Episode 5: Challenging Legal Conventions with Colin Levy

Career trajectories in the legal industry can be very streamlined. But with a little curiosity, aptitude for technology, and the ability to simplify complex information - lawyers and students can break conventions and forge their own paths.

That is what made Colin Levy, the Director of Marketing and Business Development at WordRake - the legal thought leader he is today.

A massive proponent of technological upskilling in the legal industry and a fan of the outdoors - Colin gives us a peek into the groundbreaking transformations in the industry, the way forward for lawyers, and his favorite video games.


Your blog has been a great resource for virtually anyone trying to build a career in legal or is interested in process improvement. How did you come up with the idea?

My career journey has been atypical - I did not travel the traditional route from law school to a law firm. Instead, I went in-house right away.

Unlike law firms, most corporations don’t engage in exhaustively training their legal hires. Hence, they are looking for people with some experience under their belt before working in-house. When I graduated from law school in 2010, it took me a good year and a half to find my first full-time legal role.

When I started my first in-house job, I started writing down the lessons I learned and my experiences to share them with others through my blog. During that period, I also realized that many folks were looking to change the status quo or improve existing processes with technology and innovation.

So, I reached out to all those folks, interviewing them, learning from them, and sharing their insights. It’s been a great journey and I’m continuing to learn as the legal profession slowly but surely changes and adapts.

For someone who has been in both law and marketing, what do you think about the way legal technology has been marketed so far?

In my experience, some of the best marketing by legal tech companies has focused on education and inspiration. And since lawyers love hearing from others like them, legal technology must feature lawyers doing unique things, or lawyers working with other people doing unique things. So, content marketing, putting up articles or interviews, or even webinars - about legal tech that helps the target audience organically find more information about new tools is very effective.

A lot of what legal technology does is remove process inefficiencies and improve processes for lawyers and allow them to spend more time on more strategic tasks of greater value to clients. and make work faster. But pointing that out would also imply there is something inherently wrong with the way lawyers have worked so far. For legal technology vendors or service providers, communicating their possibilities and benefits without necessarily outright telling lawyers they’ve been doing something wrong, is often key.

Legal tech companies would be doing themselves a disservice if they forgot that their users are not just lawyers. Their users are also paralegals, consultants, and a whole host of other legal professionals.

How will technology impact the “billable hours model” of law firms?

I am a big proponent of changing the billable-hours system. It rewards inefficiency and promotes behavior that encourages lawyers to spend more time on things, even when these tasks can be done quicker.

But we’ve also seen the very same model working well for law firms financially during the pandemic. For them, this begs the question - ‘why change if it works for me?

Legal technology has made people aware that it is not always necessary to spend long hours on a single matter. But to change the system, the pressure needs to be two-sided. Both from clients seeking greater clarity and accountability on their expenses, and lawyers seeking respite from a system that incentivizes working long hours. This also impacts their mental health, increases stress, and hinders their ability to live their lives outside of work.

The pandemic has contributed to that mental health discourse too. How can work be restructured to make it easier without affecting efficacy?

A combination of technology, cultural change, and leadership can help change the dynamic here.

Technology can bring in transparency, enable better collaboration between clients and lawyers and promote greater visibility into - the status of matters, how work is being done, or who is working on a particular project.

It allows for better performance measurement and knowledge management. This helps lawyers utilize and understand readily available information better and prevent reinventing the wheel at work every time. Instead, they can analyze similar matters and reference their previous actions as a starting point.

But the initiative and implementation of technology need to be top-down. Legal leaders need to educate and upskill themselves about technology, learn better business management, and promote efficiency in their departments. Leaders also need to lead with empathy and accept the imperfections within themselves and within others. Technology can help overcome our inherent imperfections, but not what leaders tell us or what we tell ourselves when we make a mistake.

On that note, what are your hobbies when you have time?

I am a big fan of the outdoors. I like to go on bike rides, hikes, or skiing - which I wasn’t able to do much last winter. But I hope to do more so this winter.

I also play online games, I like to read and write - not just legal tech, but generally.

What are your favorite games?

I’m a big fan of Skyrim and Fallout 4. I also like City Skylines - it is an easy-to-play and addictive city builder. 

Now for the big Skynet question - some lawyers fear technology might eventually replace them. How can they ensure that their jobs remain unaffected?

If you’re a lawyer constantly doing routine standardizable tasks, then you’ve got a problem because those tasks are going to be automated by technology (if they haven’t been already).

Technology can only decide based on data. So, as a lawyer, you should be spending your time on strategic work that technology cannot do alone. 

How to do that I think is by:

  1. Taking stock of the work you’re currently doing and understand what tasks are routine and standardizable and what ones are not
  2. Learn new business or tech skills when you can
  3. And if you’re tech-savvy enough, looking at other more advanced tools that can help automate and can help make your workflows more productive so you can spend more time on the most important part of your job as a lawyer which is - dealing with your clients and building relationships.

Do you also think technology in the legal industry can give way to newer roles?

Yes, and it is already doing so. There are more and more new types of career paths and jobs arising within the legal industry. There is the legal technologist - who can apply technology to an existing legal process or legal operations individuals who can do a range of things from managing vendors to developing workflows and processes to managing financial data.

Another interesting area that many folks might not know is knowledge management - managing information in firms or legal departments. It has existed for some time, but the growth of legal technology has accelerated the growth of this space. It has allowed for better insights into a lot of these different areas and how they operate.

Lawyers and law students are starting to realize that they don't have to work for a law firm or a legal department to be a lawyer or be within the legal space. There are ALSPs, consultancies, and many other diverse pathways continuing to come into existence.

I encourage law schools to do a better job of illuminating these alternate pathways for lawyers because a lot of law students don’t know about these pathways. But they do exist. And as I said earlier - more like them are coming into existence every day.

How did you learn for the future? What are the resources you looked at to upskill yourself?

Often the issue is not the dearth of resources but that there are too many, and people don’t know where to start first.

I reached out to and spoke with a lot of professionals in legal technology, to learn more about the space.

There are also two certification programs in legal technology that come to mind.

Suffolk University offers a certification in legal innovation and tech I completed in 2019. It is a 6-course intensive program, taught by some leaders in the space. It goes over some things like - project management, legal ops, process improvements.

There also is an online certification program from IFLP (Institute for the Future of Law Practice). That is another set of courses at a lower cost, online, and is accessible to everybody. It allows them to gain more knowledge within the space.

Another way to learn more is to read the different blogs that exist out there. Some great examples are - LawSites Blog, Artificial Lawyer, and my own blog where I interview industry experts.

What other skills beyond legal, do you think are important to be a successful lawyer?

For lawyers, understanding the business is important, and hence quantitative literacy is crucial. Other important skills are - project management, collaboration, and knowledge sharing, and empathetic leadership.

Another important thing is always understanding that decisions aren’t made in a vacuum. They are made in collaboration with other people. Things like emotional intelligence, fluency in the language of business, relationship-building are all additional and essential skills to be a successful lawyer.