Episode 49: Hillary H. Holmes
Partner at Gibson, Dunn & Crutcher and Co-Chair of the firm’s Capital Markets practice group
01:16:03
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Show Notes
MC Sungaila sits down with Hillary H. Holmes, co-chair of Gibson, Dunn & Crutcher’s Capital Markets practice. She emphasizes the importance of clear and candid communication when dealing with clients, making the process smoother and more meaningful. Hillary also talks about how well-managed relationships can turn into potential referrals years later and the power of chasing after opportunities instead of simply waiting around.
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Hillary H. Holmes
Hillary Holmes is a partner in the Houston office of Gibson, Dunn & Crutcher, Co-Chair of the firm’s Capital Markets practice group and a member of the firm’s Securities Regulation and Corporate Governance, Mergers & Acquisitions, ESG, Energy and Infrastructure, Oil and Gas, and Private Equity practice groups.
Ms. Holmes advises corporations, investment banks and private equity firms on long-term and strategic capital raising. She leads clients through all forms of capital markets and liability management transactions, including IPOs, equity offerings, investment grade debt offerings, 144Ahigh-yield bond offerings, PIPEs, ATMs, green bonds, sustainability-linked bonds, blue energy transition bonds, tender offers, joint ventures, structured investments, preferred stock, direct listings and spin-offs. She also frequently counsels boards of directors, special committees and financial advisors in M&A transactions, take private deals and other complex situations. She regularly advises companies on obligations under federal securities laws, corporate governance and ESG issues. She brings a special expertise in the oil and gas and energy transition industries.
She is top ranked by both Chambers USA and Chambers Global in the category that covers energy capital markets, as well as in the categories for M&A, energy transactions and corporate counseling. Named one of the 25 Most Influential Women in Energy by Oil & Gas Investor, she has been recognized as a Capital Markets Trailblazer by The National Law Journal, a Most Effective Dealmaker by Texas Lawyer and a Woman Who Means Business by the Houston Business Journal.
Clients note she is “extremely talented and has excellent judgment,” “a truly excellent corporate lawyer capable of handling complex transactions,” “an exceptionally good securities lawyer who knows the technical rules very well” and a “very thoughtful and very thorough” practitioner.
Transcript
I'm very pleased to have Hillary Holmes on the show, a Partner and Co-Chair of the Capital Markets practice at Gibson Dunn. I would say most importantly to readers of this blog, the first mother-daughter combination of folks we've interviewed. Her mother, Patricia Hunt Holmes, was on a very early episode of the show. I'm very pleased to have you, Hillary. Thank you so much for joining.
Thank you. I'm so happy to be here.
One of the things that I was interested in having you on the show, obviously, you are a partner in a major law firm, which is one trajectory that people might want to have in a practice group leader, but you're a deal maker. We've had a lot of litigators on the program. I'm very pleased to have you share that.
Another aspect of practicing law is that it doesn't necessarily mean you're going into a courtroom. I'm glad you'll be able to share that aspect with people if they're considering what they might want to do. I know your mother has legal training as a lawyer, but what caused you to be interested in the law? Was it seeing your mom in practice, or were there other things that caused you to go into law, to begin with?
When I was growing up, I did see my mother practicing law. She was a different type of transactional lawyer but was transactional. Obviously, it was the early ‘80s, and I was born before she went to law school. She went in her 30s as a second career. I saw her go through all the trials and tribulations of being a young associate. I remember when she made a partner, and my parents popped champagne in the middle of the linoleum floor kitchen. The struggles she went through being one of the only women partners at her law firm in the city we grew up in, Houston, Texas.
It was a very energy-centric and old-boys type network back then. I watched her go through both rewards and challenges, but through it all, I saw she had a real passion for it. I don't think I totally understood what it was she did other than talk on the phone a lot and move lots of papers around, but I knew she loved it. I knew that whatever I did, I wanted to do something that I loved. I stand by that principle to this day. However, I did not love coming to work every day and going do something else. I knew something about it.
I looked at public policy, but it was always around the policy side of the world, and law fits into that. Eventually, once I finished law school, during which I had worked as a paralegal clerk at a litigation firm. I had gotten a glimpse of what litigation was like. I knew that it was not for me because I saw that it was quite adversarial in my view, looking from the outside in. I wasn't interested in that. I was interested in using law as a way to help other people accomplish their goals. To be part of a team, building something, and help achieve success in a constructive and collaborative way. I knew I wanted to do some transactional work, but when you come out of law school, it's hard to know with any specificity.
You don't get a lot of exposure to that at all in law school. You think laws are either litigation or pure policy in some regard. You hardly get to even find out that it might involve appellate litigation. It’s like when I do, you read the cases, but you don't realize what's involved. It's hard to get that exposure. There are different aspects to transactional work, and how you even know or find out which thing you enjoy is something. It seems like you almost have to do either in the summer experience in law school or after.
It is important to keep an open mind as you start your law career, law school, do your summer programs, or as a young associate. Trying on all the different shoes to see which one fits is always a good idea. I knew I wanted to be on the transactional side. I never practiced litigation once I came out of law school. I worked quite a bit as a paralegal clerk in litigation, so I had a good sense of it. I was confident in that decision. I knew that it would align with what I was interested in otherwise. The other thing I thought about doing was being a banker like an investment banker.
I’m deal-making on that side on the capital or finance side of things, but I wanted to move back to Houston eventually. I'd gone away for law school and college and the time between. Once I decided to come back to Houston, back then, you couldn't have a big investment banking career without being in New York. That led me to law, and the law I ended up doing is the kind where I work on a daily basis with an investment banker. I’m doing deals on the legal side, which is a good fit for me.
You're able to find that fit. There are many other considerations in your life that factor into your career. In this case, you're like, “Where I grew up, I want to be near my family. I'm going to go there and see what's available there as opposed to available in other settings. There are a lot of other things that go into that calculus that you were able to be the legal counterpart to those investment banking counterparts that work out well. Good fit in terms of what you wanted to do and what's possible physically where you are.
Although, I don't know if that's changing after the pandemic or whether more people are open to being in different places. They say they are, but I don't know how that's going. Were you able to try out the different aspects of transactional work during the summer or at the law firms? The great sweet spot for me, the counterpart to the investment banking side, but is that where you went immediately, or did you try out some other things too?
Even though you are terrified to do something for the first time, you should definitely give it a try. You'll be surprised at how ready you are.
No, I definitely tried out various things. When I was in law school, you could clerk in the summers at multiple law firms. That's less common now, but some do it. I worked at two law firms the first summer and three law firms the second summer, and for each one of those, I made sure to try out multiple practice areas. I had a nice buffet of non-litigation options by the time I was done with law school. Basically, I had whittled it down to knowing I wanted to be in the capital markets or mergers and acquisitions, but that deal-making side. I kicked around oil and gas transactions and employment law, which is transactional in some way, not litigation employment.
I tried out public finance, which was the practice that my mother had spent her career in. I like that because it's similar to capital markets. It's capital markets for municipalities or raising capital for nonprofits, hospitals, and things like that. It's quite similar, but rather than big public companies, which is what I do. The trouble was that in the small town that Houston is, especially back then, with all the closings and the signings of the deal I went to, my mother was on the other side of the conference room. The people who knew me as a little girl was coming up and being like, “I remember when you were only this high.” I realized that was probably not the best way to kick off my career as my own person.
I ended up going to the for-profit side of capital markets. I tried a lot, and some law firms have rotation systems. They want you to go through several practice areas once you come out of law school. The firm that I joined was more open-ended. You needed to choose litigation or corporate. With corporate, you could try out as many different options as you like, but I found capital markets pretty quickly. To your point earlier, your practice ends up being partially a function of your circumstances at the time. That could be geography, but it's also the market and what legal services are demanded at the time.
At the time, capital markets in Houston were very busy and active. There was a ton of work to do. I was able to get a lot of experience quickly. It helps you go up the curve faster when you happen to be in this situation. I enjoyed it. It was fun. We would do stock and bond offerings. It was very collaborative and fast-paced. It's code-based because of its securities laws. I like rules and learning, understanding, and following them, so that was nice.
It's also a friendly type of practice because everyone on the deal, whatever side you're on, you are working towards the same commercial objective. The bankers and the company want to make money. The lawyers on all sides want to make sure no one breaks the law. The deal gets done on time and is a huge success. We all win in the end. It's not a zero-sum game like some litigation can be at times. I liked that.
Back then, everything was done in person. You spent a lot of time together until 3:00 AM in conference rooms doing these deals. You got to know each other well and each other's families as a young lawyer. That made it a lot of fun because you were in the trenches with peers, whether they be at your firm or other law firms. From those, I've developed some of my most lifelong relationships. Somebody I was at 3:00 AM as a second-year lawyer at the printer is now a partner at another law firm. We can refer each other to business and work together on deals. It's seamless.
We know each other so well and trust each other. Those relationships were special. I loved all those aspects of the capital markets practice. Pretty quickly, I latched onto that and decided if I'm going to pick this, I'm going to be good at it, which requires committing to it and focusing on it. That helped me get to a point where I was running deals as a third-year, faster than others because I knew right out of the gate that this was the match for me.
How do you get those opportunities? I know that some associates are like, “Either I'm afraid to ask, or I don't know how to be in a position where I can get the opportunities to enhance my skills, whether it's in the litigation taking a deposition or in your case, running deals. Do you have any advice for them in that regard?
I would say don't be afraid to ask, and that applies when you're a first-year associate and now, to me, many years in. You have to ask for opportunities. If you sit in your office, waiting for the phone to ring, it'll ring even less than if you walk away from it, go knock on some doors and tell people what you want. Sometimes, especially as a young lawyer or a new associate, you may not know what you're even asking for. You know the vocabulary.
Some of your readers aren't quite sure what I mean by capital markets, so that's fine. Take the opportunity to ask what those terms mean or offer to take a more experienced lawyer out to lunch or coffee and ask about their practice. You might find your future in some cup of coffee that wouldn't happen if you didn't ask for it.
As you advance and get the opportunity to be the first chair equivalent, run the negotiations or lead the 60-person calls we have on a daily basis in capital markets and everything and learn the art of doing that well. I say explain to the person that's more experienced than you and supervising you that you want to master that skill and you want to learn it. Can you observe it more? Take advantage of being back in person now. Sit in the partner's office and listen to how they handle the tough issue on the conference call or the video with the client, how they lower blood pressures, or how they get people motivated and all the soft skills that make an effective transactional lawyer.
Articulate that you would like to develop those skills. Any tips that the more experienced lawyer would like to share with you, you're open to them. You'd like to have the opportunity to test it out. It's important that you raise your hand and make clear that you think you're ready to try X if whatever opportunity you want if it hasn't happened naturally for you. I know we'll talk about mentors and stuff at some point in these interviews. It always comes up.
One sign of an amazing mentor you should grab onto is somebody who pushes you a bit into the deep end, who doesn't always wait for you to ask for the opportunities, “You're ready to go do this. Go lead the client through the purchase agreement. Go negotiate with the other side. I'll be right here if you need me, but you're ready.” Even though you're scared, it sounds terrifying to have to do that for the first time. If they say that to you, you should 100% do it. You'll be surprised at how ready you are.
They see that in you. If there is a point in asking, it's important to ask for opportunities in the context that is better. You already have a relationship, and somebody is already giving you other opportunities. You say, “I'm ready for this other one,” but also to be in a relationship with someone who is interested in your growth and basically says, “I see you're ready for this. You may not know that you are, but you are. Go ahead and take her off this aspect of the deal, the case, or something like that.” Sometimes, it's valuable to have that because sometimes you don't see it in yourself or wouldn't have asked for that.
With your particular personality or whatever, making that ask is harder for you. You don't say it like it's the easiest thing in the world, but I didn't ask as much as I probably should have. One of the skills I've developed as the years have gone by, including post partnership, is asking for opportunities internally, within the law firm, and developing your practice. As years go by, asking clients and friends like, “You should hire me for this deal. I have the skills that will add value to it,” or “You didn't hire me on this one, but I ask that the next deal that comes, you keep me in mind.”
I can point to several big lucrative deals I have done in the last few years that are a direct result of the fact that I asked for years ago. I put out the ask, and when the opportunity came, it was sitting there. I got the opportunity to interview and be the counsel for the deal. If I hadn't asked, I wouldn't necessarily have gotten the call. There's no downside. If you ask and they say no, you're in the same position you were in.
Sometimes people think about, “It's important to do the ask.” It's hard enough to make an ask but to think of it as an ongoing thing. People think, “I asked, nothing happened. I'm not going to ask again,” or “I'm done. I did the ask as though there's only one.” There's no moving part from that, but as you described it in the business development component of it with clients, you say, “You make the ask for a particular opportunity. If you're not chosen for that opportunity, you either find out why or what was your decision-making? What were you looking for?
The next time there's this opportunity, can you please put me into consideration? I'd like to be considered for that, or here are the reasons that we would be great for that.” That is that extra step people don't always take or are maybe a little like, “I was rejected. I'm not going to take that. I'm not going to move it forward,” but you're looking at it as a longer-term relationship. That particular deal may not have worked out, but I'm still competent.
There's a great fit. We could be of great service or help to you. There might be something else down the line. I'd like the opportunity to be considered for that.” That is something that some people require a little bit of resilience and persistence. People say, “I feel upset that I went for this and it didn't happen. I'm going to blink away.” I’m going forward with it. Part of that is like a mindset about that. That's one data point in a continuum of potential other opportunities.
There are three important things you're saying there. One is that this is a long game. No matter what city, market, law firm, or whatever you're sitting in, it's a small world. Keep that in mind at all times, which plays both ways in terms of getting and giving opportunities. The second thing you're saying is about resilience and persistence.
Especially as women, sometimes, depending on what market you're sitting in or what the situation is, we have to be more persistent than men. They're off too. Yet we are raised in our society to not be as persistent with career-related things. The asking needs to be transactional. Ask because you will add value to the situation.
You, on your own merit, deserve this opportunity. It doesn't have to be because you're going to do something for them. That's what you're going to do for them is an intimidating lawyer. That persistence is important. You don't ask once. You get that again, and it's all a long-term relationship, so those two dovetails.
The third thing is recognizing when there's an opportunity in the failure or opportunity in the loss. I pitch a lot. I interview for opportunities all the time because a lot of transactions are in the higher counsel based on the particular transaction. Competitive interviews all the time, or a company has decided to replace the outside corporate lawyer that they've had for twenty years.
They'll do a very competitive, robust RFP process, and we'll go through that. I have learned in all of those, the ones that I don't win, which I'll say it's the minority, but the ones I don't win, that's a learning opportunity. That's still a win for me long-term because I will learn something valuable from why that didn't work out. It only works this way.
An effective lawyer focuses on clear communication, effectiveness, and efficiency. These all boil down to impactful negotiating skills.
If you apply that lesson to make adjustments or learn from it and apply the lesson as opposed to hearing it and soaking off about it, not doing anything with it as a useful tool, even the losses or wins will increase your win rate going forward hopefully. One time, I interviewed to represent a board of directors in this big transaction.
I thought, “We nailed it. We’re totally going to get it. I've done a lot of that work in the past. I'm definitely going to get hired.” We weren't hired. Someone else was hired. Even though I did not know him very well at all, talk to the chairman and said, “Talk to me a little bit about what happened, not challenging the decision at all, transaction, but anything I should know.
This was a few years ago, and it was a very valuable lesson. He said, “This is a remote interview. You got on the video and focused too much on the team. We're all deferential to your colleagues and everything. What we're looking for is somebody who's going to come in. Tell us that it's going to be okay, and they're going to get the deal done. Here's my team. I've got all the subject matter experts, and I've got a deep bench, and don't worry about that.”
We wanted a leader, a real quarterback who was strong. Instead, it was very much passing the mic to the other team members. He did say to me, which was unfortunate that he said, “It's not totally your fault because women always do that.” Even with that comment, I learned that when interviewing for different types of roles, you're obviously going to adjust the pitch accordingly because you want to demonstrate that you fit the particular role.
What I realized was in those roles, as I got more senior, the clients were expecting me to be there, outspoken, and a strong leader. Whereas in the years before, I was a little bit younger, not that I'm that old, but a little bit younger in my practice, at least, and there was always a more senior partner above me, and I don't have that anymore.
That was a great lesson of we've entered a new chapter of my practice as you age and as things evolve. I needed to make sure to present myself that way, which I was totally capable of doing. I wasn't used to it yet, or maybe I was nervous about doing it or felt like maybe it was a little bit of a female thing. I don't know, but I don't do that anymore and haven't had a problem since.
He was straightforward.
He was because he was like, “You're obviously very talented. Your reputation is outstanding.“ It was that one problem that had us go with the man leading the all-male team. Frankly, they knew that they knew that team better. Even in the losses, you can find real value.
I think of all the soft skills, and that's part of marketing too in terms of business development. Getting better also gauging how that team works and what teamwork or leadership they're looking for. Part of that is almost a cultural aspect of what they were looking for. Possibly with a different team or maybe even a woman-led team on the other side, the teamwork and collaboration part would have been seen as a positive and valued. How you present and read the person or the team you're presenting to is almost a refinement of your skills too.
The ability to read the room and connect with the individuals on the other side of the room or the Zoom is absolutely critical to being an effective dealmaker. You need to understand where everyone's coming from. It's not the deal terms that you're working on. It's the human beings that you're working with. You have to navigate that on top of the law, the deal terms, and so forth.
Having that soft skill is valuable. Women are skilled in that area naturally. It's the way we're culturally raised. In any event, I find that skill is not useful. You're talking about interviewing for the job context. It's critical to the effective deal-making side of things too. Figuring that out, I'm never bashful about asking at the beginning of the deal or as we move through the transaction, and different deals have different levels of adversarialness in terms of, as I talked about, capital markets isn't much of that at all.
There's a little negotiation, but in the end, you're only going to get in trouble if you don't get the deal done as opposed to getting it absolutely done. I also do M&A, and that's much more adversarial and contentious. I’m still trying to get the deal done, but there's much more back and forth and give-take. In both those situations, though, it's still very important to understand the humans involved. It's not like who you're negotiating against and understanding what kind of person they are.
What's their style? How can you leverage some tools? Do you need to be friends with them? Do you need to be super tough with them? That's all doing your job. It's not personal. It's your job. We're all friends outside of work but also understand the personality of your client. It’s the little things. When I have a new relationship with a client, I will ask them down to the detail, do you like to be contacted by text? Do you go to bed early, or do you get up early? Do you have any vacations coming up or big events in your life?
I had a general counsel whose husband was having surgery, and we're doing a big deal. I needed to know that. It's not effective to be bugging her at that time and pretty private about it. When I'm doing capital markets deal, are you somebody who wants to be down in the weeds with me and want to be updated every single evening with the checklist and the minutia or do you want me to tell you it's going okay and call you when there's a problem? Understanding the personality of the client will allow you to be not just a better lawyer but a better service provider, which is key to long-term relationships.
In terms of thinking of asking those questions, those come out over time usually but thinking of them upfront. That also sends a message in terms of whether you are sensitive to how they operate their needs as a professional and how they work, early morning or not? The things that you would do with your own team internally, like, “I'm going to send you crazy emails at crazy hours, but that does not mean that I want you to respond to me at those hours, live your life, sleep, whatever, respond to them when you get them.” You lay that out. It’s like, “This is how it works, but don't worry about it.”
It's the same thing. You're all one big team together. I'm thinking about that specifically with regard to a client. Hillary, that sends a good message, and it resonates. It was something that your mom said in her interview too, which was that “We're service-oriented. We shouldn't be properly focused on our clients.” By asking those kinds of questions of your clients at the outset, that's what you're telling them.
I'm telling them that I care about them as human beings. I care about making sure their deal doesn't just get done but goes smoothly. In the deals I do, I work with the CFO, the CEO, or the general counsel. They are also running a public company. The deal I'm doing for them is not the only thing on their plate. I will never forget that. That's why it's important to be clear in the communication, very organized, and always polished in front of them so that they know you are on top of things. They can focus on running their business, doing their other deal, or handling litigation.
They've got a lot of other stuff going on. That's another question I asked, which isn't about so much intersects between the human and the entity client, which is what else is going on at the company? Are you going to be flying to another country to negotiate some joint venture while we're doing your capital markets? What times are you going to be on?
That thing is important as well. Especially the capital markets context, to help the other side understand those sensitivities as well without revealing anything you're not allowed to reveal. If I'm representing the company doing the deal, here's what's important to the company. You're representing the banks. Your job is to help the banks go through their process so that they can make this deal happen. Here’s what we should focus on. Here's what matters. Let's not waste time with things that don't matter.
For the actual deal-making component, understanding what's essential to the client term-wise, but also other things in terms of what's going on with the company, timing, and all of those factors into what flexibility you have on certain points for the deal.
Understanding in any deal what the ultimate goal is, because at this particular moment, maybe you're trying to raise $1 billion. Why do you need it now? What's coming down the pike in the company's strategy that we're managing for now? How does it fit in the larger context? Once you understand those things, the main goal of the transaction, and how it fits in larger contexts, you can help clear out the underbrush and the noise and focus on you know if you're negotiating a term of an agreement?
Do we care about that? Maybe it’s sleeved off our vest, and maybe we’re going to read it for something because they don't know it sleeves off our vest or whatever. We need to know the significance of everything, which requires having full context for the transaction which requires candid communication with your client at the beginning.
Having candid conversations in terms of what works best for them, what other stresses they're going under, or the company has at that point in time puts you, I don't want to say necessarily vulnerability, but it increases the trust because you're having those discussions. Tell me about the things we need for the deal too. There'll be more trust and authenticity in those discussions also.
One of the most important traits of an effective deal maker is clear communication, which goes to understanding, effectiveness, efficiency, and better-negotiating skills. Clear communication is critical.
Address problems right away. Just be constructive and never think about hiding it. It won't work out ever.
What advice do you have for women either starting out in law firms or who would like to become a partner in a law firm? What kinds of things should they consider? Whatever stumbles you made that you could tell someone doesn’t do that one.
We need another hour for that. I look back and learn from my own mistakes. I am big on mentoring and helping younger women lawyers or younger talents all around. This is particularly sensitive to some of the issues women have to deal with that men don't. Men have to deal with some issues. Women don't. Some of the mistakes I would've made along the way were taking it all a little too seriously and being hard on myself sometimes, especially as a young lawyer. I still do it now. I say the one trait I'd like to get rid of is my ability to play back something I did. I could've done that differently. It's spinning in my head like a VHS tape on rewind and play.
There's a difference between going back and examining that for a purpose. What can I learn from that? It’s like you do, going back and asking people, “How come this didn't work?” This is like an ongoing loop.
I’m bad about that. I'd like to get rid of that trait, and I'm working on it. Especially when I was a young associate, even some mid-level, senior-level, if there were anything that went wrong, there would be things that go wrong. You will screw up many times, probably once, big time. It will happen. That's okay. In my saying, that was such confidence. It means it's happened to everybody else you're working with and everyone you're working for. They get it. You don't have to completely hit your head against the cement wall when making a little mistake. The key would simply be to quickly bring whatever it is to the right supervising attorney's attention and come up with a suggestion for how to handle it.
I'll admit I once sent out the wrong black line of a merger agreement as a young associate. The changes weren't shown correctly to the other side. I almost hung up my law license that night. I was like, “I can't even run a black line, but it was less than two minutes of being out there. It was like, “No.” I immediately fixed it and called the partner right away. He was upstairs in a conference room, negotiating the deal. He's like, “Send out the right one right now.”
I still beat myself up pretty bad about that. I obviously still remember it to this day. The point was to address the problem right away, be constructive about it, and definitely never hide it. It won't work out ever. That's one piece of advice I would give younger lawyers if you're of that Type A like me. The other one would be, back to what we talked about earlier, but not being afraid to put yourself out there and ask for something or take on more responsibility. I was fortunate at the law firm I started at to have a mentor or a senior partner I worked with a lot like most of the time. He was very good at pushing me out there, letting me run the deals farther and farther, closer and closer to that first chair, and totally take it.
There were some things that he and others won't ever let go of. At some point, I remember a client asking us to come. We're doing an IPO for this gigantic company. I had been running it. I was a first-year partner, and they said, “We want you to come and present to the board of directors of this huge company in another city and explain to them the IPO. We want to get their approval. It's a big deal.”
I was like, “I'll check with senior partner so-and-so.” He's like, “Why do you need a senior partner so-and-so? We want you to come and do the presentation. We don't need him. You're a lawyer.” It was one of those first times as a first-year partner I was like, “You're right. I can do this.” I’m very nervous. I flew out a day early to make sure there were no travel problems. I tried my little speech 100 times. I still remember that moment on the phone with him.
I was a little more hesitant than I should have been in recognizing I was ready for some of those first-year roles. I've learned that lesson. I'd pass that on to the younger associates. Don't get over your skis, but don't be afraid to step out there. Let me say the third thing. We talked about earlier the long game. We're telling those stories about sitting at the printer as a young lawyer at 3:00 AM with lawyers at other law firms and all that. The bankers too. Now, they're the managing directors, the highest-ranking bankers at the various banks, or the CFO of whatever giant company, and all these steps. Those relationships you develop in the trenches as the baby lawyer, doing due diligence, which everyone hates.
Thinking about developing a relationship through that, of working in the trenches together, that bond.
You grow up together, and there's no replacement for that. I remember many years ago when we were baby lawyers together. You can't replicate that another way. Recognize that for two reasons, and one is the relationships you develop as even a first-year lawyer, the companies, the banks, the other law firms, or whatever. Those could be your clients in fifteen years when you're a partner or sources of referrals.
You're developing your reputation relationships from day one. The second lesson to learn from it is don't be a jerk to anybody. Once you are, it's very hard to shake that reputation, particularly if you stay in one market or practice area. The second is that you'll turn off all these opportunities that you could be developing from the start.
Newer lawyers don't consider that those relationships could, several years later, develop into something else. It's important to have those relationships, to begin with. Sometimes there's short-sightedness in terms of, “I'm going to be up for partner, and I need to have clients. You start looking around now.” It's like, “No, you need to be developing relationships much earlier. However, that might be.”
Whether it's in the deal trenches or the community, leadership positions or the bar, or other things, you're developing these relationships long before they may become a client or referral relationship. That's what makes them valuable because they're not an exchange. There's a relationship that ends up growing towards working together when you're in the position that you can trade work that way, but it's not transactional.
If you think about law firm practices transactional, you're going to be miserable—there are absolutely people who do. You don't know where opportunities are going to come from. It might not be from a lawyer or any deal person. I had a deal that came to me that was very large. One of the ways they got my name was from somebody who was a staff member at a law firm I had interacted with and been on the other side of a lot of deals. I'd spent a lot of time in their conference rooms.
Now she has a different business and whatever. They were friends who came about. She was always impressed by her. She was so respectful and friendly. It wasn't anything about my lawyering either. They'd gotten my name from a bunch of other people that I'd done work for. Having a friend say that too from somebody I didn't even know. You never know what impression you're going to make. You're always building your reputation and brand every day with everybody you interact with. It's important to be yourself and genuine. You can't fake it. If you fake it, people can totally see through it. You'll eventually probably be pretty miserable having to pretend to be something you're not all the time.
I definitely have that. It can be hard, though, because in the short-term, should I speak on that panel, or should I fly somewhere for dinner? It can seem like a hard decision. I don't know if anything's going to come from that, but I'm going to do it anyway. Sometimes it's like somebody was in the audience, and they remembered you ten years later and, you know, referred you for a particular matter or, in your case, a deal. Who would have known?
Certainly, I didn't know anything was going to happen from that. I did it because I committed to doing it or for whatever reason. There was never any sense that nothing specific was going to come from that, and nothing did right away, but it's the long game of continuing to be out there. I even had a situation where I got a job at a new firm because of something I had agreed to speak at, and the managing or recruiting partner was the chair of this organization. He liked the way I presented. When they had an opening a few years later, he was like, “I know exactly who should we call for that opening.” Who knows, basically? You never know.
You don’t. Your colleagues that you work with as a young associate at a law firm, it is certain that many of your starting class will not stay forever at the law firm. I'll go work at a company or go do something else or whatever. Those relationships within your own law firm are important. Several of my clients now are associates who I trained and went out as general counsels at public companies. I love it. It's great. We have a real personal relationship on top of it. It's rewarding.
It's great to see them go into those positions and be in the position to work with them. It's nice. Are there particular lawyers that you've looked to that you admire? You yourself are a terribly genuine person, but in terms of emulating anything, you particularly like about their approach to either deal-making or law practice.
I've always been an observer of people. People watcher as they say. I definitely had certain partners I worked the most with, but try to work with a wide array as a young lawyer so that I could observe different styles. I could observe things I wanted to pick up and things I realized I did not want to pick up. You still learn from seeing those as well. I have been very thoughtful about what skills I want to emulate. I can't say there's one lawyer in particular. Back to the mother-daughter thing you introduced at the beginning, watching my mother carry herself as a strong female transactional lawyer at a time when she had no female peers at all.
Doing that with class and grace and playing that long game, that's definitely been something I've emulated. There are other women lawyers in town that certainly I have looked up to and sought out, taking them to lunch, asking for their thoughts, and male lawyers I've taken to lunch and asked for their perspective, how did they get to where they are? What skills do they find most valuable? It's both watching and emulating but also seeking out information from them directly—no one person in particular. I enjoy pulling on traits from everyone I see.
In my practice, when I have to present to boards of directors, as an example, these complex concepts in a way that is concise and with clear, competent advice that is well-informed but presented in a very efficient way, as you would present to a governing body. I've emulated some skills I see from others, like professors or politicians. There are lots of places where you can develop skills that you can use effectively in your law practice.
Sometimes people get too narrowly within there. I can only get valuable ideas from other lawyers or somebody else in my space, but especially you've focused on relationships and clear, crisp communication. There are so many other arenas where that's valued and presented much better than lawyers can do in some circumstances known for our legally is. You can get some great ideas for presenting some complex ideas in a way that's very concrete and not simplistic but more simple from a lot of other venues.
Don't be a jerk to anybody. If you do, it's very hard to shake that reputation. You'll turn off opportunities that you could be developing from the start.
Whether it's good, speakers come in all shapes and forms, and they're not necessarily lawyers. Doing that cross-pollination, I've done that in writing, where I use different techniques or skills from different types of writing for my appellate briefs and morph them into that. Good writing is good writing. The same thing, good communication is good communication.
It's the mirror image or a compliment to what we're talking about in terms of emulating skills that you observe others but also asking for feedback on your skills as you develop something you shouldn't be afraid to do. As a young associate at the end of the deal, I was always going to the senior associate or the partner, whoever was the most involved, supervising me and saying, “What could I have done better? What did I do well?”
I’m not taking up much of their time but seeking that feedback while it's still fresh. If you waited a month and moved on to something else, they can't even remember the deal happened. As soon as the deal's over, “Can I have five minutes of your time in your office?” Get that feedback in real-time. As I started to have my own clients, and I still do this to this day, we finished the deal or came to a major milestone in the deal. How did it go? What are we doing well? What am I doing well or not, or whatever?
It’s an open question. Often, they don't have anything, but sometimes they'll have something that's either an accolade or something in particular. You're like, “Okay, great. We're going to keep doing that.” It's a suggestion on an improvement that could be made. That goes to having that trust and that line of communication with your client, and if you've opened it early on, it's not so weird when you come to that.
If you've already had the conversation about what time they wake up in the morning, circle back and say, “Are you happy? Are things going well? How do you feel about it? Anything we can be doing differently?” They're like, “No. great.” Usually, there are little things. Having that line of communication is important.
I've had some clients who, every now and then, have said, “So and so on, the team isn't a total match,” but they feel comfortable coming to me. If we're not sending the checklist every night, I want to see a checklist every night or whatever. They feel comfortable raising those points in real-time along the way so that you can make the deal more effective and the process more efficient, rather than only knowing about it on the backend.
If you don't know midstream, you can't make corrections until the end. You're like, “Okay, next time we'll do that.”
Your neck is high in it. Maybe you're going 36 hours at a time, and they'll go. Unless somebody says something, you're probably not going to pick up on the body language. Seeking feedback as a young lawyer is important so that you can figure out what skills to start emulating or not emulating.
You have a very client-centric, the client institutionally, and the people at the client. You have a very client-centric and people-centric approach to thinking about the deal, the framework, and the questions along the way that is instructive. It's good food for thought. I don't know that even though lawyers will say they're plan-centric or service-oriented, there's a way to say that. There's a way to exemplify that on a human level, which you're definitely showing by the way that you say you ask these questions and are attuned to the client.
I totally agree. They're all different types of personalities out there and different lawyers with different styles and ambitions. I find for me that the job is the most rewarding when it's all about the client and about the deal. It is not about me. I know some lawyers who are most interested in having their name on the press release or getting a certain number of deals. It's more about the kill than it is about for themselves than it is about helping a client achieve whatever the goal is. However, they define it. No new space for ego in my deals. It's all about confidence, for sure, but not ego.
I think that goes to meaning, too, like the meaning of what you're doing and why you're doing it.
It gives your work meaning. You don't mind your 36-hour stretch. You're as invested in seeing this be a success as the CFO or the general counsel, whoever the human being has been tasked with making it a success for the company. It's rewarding to do the virtual high five at the end.
Part of that, too, is making the right choice for you in terms of what you enjoy doing. I had a flashback to my own practice where I was clear that I did not want to do trial litigation because I felt badly cross-examining people. I couldn't do that to people, made them feel badly and couldn't do it. I'm like, “What will I do?” I minded spending all those hours and trials doing that work.
Once I knew and found appellate law and was locked in a room for 36 hours working on a brief like, that didn't bother me. I was fine with it because I felt like what I was working on had meaning to me and ultimately to the law that we can make change changes in the law or have an effect for our client, but beyond our clients on appeal.
It was something that worked for me in terms of it being fulfilling and meaningful, and I'm good at it. All of those things together are the perfect storm. This is what I like to do, where I can have the most impact. You have that sense of meaning when all of those things converge, and you find that thing that you feel like you can contribute to.
You talked about it a little bit in that client pitch where the potential clients said, “You need to be in a stronger leadership role.” What does leadership mean to you or look like? What lessons in that regard? You have the practice group leader position, and you're a leader of deals. What does leadership look like to you? What does that mean?
To me, it means helping other people succeed. It means doing what it takes to have others fulfill their potential and realize their ambitions. It's empowering others. Sometimes that requires leading and having them follow along the way. Sometimes it requires being behind them and pushing them. I’m a leader. I'm a very servant-oriented approach to leadership.
We didn't talk about this, but a few years ago, I only changed law firms one time and only law firms all the time. When I did, it was with a team of lawyers I practiced with for a long time. We all knew each other very well. We opened an office in Houston for Gibson Dunn. They'd never had one here before, so it wasn't like opening your own law firm or something. I know some litigators do.
It was establishing a new law firm's brand and name in a city it had never been in before. That's a very legal market that was challenging. The leadership that I saw us all embrace as a team in that regard knew each of our roles. What was going to be our role in leading this office from 0 to 50 lawyers? Having no deals to being number 2 or 3 in the city for all deals across all sectors, for five years, I've done that, but that requires strong leadership in terms of vision, purpose, strategy, and discipline.
At the same time, that flexibility and teamwork, so that everybody's rising up, realizing their success in however they define it. Each one of us brought something different to the table. That's why we made such a great team. We all trusted each other. Each person leads a different effort in a different way. If you have all those leaders doing that in a servant-based and ego-based approach, the whole team succeeds. That's been an interesting exercise in terms of leadership. I feel like I've grown a lot in that area as a result. In terms of leading my deal teams, a lot now it's about being very clear in the communication.
It’s like we talked about earlier, understanding the client's goals, the context of the transaction, and the personalities involved. When I assembled the team for a deal, there would be asymmetry and information. I will know more about all those things and the lawyers comprising the team. Assemble everyone, and by the time that meeting is over, there should be no asymmetry of information. They should know everything I know about the personalities involved, the deal's context, the deal's point, and what will define success here.
Communicating to them, “This client likes to do things this way.” The agreement must be signed by June 1st, and here is why. Being a good leader is also clearly defining the responsibilities that people have and making sure that they feel empowered to own those responsibilities. Even the summer associate who might be working on the deal here is the first-year associate to the most senior associate or the junior partner working on the deal.
You understand that the buck stops with you on this particular work stream or figuring out this issue. Make sure they have all the resources. A leader doesn't throw people into the deep ready swim. Make sure they have all the tools they need to make it happen. Ultimately taking responsibility for making sure it all happens. If something goes wrong, it's my responsibility regardless of who made a mistake on the team.
That's another part of being a leader. I had a situation where something glitched a little bit. It wasn't a big deal, but I needed to go to find like, “Here's what happened. Here's the way it's getting addressed.” It doesn't matter whose fault it was, but maybe the other side was involved. Not even getting into that with them, and I didn't. Here's how we're going to solve it. I wanted to keep you in the loop, no blame, nothing, solutions-oriented. A leader does that, too, and doesn't waste people's time by pointing fingers or anything. It takes the reins when they need to but also empowers the team to project when it's appropriate.
Every day is a new opportunity. Regardless of how hard yesterday was or how much you messed up, today is a new day, and you can earn it again.
If you have that sense of ownership as a newer attorney for however slice of the deal that you're working on, it's much better to have a sense of ownership over that rather than to be like, “I have this one piece, so I'm going to do that and go home.” It's like, “No, having that sense of ownership helps you expand the things you own over time.” It’s like your heart is in it in a different way.
Therefore, the results come out better. If you have that ownership, you get more opportunities to own more things. You see that. As a partner, you see the difference between the newer attorneys who you’re like, “They took that seriously. They had a small piece of something, but they did that to their utmost, but I’m going to trust that person with more work.”
Earning the trust of the more senior lawyers as a new lawyer is very valuable. The things you’re usually entrusted with as a new lawyer are the kinds of things that, if you focus and are organized, never miss a deadline. If you have to, for some reason, you communicate early that there’s a problem. If you do those things, you’ll earn the trust and have loyal customers internally within the law firm very quickly. That’s one of the issues.
I sometimes see them as some of the newest lawyers. They are very good at execution, delivery, thoughtful, professional, and get it done that the more senior leaders keep coming back to them over and over again. Eventually, they get the reputation like, “Call so-and-so, she’s great.” They don’t know how to say no, and their plate gets too full. Sometimes that can be challenging in terms of limited resources, and maybe there’s too much. Your work slides a bit. It’s important.
You want to be like the go-to person. You want to be the one that everybody’s like, “You have to call that person,” but you have to figure out how to balance all that. People are afraid of upsetting someone and not being available or whatever. It’s like, “We understand there are a lot of other things. Let’s figure out how all this fits together.”
It goes back to the clear communication end. Be upfront about the fact that, “I think my plate is too full. I would love to work with you. I’ve wanted to do that deal, and here it is, but I’m on these five other things. What’s your advice on what I should do?” You don’t have to figure it out yourself.
Sometimes that involves the partners talking to say, “Is this the deadline? Is this, this? How can this fit together? I’ve enjoyed this. Thank you so much, Hillary. It's been fun to learn about how you approach things, and your perspective is kind but very wise.
I enjoyed it too. I’ve enjoyed hearing about how you found your calling too. That's very interesting.
Before we close, I want to ask a few questions from the lightning round if you're ready to go. What talent don't you have but you wish you had?
I wish I could dance. I did ballet for nine years as a little girl and jazz tap, fun fact, for 6 or 7 years. I'm a terrible dancer. At weddings, I'm the one standing by the bar. I wish I could dance.
How did that happen? That's so funny. When I was young, I wanted to play the harp, but my parents said I had to choose an instrument that could fit on the school bus, which was so bulky and unwieldy. I played the violin for a year and a half badly, though. I never practiced it or anything. I was like in rebellion for the fact. It was terrible, but at least I could sing. There's that. What is the trait you most deplore in yourself, and what is the trait you most deplore in others?
The trait I deplore in myself is that feedback loop that I was talking about, lying in bed and replaying the scene and being like, “I should've done this other thing differently,” when I know good, and well, that is not going to change reality at all. It wasn't a big deal, and it's not even things that I did wrong. It's like, “I could have done this other thing. I don't even know. It’s such a waste.” I love getting rid of that trait and am working on it. In others, closed-mindedness, especially when combined with hubris, pushes my button like nothing else. I have to deal with plenty of lawyers on the other sides of deals that fit one or both of those characteristics.
I can see the hubris sometimes.
I've learned the art of hitting the mute button and letting them play it out. That skill I've worked very hard on, especially as I've gotten more senior in terms of you can't help it. Let them be the way they're going to be in the end. My goal here, again, defining how my client views success. That's the only thing I'm trying to do. I'm not here to make this person a nicer person or totally change their mind. I'm trying to align as we've defined it.
It’s accepting what you can't change. That's the way somebody is. That's part of the path where we have to go, and we'll focus on the path. I can think of only a couple of times when I was litigating, not an appeal, but in trial litigation, where I would like to try to stay classy, and somebody would start yelling or doing something. I was like, “I'm going to hang up the phone now because there's no point in this.” One more time, and I'm gone. I'm not going to take that thing, but alerting them, like, “You have an opportunity.” You chose not to take it, and no big thing. I'm going to hang up. Call me back when you've gotten over that, and we can have a solid discussion.
When you're ready to be professional, give me a call. It's important to remember that. I see more younger lawyers than ever. It might be exhaustion from the last couple of years or whatever it is, but being a little too contentious and adversarial when it's not necessary. Don't waste your energy.
I'm like, “Don't you take this? Happy to work with you later.” Who was your hero in real life?
My hero in real life it's two people. One is my maternal grandmother, 98, who passed away in 2021. My paternal grandmother turned 100. I hosted her birthday party. She lives around the corner from me. She’s had COVID twice. I'm going to live forever. I grew up spending a lot of time with them. One was in New Jersey. One was in Houston during summers and the rest of the year. They were my heroes because they were strong women who were always classy and poised. No matter what came their way, they kept their cool. They always had sage long-term advice for me. As I struggled with different choices in life or different problems I ran across or whatever at all ages, they were always there as steady guides. I'm so grateful for them.
It's amazing to have them in your life for so long, both of them. You're going to have a long life. That's good. Given the choice of anyone in the world, who would you invite as a dinner guest? You can have more than one guest if you would like to have a couple of folks together.
There are so many. I know she's passed now, but I would like to have dinner with Ruth Bader Ginsburg, not to be cliche about it these days. I always admired her and her story of not being able to get a job at a law firm as a top graduate from a top law school in her day and age simply because she was a woman. That's incredible. The tenacity demonstrated her and continuing.
Having such, as I understand it, a marriage that was based on mutual respect and support. It’s always been big for me. My husband is a huge supporter. We’re total teammates and partners, and I could not have done what I’ve done in my career without him. I would love to sit there and let her talk for two hours and learn from her.
It’s interesting doing the show because I remember, like you, those stories of Justice Ginsburg and Justice O’Connor in their time not being able to get a job out of law school, which is something that law school graduates would not encounter at all. Our time had dissipated as well, but there are others on the show who have that experience and to see how long to the chief justice of the Utah Supreme Court, Chris Durham, who said, “There were men need only apply to certain jobs.” That was the listing.
We’re talking about the early 1980s and the same thing in California with some of the larger firms, some of the women who came out in that period. We couldn’t be hired for anything like a short-term job. Nothing long-term could lead to a partnership and any of the big firms in California. How quickly everything’s changed, and the opportunities are so much faster from the get-go of women’s careers and how much further we can go as a result of that. It’s amazing to do at least a little microcosm of that evolution from individual women’s careers on this show. The last question is, what is your motto, if you have one?
My motto is every day is day one.
What does that mean to you?
It means you can’t ever rest on your laurels. You don’t have to bring the 100% insane hustle every day. It’s not meant to be that. It’s not meant to be something destructive that leads to a brain aneurysm. It’s meant to mean that you need to approach every job with your best effort and always do your best, however, defined in the context. The other side of it is that it also means back to my feedback loop problem that every day is a new opportunity. Regardless of how hard yesterday was, what you messed up, or what big wind you had, this is a new day. You’ve got to bring it and earn it again and hopefully enjoy doing it.
My mom encapsulates the same thing, both of those sides of the coin. She says, “Make this the best day ever.” Each day is a new day, and it's up to you to make it a great day. Thank you so much, Hillary, for joining the show and having this discussion. I enjoyed it and appreciated your taking the time to chat with me.
I appreciate the opportunity. This is wonderful.
Thank you, Hillary.
Thank you.