Dyane  O'Leary

Biography

Professor O'Leary is a national leader at the intersection of legal writing and legal technology. She directs Suffolk's #1 nationally ranked LIT Center as well as the law school's LIT Concentration for JD students, which was included in Bloomberg's top 10 law school innovators list in 2023.

Professor O'Leary is the author of the first student-centered coursebook on innovation and technology practical skills for lawyers. Her scholarship and speaking engagements focus on technology competence in legal practice and the law school curriculum. She has published and presented on topics such as Generative AI for lawyers, artificially intelligent legal research and writing tools and document automation, and cybersecurity basics for lawyers.

At Suffolk, Professor O'Leary designed and taught the first course on Generative AI and designed a new course called Modern Legal Practice Innovation & Tech, which covers skills in areas such as e-discovery, research analytics, cybersecurity basics, word processing for lawyers, typography, remote lawyering, law practice management tools, and digital design of legal documents. She regularly partners with industry experts and vendors to bring a real-world experience into the classroom for students.

In 2023, Professor O'Leary chaired the Association of American Law School's Section on Technology, Law & Legal Education. Her past national service includes Managing Editor on the Editorial Board for the Legal Writing Institute (LWI) Journal of Legal Writing, 2019 host representative for the Association of Legal Writing Directors (ALWD) Conference, 2021 Site Committee Chair for the ALWD Conference, 2020-21 LWI Committee Symposium on AI & the Legal Profession committee member, 2022-2024 ALWD Board Member, 2021 Awards Committee Chair, AALS Section on Tech., Law, & Legal Education, and 2022 Chair-Elect of the AALS Section on Tech., Law & Legal Education. Locally, Professor O'Leary regularly contributes to MA Bar programming and other initiatives, such as advisor to a committee consider rule changes in Massachusetts because of new legal technology.

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

• 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