#LegalTechLives with John Stewart, Partner at Rossway Swan

Ava Chisling
June 28, 2017

John Stewart is a Partner at Rossway Swan and a Florida lawyer. He served as President of The Florida Bar Young Lawyers Division and since 2007 has served on The Florida Bar’s Board of Governors. In 2013, John received The Florida Bar’s President’s Award of Merit. He was selected as Chair of the Technology Subcommittee for The Florida Bar’s three-year study on the future of the practice of law, and on July 1, 2014, was appointed to serve on the Supreme Court of Florida’s Technology Commission. In 2016, John was selected to the Fastcase 50, honoring the law’s “smartest, most courageous innovators, techies, visionaries and leaders” and speaks regularly on technology and the law, including at the 2016 and 2017 ABA TECHSHOW.

I am afraid the first question is the most obvious: How often do people refer to the comedian Jon Stewart when they meet you? And do you like the guy?

I hear it all the time. I love it as he and I attended the same college (The College of William & Mary, although not at the same time), and his last name is not actually Stewart. I think he is fantastic. Smart commentary with an edge and humor. Since he took my name and my twitter handle (I use @THE_johnstewart), I am hoping ROSS or [CEO/Co-founder] Andrew Arruda can convince him to follow me on Twitter. As I travel quite a bit these days, I have to confess the name is great for getting upgraded hotel rooms.

You may have met the right gal. I know the gang at the Just for Laughs Festival in Montreal, and by extension, your namesake. Maybe I can make things happen? Hey, @BruceHills (COO JFL) – get on it!

You are a third generation lawyer. Was there a time in your life when you wanted to be something else?

I never actually wanted to be a lawyer growing up. After graduating college I worked for a then Fortune 500 company and quickly realized that the lawyers in the company had the most autonomy and the ability to move the needle in a meaningful way. That observation really drove me to want to go to law school and become a lawyer. However, since practicing (and my entire practice has included working with my father), I have to say that learning how to practice law – in my mind the way it should be practiced – I definitely learned from watching my father and particularly his interactions with his clients.

You’ve examined technology and law via various committees and papers for a long while. What are the biggest changes you have seen, both in terms of the actual technology and how law firms adapt to it?

It’s not a particular technology in my opinion that has created the biggest change with regard to the practice of law but the sheer number and proliferation of the technologies impacting the practice. Lawyers are, by training, and often by personality, very deliberate in their thoughts and actions and the pace of change has caught the profession off guard.

For me, the most important issue now is dealing with the pace of change and working with leading companies like ROSS to assure lawyers utilize technologies to benefit their practices and their clients while protecting the core, fundamental values of the legal profession. I hope to be involved in that discussion, as I believe it is necessary to the evolution of the profession.

Last year, you were honored as one of law’s “smartest, most courageous innovators, techies, visionaries and leaders.” In the legal world, who do you think is the most courageous innovator of all time?

You may scold me for my “lawyer-like” answer but I could not settle on one person. We are now at a true convergence between the intersection of law and technology. The technologies and the legal profession will both continue to evolve. The true innovators in the legal world now need to be those who find ways to marry the two. I think it is healthy to have a natural tension between the advancement of innovation and the historic traditionalism of the legal profession. However, we need really bright, thoughtful innovators to collaborate and to bridge those two worlds for the benefit of not only technology companies and the legal profession but also the public good.

Legal Tech Lives John Stewart

Florida gets a pretty bad rap, mostly for attracting a high number of eccentric folks. Well-earned reputation? Or you’ve seen worse?

Eccentric folks in Florida? This is the first I am hearing of this. You won’t find a 3rd generation Floridian saying anything but glowing remarks for my great State. Florida is unique to be sure. I believe it is the 3rd largest by population as well as the 3rd largest Bar Association in the country, with now almost 105,000 lawyers. With those numbers and the beautiful climate, we certainly have a very diverse population which I believe only strengthens our profession and our Bar Association.

You’ve helped push the state forward in terms of tech and CLE requirements and other accomplishments. Can you give these three institutions a grade from 1–10 on how well they’re keeping pace with technology and the expectations of their “clients?”

Law Schools 5 / Big Law 5 / Regulatory Bodies 5

This is a very tough question. All law schools, large law firms and regulatory bodies are certainly handling technology and its integration into those institutions for the benefit of their clients (and students) differently and at different paces. As a result, I have a general “middle of the road” grade for each general category. The mandatory technology CLE you reference certainly differentiates Florida from the rest of the country in a very positive way. It shows the importance Florida lawyers and its leadership places on understanding legal technologies and it keeps these concepts at the forefront of lawyers and legal educators’ minds.

We can certainly do better in many areas and one which I think should be of considerable focus is how the leadership of each of these groups stays current or ahead of the learning curve so we can be more proactive for the benefit of our lawyers, clients, students and the public.

What technology do you think is most underused in the legal profession? And what do you think lawyers should just get rid of (or rely on less), once and for all?

One area that strikes me as being underutilized is advanced research tools that are now coming to market full of valuable integrations including judicial analytics and driven by artificial intelligence. Lawyers need to accept and incorporate these new research tools into their practices sooner rather than later. The second area is technologies relating generally to discovery (i.e. technology-assisted review, e-discovery tools, website capturing for evidentiary purposes). This area will just continue to grow and is one where lawyers need to learn more or engage reputable third-party vendors or professionals for assistance.

An area that has become the bane of my existence and I wish I could rely on less is e-mail. In my opinion, it is terribly inefficient, often insecure and encourages knee-jerk responses rather than thoughtful dialogue.

“We need really bright, thoughtful innovators to collaborate and to bridge those two worlds for the benefit of not only technology companies and the legal profession, but also the public good.”

I grew up hanging around The Diplomat hotel in Hallandale, Fla., waiting for celebrities and athletes to arrive. Do you have fond memories of a particular Florida landmark? Which one and why?

Well, for me there are two. The first is Walt Disney World. I grew up around the time that Disney World opened and enjoyed it with my parents as a child and now I enjoy it with my daughter. The second is from the place of my birth in Coral Gables known as the Venetian Pool. Definitely worth a visit.

Tell me a bit about your day to day practice? What’s your most prized technology in your personal life?

I have to confess it is my iPhone. It’s a business tool, a way to keep up with colleagues, friends and families and a way to find distractions from the day to day pressures of a busy practice and an equally busy life serving the lawyers of Florida through The Florida Bar Board of Governors. If you know anyone at Apple, can you get me on the list to test the 8 when it comes out?

Hey, I’ve already shouted out to Just for Laughs to get JS’s attention! Now you want me to reach out to Apple?

I have been asking this question of everyone: What non-law invention do you wish you had right now? So far, I’ve heard: robot maid, driverless car, and teleportation, among others.

I would love a driverless car. Florida is a very large state and I travel it quite a bit. If the car could drive itself and I could work during my hours on the road it would be fantastic (and my law partners would be happy). Failing that, maybe you all could get the other Jon Stewart to be my driver for a day. I am sure it would make an amazing reality show.

I will get on all of that! In the meantime, thank you for a most enjoyable conversation on AI research needs.

Ava Chisling

Ava is an award-winning lawyer and editor who counsels creative types, writes about pop culture/tech+law and sometimes creates ad campaigns. She is Quebec counsel for Momentum Law.