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“Devoted To Bridging the Gap Between Tech and Law” — Colin Levy

“Devoted to Bridging the Gap Between Tech and Law” — Colin Levy

This interview is part of Loio’s series of interviews with legal enthusiasts about the ins and outs of the legal industry.

The following is the interview with Colin S. Levy, attorney, legal tech evangelist and thought leader, writer, and speaker. A legal enthusiast by day, Colin is an avid dancer and a proud owner of two cats — “one is small, basically Napoleon in a cat’s body, and the other one is bigger and the sweetest cat one can ever imagine that wants to be loved and loved and loved.”   

But let’s talk about all things law.

What’s your story of becoming an attorney? Was it your childhood dream, a movie you watched, or a story that happened to you?

I would answer that question by saying that my mom’s side of the family was all lawyers. So, that played a little bit of a role in my interest in the law. But perhaps the biggest impetus for me to become an attorney came from the fact that I saw the law as being sort of a mix of different things that I enjoy: analyzing things, writing about things, and thinking critically about things. 

Add to this the fact that the law impacts so many different areas of life and I thought that it would make sense for me to explore it given how impactful the law is. So, all of those things that I mentioned started me down the path of wanting to become a lawyer.

Although admittedly when I was in college I did for a brief second contemplate perhaps becoming a professor instead. But I don’t regret becoming a lawyer. 

Why not? 

Because becoming a lawyer allowed me to grow and challenge myself, develop new skills, and help people. And that has been really enjoyable. I’ve enjoyed the challenge of being a lawyer. Particularly the challenges that come with being a lawyer who works in-house for companies. I have, at times, been torn between being an academic and being a professional. I always had business instincts and liked to be a part of a business helping it to grow and to succeed. So, it has made more sense for me to be a lawyer rather than an academic, but that tension remains present with me to this day. 

Do you think that this academic part of you has found a way to express itself via LinkedIn and Twitter?

Absolutely. I really think that I found a great outlet for it through my LinkedIn content, my Twitter content, and my website. So, I’ve been able to satisfy the academic side of me through these different parts of me through different mediums.

Was there a tipping point when you realized the value of technology in the legal industry? Is there a story behind it? 

I worked for a big firm prior to law school as a paralegal creating e-discovery databases. And it occurred to me that I was using technology to do quasi-legal work. And the firm was relying on that work getting done through the use of technology. So I thought to myself “Well, surely, some of this would be talked about in law school.” Of course, none of it was. And I found that to be disheartening and disappointing.

Since graduating from law school, I came to realize that it shouldn’t have been disappointing because that is how many law schools operate — currently and back then. But at the same time as I started to practice law in-house, I began to really notice how so many other industries were benefiting from the use of technology and found it disappointing that law was not really making as much use of technologies as it could be. 

So I started to want to learn more about people trying to change the nature of the practice of law and the business of law. And I started talking to folks at various companies about their experiences trying to innovate or introduce technology and/or create technology for the legal profession. And through those interviews, I got really passionate about legal tech, about helping inform and inspire others about it, and showing how technology can be really beneficial and impactful in a lot of ways, both expected and unexpected.

Hence my bio on Twitter: “Devoted to bridging the gap between tech and law.”

What are the main tectonic shifts reshaping the legal industry now? Is legal technology behind one of them?

I think that one of the shifts that we’re seeing within the industry is a shift in client expectations of their lawyers. I think that clients/customers of law providers are expecting more from their providers in terms of more business advice, as well as more holistic and responsive services. And I see technology helping bring about that shift through better delivery of services both faster and at lower costs. I also see technology being able to allow for more data-driven decision-making. For example, you can look at litigation prediction tools that allow lawyers to help provide their clients with an understanding of the likelihood of their litigation proceeding in a positive or negative way depending on prior similar cases before similar judges in different jurisdictions. 

Another shift that’s occurring is more and more pressure being put on law firms to be more flexible with regards to their billing practices. Certainly, the billable hour remains a predominant model, but I see there being increasing pressure on changing that model by providing alternative ways to the bill. 

I would also add that, thanks to the pandemic in large part, there has been an acceleration in a shift that was occurring prior to the pandemic — a shift to more flexible ways of working together, i.e. being in different locations together, but still being able to collaborate and work effectively.

One of your LinkedIn posts reads: “Legaltech is not about reinventing the wheel. It is about working smarter utilizing more digital and more automated workflows.” Which areas should be digitized asap? Which areas will never be digitized?

I would say that there are plenty of areas that should be digitized. 

One area that is near and dear to me based on my work experience is contracts and contract management and deriving data from contracts. Another area that I see being digitized is responding to common and frequent requests, e.g. intaking new clients. 

In terms of areas that perhaps are not necessarily best digitized… That’s an interesting question because I think it depends in part on what you mean by digitization. But I would say that there always is going to be an element of human judgment needing to be at play with respect to legal matters. You know, we’re not at the point yet where technology can replace human judgment. It certainly can better inform human judgment, and provide more data that a human to make a decision based on. But we’re definitely not at the point where human judgment doesn’t need to play a role at all in legal matters. 

In addition to human judgment, do you think that people actually need humans to handle their cases? Is it still important?

I think that human relationships, particularly between lawyers and clients, remain quite important. I don’t think that’s ever going to go away. 

In fact, if anything, I think that relationships are critical with respect to building and developing business, and effectively serving your clients. Because clients really want from their lawyers more than just sort of cold legal advice. They really want to have a confidant, someone that they can confide in, someone that can support their initiatives. 

What should the legal industry of the future ideally look like? How do you see the lawyer tomorrow?

I would say that the lawyer of tomorrow would be a digitally enabled one who is able to use a combination of judgment, technology, and relationship-building to effectively serve clients in ways that are effective, efficient, data-driven, and collaborative. 

A 21st-century lawyer would be one who is adept at technology and at being able to manage expectations and relationships and has a high degree of emotional intelligence. 

That lawyer will be able to better understand their client from a multitude of perspectives and will be able to provide data-driven analysis, counseling, and advice.  

When you say “emotional intelligence”, do you refer to ways of communicating with clients or managing lawyers’ mental health? Or both?

Both. Absolutely, both. I think that emotional intelligence is key for managing relationships and for managing yourself. Mental health is just as important as any other area of health and the legal profession has not devoted nearly enough attention or resources to the subject.

A lot of lawyers are driving the conversation about mental health on LinkedIn. One of them being Angela Han…

Angela Han is fabulous. I know her well. She’s done really great work in this space in terms of helping people feel more comfortable opening up and expressing their own struggles and understanding that they’re not alone in their struggles. 

Talking about mental health issues is definitely a step forward. But what do you think hinders the evolution of the legal industry? What changes need to be made to foster it? 

That’s a big question. 

I would say that in terms of hindrances, cultural norms and historical ways of doing things remain a hindrance to evolving and changing. There remain a lot of lawyers who have practiced for quite some time and remain resolute and loyal to historical ways of doing legal work. 

I think that in doing so they are resisting because they don’t necessarily see anything wrong with how they’ve been operating before. Nor do they necessarily want to be told that they are doing something wrong. To that end, I would say that the point of evolving and adapting is not necessarily about telling someone that they’re doing something wrong. It’s rather about them being able to do things better for their clients. After all, clients are the players within the legal ecosystem. 

It’s not all about the lawyers. 

Do you think that something has to change in the legal education system to prompt the evolution? 

Definitely, the way that lawyers are educated needs to change. It needs to be a more holistic education that involves learning both legal doctrine as well as practical skills like project management, being competent with the tools of the trade, negotiation, and relationship-building as well as a broader array of internships or externships. Legal doctrine is certainly important to understand, but that’s only part of what a lawyer needs to know when they go out and practice. 

Law students need to learn how to balance competing priorities and different risks, how to manage projects, and what existing tech can help them be a better lawyer depending on the area of practice. 

So, there are a lot of things that I think can be changed within the legal education sphere, but I think getting change to happen depends on the leaders of law schools enabling improvement, facilitating change, and diversifying their faculty and curriculums. Law students are one piece of the puzzle and certainly have a role to play and demand more from their law schools. But the leaders of law schools also have a key role in terms of shifting the focus of law school to teaching law students what it means to be a lawyer in today’s dynamic world. 

What is the most magical part of being a lawyer? 

I would say probably the most magical part for me is building relationships and learning new things. I’m always learning new things from those I work with and work for. I think that is really inspiring, encouraging, and motivating. That’s something that I continue to enjoy about the legal industry.  

Being a lawyer, how many contracts have you reviewed throughout your career?

Oh, gosh. I’d say that’s a large number. Thousands? If you’re talking about all contracts of any type whatsoever, it’s definitely up there. For sure. And I’ve only been a lawyer for a little over a decade!

If you could have lunch with any prominent legal industry figure, who would that be?

That’s a good question! I would say Oliver Wendell Holmes Jr. He was an Associate Justice of the Supreme Court of the United States. I have always admired him.

What is your favorite legal movie?

I have two favorite legal movies. Very different ones. 

One is “My Cousin Vinny” because I think it’s just hilarious and ridiculous. And the other is equally ridiculous — not necessarily funny, but ridiculous. That is “The Devil’s Advocate” where this lawyer ends up working for a firm that, let’s just say, has a connection to the devil. So, it’s definitely an amusing movie for that reason. 

Doesn’t it scare you? 

So, it’s funny you should ask that. No, I don’t get scared very easily in movies. I assume that is because I’m a very big horror movie fan. 

My last question is: what interview question would you like to be asked and how would you answer it? 

Interesting! I don’t think that I’ve never been asked that before.


I would say one of my favorite interview questions that I have never been asked before is what my passion other than law and legal tech is. Because I find it very important to be your whole self in all ways. So, for me, one of my biggest passions other than law and legal tech is being outdoors — hiking, biking, rafting. I just find the outdoors to be very peaceful and be a really great way for me to relax and take pleasure in the beauty of this planet that we all live on.

Thank you, Colin!

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Article by Yevheniia Savchenko

Yevheniia Savchenko is a Product Content Manager at Lawrina. Yevheniia creates user interface copies for Lawrina products, writes release notes, and helps customers get the best user experience from all Lawrina products. Also, Yevheniia is in charge of creating helpful content on legal template pages (Lawrina Templates) and up-to-date information on US law (Lawrina Guides). In her spare time, Yevheniia takes up swimming, travels, and goes for a walk in her home city.

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