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 Kiran 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.

On Hiring Scalable Lawyers

So, recently, we chatted about work superpowers — what they are and how to identify your own. What about hiring people with superpowers? And helping them further develop those superpowers? While it seems you can be precocious and clever beyond your years for a lot of roles in tech, the law is a knowledge business, and knowledge takes time to acquire (even if “learning fast” seems a bedrock skill for lawyers). Few people have experienced the type of hyper growth you helped catalyze at WeWork. Part of that growth had to have been the scalability of the people on your team. What’s the secret? How do you think about hiring lawyers – in particular lawyers who can grow with a scaling company?

Jen: Well, I am starting to sound a bit robotic (which my family does call me at times), but I had a process for hiring! Early on, I figured out three questions that I would ask every candidate I would interview, hire based on my instinct as to what made “good” responses and then evaluate based on data. I have to say, the results were phenomenal in terms of longevity and success of the hires – many of whom outlasted me at WeWork for several years (including the subsequent chief legal officers). My three questions were: Why do you want to work at WeWork? What do you think of WeWork’s mission? What do you like about what you do? These questions are designed to elicit what will make someone happy so that we can avoid burnout – every job is hard and every job has aspects we do not like, but if we can maximize the positives, people tend to learn and grow. I can go on forever about each of these and types of answers, but I will highlight just one for each.

On why This Company – I think the best fit is someone who can articulate why they are the best fit – not just why the company is great or why they are great but why the combination of the two would allow someone to unleash their superpowers. That is the best feeling for anyone. For a time, WeWork was a super hot company and we had no issues finding candidates. An answer that did not resonate related to the fact that getting to WeWork would be a resume boost – someone wanted to fill a gap or felt it would be validation.

On the Company’s Mission – I think it is important that you believe in the core business of your company. Almost every company has some stated purposes. For many years, the mission statement at Microsoft was: “A computer on every desk and in every home” If you for some reason did not care about that outcome, you will not be happy at that company. At the time, WeWork’s mission was more grounded than some of the missions that came later. It was “To create a world where people work to make a life not just a living.” Honestly, as the mission evolved to something like “Elevate the world’s consciousness”, it should screen out candidates (including me!).

On What do you Like about what you Do – Everyone has things they like and do not like about their job. It is important that the role has more things you like than do not like – again this both helps you be happy day-to-day as well as unleash superpowers. For example, if the part you like best is working with all different clients on all different matters, an in-house role that has you focused on contract negotiation will be a bad fit. You will be unhappy. As an aside, the crux of this question is not just what you like, but what do you like about what you do. So for example, some people would answer that they like the people they work with. That is not that helpful to me as the person doing the hiring because I have no idea if you will like the people on the team – that’s up to you – what I want to assess is whether I can offer an opportunity to you doing something you will enjoy.

Daniel: Gosh, Jen. You make it sound so simple. I can see the tweet thread now: “Follow these simple steps and you too can build a multi-billion dollar company!” The mission-alignment piece resonates with me (and your comment about WeWork’s mission evolution is very funny and slightly painful). Even at Credly, our small (but mighty!) company, one thing we were clear about early on was our vision — which we defined as the world we were building towards — and our mission — which we defined as our role in building that world. When we were really cooking, you could’ve woken up any Credly employee in the middle of the night and they would be able to recite both. In practice, our mission and vision served as the most effective guide for day-to-day prioritization and time-allocation. Over time, we got pretty dedicated to setting quarterly objectives and key results (OKRs), and we always started with the vision and mission at the top of the page. It was included in every onboarding sequence. It was a core element of CEO presentations. Of all the choices we made early on, that may have been one of the most important.

Seems your mission interview question served two purposes – first the one you articulated about fit, but also a second about doing your research: the interviewee will need to have known, understood and considered what the mission means to them in order to share what they thought of it. I can imagine a certain type of lawyer preparing diligently for the interview without thinking all that much about the mission, and that could be a good indicator they might not scale.

On the flip side, I wonder how much the effectiveness of these questions benefited from a combination of pattern recognition by you and talent magnetism at WeWork. When you’ve got a line out the door of people trying to come to work for you and you’re interviewing them by the bushel, you can use these questions to sift through the very best. Do you think these questions work for the more humble in-house legal departments out there who are interviewing one-at-a-time in a tight market?

Jen: I do not think these exact questions work for every situation but I do think having 3 or 4 standard questions and starting to see how they play out in the real world make sense. When I left WilmerHale, I had hired 100% of the associates (meaning over time, there was turnover but the team that was in place when I left was all hired by me in one way or another). I had some parameters there as well both in terms of screening candidates and asking questions.

At Wilmer, the team was smaller, there was not a true growth trajectory and law firms do not like to fire people. This meant the pressure was on to make good hires because you could not easily move them to some other role or transition them out quickly (even if that was best for everyone). I did use a data-driven approach and ended up hiring many associates from Cravath and also targeting Davis Polk. To the uninitiated this may seem trivial – pick top firms and recruit. But these firms were different, especially Cravath. Many of the top firms have a specialist approach – you are a capital markets lawyer or M&A lawyer or debt lawyer. At Wilmer, all associates were generalists within their larger practice area – so a corporate associate could be working on an emerging company formation, a sale of a company, an IPO or a debt capital financing…all at the same time (well almost at the same time but definitely within a year)!

Lawyers tend to feel most comfortable when they are an authority in an area so it is difficult – and not necessarily exciting – for someone who has spent five years doing M&A deals to work on an IPO. Cravath maintains a rotation system where it is embedded in the training that you move to a new area every 18 months. This meant that associates did not have time to get too comfortable before being thrust into a new practice area – with a lot of pressure. So even though partners at Cravath were quite specialized like all the other top corporate practices, the associates were not. This was an amazing fit for our practice. Also, I am sure I had a different framing than asking specifically about Wilmer’s mission – although I did have a mission statement for the emerging company group and I did have a mission for the legal team at WeWork (separate topics) – since that seems too intangible for a law firm (most law firm missions sound remarkably similar).

As a note, when I graduated college, I joined a boutique consulting firm called The Parthenon Group (later acquired by EY). They were quite forward thinking and had a very special culture. They were quite disciplined in their recruiting – hired from a small set of schools and had a grade minimum (not sure this would fly in today’s world) but also the focus was on people who were “nice and smart”. The ideal candidate was framed as an investment banker who did not like investment banking because of the culture.

Daniel: Grade minimum from a small set of schools, eh? Must be nice. Anyway, we’ve spoken a good amount so far about selecting talent from a pool of candidates. What about nurturing talent once you’ve successfully recruited someone? One of your three questions was about understanding what you like about what you do. That seems a key input to helping someone identify their work superpower. But companies change and people change. We ourselves change over the time people are working on teams. What’s worked best for you in terms of promoting lawyers on your team to execute at their highest level, and doing so over time?

Jen: This topic is of the utmost important to me: Once you have hired someone, how do you set them up for success. First, It takes a ton of time. One thing I learned about myself is that I am very good at this when I have a personal relationship with people but my approach does not scale so easily to larger groups. I have amazing relationships with people who worked closely with me but I was less effective at really figuring out pathways of success for lots of people. This is why great heads of HR are so amazing. I had the privilege of hiring one and then seeing him rise well beyond me, and it is truly amazing to watch someone who can think about the greater good for the entire employee lifecycle while balancing individual needs even though they do not know the people personally. I am not sure I am explaining this well, but I greatly admire this.

The first part of helping others is that I actually care. I know this sounds silly, but everyone has their own scorecard of what success looks like. If I were to brag, it would only be about the amazing success people who have worked for me have had. For example, I do think about how many General Counsels Wilmer and WeWork have produced. When I left WeWork, four of the most senior executives reporting into the CEO had worked for me at one point or another during my tenure at the company. I am not taking credit for these accomplishments but if it is something that you focus on, you can make a difference.

As an aside, for the person doing the work, you should approach projects you do not like and you like with the same vigor and rigor. Be opaque in your work product but transparent in your communication.

I think the key is to have a long-term view of a career but also understand that the day-to-day is what gets you there.

For example, I have taken every day of vacation that ever was granted to me at any company – including at the law firm when I was trying to make partner. That is not to say I did not have work to do on most of the vacations I took as I got more senior (not when I was more junior), but I took them. When I was an associate, I worked very closely with an amazing lawyer (who is still a tremendous advisor to me) and we would cover for each other so that we both could take vacations. I really tried to help people navigate taking time off so that they can reset and be in the game for the long run.

Daniel: Love the “be opaque in your work product but transparent in your communication,” line. It’s so easy to do the exact opposite and mail it in when the project sucks and then when you’re asked about it, gloss over the fact of your disinterest. The opposite, what you describe, seems to define “professionalism” in a way I hadn’t considered. Cool.

As for your main point about nurturing your team, my takeaways include: (a) Really, actually caring [shout out to “Radical Candor”]; (b) using the “are you happy?” question as a way into a direct report’s core interests and (c) Putting in the hours it takes to think through how to set a direct report up for success….

Actually, maybe I don’t have it all just yet. Can you say more about the “setting up for success” point? I hear you on matching people with opportunities they find exciting, but sometimes the job’s the job right? How can you set people up for success when you also need them to execute on the meat-and-potatoes, of, say, negotiating commercial contracts or responding to security questionnaires from clients?

Jen: I am going to assume that the person has the legal skills – those are the table stakes. If they really cannot do the substantive work, they need a new role. Assuming that, people have different strengths and weaknesses in terms of pacing and work environment. I am going to give an example that I think is directionally correct but has not been not fact-checked: In technology companies, there used to be a philosophical argument about continuous deployment for new code as compared to scheduled deployment. Companies have gotten more sophisticated but early on this was a philosophical debate. Amazon did both and then staffed accordingly. Product ratings was a fast team (very low risk to get it wrong) and the single-click buy-now button was a slow team (super high risk in terms of purchase friction or bad credit decisions to get it wrong). It turns out some coders liked the constant adrenaline rush of pushing code and others liked to get things perfect before launching.

When it comes to the law, I have found some people like to have many deals going on at once and some people thrive at doing one at a time. For the many deals at once, I staff them on high volume, generally low value (but lots of fun/wins) deal flow whereas one of my most trusted lawyers would get only the most important deals, one at a time. Just recently, I was meeting with the CEO at a small company. She had one employee who was excelling at her work, but did not want to go out of her comfort zone, one employee who wanted more and more work in all different areas but had trouble prioritizing, and a third employee had trouble focusing when working from home because of family interference. For the first employee, they will just run what they are doing and the executive director can think very little about that program. The second employee would be given more projects, but have a weekly 1:1 to prioritize so that they did not get overloaded. The third employee would shift to a 4 day in-office work week so they could be efficient during work hours and attend to family matters on one extra day. This was an approach that could set up everyone for success.

Daniel: Got it. Thank you. Let’s capture some takeaways before we wrap:

  1. Process, Process, Process: Having a standard set of interview questions – in particular around the organization’s mission — helps screen for people who will be durably happy working on a wide variety of tasks within that organization. And, within that context, understanding what someone enjoys doing can help you assign particular tasks and identify an attractive career pathway.
  2. The concept of a “Good Athlete” is relevant for lawyers too: As a law firm partner, you prioritized lateral hiring from Cravath and Davis Polk because of the emphasis those firms had on developing a wide foundation of ability among their associates. The emphasis on organizational mission meant that people could bring a variety of skills to bear (including in unforeseen ways) in advancing that mission.
  3. (Really) Caring about employee happiness yields performance dividends: There’s no substitute for really caring about your team members. Periodically asking “are you happy?” helps surface core interests and identify how to match people to opportunities they find exciting within the organization. Assignment pacing and work environment are two examples of inputs that can yield dividends for team engagement and help set people up for success.

Jen & Daniel are Founding Members of TechGC, a private invitation community of over 4,000 GCs & CLOs (and their legal teams) of high-growth tech companies and venture funds. To request an invitation to join as a member, click here.