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Paloma Ahmadi, Associate General Counsel, Employment, at Brex, talks about her journey from in-house, to law firm practice, and back in-house. Paloma is a phenomenal client advisor, with an interesting mix of career experiences, who provides great insight into navigating a legal career.

Relevant episode links:

Brex, The Hall of Uselessness

About Paloma Ahmadi:

Paloma Ahmadi, Associate General Counsel, Employment, at Brex, talks about her journey from in-house, to law firm practice, and back in-house. Paloma is a phenomenal client advisor, with an interesting mix of career experiences, who provides great insight into navigating a legal career.

I'm very pleased to have one of my former colleagues at Haynes and Boone, Paloma Ahmadi. She is now in-house Associate General Counsel of Employment at Brex.

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Welcome, Paloma.

Thank you for having me.

I was so interested in having you because you have a wonderful law firm-wise experience with a unique practice. You are quite adept at working with arts organizations, symphonies, and some complicated employment and union-related matters, and then in-house. I thought you had an interesting mix of experiences to share with folks. I wanted to start first with how you decided to become a lawyer and go to law school. What interested you, or what was the spark that caused you to go in that direction?

I made the decision to become a lawyer in college. In my freshman year of college, I thought I was going to be an archeologist. I realized very quickly how much science I was going to have to do to pursue that degree, so I was like, “This is not for me. Nevermind. I'm going to be an English major.” I became an English major and started looking around like, “What am I going to do with this?” I took some law classes as an undergrad. If I’m being honest, for me, that completely sealed the deal. I was like, “This is fascinating. This is what I want to do.”

At the time, I had this perception that legal practice would be a lot of reading and writing, and that's true. What my practice has become since I have been doing it for a while is a lot more talking, advising, speaking to people, understanding, and frankly, less reading and writing. That's a great thing. If my practice had stayed as reading and writing oriented and more of a lonely practice, I wouldn't enjoy it as much. The reasons I decided to become a lawyer were because I thought it would be a lot of reading and writing. I thought that's what I wanted, but I'm very happy with the way it has evolved. It turns out that what I wanted when I was 22 and what I want now are different.

The law allows that. That's what's good about the law. Before law school or in law school, you are generally only made aware of certain opportunities, whether that's in a law firm litigating or with the government. There are so many different things to do as a lawyer and so many different skills involved in them. If you like to be more isolated and read and write, you can be an appellate lawyer like me. If you'd like to be more engaged with clients and work with them on problems, they can do what you do. It's nice that when your interests change and how you want to operate changes, there's a lot of movement within the law to do that.

That's exactly right. One of my professors in law school, Professor Suk, said at one point in a thorough way, “A career in the law is 50 years.” It hit me like a ton of bricks because that was so long to me. In law school, you can perceive that your first job is critical and will make or break everything. You are like, “I have to know today what I want to do forever,” as you are considering those first opportunities.

While it's important to begin your career someplace where you are going to try and get the best training that you can, it's also true that a career in the law is 50 years. If you decide you want to learn to do something different, you can. Those decisions aren't permanent and will evolve with your interests, the market, and the needs of your clients.

That's a good reminder, especially for law students who are reading this thinking, “If I don't make the right decision right now, I'm stuck forever. It's irretrievable.” I’m like, “Get in the general right direction where you are getting well-trained and skilled. If you realize you change later and you want something else that, you can do that.”

I'm fascinated because that's where I have seen you work. You worked in Haynes and Boone, counseling, arts organizations, symphonies, and things like that with regard to their employment and union matters. That's a pretty specialized area, but it also requires a lot of tact and working with a lot of different folks in negotiations. How did you come to do that kind of work, and whether you see yourself the way I do in terms of your skill in that regard?

It's interesting that I wound up with the clientele mix that I did. This is unusual. I became a labor and employment lawyer through the internal investigations and litigation side initially while I was at my first two firms. I then went in-house in a labor relations role and got exposed to traditional labor, labor arbitration, collective bargaining, and those types of work, to which I had not been exposed to.

Learning the traditional labor ropes was what allowed me to work with the awesome organizations that I did work with at Haynes and Boone because they are unionized. Those traditional labor skills, even though I learned them working in professional sports, are directly applicable. It's the same legal framework, and frankly, has similar sensitivities. Professional sports are very much in the public eye in the same way that arts organizations often are. We keep an eye on, “How does this look? How does this theme?” In addition to, “What is the law here? What are our obligations and rights here?” Then having that balanced approach.

I love talking to my clients and being the advisor or the person who's there when they need advice. That feels good no matter what subject area of law I'm dealing with. The pandemic highlighted the need for my particular practice area and made that need feel urgent and relevant. There are some companies where employment takes a back seat. People don't consider it a real critical legal issue. The real legal issues are M&A or intellectual property.

When the pandemic happened, there were such severe disruptions in the labor force that employment bubbled up to the surface like, “This is important. This has the capacity to disrupt our business. We need good advice on this.” It created that environment where you can build those kinds of relationships with your clients and they see the value.

That's an interesting point. I was thinking in the lens or the context of the arts organizations and serving on the board of one of them. We were like, “We are all about our people. If we don't have people playing the instruments, we don't have an orchestra.” Working through all of that was pretty clear on what the priority in that setting was. I'm sure, to varying degrees, a lot of other organizations and companies had that realization also.

Regardless of what the positioning had been beforehand, we are confronting the same very serious problem, which is that in some jurisdictions, it was arguably illegal to come to work. The type of work that you had been able to perform before the pandemic might not be lawful or might not be lawful in a way that makes you any money.

It may be technically lawful, but that number of hours in that setting is not going to be feasible. This has been a thread across different folks who have been on the show, too, which is that all the pieces of the puzzle end up fitting together to make sense to where you are now or where you went next in your career. You were talking about the different building blocks positioning you to be in a great skillset to work with, in particular, arts organizations. They do have a very special union and set of questions. They also have this, “We are in the limelight. No matter what we could do, it doesn't make sense for our patrons, donors, or community to take that hardcore position. We need to figure out something else that works and works for everyone.”

It's important to begin your career someplace where you'll get good training.

Those were all pieces you got from different experiences and put together that then lead to other opportunities. I wanted to highlight that because that's a similar thing where people say, “I didn't think about it, but afterward, it made sense. I have all of these different skillsets together. I'm the only one with them, or no one has it in that combination that I have.”

Although I will say, especially for law students reading this, it can sound linear when I talk about it. At the time, it felt anything but. Looking back, I was like, “I liked this and that. I had a strong reputation for this or that.” Those are things that I know now, but I did not know when I was 25. Nor when I was 25 and graduating law school was it my plan, like, “First, I'm going to be a white-collar criminal defense lawyer, and then I'm going to practice in a boutique in Texas. After that, I’m going to go in-house in professional sports.” All of those things were decisions that I made at the moment when the opportunity arose or the need arose, but there was no ten-year plan.

That's fair to reiterate and make clear because it can look like, “It all makes sense.” They were all intended to go in a particular direction. Both can be true that they weren't intentional, but then, when you look back, you go, “All of these pieces fit together. It makes sense.” At the time, I wish we had that sense where we are like, “This is the clear next move which would help fill in this gap.”

When you were saying you took opportunities, there are two things in there. One is that you were open to the opportunities. You weren't blindfolded. You were like, “That’s a good opportunity.” You also built up the skills to be able to be in the position to take that opportunity. All of those things go together. Even if you don't have some 10 or 15-year plan laid out, you were good enough to go. You were like, “I'm willing to take a chance on that opportunity. I have the skillset for that.”

Sometimes, people are hesitant to do that. Opportunities can show themselves to you, but you might be a little concerned. You are like, “I'm not quite ready. I need one more piece of the skill puzzle before I can apply,” or, “Somebody with more experience should do that.” We tend to talk ourselves out of things sometimes.

Law is an apprentice business is important. Having those lawyers who are more experienced than you and have done certain things before, that's where their advice is so useful. You can have that conversation of like, “I'm ready for this next thing. Is that dumb? Am I wrong? Talk to me about this.” I remember when I wanted to take my first deposition. I was like, “I'm ready. I want to take my first deposition.” I was talking to the senior associate and saying, “I can do it. I know the most about this witness. I am prepared.” She was like, “Okay.” The fact that it had never occurred to her that I wouldn't take that witness was helpful. I had a lot of self-doubt about it, but she, who had been there before, was like, “You can take that position.”

I'm sure in her head, she was also making considerations, like, “He’s not the most critical witness in the case. It's okay if it's her first deposition. It’s unlikely to turn into a slugfest. I know the demeanor of this opposing counsel. This will be fun.” Those are probably also things she was thinking about. Putting yourself out there for those opportunities and talking to mentors in the profession to see, like, “Am I underselling myself? Am I ready for this? What do you think,” is so useful.

How do you approach someone to be a mentor to help you? They may not even be a long-term mentor, but a mentor to mentor you through a particular situation or circumstance. It's always that first question, “What does that look like? How do you ask that?” You have pushed that a little bit further in terms of, “I want to bounce things off people. I'm thinking this. Am I out there thinking that this is a good next step for skill building?” In that process, you can find out whether you are a little overly ambitious at that point. Is there something else that you need to do to get ready to be in that position?

You have also brought that person in as a teammate towards what it is that you want to accomplish. That is also another thing that you are very good at and why you enjoy the in-house aspect too. You are working with people and you are good at moving them forward towards a goal. Even if they are against each other at first, you are like, “Okay.” I think about that in negotiating, but bringing everyone together to move forward is important.

It is persuasion. I always remind myself that if I'm finding somebody behaving in a way that I don't understand in a negotiation or a professional counseling interaction, they are probably pursuing an objective and I haven't figured out what it is. I can't tell you the number of times when I have a client say, “The counterparty's being crazy.” I say, “I don't think they are crazy. They are probably pursuing a different objective than we are. We were thinking that their objective was X. It sounds like their objective may be Y. Y may not be something we value.”

Thinking about how I can understand the other side's behavior in order to gain an advantage is also useful in persuading when I’m trying to build a coalition around an idea. Everybody has their objectives, viewpoints, and priors. Taking those into account to build that puzzle and put all those pieces together to say, “What's going to speak to this person? How can I put that together? How can I be the best advocate for the idea that I have in this scenario?” It's not something that you do in the courtroom. It’s something that you do as a lawyer. You are persuading. You are persuading someone like, “Listen to me, I know what the law is. This is what the law means in our situation. Here's my recommendation going forward. You have to have reasons why they should do what you say.”

It's always the challenge and negotiations generally, but by uncovering their why and their motivations, people are going to be forthcoming about that. Sometimes, it's not that they are not meaning to be forthcoming. They think the same thing. They are like, “Doesn't everybody want X? The other side's acting crazy.” It’s hard. When you are in an adversarial sense, it's a little bit harder. How would you tease that out if they don't want to tell you what their interest is? That's a little different than having people internally in your organization and trying to figure out their individual motivations as well as the larger goals of the company.

That's something I don't think that people think about in terms of practicing law. There's the law, but then there are also the personal interactions, the business aspects, and the persuasion in terms of working with people on legal problems. That's another layer to what we do. There are ways to do it in a productive way and there are ways to do it unproductively.

That is a very gracious way to say it.

It's interesting because you have been in practice, then in-house, and then in practice, and then in-house again. How did you decide to go to your first in-house position in the sports setting and now, you are in a different setting? How did you decide to do that? What do you enjoy about being in-house as opposed to outside?

The first time I went in-house, I had been fervently assured that the opportunity would never materialize. I was shocked when it did. I’m being a little bit flippant, but I had interned for Major League Baseball when I was in law school. One of the things that they are very transparent about with interns is that there's no job at the end of the internship. They are like, “There is no opening. There is no open role. Do good work, but then please plan to go on and get a job,” so I did.

I interned for a while in law school for Major League Baseball in their New York office and the office of the commissioner. I was told, “There is no job for you here.” I said, “That’s great,” and went and joined Kirkland & Ellis in DC. I was working on white-collar criminal defense, doing some litigation, working with amazing lawyers and learning a ton from them, and living in DC. I then met my husband. He is Texan, so we decided to move to Houston. I was practicing in a boutique in Houston where I'd gotten a lot more employment exposure. It was a litigation boutique, but at the time, was doing a lot of employment litigation. That was a nice transition for me towards more specialized employment practice rather than internal investigations.

I had been there for eleven months. My husband and I were shopping for a house because the lease on our apartment was about to end. I had every intention of staying in Houston. I got a call from my internship boss saying, “I told you this would never happen, but there is an open position. Would you like to interview?” I was on the plane before I stopped talking in that conversation. I was so excited about the possibility of being able to work with them

It was something that you never thought would happen. They told you, “This is not going to happen.”

If you decide you want to learn to do something different, you can. Those decisions aren't permanent and will evolve with your interests in the market and with your clients' needs.

They were like, “This isn't a thing,” and I was like, “I believe you.” It turned out that it was a thing. I got a job as a lawyer on the labor relations team for Major League Baseball. In addition to doing traditional employment, I was also doing labor relations. I got a lot more exposure to international work and immigration in that context and got some fun, special assignments that I would not get anywhere else.

There was this moment when I was standing in front of the dugout in the national stadium in Havana. The Rays were getting ready to play the Cuban national team. President Obama was going to be there. It was the most unbelievable, crazy, and historical project I'd gotten to work on. I was standing there on the warning track and was like, “I am here right now.” When you work in professional sports, you are not supposed to be blinded by the lights. You are supposed to be like, “I’m a professional. I have seen this before.” I turned to the baseball executive to my left and he was like, “This is cool.” I was like, “I know.” We had this moment of being like, “We are going to not be shocked here. Right now because this is so cool.”

You have to acknowledge it and suck it in for a minute.

It was one of those things where they told me it was never going to happen, but I got incredible opportunities. Going back into private practice was also one of these moments where the opportunity showed up. I was on maternity leave. I had my first child. I got a random call from a running buddy of my husband’s saying, “You are a lawyer, right?” I was like, “Yes.” She was like, “Moses is from San Antonio, right?” I said, “Yes.” She said, “I have an opportunity to join Haynes and Boone in San Antonio. I was like, “Yes, please. This sounds amazing. I didn't know this job was available. I didn’t even know this was a thing. This sounds wonderful.”

I'd heard of Haynes and Boone when I was practicing in Texas before. I knew some of the lawyers there, but it was one of these things where I didn't realize that there was an opportunity to practice exactly the kind of law that I wanted at the level that I wanted with amazing colleagues in my husband's hometown. It was all the stars aligned. I was like, “I'm not saying no to this.” I wasn't particularly looking for a job, but I was like, “This is amazing.” It was wonderful.

Deciding to go back in-house again wasn't exactly the same. I'd reached the point in my career where I was starting to try to be more intentional about my growth as an attorney. I didn’t try to be intentional, but there were specific things that I wanted to do with building. I wanted to build something. I wanted to build programs and help run them in a more hands-on way. I had this feeling that I would learn a lot from doing that where I wasn't getting exposure as outside counsel.

I loved being in-house the first time and the opportunity to build programs, but as a more senior lawyer, my thought was, “I now have even more to offer. I'm a lot more experienced. I know a lot more. I have seen a lot more. Now is a great inflection point in my career to try and build something.” The opportunity with Brex came about through some friends that I had who told me, “Our mutual friend is at Brex. You should talk to her,” and I did.

She said, “We are scaling the legal department. We are growing fast.” We wound up in conversations for a while, but the more I learned about it, the more I was like, “This is an amazing opportunity. Brex is growing so quickly. They are doing innovative things in the area of employment. This is something I would love to be a part of if I get the chance.” I got a chance, so I said yes.

We were talking earlier, too, in terms of the pandemic having a major impact. One of those is how and where we work. Whether people are in one location or they are not in any one location, or hybrid, or purely remote, that poses a whole range of new questions with regard to employment law and how it's going to apply to the company. That's another opportunity here.

That's exactly right. I like to say that what I'm working on is the future of work. We are trying to create the future because we are a remote-first company. We are innovative. We are growing quickly. We are figuring out ways to build culture and productivity and support employees in this way. I like to think of it as the new world.

You see a lot these days about return-to-office memos and back-to-work memos. There is no back. Time doesn't move backward. You can't rewind the experiences that we have all had over the past several years. We have learned a lot about ourselves and the ways that we work well and the ways that we don't. Companies, if they are being honest with themselves, will find that there's quite a bit that can be done remotely or more flexibly with similar productivity. They may also have identified areas where there aren't.

One of the things that I think a lot about for lawyers is training young lawyers in the remote work environment. It is an apprentice business. When I was a junior associate, part of my training was I would get invited into somebody's office and be told to sit there silently and take notes. Nobody would know that I was on the call and I was not to bill for it. My role there was to listen to how these things are supposed to go. Before I ever did a meet and confer, I had sat in a senior associate’s office with my notepad, listening to her debate and discovery objections. She was like, “Why do you need that? That's unreasonable.” I was like, “What kinds of things do I say? How is this supposed to sound? What words do I use?” That’s what you learn through that process.

Being a fly on the wall for those is so helpful because there are so many things that you do as an experienced lawyer that you don't even know you are doing. If you were to explain to someone, “Here's what you do,” you would miss at least half of what you do in that circumstance. You can explain it, but then somebody has to come in, hear it, see it, touch it, feel it and then develop their style around that too. That's a concern. I certainly have had that concern in terms of where you are going to have those opportunities to have that fly-on-the-wall apprenticeship stuff and all the things you soak up from being around people doing other parts of cases.

If I'm around people and we are in the office with the associates, I can get a sense of their mood or where they might be out on a project. I can drop in and be there before they even know that they need somebody to consult with. I am able to redirect them before they start going off a cliff somewhere. That's harder to do when you are not in the same setting where you are like, “I can't get your vibe.” I have to figure out something different to have the same impact and to help people improve and get trained. That's a question of how can you adjust that and get something equivalent if you are not in the same workspace.

When I was at the firm, one of the things that I did was force myself to be way more intentional. In the in-person environment, you could maybe take for granted that you were doing the teaching that you were supposed to be doing as a senior lawyer. In the remote environment, you cannot take for granted that you were teaching. You have to add it to your calendar.

Instead of just sending the junior associate the markup, you have to also send the markup, block the time, explain the markup, and let them digest the feedback. Create more space for that kind of discussion so that they can be comfortable enough to say, “I liked my introductory paragraph and you took a machete to it. I don't understand why.” For me to have the candor to explain, I’d be like, “I put things very differently than you. Your way is not bad, but this needs to be my voice. That's why your introduction got red pens.”

What role are you playing on the front lines? The company is growing. The company is remote-first. How does that look in terms of your strategy, challenges, or how you are part of that change within the company?

More broadly, the number one challenge for the in-house lawyer, especially when you are new to an organization, is that people need to remember to call you.

They are encouraged to call you. It was a helpful experience when we called you as opposed to saying, “We have to now call legal. They are going to tell us we can't do what we want to do.”

Understanding the other side's behavior to gain an advantage is useful in persuading when you're trying to build a coalition around an idea.

People have to remember to call you and find that it's a useful partnership. More broadly, I do try and spend more time intentionally in relationship building on things that are non-controversial and things that are me trying to be helpful. That's helpful work from a business partner standpoint. From a lawyer mentorship standpoint, the in-house team at Brex is on the senior side. We don't have any junior attorneys. We have tended to hire folks who are a bit more senior.

With that said, one of the things that we are good at is setting up that one-on-one time with colleagues even if you don't necessarily work with them. For example, I spend a lot of time talking to our M&A guys even though I'm an employment lawyer. There’s a narrow subset of issues we might work on together. Knowing what they do and understanding how they are thinking about things that the company is facing even if it's not something I'm directly involved in is helpful for me to directionally calibrate my advice. If I know what their internal clients are doing and they know what my internal clients are doing, it's that added layer of coordination.

Being intentional about that kind of communication even if it's not necessarily a mentorship and we are more of peers is still very valuable. I will learn a lot. I have my practice area. I do not profess to be a securities lawyer or any other flavor of a lawyer. We are all going to spot different issues. I'm a litigator by training. I'm going to look at things very differently than someone who has been completely transactional in their practice. It's a wonderful mix to continue to encourage. When you are intentional about it, that kind of growth can happen. If I was head down in my silo and never bothered to network within my own department, I wouldn't have the benefit of any of their experience.

That puts you in the position of when things don't happen as a particular type of legal problem either. There are larger concerns within the company. If you have an understanding of that before something hits your purview, then you can have a more holistic answer to that question. You could say, “We need to engage this person in thinking about this problem.” It helps you problem-solve better and also think of things more holistically for the company. To have those relationships in advance before something becomes mission-critical makes everything much easier.

I completely agree. For the law students out there, legal problems don't show up with labels. No one calls you and says, “I have a torts problem.” That is not what they say. They will call you and they will say, “You will never believe what happened.” It's you as the lawyer to say, “This sounds like X. This sounds like Y. I know what kinds of lawyers I need to bring together to solve this for you.”

That's where the spawning of issues comes in handy. That's why the bar exam is the way it is with a lot of those questions. We are like, “First, we have to figure out what kind of creature we have out here that we need to think about what kinds of issues.”

I stole that example from my torts professor. He was the one who told us, “No one's ever going to call you and say, “I have a torts problem.”

People don't think that way. We do. That's why we get called in. Also, having to do that, we have certain analytical skills. We problem-solve in a certain way because of the legal training even if it isn't a legal problem. I firmly believe that's one of the things you add, whether you are serving on a board as a lawyer or in-house in a company that you can look at problems and help problem solve in this very analytical step-by-step way that is unique. It’s not something that business people tend to go towards that decision-making unless they have legal training as well. You do add something to the decision-making besides just knowledge and application of the law. It's helpful to go through that and figure that out.

I agree, but I'm biased because I am also a lawyer by training.

It is interesting. I noticed that serving on non-lawyer boards, nonprofit boards, arts boards, and things like that, we will sit down and go, “The problem is here. Let’s break it down. Let's go through these steps.” People will look at you in complete amazement. They are like, “We never even thought of breaking down the problem that way.” We are like, “That's how a lawyer would do it,” without saying it’s the only way. It is one way to approach it, which can lend some order to the process instead of people running around going, “What are we going to do with this?” We are like, “What do we have here? Let's break it down and work with that.”

The only way to eat an elephant is one bite at a time.

What kind of advice do you have for people who might be considering going in-house? What training is helpful? What things should they consider about being in-house that they wouldn't think of litigating outside? Maybe there's something they might not take into account or would be surprised by.

As an outside litigator, you get to go to court. You get to stand up in court. You get more time with your thoughts and with your arguments. As in-house counsel, the pace of your work is much faster. You are not going to get a week to think about what you think about an issue or to prioritize and triage issues. You are often making decisions much more quickly than that. That's where having trial court level experience where the practice is more fast-paced is helpful for somebody who's considering an in-house role.

The biggest difference for a litigator between in-house and outside counsel is the way that you are expected to write. As an outside lawyer, you will often write things that are very long and dense. It wasn't until I got more senior that I started doing the kinds of writing exercises that are the most directly useful for in-house practice. It was not until later on in my practice that I got experience writing talking points, scripts, and very high-level summaries to empower someone to explain something. Those are the kinds of documents that you probably never had to write in law school but are critical to in-house practice.

In-house, you are writing very short Slack messages, instant messages, and maybe emails if you have got something longer to say. You have way fewer words in which to make your point. It’s that sort of practice of distilling what's important, triaging making judgments about, “Which are the risks that we need to focus on?” I’d be like, “There are 50 possible issues and I'm glad we spotted them all, but now, I'm the filter.” I’m saying, “There are technically 50 things that could go wrong. The most probable are these three. We are going to talk about these.”

You have to understand that you have to communicate simply, plainly, and persuasively to a non-lawyer. You have to give confidence the same way you do as an outside attorney. You have to show that you are prepared, you know what's going on, and you have studied this, thought about this, and you are advising about a good decision. Those are the fundamentals. The biggest difference for in-house practice is the speed. The most useful thing you can do is practice your short form. You do that by writing your emails, bullet points, talking points, and things that are one page and less.

That translates the same valuable information for outside counsel too. Outside counsel generally knows that, like, “They need something shorter or something more easily digestible. How can we make in-house counsel's life easier in whatever they have to deliver inside the company?” When you put it that way In terms of bullet points, text messages, or Slack messages, that is a visceral image of what it is you are doing.

Sometimes, I will get things from junior associates. They are like, “We have done this long analysis. We have this memo.” I'm like, “You can have that attached to whatever it is that we are sending in case someone wants a more deep analysis, but there is no way that is what we are sending to someone who has to make this quick decision. We need an executive summary.” How is that written in a way that's helpful to you to use and then communicate things to others within the company? I have never heard someone describe it the way you have in terms of, “Here's what I have to deliver. Here's how it looks.” That is a different thing than what you would imagine.

If it is an email, it’s 6 to 8 sentences and one of the sentences is bold. I want to be very clear. There's the routine advising, which happens in that very fast, condensed format. One of the things that Brex is good about is people do read long memos. I was shocked by this when I came here because as outside counsel, I often had the experience of sending my beautiful memos with dozens of footnotes into the ether, never to be heard from again. At Brex, people do read your memos. It’s lovely. I also try to respect people's time, because if I'm going to ask you to read something long, it better be really important. If it's not one of the key business objectives but I have written a ten-page memo, I have misallocated my time.

You have to be way more intentional in an in-person environment.

That's how I think of that in terms of how we are going to prioritize the executive summary and the key points in the cover email. We’d be like, “Here's the long discussion. If you want to dig into that or have others dig into it, here it is.” It's not that we haven't done that. When you are saying quick responses like that or bullet points, you have to understand something quite well in order to boil it down to make the decision of what are the most important things. You have to have thought and consider all the other stuff. Even if you are moving fast, it doesn't mean you are moving in a shallow way or that you are thinking shallowly about things at all.

That's where the expertise comes in. When you have the experience to know, you are like, “I'm aware of this general area of the law. I'm aware of the most recent developments.” You double-check and you are like, “Is there anything new? No? That’s great. My knowledge is current. I can proceed.” You do those kinds of checks. Sometimes, it’s a phone-a-friend. You say, “I know you looked at this very recently. I didn't, so tell me if I'm right.” That gut check from your colleagues can be helpful.

Those are great. It’s honestly in a way that I haven't heard and the most succinct that you can go, “I need to think about that in terms of how the messaging is.” People will come back and say, “I need to think about how I do this.” You need to ask these questions in different companies. Ask the questions, “What is the most helpful to you? What's the best format?” People sometimes assume it's exactly the same as the way they are communicating.

That's right. Matching your client's preferences is always a good idea.

That’s right, and to what the business side is curious about as well. You have had amazing opportunities that have come to you and people who have been great in terms of training you as well. What about mentors and sponsors generally in terms of their value, what that looks like to mentor and sponsor, and how you pay it forward?

In terms of mentors and sponsors, I have been very blessed in that way to have senior lawyers who believe in me and are rooting for me.

I think about that in your story about the job that was never supposed to happen in Major League Baseball. You got the call from a person that you worked with when you were in the internships. That was someone who was impressed by you and wanted to make sure you had that opportunity.

Paul Mifsud was always a champion of mine. I was thinking back and trying to think of everybody because I’m terrified I'm going to leave somebody out. I have had so many wonderful mentors, but Paul Mifsud, Dan Halem, Steve Gonzalez, and Jorge Perez all at baseball were wonderful to me during my time there. When I was at Kirkland, Savaria Harris who's now in-house at J&J was a senior associate who helped me develop. Laura Fraedrich who was there at the time also helped me develop. There are so many. I have been lucky in my career that there have been a lot of people who I feel are in my corner and rooting for me.

Now that I am more senior, the other thing I do have is my law friend kitchen cabinet. It's peers. It's people who are roughly my same seniority who do different things than me. We are all lawyers. We are all women of about the same age, and we are all moms. I view them as my gut check. If I'm in negotiations for my comp, I’d be like, “Is this good? I'm having this experience. Am I being crazy? Is this weird or is it me?” Even being able to do that quick question of, “Do you know somebody who's done X?” At this point, the answer is usually yes. I do know somebody who's done X. That sounding board of close women lawyer friends has been invaluable as I step into this new phase of my career because we all know stuff. It's great.

Everyone's getting elevated in their knowledge and they can help everybody else more. I liked your description of it as a kitchen cabinet. Some people talk about it in a way that I think sounds a little bit more daunting. They say, “Your personal board of directors,” which sounds a little bit more formal and a little bit more removed. Everybody’s above you and you are all this kind of stuff.

I liked your description of it, and that often is what it is. You are good sounding boards. You know everybody has each other's back. You can be authentic in asking your questions. Also, what goes in the kitchen cabinet doesn't leave the kitchen cabinet. It's nice to have that space to ask questions to help grow in the next phase. I love that kitchen cabinet phrase. That's good. It's always neat to see others grow too. You can see them growing in their capacity and in what they know. It's a little bit of a marker of how far you have grown, but also, it's great to see it in others. It’s inspiring to have that group where you can see that and you are pleased with their growth.

That's a great way to close with the great, supportive women's kitchen cabinet kind of thing. I hope that we inspire many more people to build the same thing for themselves and their women colleagues as well if they don't have it already. Before we leave, I wanted to run a few of the lightning-round questions by you and see what you have to say. The first question is which talent would you most like to have, but don't?

Singing.

You can be the audience. You can be the appreciator. You always have to have someone appreciating the art. That's how I feel about painting. I'm like, “Somebody has got to admire the painting. Even if she can’t make it, at least she's there.” You need an audience.

That’s fair. I also do admire great paintings.

What trait do you most deplore in yourself, and then what trait do you most deplore in others? It might be the same.

Procrastination. Procrastination is a manifestation of cowardice at some level. That's why it bothers me so much. Pull the trigger and do the thing. It's not scary. It's only scary if you make it scary. There are things in this life that are scary that we do all the time. I procrastinate about dumb stuff and I shouldn't. For me, it's like, “I need to call to make a dentist appointment.” I'm procrastinating. What do I think is going to happen if I call the dentist? Nothing. It's an irrational failure to do something. I don't like that I procrastinate and I don't like it in others either.

I have a writing list each week. There are the personal things, work things, and various things that need to get done. The work thing is fine, but then there are funky things like that. I’m like, “How come you are not taking care of that? It's not that hard,” but it happens. They are things where you are like, “I have talked to people all day long. Why am I worried about calling this particular person? I don't know.” There's some weird thing about that. You are like, “Do it.” Who are your favorite writers?

I have so many. I love Mark Helprin and Ernest Hemingway. I also enjoy Georgette Heyer. If I like Georgette Heyer, I also like Jane Austen. I also like Elizabeth Peters on the fiction side. On the non-fiction side, I feel like I don't have as strong preferences. I don't read a ton of non-fiction, to be honest. One of the things that I have recommended to others frequently and find myself coming back to a lot is the essay collection by Simon Leys called The Hall of Uselessness.

People must remember to call you and find it a useful partnership.

There's an essay in there, in particular, Lies That Tell the Truth. It talks a lot about fiction. Usually, I tell people to read this essay when I want to know why I read so much fiction and so little non-fiction. I find it powerful. That one sticks out to me. There are some journalists who are wonderful. Ron Fournier is a great writer. There are some sports writing that I love, but the names are falling out of my brain.

The journalists who are great storytellers put you in the scene. Good writing is good writing in so many different contexts. It can be inspiring.

I didn't even think about judges on that when I should have. If I'm adding non-fiction, it’s Bryan Garner. I find it compelling the way he writes about writing. Justice Scalia was so fun to discover as a law student. I didn't realize lawyers had a sense of humor until I started reading some of them. I’d be like, “Was that sarcasm?”

There was a collection of his writings that his son put together and published a couple of years ago. They are not legal opinions, but his lectures, other writings, and that sense of humor come across. If you haven't read that collection, it's pretty cool. I have certainly enjoyed it. The point that you are making is that when you think about your favorite writers, there are so many different settings in which that can be true. Some people think about fiction or a certain kind of question when you ask that. You are like, “Here are all the different ways. I have different places I'm following writing that I enjoy.” It can be anywhere. For what in your life do you feel most grateful?

A lot. Number one would be my family. I'm very grateful for that. I feel lucky to have my husband, my kids, and our extended family.

You are all at least near his family. It's nice to have that, especially with kids. In so many ways, I say nice but it’s also essential. Given the choice of anyone in the world, who would you invite to a dinner party?

We were talking about Justice Scalia. I feel like he's top of mind, and I feel like that's part of why he's coming to mind. I feel like Pope Francis would be awesome at dinner. I feel like he would be delightful. There are so many possibilities.

I can imagine Scalia and Pope Francis together. The combination of the dinner guests itself would be its meta-story of interest.

I'm very curious about what Eleanor Roosevelt would have been like. I'm curious. I want to know. That would be another person that I would invite. There are so many people. Also, with the pressure of having them to dinner, the first thing that jumps into my mind is, “What on earth would I serve?” When the Pope is coming to dinner, what does one do?

The first thing I would think would be like, “Do I have to cook or can I have someone else do it?”

That was my thinking. We are on the same page.

I can be hosting, but I should not be cooking at all.

My husband's an excellent cook. He probably could.

You are like, “I have a good person to do that. Not me. We are going to divide tasks.” Here is the last question. What is your motto if you have one?

This is a paraphrase of Thomas Edison, “The opportunity is missed by most because it's dressed in overalls and looks like work.” It can be easy to look at other people's successes and perceive for whatever reason that they were easy. I have never met someone for whom that was true. The quote, “The goose laid the golden egg and flew off,” doesn't usually go like that. There are usually years of hard work, effort, focus, and determination behind some of the meteoric successes that you read about.

It’s also saying, “What about your own opportunities? Why isn't the right opportunity showing up? Why isn’t the right opportunity descending from the skies?” Are you working to put yourself in that position? Have you done the work and put on the overalls? Did you go and pursue that opportunity? Success doesn't descend from the sky. You earn it. Especially in these social media-driven perceptions of success, somebody else's success can look easy. It’s tremendously comforting to remember that at some level, it isn't that like. Great success and high achievement are hard. Take hard work.

Matching your client's preferences is always a good idea.

It took many years of cumulative work that went into leading to that moment. Everybody's going, “Look at that achievement.” I’d be like, “It was all of this built to there.” That’s especially true to the law.

When you read about these tech leaders, they are 25. When you read down in the article, you learn that they have been coding since they were eight. They have been functionally working since they were twelve. If you started your first job at 22, you are not behind. You are just on a different trajectory. Calibrating that is important.

That reminds me of Malcolm Gladwell on his 10,000-hour rule. If you are Bill Gates or somebody else you are talking about who started those 10,000 hours much younger than everyone else, then everyone’s got the 10,000 hours. When you are starting and focusing on it, then it's going to be a different timeline. Thank you so much for joining the show and having this discussion. You have a refreshing way and unique Paloma way of phrasing things. It gets to the heart of things. You have done that here. You have given me food for thought, and I'm sure it’s the same for the law students and newer lawyers as well. Hopefully, we can help them move forward in their trajectory with some of the wisdom that you shared. Thank you so much.

Thank you. This was so fun.

It was enjoyable. Thank you.