Looking Back at My Time as a GC — How I Learned to Stop Worrying and Love Legal Disruption

By Jerry Levine, Chief Evangelist and General Counsel at ContractPodAi

“Plan for what is difficult while it is easy, do what is great while it is small.” Writer, strategist, and philosopher Sun Tzu certainly got human nature right in his ancient Chines treatise, Art of War.

When I was a bengoshi no tamago (that’s Japanese for “lawyer egg” — and just a cute way to say “law student”), I took the opportunity to evaluate my life, discover leadership, and chart a new course for myself. Truth be told, like many law students, I wasn’t sure why I went to law school at first — other than it seemed to be a good choice for a kid from New Jersey. One of the more interesting areas I studied, though, was the history or Asian legal systems. I absorbed Confucian concepts and even learned how Sun Tzu’s Art of War inspired modern military and civilian law, not to mention day-to-day boardroom antics. Actually, I still go back and read The Art of War to this day (Perhaps not cover to cover!). It simply answers questions that can be applied to just about any business scenario: How do you come up with solutions to issues exactly? How do you make ‘a plan of attack’ to achieve true success? When you endeavor to accomplish anything, how do you build a sturdy team before fully executing?

I’ve learned a thing or two during my time as a general counsel (GC) and technologist, too. I’ve learned how to make sound strategic decisions, identifying counterparties’ needs and weaknesses so that I can adapt accordingly. That’s because as a good legal leader, I’ve had to remain bold, wily — and, yes, even ‘artful’ — in my ways and dealings. At the same time, I’ve had to remain sincere and humane, setting the workplace tone, pace, and expectations with some modicum of balance.

Here are a few other things I’ve learned throughout my career and professional interactions.

The Practice of ‘Awesome Law’

I’ve had quite an interesting career path, to say the least — and especially compared to other GCs. But I started out in a very traditional way like most other legal professionals.

With my eyes set on becoming a litigator, I first joined a medium-sized firm with lots of high-profile clients in the pharmaceutical, energy, and media industries. I wasn’t happy, though. I strongly preferred working on technology projects at the firm over going to court, and always tried to pick up corporate law assignments instead of engaging in motion practice. As a result, I very aggressively multi-tasked, starting my own law firm focused on technology start-ups, advising sports teams on privacy law, dealing with eDiscovery and computer forensics — and, basically, working all of the time. Later, I was hired as a GC and corporate secretary by a technology company — its very first. The organization wanted someone who not only understood the law, but also emerging technology. In January 2021, I then joined ContractPodAi as general counsel and chief (technology) evangelist. I now advise customers, helping them transition toward having more digitally driven legal operations.

Let’s face it, as legal executives, we need to spend less time in an endless sea of administrative tasks. We need to become what I like to call “awesome lawyers” — attorneys who serve as strategic leads and transformative figures within organizations. In fact, I’ve always referred to my own practice as “awesome law,” in the truest sense of the term. I have focused my energy on deploying strategic solutions and bringing the latest technology into legal departments and companies.

Disruption Pays Dividends

In the various roles mentioned above, I have seen firsthand how disruption benefits corporate legal departments — how using artificial intelligence-based systems help legal departments work more efficiently and effectively. But although other industries have modernized through AI and automation, the legal industry has been stuck on the wrong side of the proverbial technology gap.

It’s time for legal’s approach to technology to become disrupted — that its digital evolution was sped up. Legal teams, for starters, need AI to simplify and streamline their most standard, ho-hum, and repeatable tasks.

The good news is the majority of lawyers are now ready for automation, many surveys have suggested. Here’s the rub, however: corporate legal teams just aren’t set up for success at the moment. Even though in-house attorneys know the value of having the time to tackle higher-level, strategic work, they receive little support in the form of legal tech investment. Nevertheless, with in-house legal budgets increasing and expectations of legal teams growing, there’s a significant opportunity for companies to invest in something like AI moving forward. This will facilitate legal digital transformations, which will have outsized, strategic value.

Fine Line Between Positive and Negative Disruption

Without question, though, disrupting the legal industry can be equally positive and, let’s just say, not so positive.

Naturally, positive disruption makes legal professionals’ lives easier. It vastly improves the way in which they operate — and helps them find brand-new ways of working. It helps them to achieve far better results in a much shorter timeframe. Disruptive technology, more specifically, is about supporting people and functions, not hurting them.

Now, here’s the caveat: something like AI is incredibly disruptive, but it can be a source of negative disruption when implemented without concern for the people using the technology (or humanity, itself!) That means disruption for the sake of being disruptive. Alternatively, lawyers would do well to ask if they’re truly trying to improve people’s lives and, if they are, whether or not their technology is positively impacting the people using it. Basically, they must think deeply about the human aspects of the legal work they’re doing, not just legal tech exclusively.

Three Pieces of Legal Advice

For in-house attorneys, I have three pieces of parting advice. Firstly, keep in mind that lawyers program relationships. It’s their role to shape the relationship between parties. Contracts and other legal documents make for really good legal code, fortunately enough. With agreements, for instance, lawyers can define rules and setting guidelines, and build a system for how parties will work together. In other words, they write code for the many ways in which humans interact with one another (This is a concept for technology developers to keep in mind, too!).

Secondly, putting in tremendous effort in legal departments is obviously important. However, attorneys need to get results from that maximum effort. If they continue doing the same thing with no result, is that not the very definition of insanity? Ask instead what result needs to be achieved and what efforts are needed to get them.

Lastly, but not least importantly, it’s crucial to realize that there are no “problems” per se. There are only “issues.” My mother would share this old adage when I was younger, and to this day, I hardly ever use the word, “problem.” It only makes a given challenge appear all the more unsolvable. When framed precisely the right way, then, just about any obstacle will have one clear solution or another.

Ultimately, we lawyers are operating in a drastically different world today. In fact, we’re in the middle of a period that is more difficult than ever anticipated. We need to ask ourselves tough questions like how do we adopt the legal tech that is available currently, and use it in a way that not only benefits legal teams and companies, but also humanity. Also, how do we go about freeing ourselves up — to do what we do best as legal practitioners?

At the end of the day, we need to create a more positive future for our profession. We need to determine the best path possible — for the most people imaginable — using advanced legal technology and prioritizing positive disruption.

But remember, too, what Sun Tzu also wrote in The Art of War: “Never venture, never win.”

Jerry Levine is the Chief Evangelist and General Counsel at ContractPodAi. He uses his experience to support ContractPodAi’s continued product and delivery innovation in legal technology and digital transformation.