Women of Legal Tech: Dyane O’Leary

The Legal Technology Resource Center’s Women of Legal Tech initiative is intended to encourage diversity and celebrate women in legal technology. This initiative launched in 2015 with a list of innovators and leaders in legal technology and with this year’s additions, that list now includes 141 talented and influential women leaders.

Every Monday and Wednesday, we have featured a woman from our class of 2022. Today we have Dyane O’Leary!

Dyane O’Leary is the Associate Professor of Legal Writing; Director Legal Innovation & Technology Concentration at Suffolk University Law School.

Three points to summarize you and your work in legal tech.

I work to integrate technology competence skills into the law school curriculum and introduce all students to the ways innovative new aspects of law practice will impact their future careers. Topics such as security, mobile lawyering, document metadata, electronically stored information, legal research analytics, and automation aren’t merely “nice to know” topics as they might have been decades or even years ago. They are just as fundamental for the modern law student as drafting a case brief or preparing an office memorandum.

How did you become involved in legal tech?

I’m proud to be part of a law school that values innovation and technology and strives to prepare law students to contribute in new and meaningful ways as the profession continues to change. Suffolk Law has been ranked #1 in the country for legal technology and Dean Andrew Perlman started the nation’s first LIT Institute. Our clinical LIT Lab model is continuing our tradition of innovation and bringing sponsors, partners, and our students together on some exciting initiatives in the access justice and “justice tech” space.

What projects have you been focused on recently?

For the last year or so, my primary focus has been a student-centered course book on legal innovation and technology. There are plenty of scattered sources such as blogs and articles for practicing lawyers on these topics, but no one comprehensive source to introduce law students. Legal Innovation & Technology: A Practical Skills Guide for the Modern Lawyer will be published by West Academic later in 2022 and offers background explanations, hypothetical multiple choice scenarios, extension exercises, tips, quotes, screenshots, and more. My work has always been student-focused and I’m proud to have created what I think will be a helpful resource for many of them.

What do you see as the biggest challenge in legal tech today?

I’m not sure that it’s the biggest challenge, but one challenge I see everyday with my work with students is the assumption that as digital natives, this next generation of lawyers will be tech competent simply because of their age and life experience. They are indeed tech comfortable, but I’ve been surprised that many lack familiarity with what many of us would consider basics such as track changes or hardware security settings. A challenge will be to celebrate and recognize this next generation of lawyers without presuming they’ll always know how to seamlessly transition their personal electronic lives to their new professional ones.

Has the pandemic changed anything about the way you, your firm, or your organization does business? Has the changes that have resulted from the pandemic improved or altered your work or how you do it?

I worked on distance education initiatives well before the COVID-19 pandemic as Suffolk Law explored and formed its hybrid JD program. Innovation and technology skills can and should be taught anywhere and by any means, whether in a physical or virtual classroom. I’m inspired that the forced distance learning and “Zoom school” my students have experienced will help position them to be excellent remote lawyers in our digital world, just as they were excellent remote students.

What legal tech resource helped you the most in your legal tech career?

Newsletters and curated content such as my Suffolk colleague Gabe Teninbaum’s Lawtomatic newsletter. With so many sources of information on a topic changing everyday, I’m grateful others can help do the work for me and digest news into snippets I can manage to review on my daily commute!

What do you see as the most important emerging tech, legal or not, right now?

The legal research and writing teacher in me has to go with analytics on this one. It seems like companies such as Fastcase are giving lawyers new tools and techniques all the time to help us make information come to life – whether that’s judicial decisions, internal firm metrics, client and potential client docket metrics, etc. Research when I was in law school meant books, online cases, statutes, etc. Research today means so much more than primary law. It’s real-time information at our fingertips that may not make or break a project, but it’s certainly not going to hurt.

What do you see for the future of legal tech?

One hope I have for the future of legal tech is more efforts at broader open source collaboration across jurisdictions. So much is already being done – including in Suffolk’s LIT Lab with respect to its document assembly line project – and I hope that the future sees more collaboration and sharing of innovative approaches. One jurisdiction doing amazing things is terrific; 20 jurisdictions doing it is that much better.

What advice would you give to other women who want to get involved in legal tech?

Own your lane and don’t worry if it’s a narrow one. I don’t code and am not particularly interested in software or the entrepreneurial side of legal tech as a broad concept. I used to shy away from that fact or feel like I needed to “fake” interest in it among certain groups, etc. I don’t. My lane and my passion is still student work, and I’ve found a way to connect my substantive legal tech interest to my interest in skills teaching. The only way an interest will be sustainable is if it’s a real one. Find your real one and hold on to it.

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