Well, that is not exactly what I used to say when I was a kid. But had I known such a thing existed, that would have been my saying. The truth is, I wanted to be a lawyer as far back as I can remember. Yet, I never knew how much I’d love it until I became one. Then, as the years progressed, it morphed into something even better.

In January of this year, after more than 13 years at Microsoft, including my last role as Assistant GC of Legal Operations and Contracting, I embarked upon a new chapter in my professional life. Much to my delight, I have received countless congratulatory wishes and kind words of praise.

What has surprised me, however, is the number of times people expressed to me their envy. In very honest and genuine conversations, many of my colleagues throughout the industry have expressed to me how jealous they are that I took such a leap. They often added “I’ve been thinking of doing something similar for a while but have not had the courage to do anything about it.” Thus, when Bill suggested that other mid-career professionals would be interested in how I chose to make this move, I agreed to write this post.

I am not writing this post to describe what a great leap this has been and to recommend it to everyone. I have no idea if it was, in fact, a great leap. I’ll only know years from now when I can reflect and assess my success, and judge whether it met my standards. I am writing to explore what it is about the current market that made me think it was in fact ok to take such a risk.

Our mental habit of ‘Playing it Safe’

Lawyers are known to be risk-averse, “play it safe”, “consider everything that can go wrong” kind of people. We are trained that way for 3 years in law school. Then we are rewarded for helping our clients think about all the bad things that could happen and try to help them avoid those things from happening or mitigate the damage if they do happen.

But when the universe starts sending signs and hints, and tangible viable opportunities appear, I suggest that it is time to listen. In my case, I listened with one ear while my inner lawyer was saying, “keep doing what you’re doing” and “that’s crazy – look away!” I have always seized opportunities when they arose in the context of my regular career path. I also didn’t shy away from challenges. But like many lawyers, I am not one to seek out great risks. Yet, the cumulative signs and hints were too compelling to ignore.

The legal industry is going through an intense period of unprecedented change. To really be a part of that exciting journey, I had to decide what role I wanted to play. That was obvious for me… I wanted to be a game-changer. I wanted to not only provoke spicy conversations about the practice of law, but I also wanted to help change the delivery of legal services.

So how was being in one of the world’s most innovative companies not enough of a platform to impact such change? Here is the inconvenient truth: Impacting broad-scale change is hard anywhere. Further, the bigger the entity (law firm or in-house department), the bigger and heavier the boulder we have to push up on the hill. Everyone’s journey is different. But for legal professionals, I think something is happening across the industry that is causing us to re-think our careers and our goals.

The satisfaction of sharing knowledge and know-how

After more than 13 wonderful years at Microsoft, I felt that I had reached a point of achievement that was very satisfying. Yet, the interest from others in what I had accomplished began to send signals that I could not ignore. At first, it was flattering to be called for advice and insights. I was called by very prestigious companies and law firms wanting to know how I had carried out what I saw as quite obvious and necessary. Every conversation was energizing, promising and just plain exciting. I found myself getting great satisfaction in helping other people think through their problems. After enough of these conversations, I had to admit they were becoming a highlight of my day or week.

At the same time, something else was brewing. Legal tech was exploding. I had very quickly become quite capable of filtering out the “vaporware” (techie speak for software that provides little actual value in solving business problems). There was a lot of focus in the legal industry on legal technology and how it was changing the legal profession. Unfortunately, writings about robolawyers, blockchain and automation are outpacing the ability of most readers to absorb this new information.

Although new innovations can be very energizing, new technology also creates a bewildering array of complex choices for buyers who are generally not well-versed in technology. Lawyers certainly fall into this group.  What is real? What is useful? What will be here five years from now? All of those questions began racing through my mind. I wanted to be the one that companies and law firms would turn to for answers.

I was also getting some subtle, and not so subtle, hints from experienced, well-respected industry leaders. They were telling me there was more I could offer and that my biggest challenge would be picking amongst the many opportunities coming my way. Although these conversations boosted my confidence, I still convinced myself they were just saying those things to be nice.

Taking the leap

Then one day it happened – a revelation – like that proverbial light bulb going off in my head. I realized it was time for a change.

The light bulb was one particular conversation that solidified the comments that I had stored in the back of my mind for the previous many months. A group of lawyers from an in-house legal department were sitting in my office taking notes on the ideas I was suggesting. And then they asked if I could recommend a consultant to help them. Of course, I could and would send them a few trusted names.

“Wait a minute!”, I said to myself, “I can do this. …  I should do this.”

Meanwhile as that light bulb went off and shone so brightly, I was having conversations with a small but powerful start-up called LawGeex. They were offering advanced AI-based automation for the review of contract terms. I was VERY familiar with reviewing contracts and had been desperately exploring solutions for the contracting work I was overseeing in my job at Microsoft. I was impressed with their approach to content marketing, the founders’ philosophy on building a company, the reputation it had so quickly gained in the industry and of course their advanced technology. Candidly, I had always felt like I missed out on that start-up adventure that others had always spoken so fondly about. It sounded thrilling: fast-paced, high-energy, all-in, purposeful. I really wanted that experience. Contracts + AI + start-up. Could there be a better fit for me?!

So, I decided to be really frisky. I wanted to try both – start my own law firm & consultancy (more on that below) and be a part of a start-up. I was fortunate that LawGeex saw the potential of having me on part-time basis and engaged me as their Chief Legal Strategist, while still allowing me the time and space I needed to develop my own new business, InnoLegal Services PLLC.

InnoLegal Services, Inc.

You may be wondering, “So what is InnoLegal Services? A consultancy? A law firm?” Well, it’s both. Let me explain.

I am a strong believer that law firms today can’t just practice law and hand off artifacts, output and advice without also providing a more holistic solution on the real needs of the business that the lawyers are trying to support. Every law firm should also be a consultancy. Lawyers need to provide sound legal advice, coupled with operational insights about HOW the engagement runs.

The HOW covers a variety of aspects of the practice of law that were often ignored or happened organically. For example, why should a corporate client have to ask a firm to tell them how many litigation matters are pending with that firm? Or how many contracts have been negotiated? Or how long either has taken? There should be basic sets of data insights that are always being provided. Beyond that, the law firm should work with its clients to figure out the best ways for taking in work assignments and returning deliverables. There should be feedback loops created, and collaboration technology used (not that Outlook isn’t amazing, but it is not intended to be a workflow system, though that is what lawyers use it for). The list goes on.

You see, operating as a law firm, I can deliver all sorts of other professional services under that umbrella. But the reverse is not true. So, why limit myself to a consultancy, if I can also be in the position to provide legal advice on the HOW? Yes, that’s right. There is an element of legal advice that is part of the HOW. Helping a legal department figure out what legal risks it can reasonably take in its contracts, will inform their corporate policy, which then informs the process for contract review. So, the practice of law and consultancy are actually very clearly connected. At least that’s my theory!

One engagement at a time

Even as opportunities presented themselves with large prestigious firms, I learned how painfully slow any change in those big institutions would be (not for lack of interest, but because of the difficulty of implementing broad scale change). Thus, I decided to start simple.

I am very excited about the idea of experimenting with the mix of technology, law, and process and thus helping law departments and law firms engage more effectively, one engagement at a time. Equally exciting is my role as Chief Legal Strategist for LawGeex. In that role, I work with all aspects of the company and product. I also get to consider interesting business models and operational scalability, all while applying my years of experience in contract negotiations, team-building and providing solutions. Come to think of it, I am also applying many of these new skills to my own business.

I suppose I am Chief Legal Strategist of two start-ups: LawGeex and InnoLegal Services. I’m not sure it can get more exciting than that!