21st Century Lawyering: Spring 2026 reading list
The readings I assigned in 21st Century Lawyering, a course on legal technology and generative AI for law students, in Spring 2026. Classes are numbered by week and meeting (1-1 is the first class of week one). Times are the estimates students were given for the required readings. Links were checked in August 2026; where a link had moved, it points to the new location.
1-1Introduction to Legal Technology & Technology as Problem Solving
Required
- A Rant about "Technology"
- From Scriveners to Typewriters: Legal Technology in Historical Perspective (16 Green Bag 2d 435 (2013))Skim.
- Legal Technology Overview
Optional
1-2Introduction to Legal AI
Required
- A Generative AI Primer for Law Students (SSRN, Aug. 2025)
- The Shape of AI: Jaggedness, Bottlenecks and Salients (One Useful Thing, Dec. 2025)
- Generative AI is not a 'calculator for words' (The Conversation, Aug. 18, 2025)
- The fallacy of the calculator
- 85 AI & Automation Use Cases for Solo and Small Firm Lawyers (Google Doc)Skim.
Optional
2-1Technical Basics of LLMs
Required
- Generative AI exists because of the transformer — This is how it works (FT interactive)
- Why AI chatbots lie to us (Science, July 2025)
- Why You're Thinking About 'Reasoning' All Wrong (WordRake, May 2025)
Optional
- Talking About Large Language Models (arXiv, 2024)
- A jargon-free explanation of how AI large language models work (2023)
- The architecture of language: Understanding the mechanics behind LLMs (Cambridge Forum on AI, Law and Governance, 2025)
- Pre-Training vs Fine-Tuning vs RAG: Which AI Approach Fits Your Business in 2026?
2-2Introduction to Prompting
Required
- Mastering AI Prompts for Legal Professionals: Practical Strategies and Tools (AALL Spectrum, reprinted on Slaw, Nov. 27, 2024)
- Effective Prompts for AI: The Essentials (updated May 30, 2025)
- The Intent Pipeline: Why Most Prompt Guides Miss How People Actually Use AI (Medium, Dec. 2025)
Optional
- AI company prompting guidesAnthropic (Claude)Google (Gemini)OpenAI (ChatGPT)Lexis+ AIChoose one.
3-1Legal Design: From Pain Point to Use Case
Required
- Design Problem Statements: What They Are and How to Frame Them
- Needs Assessment, Process Mapping, and Goal SettingStep 1 only, and within it the Needs Assessment and Process Mapping sections.
3-2Evaluating Legal Technology
Required
- Evaluating Legal Technology: A Checklist (Slaw)
- Defining and Using Legal Metrics That Actually Work (Ironclad)
- The Verification-Value Paradox: A Normative Critique of Gen AI in Legal Practice (arXiv; forthcoming Monash U. L. Rev.)Read selectively.
- Legal Tech Leaders Share Practical Approaches to Selection, Evaluating and Managing AI Tools
4-1Ethics of Legal Technology
Required
- Generative Artificial Intelligence Tools: ABA Formal Opinion 512 Provides Needed Guidance on the Benefits and Burdens of Lawyers' Use of GAI (The Bar Examiner, Fall 2024)
- Ohio Rules of Professional Conduct, Rule 1.1 and Comment 8Pp. 5–6 only.
- Technological Proficiency Is an Ethical Duty
- Be Reasonable, People! AI's Impact on Legal Fees (ISBA AI Law Section Newsletter)
- Talkin' 'Bout AI Generation: Copyright and the Generative-AI Supply Chain (72 J. Copyright Soc'y 251 (2025))Pp. 251–254, § III (261–275), and § IV (276–285).
Optional
- Updated U.S. Map of Copyright Suits v. AI (ChatGPT Is Eating the World)
- ABA Formal Opinion 512: Generative Artificial Intelligence Tools
4-2Security & Confidentiality
Required
- Formal Opinion 2025-6: Ethical Issues Affecting Use of AI to Record, Transcribe and Summarize Conversations with Clients
- How Attorneys Can Ethically Use ChatGPT for Client Matters Without Redacting Everything (MyShingle, Nov. 2025)Read critically; it is advocacy. Since revised and retitled to cover general-purpose tools beyond ChatGPT.
- Shadow AI: The IT Risk We Can't Ignore (ABA Law Practice Magazine, Sept./Oct. 2025)
- 'Tip of the Iceberg': Lawyers Look to Address Risks From Gen AI Transcription Tools (Law.com / Legaltech News, Sept. 23, 2025)
- Vendor Contracting ChecklistSkim.
5-1Advanced Prompting & Context Engineering
No readings. Students set up access to Gemini, NotebookLM, Westlaw CoCounsel, and Lexis Protégé before class.
5-2LLMs and Legal Work Lab
No readings. An in-class CoCounsel lab working from an appellate case file and a set of merger agreements.
6-1Building Legal Technology
Required
Optional
- An Introduction to QnA Markup (video, 15–20 min)
- Claude legal plugin: triage-nda and brief skills (GitHub)triage-ndabrief
6-2Vibe-Coding & Legal Data Sources
Required
Optional
- The Non-Technical Guide to Vibe Coding with Google AI Studio (Medium)
- Vibe-coded legal tool collectionsJamie Tso's appsLegalQuants
- Vibe Coding a Harvey Competitor: Fun Demo, Expensive Reality (LinkedIn)
For reference
- Legal data sourcesPACERCourtListener / RECAPSEC EDGAR API
- RSS Feeds, PACER, and the Fight for Access to Federal Docket Information (RIPS Law Librarian Blog)
7-1Hallucinations: Causes, Detection, Mitigation
Required
- What the Science Says About AI Hallucinations in Legal Research (AI Law Librarians, Feb. 19, 2026)
- Declaration of Celeste H.G. Boyd, N.Z. v. Fenix International Ltd. (C.D. Cal. 2025)Appendix A.
- 18 Lawyers Caught Using AI Explain Why They Did It (404 Media, Sept. 2025)
7-2AI-Enhanced Legal Research
Required
- Teaching Legal Research in the Generative AI Era: When Source Blindness and Source Erasure Collide (RIPS Law Librarian Blog)Part 1Part 2
- Google Search's AI is (or should be) about cognitive load
- Legal Research Trapping You in an 'AI Tunnel'? Use a Toe-hold to Get Out (AI Law Librarians)
- United States v. Heppner, Memorandum & Order (S.D.N.Y. 2026)
8-1Microsoft Word & PDF for Legal Practice
Required work is Procertas training modules (a Word trainer and the PDF for Legal trainer) rather than readings.
8-2Excel & Data Literacy for Lawyers
Required work is the Procertas Excel for Legal trainer rather than readings.
9-1Algorithmic Bias & Discrimination
Required
- Against Predictive Optimization (interactive web paper)
- Hiding in Plain Sight: An Empirical Study of Prosecutorial Bias in AI Legal Analysis (27(1) Colum. Sci. & Tech. L. Rev. (2026))Pp. 3–10 and 47–53 only.
- Complaint, Nippon Life Ins. Co. of Am. v. OpenAI Found. (No. 1:26-cv-02448 (N.D. Ill. Mar. 4, 2026))
9-2Agentic AI
Required
- Welcome to Law Town
- The Claude-Native Law Firm (LinkedIn)
- How to Crash the Legal Tech Market (Geek Law Blog, Feb. 2026)
10-1Tool Presentations
No readings. Student presentations.
10-2Access to Justice & Technology
An asynchronous module.
Required
- Thinking Upstream in the Legal Ecosystem (video, about 41 min)
- So You Want to Create an A2J Tool
- Measuring What Matters: A Quality Rubric for Legal AI AnswersPp. 4–5 (§ 2.2), p. 7 (§ 3.1), and pp. 10–11 (§§ 4.1–4.3).
11-1Review & Connections
No new readings.
11-2eDiscovery, Litigation Analytics & Transactional Technology
No readings. Taught through an eDiscovery simulation.
For reference
12-1Business of Law & Technology Economics
Required
- Fighting the Hypothetical: Why Law Firms Should Rethink the Billable Hour in the Generative AI Era (20 Wash. J.L. Tech. & Arts (2025))Parts I and III; Part IV optional.
- How Professional Services Firms Dodged Disruption (MIT Sloan Management Review)
- AI Won't Automatically Make Legal Services Cheaper (Lawfare)
- Services: The New Software
Optional
- AI in Professional Services 2026
- Legal Trends Reports20242025
12-2Change Management & Technology Stacks
Required
13-1Courts, Productivity & Remote Practice
Required
- Artificial Intelligence in Federal Courts: A Random-Sample Survey of Judges (27 Sedona Conf. J. (Apr. 2026))Pp. 5–7, 13–20, 34–41, and 49–59.
- People with ADHD, Autism, Dyslexia Say AI Agents Are Helping Them Succeed at Work
- Managing a Modern Law Office That Is Paperless and Remote
- Remote Work in Law Firms 2025–2026: Transparency Report, Policy Rankings & Negotiation Playbook
Optional
- Judges Increasingly Using AI to Draft Rulings and Prepare for Hearings (Apr. 6, 2026)
- How ADHD and AI Work Together Better Than Any Productivity System I Tried (HackerNoon, Apr. 2026)
- Lived Experience: Using AI as an AuDHD Adult (Feb. 2026)
13-2Will Robots Take Our Jobs? (Part 2) & Course Synthesis
No assigned readings.