Breaking In, Leveling Up, and In-House Wins with Billy Rusteen

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Visit imans dot Ch today. That's Edmond, and use promo code ITL 50 to claim your 50% discount on NCA exam preparation courses. Today I have the opportunity to interview Billy Resting. He has a super cool career in lots of big tech companies in house, including Microsoft as well as GitHub. And now he's also has his own business where he teaches lawyers how to become inhouse lawyers. So thank you so much for taking the time to being in the podcast today, Billy. Yeah, thanks for having me. Claudio absolutely. And to start over our conversation today, I'd love for you to start by introducing yourself to your our audience. Yeah, sure. So as you said, I'm Billy Rustin. I've been a lawyer for about graduated in 2009. So I think that's my math is correct. That's about 15 years is a long time. I graduated high school in 09, like I said, and that was the start of the great Great Recession. I noticed my last year at the start of my last year of law school, all my classmates were getting offers were sanded and or deferred and they weren't going to the jobs and the firms that they wanted to go to. So I ended up, so I ended up taking a job at an insurance law firm doing insurance coverage work. And I eventually, you know, took another job in another firm doing insurance related work. And at some point I realized, hey, I don't want to do this for the rest of my legal career. And that kicked me off on this journey to where I am today, where I didn't really understand how applying for in-house worked. And you know, it turns out it's pretty hard when you do insurance. And in my second firm was doing insurance and asbestos litigation. And you know, it turns out insurance and asbestos litigation, there's not a lot of jobs in house for lawyers who specialize in those. So what? So I had to learn over time. It took me about a year and a half to find my way in house, but I had to learn a bunch of tips and tricks and, you know, skills and strategies to get my resume seen because I initially started off just applying for jobs. And over the years I started. So I started my career in house doing as actually contracts manager and then I worked my way up to doing commercial contracting. And then I moved, as you said, to Microsoft, where I was actually at a small startup in 20, I think it was 20. So I started like 2015 and Microsoft ended up acquiring that company. And so that's how I got into Microsoft. And then I threw just sheer luck. I became a product counsel. And then then I moved over to GitHub, which Microsoft acquired later. And then I moved to Databricks after Microsoft. And so anyway, so now I do partnerships for them as well. And you know, it's given me a, over the years of my, and I've done coaching the entire time pretty much. And the thing that I have seen with this wide array of experiences, you know, all that every, I've seen all sides of the business of law and what it takes to get in house. And so it's giving me a a good perspective to help others which I enjoy. Amazing. I love that you mentioned a little bit more about your background and how you got into the positions that you got you. Because I feel like as somebody who's starting my legal career right now, and it's the situation that I see with my colleagues as well, that we get a little bit concerned about our first job. It seems like, you know, if you don't get that big law job on the first year, it really will limit your possibilities afterwards. But honestly, time and time again, the more people coming to the podcast and share their stories, the more I really realized that there is definitely lots of ways to to steer your career into the direction you want. And it's awesome to to get to hear from you today here. Yeah, of course, you know, there's no, there's no one-size-fits-all approach to finding your, your ideal legal career. And as long as you have some some pluckiness and stick to it in this and you have a little bit of thick skin and can take some rejection, I think most people can get to what they want to do. Amazing. And if I may ask then you've been doing this for for quite a while now. Was there a specific point where you realized you didn't want to be quote UN quote, just a lawyer, but you also wanted to help other lawyers to getting housed? Yeah, so this is a this is a story actually that goes way back in time. So I'm the oldest of four boys. And when I was when I was in high school, my mom signed me up to coach my youngest, my youngest brothers basketball team. And it turned out I really enjoyed coaching. It was fun. And, you know, there was a strategy aspect that there was also an aspect of teaching these 7th and 8th graders how to play basketball, right? And I started that kicked off this journey, this parallel journey where when I was an undergrad and when I was even after a school and now that I have kids, I've always kind of coached, you know, I've coached basketball for the most part, and I've done some other, I've done some other stuff like track and field, but you know, mostly basketball. And then now, you know, I coach baseball for my kids. But I've always, I've always just gotten hooked on, you know, helping someone connect the dots and gain confidence in something new. Because I always, I always come out of from the perspective of someone who is always good in sports. But I needed someone to really hold my hand and explain to me like, you know, why you do this particular thing. And so, you know, that scene instinct carried over into my legal career and as a result of my coaching experience. So I, I, when I found my first in-house job, I remember I had some lost school classmates who said, Hey, that's amazing that you did this. How do you do, how did you do it? Can you talk to me about it? And after like the second or third person told me, and then I had a, I have a friend who's a legal recruiter and he said to me, Hey, I have some friends or I have some, some, some lawyers who are submitting applications to become for me to recruit for them. And I can't place them because they don't, you know, they're like, they have my experience, which was insurance or asbestos or family law or something that wasn't like traditional, traditional in-house law. And so he said, Hey, you should also like, think of coaching these people. And so that really like kicked off my, my coaching career, which which I realized, you know, there's like very little practical guidance to go in, in house. You know, lawyers aren't lawyers, in my experience, aren't great about information sharing. You know, I think it's a profession where we, we tend, we like to talk a good game about sharing information, but we tend to actually hoard information because, you know, that's how you make partner, right, Is by like hoarding your clients. And it's like you go to law school and you wanna, you know, you want to be the top of your class and there's not really, you may have a study group or something, but there's not really an incentive to help others when you're, when you're in law school, at least in my observations. And so, yeah. So anyway, so I just, it's just a natural progression from my, from my coaching career to now helping lawyers go in house because it's, I enjoy helping people. I like seeing the success and it really jazzes me up when I see people, you know, make like the, you know, you see the light bulb, like the, the proverbial light bulb flicker in there in their mind. When, when they believe, they finally believe that, that they've, they've had a hard time. They come to me. And then all of a sudden they've now found a, you know, they've gotten their first interview or like they have made it to the, the offer rather, they've got an offer. So those are the cool things for me to see, But I just really enjoy helping other lawyers navigate this path that no one really teaches you to take. That's awesome. And I see that you might work with some lawyers who really don't check those traditional boxes of or you got to do XYZ or you got to start your career doing this. And I think there is, it's always interesting to see, you know, what most people get wrong and, and what they, you know, might be doing wrong with their resume. Or even if you're a student getting out of school and you do have a few options, which one is best? But from your observations, what are some things that that people get actually right and that usually surprises? You yeah, I, I think that the biggest issue or biggest thing that I'm always surprised by is I don't think that, you know, if you're not fancy law school, big law pedigree, those are my observations don't really matter much. Really the primary key for anybody, whether you're you went to a fancy law school or you have a big law pedigree, is you need a willingness to learn. You know, it's very, it's the, it's the attorney. So I constantly observe who are curious and it's not they're they're they ask questions, right? They're not afraid. Law law school again, to not to not to dump on law school during this podcast. But you know, law school is like teachers would be the Socratic method and they ask you hypotheticals and you know, there's sort of this like when you don't, when you don't answer the question or you don't know the question, there's sort of this underlying current of, you know, Hey, you failed, you didn't know the answer to this, this question. And I think that's that teaches you the wrong mentality because it teaches you like a fear of failure because you have this like, oh, shoot moment when you're called out early. So I did when I was in law school, you know, you're like, Oh my gosh, I just got called on like what I and then you start panicking. And so I think it's really like, it's the it's the attorneys who are able to kind of like ditch that, that like, I need to know everything mentality. And we're curious. I'm like, hey, I don't understand this issue. Will you explain it to me? And I think when you go in house, you know that the restraints on your time are a lot different because you're not under the crush of the billable hour. And so whether you're working with sales people or engineers or senior lawyers, you know, people will take time to explain things to you if you don't understand. But you got to ask and you got to be willing to learn and roll up your sleeves and think about it a little bit because, you know, the more repetitions and the more curious you are, the better, the better you are. And anyway, that's a skill that I think just transcends where you went to law school, what firm you worked at. And you can learn that skill along the way too. But that is what I think makes you become a really great in-house lawyer. That's amazing. I was thinking here of like, what would be something or, or some story that maybe you could, how is that could be something that our listeners could really relate to you. And I'm wondering if there was a time when maybe a client surprised you in some way. Maybe it could be, you know, somebody who didn't have much of that self-confidence of going to and, and in-house role, but really want ensuring the long term and, and they ended up, you know, lending that job maybe more easy than they thought. I'm wondering if there is any success story like that you could share with us? Yeah. So you know, this story is I had a student come to me awhile back who actually had great, he had great experience. He had been in house for many years. He had to. I don't, I'm forgetting the exact specifics, whether he was general counsel at one point. What point is he had, he had a great, great career, a great experience. And he, something happened where he wasn't in his current job and he had spent many months, you know, he felt like he was out in the wilderness and he was not having any luck getting anybody to, to interview him. Or when he did get interviews, they, he thought they went well, but they didn't go anywhere. And he just wasn't having any luck finding, finding his next job. And you would think on paper, I always tell my students that the hardest in-house job to get is your first in-house job because the jobs are not very plentiful. And there's a lot of in-house lawyers who are competing for those jobs. And in this case, it was totally the opposite. You know, this person had a great resume and it just seemed like they were just not having any luck, even though they had great in-house experience. But really, you know, this was where I, and we'll talk about this a little later, I'm sure too. But, you know, I think I felt like he was just really psyching himself out. There wasn't much that I could tell him. It was more I felt like I became, even though I'm not trained as a psychologist, I feel like I was more just a like a, you know, kind of like, I don't mean this is like a, a negative way, but I was just kind of like a shoulder to lean on another voice to like a voice and encouragement for him. And, you know, I just told him, I said, Hey, this is sometimes you, for whatever reason, you, you might, you might provide an answer to an interviewer's question. You don't know what the interviewer has been through. You know, they might, you might have said something that just like, that's a, that's a red line for them, right? And it might be the most innocuous thing like, you know, and you just you have no idea. So, you know, the odds are, you know, the the more I so I kept encouraging them, hey, you got to put yourself out there. The more you interview, your eventually going to find one of these. You have great experience. And so I really just found myself, you know, so it was surprising because I wanted and finally I got him believing that it was, it was he could do it. And you know, I'm happy to report. I think a couple of months ago he started a started an in house drive and loves it. So it's great. But yeah, it's you know, it's your, your equal parts, you know, your, your equal parts coach. And sometimes you just have to it's not even really coaching. It's just like giving them a voice of encouragement, just like in this situation. Solutely. That's awesome. If I were to ask you as well, is there one small mistake that you see repeatedly that, you know, lawyers will be making it over and over again? Maybe something that quite often you have to kind of go over with or and that could be, you know, either in the resume interviews or even in the way that they go about applying for things. Like Claudio, we could talk about, we could spend a whole interview talking about this. So you know, my, I wrote down, I wrote down a couple of thoughts that that I've noticed. And so I do a lot of rest to me reviews. So resumes, especially legal resumes, they suffer from what I call a sea of sameness. So most lawyers, they fill their resumes with a bunch of buzzwords, things like a draft, negotiate, redline, streamline, you know, all these things that don't, all these things that they mean something to a lawyer, but they don't really tell the story of what he did. And So what I try to, what I tried to tell lawyers is when you're like, the example I always give is if you're applying for a commercial legal role, you're going to negotiate commercial contracts. Or if you're going to negotiate procurement vendor contracts, it's the same thing. Your first bullet should describe the types of agreements that you've negotiated. And it should be because the assumption if you're applying for the job is that you know how to negotiate. But if you bury it on your third or fourth bullet, most people are going to assume that your first bullet is the most important thing that you've worked on. So I think that's one, that's one critical point that a lot of people miss. The second critical point is this is particularly for law firm lawyers is law firm lawyers write their resume and there's, this is no fault of their own. They don't think about it is they write their resume like when they're applying for an in house job is if another law firm lawyer is going to be reading the resume and it just doesn't speak the language of the in-house lawyer. So these lawyers, oftentimes I, I advise them to take a look at job descriptions in house job descriptions and start thinking about what kind of words are used, what words and phrases are used in those job descriptions, because those could be helpful road map for you how to describe your experience on your resume. And in today's day and age with, you know, ChatGPT and Claude, you can, you can just take a couple of those job descriptions, post them into ChatGPT. And you can also put your resume in there and say, you know, something like map by, you know, map my experience using the, you know, buzzwords found in these, you know, three job descriptions. And that will go a long way towards towards improving your resume. No, that's amazing. Quite a good tip that I feel like everybody could benefit from, maybe not even only people wanting to go into the new space, but really trying to, you know, stand out a little more in the in the job market. And I'm also curious to know about, you know, once one of your clients gets a job, do you also work together to know, you know, the the first few weeks or are there, you know, rules of what you do, what not to do? Do you have any any general guidelines like that? Yeah, well, you know, it depends. So first, yes, I have actually in my course I have a lesson which is, you know, essentially, hey now you got the job. What do you, what do you do now? And I, I sort of tongue in cheek say it, but it's true. You need to start thinking about your next job when you start your first job. And now, of course, I don't mean like you should start applying for your next job the day you get your first job, but you're, you're really in what I call the story accumulation business. And what I mean by that is when you go to an interview, eventually you're going to interview, you know, the odds are very high that you're not going to stay at whatever in-house job you've been at your entire life. And so you're going to have many in-house jobs. You're going to interview many times for different roles. And so your goal is an in house lawyer. You know, besides being an excellent in-house lawyer and a good partner to the business is you want to accumulate stories, meaning like you want to talk about the these things that have an outsized impact beyond just your day-to-day role. And so, but part of being able to tell those stories is gets to your question about the first, you know, 90 days, right, which is you should just focus on the things that are key to the business. So I keep going back to this commercial lawyer example, But you know, one of the things, and even if you're a product lawyer, it's still the same is you should understand the products. What do they do? You should understand the, you know, if you're a commercial lawyer, you're going to be negotiating your, the terms of service with your customers. So you should understand what your terms of service say. You should talk to other lawyers and ask them what, what are the things that customers typically negotiate? And like, why do they negotiate? And if you're, and if you're a company that's big enough, they might have a, they'll probably have a, a legal playbook that you can go and review and see, Hey, these are the fall backs that we get. And here's the provisions that, you know, you have to, you have to learn those because that's, that's really the table stakes is when you, when you understand these, how, how your job works and you understand the product, it all fits together into this like beautiful, you know, mixture, right? It's like a recipe. And then that when you understand all that, that is when you get into the next phase, which is where you get, which I called story accumulation, right? Is your, that's when you're able to like add the real value to the business because now you're doing the day job or what's required of you and you're doing a great job. But then that's when you start thinking like, Hey, you know, I have noticed that this same issue keeps coming up every single time. What's the way we can streamline this? Or hey, maybe there's a, maybe there's a problem over here or, you know, if you're on the, if you're on the vendor side, right, which is just the flip side of commercial. Maybe you say, hey, I've noticed that we're, we're getting the same type of agreement in, but we're not really negotiating it. Maybe you just create a, you know, like a one page writer that says, you know, here are the key terms that we we require in every contract. And then those, and then that way you just eliminate negotiation. And so, you know, maybe that's like 10% of your day, right? You spend reviewing these agreements that you never redline. And now all the sudden you freed up 10% of your time. And that goes into the, the account again of story accumulation. So now when you go interview again later, you have this great story. Like, Hey, I saved, you know, I saved 10% of my time or 10% of the contracts I reviewed by, you know, streamlining this process. And here's what I did, and here's the impact it. That allowed me to do all these other things that I wouldn't have normally been able to do. So those are the things I think you should look for, you know, and that's obviously way beyond like, you know, your first like couple months in the role. But you know, the table stakes are what you got to start with and build that great foundation that allows you to excel later on in your career. Amazing really, I think that one of the, the very helpful like resources that you have as well is, is what you end up doing a lot of LinkedIn of like, you know, putting a, a whole list of different in-house roles. They're available sometimes not only in the US, but including, you know, Canada. I've seen you do it if you European countries as well. So really comprehensive and I find that amazing in a way. It's being really nice to see, you know, you're helpful tips and all of that. And I'm wondering as well if you, if you have any kind of advice that maybe you give two lawyers, you know, trying to build their own online presence in a way that feels natural to them. And, and in that same point, have any of, you know, the lawyers that you've interviewed or do you, that you worked with, have, you know, kind of is there a correlation between, you know, having that online presence and actually getting jobs or that's usually more of a no instrument for networking and, and keeping those connections alive afterwards? Yeah, I, so this, this one, I go back and forth on about whether it's whether a, an online presence is helpful to lawyers on LinkedIn. You know, the, the general advice or I guess the general, general observation I've seen is I, I can't, I've never noticed a correlation between someone's posting and whether they get, they get jobs. I don't know if it's true in other, other industries, but it doesn't seem to be, I don't think I've met anybody who said they got a job because of something they posted on LinkedIn. I do think that if you're working in a law firm, posting on LinkedIn could be a good way to draw the attention, to draw the attention of in-house lawyers, right. Because you, you're seen as a subject matter expert. It's similarly like presenting at CLES is another great way to do that. But, you know, I think in terms of trying to grow your online presence, I think, you know, first you have to get over, I guess the, the cringe factor of like, you know, posting content and like feeling like what other people, you know, you care about what other people are thinking about you. But I think you really just have to be authentic, right? And think about what, and this advice is not dissimilar from what I hear other people give, but you know, think about something that you're that you're interested in and that you know a lot about, because I think that that passion and that interest will people can read that, right? If you're just writing a you know what, I think it's like the term of art now these days is for with AI generated content to slop, right? And people can, can identify the AI, the AI generated slob. I think you know better than better than you realize. And it's OK to use AI to like help you come up with ideas and maybe refine your post or give you like a first draft. But you know, you should always be the one writing and editing it. You know the one. The one other thing I think that I notice lawyers do a lot is lawyers are really bad at humble bragging. I think, I think it's, it's perfectly fine and acceptable to be proud, proud of what you've done and highlight your accomplishments. But I do think, you know, you have to be careful about how you do it. Otherwise it can't rub people the wrong way. And, you know, I think I think honestly, oftentimes it's better to keep it keep things short and sweet. Like, for example, you know, I'm I'm honored to, you know, like received, you know, ABC award last week. But then I think you kind of you cross the line into like cringe worthy and, you know, embarrassing when you know, you post something about an award or nomination you received. And you know, you say like I, you know, you and, and you touch it in a wave. It's just like it turns people off, I think. And it's like, you know, I had a really awesome time at this conference and I was humbled to be on stage with, you know, this, you know, insert the name of a super important person. And and then I was presented by an award from this other super important person. And it's like, you know, nobody wants to hear that. It's just like, just describe the award and the work you've done, you know, and like let your work speak for itself. But you know, I think you could talk to probably 10 people and they have 10 different takes. And so I'm just one person. It's like resumes, right? Everyone will have a different resume tip. But you know, there's also gets me thinking though, I'm going to have to follow my own advice when I post about being on your podcast when this comes out. So it's a good question. Got me thinking. There you go. No, that's great. While you wrap up today's episode, I wanted to do a quick with a little bit of a lightning round with you. So I wanted to ask you, you know, if there was kind of one phrase or or one thing that you see in each or in lots of the in-house job descriptions that you could delete, what would that? Be Oh, this is an easy one. I would delete any, any job description that describes a job as corporate counsel. But what is really describing is the head of a legal department. This is a I posted about this before on LinkedIn, but that was a huge pet peeve of mine as people just have unrealistic expectations and you know, they'll, they'll say it's a corporate counsel role, but it's like they really want, you know, the head of privacy ahead of product, kind of commercial ahead of compliance. And I don't think that does a favor for anybody, the company or the lawyer who gets that. Job Amazing. Is there anything about law school that you wish it were completely different? Yeah. I do. I was actually talking with a friend this morning about this. You know, I think, I think law school, I think law school could be done in two years. So that would be one, that would be one thing I wish was changed. The other thing is I, I wish there was less focus on learning the law. You know, like there are some important things you need to learn, like Civil Procedure and criminal, you know, criminal law and things like that. But I do think there is not enough emphasis on like learning, but like learning how to do things. And there's I think there's a you get in a lot of lawyers are done a disservice when they go into and firms are done a disservice when lawyers going to practice. And they spend the first probably couple years just molding these lawyers into a lawyers who are actually, you know, can produce work product that they can sell. And so I wish there you would spend, if you were gonna spend three years in law school, maybe that third year I spent less on learning, you know, nuances of the law, right, and more learning about we're learning about, you know, hey, how do you write a brief? How do you research? How do you write a memo to a partner or to a client, things like that. I think law school would be great if it if it changed that model up a little bit. Although it has been 15 years since I've been in law school. So maybe this has changed? Well, as somebody who's graduated maybe a little bit more recently, I think there is a there's definitely the push and the willingness and, and all of that. But yeah, I don't, I don't know if in our lifetime we'll see a complete shift. I think that's very interesting to keep, you know, thinking about ways that that can be implemented. And I think that more and more professors and and schools are trying to integrate that into the curriculum. But it's definitely still something that that can be worked on. And military finished the lightning round here. I wanted to ask you, is there, is there a question that you never get asked but you wish people would ask? Claudio OK, so I wrote this down and this you actually asked the question. So the question is that I wrote as what should I focus on after I land my job? Because so many people focus on landing the job, but they don't think about what they should be doing after that. And so I think if they focused on that, they would or they, they spent a little bit of time thinking about that, they would do themselves a humongous, humongous favor and really go in, hit the ground running. Fantastic. Well, I really appreciate you taking the time to share all of these insights and so much about your career and the work you do. If you could also tell our listeners of like, how could they reach out to you? How could they learn more about your coaching services as well? Yeah, for sure. So you can find me on LinkedIn, Billy Rustin. I also have a course called my in-house coach. It's just BW w.myin-housecoach.com. And you can also feel free to reach out to me, e-mail me at hello@myownhousecoach.com. Amazing. Thank you so much for once again for being the podcast and thank you all for listening. Thank you.