State Question: How do you see the Legal-AI partnership, Legal education and AI adoption evolve in the next 5 years? Looking back, what do you wish you had learned in the past? Breakout Session Organizer: Jason R. Baron, Univ. of Maryland, College Park Title: Law Practice in the year 2030: What should we expect? A tradition at the LegalAIIA workshop and preceding DESI workshops has been the opportunity to discuss in smaller groups an overarching topic of interest to the greater workshop, with a "reporter" from each breakout subgroup serving as one of the final panelists. For the Second LegalAIIA workshop, we will be asking breakout group participants to imagine law practice in the year 2030: 1. How AI is Changing the Legal Profession What do rapidly developing technological capabilities mean for the delivery of legal services? What types of legal services will be most affected? How will the increased use of AI/IA change the way in which lawyers deliver services through collaboration with legal tech, innovation, engineering and marketing professionals? How will law firms respond to these new developments? What will be the challengers or obstacles the profession will encounter along the way? What research may be needed to overcome those obstacles? 2. AI & Access to Justice Will emerging AI/IA technologies increase universal access to legal systems through new ways to deliver legal services? Will these technologies serve to widen present disparities? Are online courts implementing AI/IA tools and techniques feasible? What other ways might AI/IA be able to increase access to justice, especially for historically disenfranchised populations? 3. The Human Role in AI In an environment increasingly dominated by large scale language models such as transformers, as well as other AI advances, what role does human interactivity play in solving legal challenges? Or is the human role limited to providing training labels? Can human interactivity and decision-making enhance the results above and beyond that which is capable by purely machine-driven approaches? What new roles may be developed for human interaction with machine learning systems in order to increase their contribution to the overall well-being of society? 4. The Evolving Role of Deep Learning in the Legal Space Given the increasing power of deep learning and the evolving capabilities of transformers that result, in a variety of both general and domain-specific deployments, including the legal domain – through applications of text classification, summarization, translation, question answering, as well as increasingly accurate prediction – what should the road map look like with respect to the legal domain’s adoption of these capabilities? Are there any constraints that should exist in the deployment of transformers, from the perspective of technology, legal governance, ethics or other considerations that might limit the scope of their possible applications? 5. The Future of E-Discovery What improvements in e-Discovery search techniques are envisionable (e.g., what would TAR 7.0 look like?). How would deep learning techniques assist in facilitating e-Discovery searches? In what other ways will new developments in e-Discovery technologies and applications transform the legal and especially litigation landscapes? The organizing committee would like to sincerely thank all authors for their submissions and participation in the workshop, the program committee for its all-important task of reviewing, the keynote speakers and panelists for their time and preparation, and the workshop attendees for their active participation. The LegalAIIA 2021 Organizing Committee Jack G. Conrad, Thomson Reuters (Co-chair) Jeremy Pickens, OpenText (Co-chair) Jyothi Vinjumur, Walmart Hans Henseler, University of Applied Sciences Leiden and Netherlands Forensics Institute, Jason R. Baron, University of Maryland, College Park Daniel Linna, Northwestern University The LegalAIIA 2021 Program Committee Amanda Jones, H5 Apoorv Agarwal, Text IQ (Relativity) David Lewis, Reveal - Brainspace Douglas W. Oard, University of Maryland, College Park Alan Lockett, CS DISCO Dan Rubins, Legal Robot Antigone Peyton, Ridgeline International Fabrizio Sebastiani, Italian National Research Council Amy Sellers, Cardinal Health Gineke Wiggers, Leiden University These proceedings are published online by the LegalAIIA organizing committee as CEUR Workshop Proceedings http://ceur-ws.org Copyright © 2021 for the individual papers by the papers' authors. Copyright © 2021 for the volume as a collection by its editors. This volume and its papers are published under the Creative Commons License Attribution 4.0 International (CC BY 4.0). Proceedings volume compiled by: Jack Conrad Thomson Reuters TR Labs – Research 610 Opperman Drive St. Paul, MN 55123 USA