Jen Berrent & Daniel Doktori worked together at WilmerHale where Jen hired Daniel as an associate. The goal was to build an emerging companies practice in New York City. One day, a couple of guys named Kieran and Greg approached to see if there was any interest in buying lunch for a group of seven or so general counsels of tech companies. So was born the first-ever TechGC event. Shortly thereafter, Jen left WilmerHale to become the General Counsel of WeWork, and a couple years later Daniel left to become the General Counsel of Credly. In the time since, Jen and Daniel have remained close and talked through the gamut of topics of building a life and career as a general counsel.

In this series, they speak about on building a successful life and career as a general counsel. Stay tuned for part 3!

On Lawyering in a Business Context

Jen: I thought the cross-over role of General Counsel with a business role was difficult. The GC not only needs to provide sage legal advice but also needs to focus on how to operationalize the legal team (even if it is a team of 1). In that vein, legal should balance and augment the business team but remain a trusted advisor. You relished the combined role. Why?

Daniel: When I joined Credly, the company was tiny — five people. At that size, we were way too small to need a full-time lawyer, let alone a full-blown “general counsel.” But Credly really did need a Swiss army knife type who could execute a lot of different jobs well enough as we grew. Contrary to the prevailing stereotype, I think many lawyers have the capacity to manage eclectic responsibilities, and I’m bullish on lawyers as early-stage hires. Good lawyers get smart fast on a wide variety of topics. They listen exceptionally well. They execute reliably. Ultimately, though, it’s an appetite thing. Not all esquires want to marginalize their legal training to make space for non-legal responsibilities. Why did a legal role in a business context appeal to you?

Jen: I have always been fascinated by business and building companies. I went to business school as an undergraduate and joined a small consulting firm in the mid-1990s and then worked in strategic planning at American Express. In business, the career path seemed filled with managing people and projects but devoid of analytic rigor that my nerdy side desired. I toyed briefly with getting a PhD before deciding to go to law school. There are endless possibilities with being a lawyer. Personally, I recommend becoming a lawyer to anyone who has an inclination. Where do you fall on recommending law as a career?

Daniel: Huh. I’m surprised to hear that you so freely recommend a career as a lawyer. That’s rare in my experience; I’m frequently surprised at the ubiquity of self-loathing lawyers. In the corporate context, it’s possible that negativity stems from the dynamic of lawyers serving as the “designated readers” of stuff with which their colleagues can’t be bothered (a thankless job to be soon replaced by AI). But I don’t feel like that. It’s possible that my initial experiences in government influenced my perspective. In government, there’s not much that can be done without a lawyer involved. From speechwriting to policymaking, lawyers provide insight, guardrails, language, and assurance that is, as they say, sui generis

When I was in law school, I took a course taught by tech scholar Yochai Benkler, author of the Wealth of Networks. Something that stuck with me was Professor Benkler’s characterization of lawyers: “Lawyers are the engineers of the social sciences,” he said. Sure, you can make a drawing of a building or a wireframe of an application, but you can’t build either without an engineer. Professor Benkler’s comment has rang increasingly true to me over the years: you can dream up a policy or a new product all you want, but it takes a lawyer to make it a reality. That fact means lawyers get to be in the room where it happens. Once you’re in there, the combination of your skills and knowledge help decide your influence. I dig that. 

You were in the room where it happened at WeWork. How did you think about your own career as a lawyer (who started as something else), and how did that influence your ascension to something else when you became Chief Operating Officer of WeWork?

I think [being a lawyer] is one of the most fascinating fields if you are interested in a long career – it is truly the practice of law in that the more your practice, the better you get.

Jen: First of all, I also took a law school seminar with Yochai Benkler that was quite memorable. One thing we debated was the ethicality of adding in a location tracking device to every phone – this was in 2000 so well before the iPhone. He was prescient about the issues we were going to face.  

Anyway, I 100% agree with you about the benefits of being a lawyer. I think it is one of the most fascinating fields if you are interested in a long career – it is truly the practice of law in that the more your practice, the better you get. Each bit of experience adds to your ability to provide good advice. 

I like the rigor of being a lawyer.  You need to weigh factors that you may or may not control in a broader context – it is not just what you want to do, but what you can do and what you convince other people to agree to do. You need to think what possibly can happen in the future without getting too far afield from what actually will happen. When I negotiate, I have a systematic approach to analyze all of the points at hand and I never think of one point alone – it is always a package of points. If we move a little in one direction on one topic, I need to have a strong sense of where I would move on a seemingly unrelated topic. This allows me to play the statistical game of foreseeing the future correctly much more frequently – because I am covering more scenarios.   I see the assessment of my negotiation playing out over years as a business deal unfolds in the real world.

As I became more senior in my career, combining legal acumen with business strategy was incredibly appealing. I loved building a practice at a law firm, but I found the role of advisor less fulfilling than I had hoped. To me, the most rewarding parts of the job were advising founders and working with a team of lawyers. I wanted to go deeper in those roles. When I joined WeWork, I believed in the mission, I believed in the CEO and I believed that I could actually be helpful in building the business. I had zero ambition to become COO. In fact, my favorite job – by far – of my entire career was the brief period (about 18 months) I served as General Counsel of WeWork.  After taking on operational roles, I became Chief Legal Officer so was the most senior lawyer but other (amazing) lawyers served as General Counsel during my tenure.

Daniel: An endorsement for career patience: the more you practice, the better you get. Funny how counterintuitive that rings in our wunderkind era. That can be hard to swallow when the entrepreneurs have success so early while legal requires the build-up of knowledge over time. On the other hand, it seems important to avoid getting stuck in a rut.

In those first days as an associate, I remember vividly how we were coached to aspire to become a “trusted advisor” to our clients, and maybe one day you too would see your deal on the front page of the newspaper. There was something so unsatisfying about that to me – you could become expert in a particular transaction and, ideally become the go-to person for that thing (I always think of Bob Barnett, king of big book deals, as the epitome), but you never really “owned” the outcomes. It was someone else’s achievement and you helped. And, worst of all, if you don’t love doing that one helping thing, it’s terrifying.

I remember practicing for a very few short years at Wilmer and worrying “am I only ever going to be good at seed financings for startups?” For me, going in-house and focusing on the operational side helped me feel that sense of ownership and satisfaction. There’s a difference between going in house and converting fully into an operational, non-legal role. How did that happen for you?

Jen: One of the key factors for why I moved to operational roles is the work I did on systemizing the real estate leasing process. There is a skill and an art to doing deals, but there is also an ability to create standards and process. Together with two other folks from the legal team, we white boarded the lease negotiation system, which eventually became the backbone of WeWork’s real estate acquisition process. There were a series of controlled gates that allowed for multiple pathways of work to occur based on deal progress. I like to say that you know the system was built by lawyers because the endpoint (Gate A) was signing the lease – it should have been opening the building (we needed to add a Gate AA) to correct for this!

Daniel: Ok. Well, now I’m fully intimidated. Do you have advice for, you know, normal people? 

Jen: Ha. You know, one question I get asked a lot about is the “imposter syndrome” – Do I have it and how do I cope with it? I have thought a lot about this and in some contexts have over-indexed for experience so that I can feel confident in my qualifications for a role. When I joined WeWork as General Counsel, I had been a partner at a large law firm (WilmerHale) and so had some level of confidence in my legal abilities at least. I learned recently that the term as coined by the original psychologists was Imposter Phenomenon rather than Imposter Syndrome. I think this is an important distinction – the phenomenon can pop up at any time. I do not think I have met anyone who is successful who has not been pushed out of their comfort zone enough to question whether they have what it takes. This comes up in a lot of high stakes situations.

If you think about [impostor syndrome/phenomenon] not as a diagnosis of a psychological condition (such as clinical depression or anxiety) but rather as a phenomenon that occurs for everyone (like sadness or stress), then I think it is easier to confront and address the self-doubt.

I have had in my office for many years the Eleanor Roosevelt quote: “Do one thing every day that scares you.” A very close friend gave this to me when I was going through personal exploration and it has helped me frame being afraid. Facebook used to refer to a quote asking what would you do if you were not afraid? I found that Facebook framing to be a more difficult construction of the same concept. We are all afraid at times – if not, oftentimes. How do we face that fear and push ahead? Every human makes mistakes, so as a human I should be totally unsurprised and unfazed when I too make a mistake. If you can hold the fear in its place, then you can figure out the tools you need to perform while still having a sense that you do not belong, that you are not good enough, that you do not have the talent.

Daniel: Inspiring stuff, Jen. And also comforting in a way. Some takeaways for the folks: 

  1. Lawyers make good operators when they build systems. Translating business processes into definable, repeatable systems can leverage legal skills into significant business value. Once you’re in the room where it happens, your ability to execute generates credibility and opportunity.
  2. Law is a practice: The more you practice, the better you get. While that reality can seem frustrating in a high growth tech startup environment, the flip side is that succeeding in the law doesn’t require a stroke of inspiration or unique insight. There is no need to be the world’s youngest anything in the practice of law.
  3. Feeling like an “imposter” is a phenomenon, not a syndrome. Syndromes are like illnesses while phenomena simply occur. We avoid illness and we manage phenomena. Feeling like an imposter can be a sign that you’re pushed beyond your comfort zone, but framing it as a phenomenon helps you manage the fear inherent in that discomfort.