Dyane  O'Leary

Biography

Professor O'Leary is a national leader at the intersection of legal practice skills and innovation and technology. She directs Suffolk's #1 nationally ranked LIT Center as well as the law school's LIT Concentration for JD students (included in Bloomberg's top 10 law school innovators list in 2023) and the JD/LLM and LLM in Legal Innovation & Technology degrees. Professor O'Leary designed and co-taught the first course on Generative AI at Suffolk in 2024 (one of the first such courses at any law school in the United States) and designed two new courses: Generative AI & Delivery of Legal Services and Modern Legal Practice Skills: Innovation & Tech.

Professor O'Leary authored Legal Innovation & Technology: A Practical Skills Guide for the Modern Lawyer, regarded as the first student-centered coursebook in the field. Her scholarship, consulting, and speaking engagements focus on technology competence and training in legal practice and the law school curriculum, as well as ethics, policies, training, use cases, and adoption of Generative AI tools and associated workflows. Professor O’Leary regularly partners with industry experts and vendors to bring a real-world experience into the classroom for students.

Professor O'Leary’s past service roles include Chair of the Association of American Law School's (AALS) Section on Technology, Law & Legal Education, Managing Editor of the Editorial Board for the Legal Writing Institute (LWI) Journal of Legal Writing, Board Member of the Association of Legal Writing Directors (ALWD), and contributor to the Thomson Reuters Institute/National Center for State Courts AI Policy Consortium for Law & Courts.

Education

• Suffolk University Law School (JD, summa cum laude); winner of Daniel J. Fern Award (highest GPA) Villanova University (BA, summa cum laude)

Selected Publications

Books

• Legal Innovation & Technology: A Practical Skills Guide for the Modern Lawyer, West Academic Publishing (2022).

Articles

• Disconnected Connection, (posted draft Feb. 1, 2025).
• Life Beyond Zoom: The Promise of Emerging Virtual Court Alternatives, 62 Washburn L.J. 587 (2023).
• Life Admin When Life Turns Upside Down: A Book Review (of sorts), COVID Care Crisis Symposium (2021) (with Professor Sarah Schendel).
• Smart Lawyering: Integrating the Duty of Technology Competency into the Legal Writing Curriculum, 19 U.N.H. Law Rev. 197 (2021) available at . 
• License to Hack, 94 N.Y.U. L. REV. ONLINE 234 (2019). 
• Flipped Out, Plugged in, and Wired Up: Fostering Success for Students with ADHD in the New Digital Law School, 45 CAP. U. L. Rev. 289 (2017). 
• A-I is a G-O, 26:1 Perspectives: Teaching Legal Research & Writing (2017)

Media

• Podcast Guest, How AI is Changing Legal Education
• Judge Rejects Lawsuit With Dragon Logo, (April 29, 2025) (quoted)
• GenAI is Not a Legal Tool. Or is it?, 68 BOSTON BAR JOURNAL 2 (2024)
• Charting a (New) Course: Generative AI for Lawyers, LEGAL WRITING MATTERS BLOG (Feb. 5, 2024) (with Colin Black)
• Keeping Pace: Creating a (More) Modern Mindset (State Bar of Texas Annual Meeting 2023), guest on Legal Talk Network podcast
• (Tech) Actions Speak Louder: Developing Tomorrow’s Legal Thinkers, Problem-Solvers, & Builders [PDF], THE FUTURE LAWYER (2019) (with Gabriel Teninbaum)
• Submitted By: Legal Writing Robot, BBO# 55555, LEGAL WRITING MATTERS BLOG (Oct. 3, 2019).
• Teaching a Hybrid Legal Writing Course? Lessons From Two First-Timers, LEGAL WRITING MATTERS BLOG (Sept. 19, 2019) (with Rosa Kim).
• 1Tech Year, LEGAL WRITING MATTERS BLOG (Sept. 5, 2018).
• Legal Texting, LEGAL WRITING MATTERS BLOG (August 12, 2016).

Honors and Awards

Professor O’Leary was named a “Women of Legal Tech” by the American Bar Association Legal Technology Resource Center in 2022. In 2021, she was recognized as a Fastcase 50 Honoree (an award recognizing innovation and leadership in technology and law) and was also elected as a Fellow of the College of Law Practice Management. She was recognized by the Association of Legal Writing Directors with an Outstanding Service Award in 2021 for her leadership with national conference planning and received Suffolk University’s Creating the Dream Award in 2017 for her efforts at supporting a diverse and inclusive environment at the law school.

Bar Admittance

• Massachusetts, 2005
• U.S. District Court (D.Mass.), 2006