#148: C.J. Mahoney - Microsoft General Counsel, Former Deputy US Trade Representative, & Law Firm Partner

Jonah Perlin [00:00:01]:
Welcome to How I Lawyer, a podcast where I talk to attorneys from throughout the profession about what they do, why they do it, and how they do it. Well, I'm your host, Jonah Perlin, a law professor in Washington, D.C. this episode is sponsored, edited and engineered by my friends at LawPods. LawPods is a professional podcast production company focused solely on attorney podcasting. I absolutely love working with them. And if you're considering becoming a legal podcaster or just want to learn more, check them out@lawpods.com and now let's get started.

CJ Mahoney [00:00:38]:
Hello and welcome back in today's episode of How I Lawyer. I'm excited to welcome C.J. Mahoney to the podcast. C.J. Is currently the corporate Vice President and General Counsel at Microsoft. Prior to joining Microsoft, C.J. Served as the Deputy United States Trade Rep, a position to which he was unanimously confirmed, and before that was a partner at Williamson Connolly and a law clerk to Associate Justice Anthony Kennedy. A native of Kansas, C.J. Is a graduate of Yale Law School, Go Bulldogs. Where he was the Editor in Chief of the Yale Law Journal and Harvard University. Go Crimson. But most importantly for me, C.J. Was one of my first legal supervisors when I was a summer associate at Williams and Connolly 15 years ago.

CJ Mahoney [00:01:13]:
In that role, he taught me so much and treated me with a level of kindness and care that I still remember and appreciate to this day. And that's what is so exciting to have you on How I Lawyer. So thank you so much, C.J. for doing this and so nice to be back in conversation together.

CJ Mahoney [00:01:27]:
Jonah, it's great to have the opportunity and to get reacquainted. Remember quite well the religious liberties work that we worked on when you were a summer associate and some of the rabbinical anecdotes that you put into our briefs. And it's been great watching your career flourish since then.

CJ Mahoney [00:01:42]:
Absolutely. Well, look, thankfully I'm on this side asking the questions and we get to tell a little bit of your story. And I always like to start those stories by asking a little bit about how you decided to become a lawyer. What's your legal origin story? And was lawyer always the plan for you?

CJ Mahoney [00:01:59]:
It more or less was always the plan, or at least one of the top two or three plans. It really kind of goes back to the small town I grew up in in western Kansas called Russell, which is a town of about 4,000 people. Lawyers in small towns are quite well respected. When my best friend's dad was a lawyer, was very good family friend, somebody I admired, continue to admire. He was the county attorney for a long time while we were growing up. They had a nice life. So I always kind of looked up to him. And as I thought about what I wanted to do growing up, that was something that was.

CJ Mahoney [00:02:31]:
That was first on my list. I was always a humanities person. I like history and government classes. I was actually a reasonable math student back in the day. But then when I went to college and encountered people who were really good math students, I realized that that was not where my comparative advantage was going to be.

CJ Mahoney [00:02:49]:
Right.

CJ Mahoney [00:02:49]:
So I was always. Law becomes the default career path for a lot of people who are reasonably intelligent but don't excel in math and science. And so I think for, you know, for a lot of college, I was kind of on that default path. And then I was lucky enough, which is not where everybody gets. But I was lucky enough where I went to law school and actually really liked the substance and really liked practicing law. So it ended up working out for me.

CJ Mahoney [00:03:12]:
Yeah. Sometimes you just have to take the. Take the jump and see what happens and deal with the consequences either way. The other interesting thing about that story, right, is you've practice law in very different ways than maybe that lawyer that you remember and looked up to back in Kansas. Yale Law School, Supreme Court, head to Williamson, Connolly. Don't go all the way back, but back far enough to sort of tell us a little bit about, or tell me a little bit about what you thought you might do once you actually started practicing law and headed to Williams and Connelly. What was that decision like, and what kind of work did you want to do and what kind of work did you end up doing?

CJ Mahoney [00:03:46]:
I think when I decided I wanted to be a lawyer and wanted to go to law school, I don't really think I had a great idea of what that meant, frankly. I wasn't necessarily somebody who watched a few Good Men and legal movies and thought, gee, I really. I want to be Atticus Finch in the courtroom. I didn't necessarily have that burning desire. I think I liked the idea of being somebody who was introduced as a lawyer probably more than anything else. But that also gave me some flexibility to figure out what. What I wanted to do. And I got on the appellate clerkship bandwagon that a lot of people get into in law school and ended up looking for Judge jasinski on the 9th Circuit and then for Justice Kennedy again, really, because that was kind of the thing to do.

CJ Mahoney [00:04:30]:
And they were both great experiences, very different experiences, but good experiences in their own way. But it did make me, especially after going to Yale Law School, which is. Has the reputation of being very theoretical and it's really very con law, appellate law focused. Having done two appellate clerkships, I thought to myself, gee, this is. It's interesting that there's been so much focus in my time in law school up to this point on what happens in the courts of appeal when that's really a very small part of the litigation system, certainly a really small part of the overall practice of law. One of the turning points for me was actually when Judge Kaczynski sat by designation in did a trial when I was working on the Ninth Circuit. I thought that was really, really interesting. And I also realized, I think, especially the next year, that the Supreme Court is as dazzling as some of the top Supreme Court advocates that I saw were.

CJ Mahoney [00:05:22]:
At the end of the day, I really don't think that their advocacy in a case where both sides were well represented, I didn't really see that many instances where I thought that the advocacy really made that much of a difference in terms of who won or lost the case, because a lot of the cake had already been baked by the time it got to the courts of appeals and certainly to the Supreme Court. And there was just so much else to learn. And so I like. And the other thing was I was with a bunch of both in law school and the court of appeals in the Supreme Court. I was with a lot of really smart people who all wanted to be appellate lawyers. And I thought, do I want to relieve. This seems like a pretty saturated market, so maybe I should think about doing something a little different. And that was where I all of that combined to make me interested in wanting to learn how to try cases.

CJ Mahoney [00:06:06]:
And Williams and Connolly in Washington was a fantastic place to do that. And I was then there for the next 10 years, which was a great experience.

CJ Mahoney [00:06:14]:
Yeah. So it's so funny because one of the things that I talk about a lot is sort of what I call like the LinkedInification of careers, where everything sort of looks like from the back end, that it was all planned in advance. And even hearing your story right, which looks sort of like this expressly linear kind of career track. And the way you describe it is not quite so linear in the sense that it was. Let me see what the next situation looks like. Let me see what I like about it. Let me see what I'm missing or what I think I might like more and let me try something new. Is that an accurate description?

CJ Mahoney [00:06:48]:
Oh, absolutely. I mean, my career path has not been. I mean, again, I can see where at certain points you would think that it was very linear. But I was always very cognizant of the fact that it is a very competitive profession. And there are a lot of really great smart people who were in this profession. And no matter how great and how smart I thought I was, figuring out a way that I could distinguish myself and separate myself from the herd was always something that I was interested in doing. And so again, when I was a court of appeals clerk, I thought going from that, combining that with actually learning how to try cases. When I was trying cases at Williams and Connolly, I was always looking for a place.

CJ Mahoney [00:07:21]:
And I ended up doing a fair amount of international arbitration, international litigation, as a place that would be different than when I had the opportunity to go to USTR and add trade to my portfolio. That was another way. And none of those things. I wasn't. I didn't actually was. I didn't take one international law class when I was in law school. I didn't. I always.

CJ Mahoney [00:07:40]:
But I was always kind of open to where the opportunity would be. And that ended up serving me really well. And I really would have been surprised, you know, probably at any point in my career if you told me what I was doing, I mean, except for at Williams and Connolly when I first started. But if you told me when I was in law school or when I was at Williams and Connolly, that I would have gone to ustr, that I'd be at Microsoft now. Like, I just wouldn't have predicted that that would have happened. But it was being open to opportunities, frankly, sometimes being open to opportunities. And the opportunities I always found always come at with a lot of inconveniences and at inconvenient times. And you have to be willing to get over those if you're, if you're going to take advantage of them.

CJ Mahoney [00:08:17]:
But it was. And part of it too, was being at Williams and Connolly for as long as I was. A lot of people go to a law firm for a couple years. A lot of people will stay at a law firm for all their lives. I've done kind of a middle path of being in a law firm for 10 years. And for me, that was a great thing to do. I felt I built a really strong foundation for my career that then gave me a lot of options.

CJ Mahoney [00:08:37]:
I love it, and I want to go to the USTR role next. But before I do, one of the things that I've been doing this summer is writing this newsletter for summer associates and junior lawyers. And one of the questions that I got that I think you would have some particularly good insight on is how you start that new job or that new area of law or that new task that you've never done because you are a clerk on the Supreme Court, like every law student's dream. And then you go to a firm, and I imagine you sort of start at the beginning again and have to learn this whole new way of thinking, trying cases, new strategy, and frankly, new skills that you've never heard of or seen before. Any recollections about how you go about starting something new when you're really starting at the bottom, even though you felt like you maybe had been at the top before?

CJ Mahoney [00:09:24]:
I guess over time, I became comfortable with those uncertain situations, and I developed maybe not always a completely justified confidence, but some confidence that most things I'd be able to figure out, because at the end of the day, most things are not, especially in the law. They follow some pretty basic principles. And in order for enough people to understand them that we can govern society with these laws, they kind of have to be intuitive, so you can kind of figure them out. And it's certainly in litigation. I think litigation is such great training for a lot of what I do now and what I've done in other contexts outside of litigation, because it's really about figuring out how you can come up to speed in a new area very quickly and learn new facts, learn new areas of the law and synthesize them, reduce the complexity into something that you can talk to lay people about and like that, in and of itself, you can build. Like, if there's something I've. Any skill I've gained and I've learned in my career, I think it has really been that, and it's been great for me because it's just. It's.

CJ Mahoney [00:10:29]:
It's allowed me to operate in a lot of different areas.

CJ Mahoney [00:10:32]:
I love that. Well, the next area after you were at the firm is you end up being nominated and ultimately confirmed as Deputy U.S. trade Representative. Talk to me a little bit about how that came about and also your thought process of going from the law firm and being a law firm partner, which some people see as sort of, again, the last job you'll ever have, and you're taking a big jump going to represent the United States in that role. So talk a little bit about that.

CJ Mahoney [00:10:54]:
Yeah, it was a totally unexpected turn in my career. I remember when, actually, when President Trump was first elected in 2016, I was doing a mock jury exercise in New Haven, Connecticut, for a trial that I had that began after the first of the year. And at the time thinking to myself, wow, this is such a surprise. I bet that they didn't have much of a transition. I just bet they don't have people lined up for all these jobs. I wonder if there's, if that's maybe an opportunity I ought to be interested in. But then I had a trial, and I didn't really think about it again until I finished this trial in like, like late January of 2017. And I came back and this is a case that had taken up probably about a year and a half of my life.

CJ Mahoney [00:11:38]:
It was, it's a big criminal securities fraud case. And I came back, I ran into one of my partners in the hallway and is oftentimes is the case when you go to trial and that is kind of all consuming. You come back and you kind of have to rebuild your pocket and figure out, you know, what your next thing was going to be. And ran into one of my partners who said, one of my really good friends was just nominated to be the U.S. trade representative. You want to go talk to him? And then I got a call from a mentor and long term longtime family friend who was former Senator Bob Dole, who's from my hometown of Russell, Kansas, who said, my former chief of staff is going to be the US Trade Representative. Same guy. You want to go talk to him?

CJ Mahoney [00:12:19]:
Wow.

CJ Mahoney [00:12:20]:
And so through these two mutual connections that I had to Bob Lighthizer, who I'd never met before, I got introduced to him. And at the time, I remember thinking, well, you know, maybe they'll ask me to do something in the General Counsel's office. How do I. If I'm offered something, I'm have to figure some polite way to decline this. And then to my surprise, the job that they wanted to interview, interview me for is to be the deputy U.S. trade representative, the number two position in the agency. And, you know, I think that the fact they were looking at me owed some of the fact they didn't have, you know, that at the time they didn't have a lot of other candidates. But it also reflected that Bob was of the view that what he really wanted at USTR were strong lawyers who could advocate for the United States.

CJ Mahoney [00:12:57]:
And he knew, having been a litigator himself, that strong litigators can learn the substance of almost anything, at least well enough to be good advocates. And so I thought, and at this point, I'd been a partner for a couple of years, so I was a position where I could step away from my practice. And it's one of the nice things about practicing law in Washington is it's kind of an expectation that people are able to do that and then go back to a law firm. So I thought this was a way that I could expand my horizons, do something different, learn a new area of the law. And at the worst case scenario would be that I did this for a couple years and it was like a sabbatical. And then maybe it would, on the upside, maybe it would lead to something else. And I'm really glad that I did it. I didn't know anything about trade when I went into the job.

CJ Mahoney [00:13:41]:
I had done some international work, but I hadn't done anything around trade. But I just really treated it like a case. I read, I bought books, I read articles, I talked to experts and I. And fortunately, because of our efficient Senate confirmation process, it took me about a year to get confirmed. And so I had a lot of study time. But it was, and it ended up, ended up being another just fantastic, life altering experience.

CJ Mahoney [00:14:07]:
Yeah. And talk to me a little bit about, I mean, that's not something I've ever had somebody on the podcast who's had that experience, what's that job like and how is it different? How is it the same as being a litigator or a big law partner? Pull back the curtain a little if you can.

CJ Mahoney [00:14:19]:
In some ways, I was struck by the similarities more than the differences, because the way that I approached the job was I was Bob's lawyer, USTR's lawyer, and I had a job to do. And in my case, the job was to renegotiate the North American Free Trade Agreement. And it was a negotiation which, and I hadn't been a deal lawyer, I'd been a litigator. But as a litigator, you're often negotiating, negotiating over discovery requests. You're negotiating settlements, particularly settlement negotiations, probably prepared me to, to be a trade negotiator more than anything else. Because oftentimes the settlement negotiations, what you're doing, like once it's time to settle, you kind of have to figure out something that works for both sides.

CJ Mahoney [00:14:59]:
Right.

CJ Mahoney [00:14:59]:
In order for. And that's what trade negotiations are all about. You just, I mean, this idea that you just ground somebody in the dust, especially when you're dealing with countries that have their own politics, that doesn't really work. You got to figure out what both sides want and listen very carefully to how people articulate their objections. And so I really felt that being. And also with all of the disciplines you have to deal with as a trade negotiation, particularly as A more senior negotiator. You couldn't be an expert in a subject matter expert in telecommunications and in digital trade and in the dairy sector and automotives and everything else. You had to learn enough so that you could be competent so you could understand the issues so that you can.

CJ Mahoney [00:15:36]:
And cross examination skills was something that I also felt was really, really helpful because a lot of what I had to do in that job was to cross examine some of our own subject matter experts at USTR and in the US Government and in the private sector about what really mattered. And so it was, it ended up being a really fantastic experience. And it also just taught me too that my skills as a litigator were valuable in a context other than litigation. It also showed me when you, when you're being, when you're a litigator and that's what your life is just you try cases every year. It's easy to kind of think that litigation is what the world is, when litigation is actually a pretty small slice of the world. It's a small, it's actually a fairly small slice of, it's certainly a small slice of what companies do and it's a pretty small slice of what the overall practice of law is like. And so it was a great, it was a confidence building and a certainly horizon expanding experience.

CJ Mahoney [00:16:26]:
Yeah. And again, what I love about that answer is I think so many times people self select out of opportunities because they say I don't have the experience yet. And in reality we don't have experience until we've tried it. The metaphor I use with my students all the time is every pilot needs to land a plane for the first time, but they don't get on the loudspeaker and say, everybody, just so you know, this is my first landing. Right. You have to do it and you have to have enough practice and experience. And I love how you talked about the various skills that you were sort of able to use from litigation. And you've had some experiences that are relevant, but they're going to be in a new context in a new way.

CJ Mahoney [00:16:57]:
And everybody's kind of learning on the fly as well.

CJ Mahoney [00:17:00]:
I've kind of had a, one of the things in my career like, and I perhaps to some extent it comes from having worked with a lot of expert witnesses and having cross examined some expert witnesses and worked on reports that dismantle the report of very well credentialed experts. I've kind of rebelled against the idea of like uber specialization because I think that if you, a lot of people will Use specialization as a way to kind of build a motor around themselves and say, well, you know, other people can't understand this because the barrier entry is sorry. And that's, that is the case. I mean, you couldn't be a nuclear scientist or a genomics researcher or a, you know, a data scientist or somebody that builds large language models if you didn't have a great deal of subject matter expertise. But I think in the law you really have to have an ability. You think about if you're going to explain things to juries, if you're going to explain things to counterparties, if you're going to explain things to regulators. The superpower that at least a lot of lawyers have is in taking what is complex and making it something that is understandable. And, and I, I just also, at some point, I realized as well that if I don't understand something, probably not because I'm an idiot and I'm too dense to understand, it's probably because something isn't communicated as clearly as it, as it should be.

CJ Mahoney [00:18:13]:
And if there's just one thing that I think I have learned how to do, it's how to take complex facts and situations and put them in a way to where different people can understand them. And that can just. It's a very basic thing, but I found that it's something that is really key to being effective in a lot of roles that I've had.

CJ Mahoney [00:18:29]:
And just brass tacks, like, how do you do that? I mean, you know, not on a big scale, but just, you know, if you're learning something new. Are you, are you the kind of person who's like reading everything you get your hands on? Are you talking to people? Are you taking notes like brass tacks? What's your approach to learning those new things?

CJ Mahoney [00:18:44]:
I think that for me, one of the. Yes, you have to read, you have to talk with people. I think for me, one of the key things is putting things in my own words. And so I will often, if I'm talking to somebody, I'll say, well, okay, if I'm understanding this correctly, let me just summarize. And just so that I understand it, I think also putting things down on paper, writing them down is really, really important. I think it's important not only for communication, but it just hones your own thinking. When you see something on the page, sometimes you just counter arguments that you didn't see. Weaknesses that you didn't appreciate when you were just talking can become that much more apparent.

CJ Mahoney [00:19:16]:
So I think that just that. But a lot of It I do think having a, having a dialogue and having a conversation and forcing experts who oftentimes will want to put in all kinds of caveats and jargon and every, you know, and making if, if you think about it, if I have to explain this to a lay audience, there's one of my. I love you ever seen this movie Morgan Call with which is a great, it's a great scene in it where Jeremy Irons is the, the CEO of this investment bank that's about to go under and they have this young, young really smart analyst who's figured out that these mortgage backed securities that the company has are worthless. And he is the guy launches into this kind of technical discussion. He's like okay, explain this to me as if I'm a small child or golden retriever. And I really think, I always think about that because I think that's how you have to simple it. There's no. They're not there should I think people think there are rewards for making things more complex.

CJ Mahoney [00:20:10]:
There's actually there should be rewards for making things more simple.

CJ Mahoney [00:20:13]:
Well said. Well said. Yeah. And it's funny, I'm having flashbacks too. Fifteen years ago when you were my supervisor as a senior associate, not even as a partner and I remember you saying to me often let's see how it writes, right. Like let's just see how it goes. Explain it to me. That's enough for me to get you to spend time to put it on paper but let's see how it writes.

CJ Mahoney [00:20:30]:
Because I'm not convinced one way or the other the argument's gonna work.

CJ Mahoney [00:20:33]:
Yeah, I just think that process of writing and it's something as an in house lawyer, I really try to encourage people on our team to spend more time writing because even if, I mean even though we're not filing most of the house lawyers or Microsoft or not, you know, we're not necessarily writing pleadings or things are going to be that are going to be scrutinized by an external audience. I just think even if, even if you end up not actually sending the memo, sometimes just having the exercise of having written the memo is really helpful in sharpening your thinking. I've also found too that sometimes just putting things down and when you're trying to drive consensus with a group is putting things down. Laying the facts out in ways that are, that are clear allows people to get on the same page. It can both sometimes mean that disagreements that people are having in a room that seem very heated when you actually put them down on paper, you realize that they're actually the distance isn't as great. And then on the other end of the spectrum, sometimes you're in a meeting where there's a lot of kind of superficial agreement that people are talking past each other and when you memorialize it, you write it down, people realize, oh actually no, that's not what I meant. So I just, I'm a huge fan of writing and it was something, something I really enjoyed doing and it was probably, I was, I was really happy when I was like writing a good brief where I felt they had a good argument. I love doing that and unfortunately I don't get the chance to do that as much anymore.

CJ Mahoney [00:21:48]:
But I really did like that. And again as I, as I found out in my career, those skills serve you even when you're doing something other than writing in a brief for corporate fields.

CJ Mahoney [00:21:57]:
Yeah. Well, now that I've had you sort of reminisce about the golden days of brief writing, let's talk a little bit about your move to Microsoft. So you finish your time with the trade represent and you decide not to go back to the law firm but instead to go in house at Microsoft. Talk a little bit about sort of how you thought about that next move post government service.

CJ Mahoney [00:22:13]:
Well, there were things when I went to usdr I had a couple being able to see it was a great thing to be able to do to really kind of, you know, mid career or I wouldn't say it was early career at that point I was like my early 40s when I was stepped away from Williams and Connolly and went to ustr and I just, I had the ability to kind of reflect on a big chunk of my career and really think about where I wanted to go next at that point. I'd been a litigator, I'd tried several, I'd try about a dozen cases or so when I was at which for people who are litigators, 30, 20 or 30 years ago wouldn't seem like a lot. But today in big law firms it's hard to get that many cases under your belt. So I felt I was, was at a crossroads. I'd had that experience but then I now then I'd have the USTR experience with negotiations and policy and what I really wanted to do next was something that would allow me to draw on both sets of experiences. And as I thought about it, I came to the conclusion that I was going to be more valuable with the kind of jack of all trade skill set that I had built at that point to a company as an in house lawyer than I would be going back to a law firm. Because a lot of what a company, particularly a big global company like Microsoft has to deal with are not just narrow legal issues, they're geopolitical policy issues. And I was in a position where I'd done both things.

CJ Mahoney [00:23:34]:
And so I liked the. I also really liked it as much as I liked practicing law at Williams. And finally, what you do, you're dealing with problems are very important problems, but you're dealing with a discrete set of problems for multiple clients at once. And when you go to work, for my example, a federal agency or then Microsoft, you're dealing with one client and then all of the problems that they have. And I did, I like that transition. I liked the kind of the stability of dealing with, with, with, with one client being part of an organization that has a mission. And not because I mean some of the. I loved and you know, I had a great experience at Williams and Connolly, but there was always a little bit of a sense that you really didn't.

CJ Mahoney [00:24:16]:
I would only know my clients in certain instances. And then you do great work for people and then you never hear from them again. Right. That's just the nature of the business. And so I liked the pros and cons with everything. But I did like being having one client.

CJ Mahoney [00:24:28]:
Yeah. And it's funny when I've heard I've had people both in house counsel and outside counsel on the podcast and it's funny that people tend to gravitate toward one more than the other. They either don't like being in the same rooms, focused on the same client. And there are folks who really thrive in the ability to be that jack of all trades. Are there things that you wish you had known when you were outside counsel that you now know now that you're in house?

CJ Mahoney [00:24:52]:
I think one of them is just again with how I thought about litigation when I was a litigator. It's different than how I think about it as an in house lawyer when you are a litigator. And I think also Williams and Connolly is maybe a little different too because we were generally hired when people had, when there was no hope of doing anything other than winning a trial.

CJ Mahoney [00:25:12]:
Right.

CJ Mahoney [00:25:13]:
But again, that's really not the, I mean that's not a good position yet if you think about it. No, we did well. People always talk about bet the company cases and it was a big kind of more distinction if you'd said I had this bet the company case. You think about it. If a company gets to the point where their future is bet on something as uncertain as litigation. Something has gone wrong, something's gone terribly wrong, somebody's made some bad judgments, somebody's being irrational. And so it's really not a place that any business ever wants to find itself in. So I, and another thing too, I was, I will say, unfortunately at Microsoft, we've got a good recorded winning cases when we do take them to trial.

CJ Mahoney [00:25:54]:
So we're good recorded at working through, through things without litigation. The burden of litigation on a business in terms of executive time distraction, I mean, not to mention just the hassle and cost of document review. It's really, it's significant and I don't think I quite appreciated how significant it was until I was in house and realized and especially in a, you know, in a business that is as dynamic and competitive as ours is right now. And I mean I, anytime our executives have to take time out of figuring out how we're going to win the AI race to sit for a deposition, I mean that's really, that's valuable wasted time. And so against the need to avoid litigation and the burdens that it imposes on companies was something I didn't quite appreciate until I was in house.

CJ Mahoney [00:26:42]:
One of the big changes, and you sort of have hinted at this a couple times, both as you got more senior at the law firm, but especially now in your roles at Microsoft is managing people and managing experiences, but mostly managing people. And I guess I'd be curious if you have thoughts or recommendations for people who are starting their management journey that could be someone as junior, as a mid level associate or senior associate like when you were first managing me 15 years ago as a summer to the kinds of things that you're teaching the folks that work for you today. Any thoughts on management?

CJ Mahoney [00:27:12]:
I'll just give you a couple. I, I think one of the most important, I think probably the most important thing that you can do as a manager is to build trust with the people you're managing and convince them that you are in their core. Because if you do that, I think everything else is easier and if you don't do that, everything else is harder, if not impossible. Because if you don't have that trust, you don't have clear communication. I mean one of the most important things that you want people you're managing to do is they feel comfortable bringing you bad facts, bringing you bad news and not fearing what your reaction is going to be in the moment. And this isn't something that I've come about. I've come to this conclusion Just because I like to think I'm a nice person. But it's not just because of that.

CJ Mahoney [00:27:54]:
It's in my interest as a manager to know the bad facts. One of the things that Brendan Sullivan instilled to me when we were at the firm was I always felt, for whatever reason, from day one, when, like when Brendan had some argument he wanted to make or some narrative that I didn't think quite worked, I just felt comfortable in those meetings saying, you know, I think this doesn't quite work because of this fact. Now, it was always helpful if you could then pivot it and say, well, but what if we tried this instead?

CJ Mahoney [00:28:17]:
Right?

CJ Mahoney [00:28:17]:
People do the former very good, but not the. Not the latter. But again, having that trust, I also just think that it also just makes feedback so much easier to give and so much easier to receive if somebody is telling you something. And feedback is just always tough at this point, it's tough for me to receive feedback from my boss. But when you are in a relationship with the person who's managing you and you realize that they're doing that not because they want to be mean, not because they want to knock you down, not because they want to abuse you, but because they really want you to be better. And it's very hard for us to be objective in evaluating our own performance. But if somebody can sit you down and say, you know what?

CJ Mahoney [00:28:56]:
I'm just.

CJ Mahoney [00:28:57]:
I'm looking at something that you're doing, and it's going to get in the way of your success if you don't change it. I just. I think that. And if you can develop that kind of a relationship, I just think that that, that is. It's. It's really works in both ways. Another thing that I think is really important is people are especially junior lawyers who become managers. There's a certain amount and, you know, maybe less than there used to be.

CJ Mahoney [00:29:16]:
But I said, I do think that there's a certain amount of pacing in our profession. And so sometimes when people get, you know, move from being the junior associate to the senior associate to the junior partner, they will sometimes see that as an opportunity to inflict pain on others that reflects the pain that was inflicted on them. I think that's a really terrible way to manage. And it's just. And it's a dumb way to manage because you want to be the kind of manager that people will want to work for. You want to be the kind of manager who has a track record of managing younger lawyers who then were able to take that experience and leverage it and go on and achieve more. There was. I loved it when people that had worked for me became partner or got on another big case because of my recommendation.

CJ Mahoney [00:30:02]:
And frankly, even if some of those people, even if they end up. You end up working with her, you don't end up working with them again. You lose them to somebody else. You lose them to another law firm, you lose them to another company. I just think that it is a. Over the long run, the benefits to the manager. I love it when good behavior is actually reinforced by incentives and you get good people to work for you if you develop that kind of. That kind of reputation.

CJ Mahoney [00:30:24]:
So it also just makes. I just think it makes your working environment, you know, much more pleasant. People think that this is really all about that we have kind of a bargain here and that you'll work hard for me and then I'm going to support you and make you in your career, make you a better order.

CJ Mahoney [00:30:37]:
Yeah, I mean, I love a lot of that. One of the things that I try to train my students from day one is to see feedback as a gift and not as a bomb. But that's not how it's received. Right. And that's. And I think it's important, as you say, to sort of admit that feedback is not easy to receive. By definition, it is telling you what you have done less than the supervisor wants. And that's painful to hear.

CJ Mahoney [00:30:58]:
The famous red ink. Although I don't know that we even have red ink anymore, but you know what I'm talking about. Red ink, it's hard to see. And if you see it instead as somebody who is taking time out of their busy schedule to make the work product better as a path to making you better at your career, then feedback becomes a gift. And I think it's. I think the part that we forget that I really want to highlight, that you just talked about is there's an interpersonal piece to that as well. Right. If you feel like you're supported by that person, then by definition you're going to see that feedback differently.

CJ Mahoney [00:31:31]:
Yeah.

CJ Mahoney [00:31:31]:
And you're right. People are going to come back and want to keep working for you. I mean, I remember I worked with you as a summer associate, and guess what? When I got back to the law firm two and a half years later, three years later, I said, hey, can I work on a case with you again? And that may not have been to your benefit, but it was certainly to my benefit.

CJ Mahoney [00:31:45]:
It definitely was, John.

CJ Mahoney [00:31:47]:
And so that's the kind of thing that you don't Know, that's the other thing is you don't know how many opportunities are going to come back to help you. But you're absolutely right that even if they don't come back to help you, everybody kind of wins.

CJ Mahoney [00:31:58]:
Yeah. Another thing, you know, another thing is I'm thinking about this I think is really important and I've always tried to do do is there is the feedback that I give to people one on one and then there is like the feedback that I give when kind of more official channels. And I, I have always tried to be. A lot of times people will give, will say will be very kind of soft in their feedback one on one. But then they'll be very sort of harsh about it in a different setting when they're talking about the person, when the person isn't in the room, you want to do it precisely the opposite. I think you want to develop the kind of relationship where you're really, you can really give honest and sometimes kind of raw feedback in private settings. But then, but then I think just be, you know, more, a lot more deliberate about. Because sometimes when you give, when you relay feedback to somebody else, if you're just like a small anecdote, somebody doesn't have the whole context that's small mistakes can take on outsized importance.

CJ Mahoney [00:32:52]:
And you know, I saw just at various points in my career I've seen that happen where I thought it was, was unfair. And so I just, I think you really need to kind of strive and it, it is difficult. And I, and I do find that being. If you, you try to soft pedal feedback sometimes the ways in which you soft pedal it will depending on the person it will just, it won't necessarily sink in. But again it's another reason why just it's easier to have really honest communication if you built that level of, of trust. And so I think that's gotta be your first and really kind of overriding early goal with any new person that you manage is to build that trust.

CJ Mahoney [00:33:26]:
I love it. I think we're getting close to the end. So I got two more questions I want to try on you and we'll see if I can squeeze a third one in. As a good former litigator myself, just.

CJ Mahoney [00:33:35]:
Don'T ask too many. That's always the answer.

CJ Mahoney [00:33:36]:
Yeah, right, exactly. Well, so the first one is, you know, I imagine and you sort of have mentioned this a couple times that you're at a company right now at Microsoft that's really at a unique vantage point about the future of society, of technology and where we're going. And I guess my question for most of my audience, which is law students and junior lawyers, is for those folks that want to work in this space at the intersection of law and technology in the future, where do you see both the profession going and sort of where do you see the big places that lawyers might play a role?

CJ Mahoney [00:34:11]:
Well, the thing that I think is really interesting and I think being an in house lawyer, the technology company right now is just fantastic and I think it's a historically interesting and consequential moment because we're dealing with two things. We're dealing with this massive technology shift driven by AI at the same time we're dealing with the breakdown of the neoliberal order, political polarization, increased regulation of the technology industry. And both of these things are happening at launch. You could have. The political trends would be challenging enough, but the political trends at the same time this technology shift has happened. I think just you know make it's a really interesting, creates a lot of demand for, for, for lawyers. But I actually think that the, the skills that you need to, to serve your clients well at, at this moment, it's, it's not just knowledge of the technology. I mean that's important, but the technology is also changing so quickly.

CJ Mahoney [00:35:05]:
You know, I don't know that I would tell lawyers who want to get young lawyers who want to get into this industry that's like the most important thing is like to learn how to code or learn very discreet thing about technology law. I think it's really about building these skills of figuring out how you absorb, synthesize and simplify complex information, apply it to legal frameworks. The other thing is that a lot of the question, the really tough questions that we have to deal with in a company like Microsoft are not just narrow legal questions, they're political questions, they're kind of public relations questions. And we really have to evaluate a lot of the problems that we face in all of through, through all of those different lenses. And like one particular lens would lead you to recommend one course of behavior, but when you apply all three, that leads to a different one. And so I think it's, I think a lot of that is. It's just really, really important. I mean I think probably if you were going to be a technology lawyer like in the late 90s during the dot com booms, knowing how to do IPOs was probably like the most important thing you how to do where now I think that knowing something about geopolitics, economics, public policy, those things are really as important as understanding a lot of the stuff that traditionally been in the, in the toolkit of a traditional tech lawyer.

CJ Mahoney [00:36:18]:
And how do you see AI both being part of the problem or the thing that we're solving for and part of the solution of being able to synthesize information, learn information, create information more quickly. Like how are lawyers going to be using AI in some ways to respond to the challenges that it brings?

CJ Mahoney [00:36:35]:
I think it'll be, I mean I think it'll, it'll come in a, in a couple of different ways. In some ways that actually that concern me a little bit frankly because I think that certainly AI is a. One thing that AI does pretty, does a pretty good job with right now is synthesizing information, coming up with, with summaries. But as you know, the summary points are not all you need to know as a lawyer in dealing with. So it clear clicking down and figuring out actually like reading the cases, reading the underlying sources, understanding the difference in the credibility between different sources. Like those are things that AI does not do a good job with right now. And so I mean I do worry a little bit about a generation of law students and young lawyers who are going to be trained on summaries rather than trained on. I always liked actually printing off the cases and I walked around, I spent a lot of time walking around and lugging, you know, lugging binders full of printed out cases on airplanes and very.

CJ Mahoney [00:37:32]:
Because I always felt too that I just, I felt I absorbed more and I would. The ability to circle things and you could, of course you can do a lot of that with tablets like Surface now. But it was, I just, I think that that stuff is, that that's really important getting your hands dirty and understanding the facts. But the AI can be helpful with that and it can help you get, you'll get quick answers when you need them. But there's going to be. I think you're going to have to figure out people are still going to need to be able to get their hands dirty and the best lawyers will figure out a way that you can use AI in ways to make you more productive and efficient. But not. But still learn how to do it.

CJ Mahoney [00:38:08]:
Still learn how to do it the hard way.

CJ Mahoney [00:38:09]:
Yeah. And I mean that's the challenge from my full time job perspective of teaching legal research and writing is teaching writing in an age where AI is both more present and better than it was even 18 months ago. That's a big conversation that everyone who does what I do is having at this very moment. And I'm sure They're having it at my kids school also on how they're going to teach elementary school kids how to write as well.

CJ Mahoney [00:38:29]:
Well, I go back to, go back to the point too where to me writing is not just about communication, it's also the writing process helps you think and helps you hone your arguments. And at least for me that was just, that's critically important. I think you've heard an earlier generation of lawyers who some of them were, I think really good because they had to learn how to do that by dictating into, into a microphone and they couldn't even go back and do all of the iterations. I, some of those people are probably quicker on their feet and more smooth in their communication than we are because they had to learn that way. And so I think people who need copilot or chatgpt to draft briefs I just think are probably not going to, are not going to go through the process of legal reasoning in the same way if you rely too heavily on those tools.

CJ Mahoney [00:39:14]:
Right. It's how to turn the technology into a net benefit, not a net loss. And I think the point you make is one that I've seen with my own students is that actually it can sometimes force you to write more because you can get more feedback. Right. You can try things out, look at things a different way, have a thought partner when, when a high powered, high charging lawyer thought partner isn't available to you. And those are the places where it actually might help solve some challenges instead of just create them.

CJ Mahoney [00:39:41]:
And it can also, I think it can, it can make some of the rote tasks easier. It can help you find errors and things. I mean it always just struck me that how many times you read a brief, hundreds and hundreds of times and like still on the last read we'd find some title or God forbid, once it was published, you'd find some type out. I'm hoping that younger lawyers are spared some of those, some of those indignities. Maybe some of the. I remember some of the logistics of having to file stuff in different courts sometimes was so difficult, I think sometimes by design.

CJ Mahoney [00:40:11]:
Yeah. And I remember, you may not remember this, but I remember when you were a senior associate, you had a couple of Post IT notes on the bottom of your computer screen and I once asked you about the Post IT notes and you it's my checklists for when I'm filing so I don't screw it up because I've already screwed it up once before.

CJ Mahoney [00:40:27]:
Yeah, I found in some of those, you know, every single bullet on that list was something that was a result of some unpleasant experience. But I just, I felt you needed to have these like, systems in place because I, it's like, it's most important to know your weaknesses. I always just found I had to like, I could edit for arguments, I could edit for tone, I could edit for typos, but I couldn't do all that at once. And so I had to have process you set up. And a lot of those checklists were ways that I did that.

CJ Mahoney [00:40:52]:
Love it. Love it. Well, look for. My last question is the same that I ask everybody, which is for a piece of advice and you've given a bunch. But what's one thing that you sort of share with more junior lawyers or something? You wish you knew when you were just getting started in our profession that, you know now I just, I think.

CJ Mahoney [00:41:06]:
That there's a just, there's a real benefit to just sticking it out through the hard times. And I look back at my experience of staying in a law firm for an extended period of time and I know a lot of people who, and people have had great careers and done different things. And one of the, I should say is that generally when people give you advice, they generally say, do what I did to validate their own experience or they had some uniquely bad experience. They say, don't do what I did. And people can over pivot on that. Over pivot on that as well. But for me, having staying at Williams and Connolly for as long as I did and building that foundation, that strong foundation was really the best thing that, the best thing that I've done in my, in my career. And I was a, I was a better lawyer as the longer I got there, I think that the better I, the better I became.

CJ Mahoney [00:41:49]:
Like the difference between where I was at like year two and year five, but then like where I was at year six and you're seven and you're eight in those later years, I really got a lot better. I mean, I really think I kind of like when I left was. It wasn't really until I left that I felt like I was actually, I kind of knew what I was doing, ironically. But so I just, you know, when people are, you know, in the middle of some big discovery fight or document review or, you know, in some case that is, there's a lot of benefit to, to sticking it out and making sure that when you, I think law firms do an excellent job. I think it's really, I think the training that you get a law, particularly a good law firms and law firms that value training young lawyers is invaluable and making sure that you if you sticking it out there and getting as much of that training as you can, I think there's a big benefit. Even if that isn't. Even if you don't want to be a law firm partner, you don't want to stay there for as long as you can. Being at a place long enough, you know, sitting yourself down in the chair and learning the craft from people who are really good at it.

CJ Mahoney [00:42:46]:
I just think this is a really important thing to do.

CJ Mahoney [00:42:49]:
I love that it's a great place to end. And again, congrats on the new gig at Microsoft and thank you again for taking the time to do this and for your kindness over the last almost a decade and a half knocking on two decades. So thank you so much and look forward to keeping in touch.

CJ Mahoney [00:43:04]:
Thank you so much, Joan. I have very fond memories of our working together and again, it's, you know, I'd love. I've really enjoyed watching your successes over the years. Congrats on all of it, especially on the podcast.

CJ Mahoney [00:43:13]:
Thank you so much again.

Jonah Perlin [00:43:15]:
I'm Jonah Perlin and this is the How I Lawyer podcast. Thanks to podcast sponsor LawPods for their expert editing. If you're a lawyer considering starting your own podcast, definitely check them out@lawpods.com and thanks to you for listening. If you enjoyed the episode, I hope you'll consider sharing it with friends and colleagues or on social media. And of course, if you haven't already done so, please sign up for the email list@howilawyer.com or subscribe to the show wherever you listen to podcasts. As always, if you have comments, suggestions or ideas for the show, please reach out to me at howilawyermail.com or jonapurlin on Twitter. Twitter thanks again for listening and have a great week.