The Evolution of a Contracts Lawyer: Shaun Sethna's Path of Discovery

This is the full transcript of You Can Contract's episode featuring Shaun Sethna, General Counsel at Tech GC.  In this episode, Laura Frederick chats with Shaun who shares his journey from patent law to commercial contracts. He discusses the challenges he faced while adapting to contracts, the imposter syndrome he experienced, and the value of learning from colleagues and opposing counsel.

Laura Frederick: Welcome to this episode of You Can Contract. Today with me I have Shaun Sethna. Welcome Shaun.

Shaun Sethna: Thank you, Laura. I appreciate your having me on.

Laura Frederick: Oh, I'm so excited to have you. And we've become friends over the last probably two years or so, talking contracts on LinkedIn. Well contracts and other things, too.

Shaun Sethna: Absolutely. Yeah, you were definitely one of the first people when I was starting to get active that I saw putting out great content right away. And and I appreciate how you've reached out and we've been able to, chat and work together on some things.

Laura Frederick: Yeah, you were in one of the workshops we did last year, and it was fantastic. I really appreciated your practical approach. So tell us a little bit about you and where you are right now and what you're focused on.

Shaun Sethna: Just about two months ago I started a new job for the first time in 10 years.

I'm the general counsel at TechGC TechGC for those who don't know, it's a community. For for in-house lawyers generally focused on technology companies that we try to basically provide you the tools to be able to do your job better, whether that's through content, networking opportunities software platform, et cetera.

So I've really been enjoying that. And in addition to the GC role, I'm also taking on HR and also helping with a lot of the legal content. So it's been a, it's been a really good mix and a really exciting challenge.

Laura Frederick: We'll start at law school cuz that's usually where most people start working with contracts. Did you remember liking contracts or learning anything about contracts in law school?

Shaun Sethna: Sure. I took contracts the class that we all take, and I think I, I did reasonably well in it, but I do remember like in the middle of it, or maybe towards the end as I was studying for my final exam one of my friends from college asked me who was not in law school or anything.

He asked me a general question about contracts or something like that, and I said, I'm actually studying for contracts right now, and I've gotten through the whole semester and I have not seen a contract because we are just reading cases all the time. And when I look back, and I think this will probably come up in, in LinkedIn when we talk to people who are in law school and how things can be better, I'm pretty sure I did not see a contract during law school other than if you count like the lease that I signed for my apartment that's just how it was, at least back then.

They had started to offer various clinics, and I'm sure if I had done that, I probably would've seen some, but it was not part of the regular coursework.

A lot of schools are starting to do better. It's a long road I think.

Laura Frederick: You graduated law school without seeing a contract, and then what kind of work did you do out of law school?

Shaun Sethna: When I started I was an IP associate at a large law firm. I did mainly patent work, both on the litigation and transactional side. So I still didn't really see contracts much until maybe a few years in.

I started helping with IP due diligence for M&A transactions. Maybe look at the IP sections of a purchase and sale agreement but certainly not a meaningful part of my day-to-day job either. And so I was there for about five years before I went in-house.

My first in-house job was at Schlumberger, a big oilfield service. Oh yeah, I know them. And at least I got the same introduction to contracts that a lot of people get, which is NDAs. And so I started dealing with those a fair amount and that was probably the first time it came.

That's interesting about the NDAs because they're ignored by a lot of people. They're just like, whatever sign the NDA. Other people are like, you gotta be careful. You gotta be careful. But it's really hard to balance those two dynamics of being such an ordinary business document and when is it important. Every single NDA isn't that important.

Laura Frederick: There are some that are though. Do you have any advice on what you learned from that experience about NDAs?

Shaun Sethna: Yeah. I love how you hit on that theme because I feel that lawyers seemed to fall into one of two camps. So one camp saying, eh, it's not a real document. It's basically just saying shake hands say, yeah, I'm gonna try to keep it to myself.

And the other camp was like, no very serious document. You need to extensively negotiate every single thing. Their risks all over and I don't find too many people in the middle, but you actually hit on something, which I think is exactly the right thing that it depends. There are somewhere it is probably not a big deal.

You just need to have something reasonable in place and move on. And there are some where they are absolutely a massive deal. I think the situations that come up are when you really need to drill down are certainly if you're entering into an NDA with a competitor or a partial competitor where, you know, yes, you may be the client and they may meet the vendor in this context, but there's a tremendous amount of overlap in the services that you offer.

You wanna make sure that there's no, if you're independently developing things on your own, that there's no argument from them that, oh, you took our confidential information to do that. Those are risks that I think the crowd of, just shake hands and move on. I think they sometimes gloss over that.

So that's definitely real. And then certainly in the context of a potential M&A transaction or with the potential financing when you're dealing with, especially if you're a public company, material, non-public information, there's a lot. There are a lot of clauses in there that will need to be heavily negotiated and customized.

And yes, that may mean it may take a couple of weeks to get the right NDA in place, but hopefully, it doesn't take that long and you can make things more efficient. But that is almost always time well spent. We could probably talk NDAs for days. It's an important document. I really enjoy them. A lot of lawyers don't, but I like that it's more of a puzzle cause it's only a few pages and it's always a challenge. So anyway, we'll move on from NDAs.

Now you've been doing NDAs and how did you transition more generally into other contracts? So that wasn't until I went to my third job.

Okay. So I was at Schlumberger for about two and a half years. And at that point in my career, I still very much saw myself as an IP lawyer. Largely patents. But I had started moving beyond that and I thought, hey, if everything breaks right for me I would love to be a Chief IP Counsel one day, and that, that's what my goal was.

And that's now probably, we're talking about 8, 9 years out of law school. And so I went to a company called Altisource and there I actually was, that wasn't my title, but I was the lead IP attorney for the company. And I thought, okay, this is what I wanted. And I thought, do well here, maybe then try to be that same role in the larger company, et cetera.

That was my plan. But two weeks into the job it was clear they had an additional role for me, which I wasn't expecting, never came up in the interviews or anything like that, which was to be essentially the generalist for all the technology businesses. So then within two weeks, I was looking at leases that the technology team needed to sign. I was looking at all their software licensing agreements, SaaS agreements, et cetera consulting agreements. I had never really done commercial contracts before. And eventually a lot of imposter syndrome. And wondering, Hey, like I'm teaching myself here. Am I getting this right? Am I making huge mistakes? I don't know, I'm gonna get caught one day. But I really did enjoy learning it. I really did like that kind of work.

And that just went on and started getting more and more comfortable eventually. I shouldn't say eventually, it's less than a year later I started taking on M&A work, which is, what is that? Other than a lot of big contracts in one transaction. And I really started to enjoy it.

And that's when I realized, okay, like the whole IP thing, that's just what I thought I wanted to do. But this is something that's far more enjoyable to me.

Laura Frederick: I love that story of that transition, and I had that so many times in my career where I was. This is perfect. The job I have right now, I love it so much. Okay. I just wanna do this with this little tweak at some other company. So I think that's great to tell the story of how you just evolved and followed what interested you.

Shaun Sethna: Yeah, absolutely. And with me, at least until that moment, I did not think I was the kind of person who always likes learning new things. I thought that was very much I want to focus on. I want to do well and get better at this narrow set and maybe gradually expand. But that kind of transition happened relatively quickly. You're talking about a span of six, seven months that made me realize, no, I'm the kind of person that I like learning new things and keep expanding. Even if that means I don't have the time to get deep into any one topic anymore. Getting that breadth of experience is really satisfying to me. Yeah. That's so cool.

Laura Frederick: So those years when you were figuring things out, did you have resources available to ask? Were there lawyers around or outside counsel? How did you figure things out you couldn't figure out on your own?

Shaun Sethna: Yeah, so certainly on the M&A side, yes, I relied a lot on outside counsel to bring me up to speed and they were absolutely fantastic and very helpful in that in terms of the everyday commercial contracts.

Not so much, to be honest. I did a lot of figuring it out on my own. When I really screwed up. Yes, my, my boss was there, he would notice something, we'd talk about it, et cetera, but he didn't have time to look at even, 20% of the contracts that I was signing off on.

And you figure it out over time, as so many people do. But I wanna call out that a lot of the places where I've figured out over time were from learning what people more junior to me were doing. There were some contracts that I was just responsible for, but for a lot of the more minor contracts, I was reviewing the work of somebody else.

And I would learn from them. And when people are doing, if that is their main job, they're gonna think of things they're gonna think of, better language, et cetera. Sometimes that I haven't thought of. And that's great and you should leverage that. And you should never be too proud to, to think, oh no I'm much more senior to them.

I'm sure my way's better. So I learned a lot from them. Learned a lot from opposing counsel. At times they mean they'd come back with something and I think, huh yeah. And next time I'm on the other side of this deal, I'm gonna do exactly that. And, get better over time from things like that.

But I think those were two really big sources for me that I think people don't talk about a lot. They usually focus on mentors who are teaching you, but there's a lot of value in those other sources as well.

Laura Frederick: That's why your story is so important and really why I wanted to start this podcast cause there are so many different paths to learning about contracts.

It's not just one straight path. Everybody has some wandering around and figuring it out. When you're learning contracts, it really is that lifetime of learning, like you were talking about. I think those are the people who really enjoy contracts the most are the ones who like ongoing learning. I think there's also an element of being comfortable knowing that you don't know everything and doing your best.

It's almost like the emergency room medicine approach. As opposed to the surgeon who's doing everything precisely, always. I think of it as the ER doctor who's okay, stick a bandaid on it. Send them out.

Shaun Sethna:  I love that analogy, Laura, that is fantastic. That's a great way to look at it.

Laura Frederick: And then hopefully people hear that and hear stories like ours and they say, oh, I'm figuring it out too. And that's okay. It's not some false standard that we're all so genius and we all know the answers. We don't, we never do. We just keep learning.

Shaun Sethna:  Yeah, absolutely.

Laura Frederick: You were working in commercial, you were doing M&A. Do you like one more than the other now that you've been doing them both?

Shaun Sethna: That's a good question. My instinct is to say M&A. There's something about it. Maybe it's just the energy of it and the excitement in getting to close a large deal. But at the same time, when I say that, I've been part of deals that just stagnate after a while and you get deal fatigue. And that does happen with M&A. That's probably more likely with M&A than your typical commercial contract. Then it does start to feel like a slog.

And that is not enjoyable. So I hate to be wishy-washy here, but I think it's good to have a mix of both. It really does. They each bring something new to the table. And I'm not saying it's not just doing some M&A and doing some commercial contracts, but even while you're working on a big M&A transaction, it's really fun to have some smaller commercial contracts to do at the very same time.

So if you feel a little stuck on one, you can go to the other and feel like you're making. Yeah. And I think it's great too because you, by trying out these different kinds of contracts, you really get exposure to the different things. Because I did some large outsourcing deal that was a big part of my practice in my law firm days, and these are eight months full-time, nothing but one particular deal, and I hated it.

And it was that deal fatigue. Some people just thrive on that level of deal. But I didn't like it. And I did some M&A support. I hated that too. Maybe it was because I felt big when I did my commercial contracts.

Like I'm in charge of this deal. I'm important. And when I did M&A, I'm a cog of a hundred people. Yeah. So maybe that was part of it. Yeah, it's definitely interesting to see who's drawn to what and even ourselves, like you were saying you didn't know you were gonna like M&A and you found it fun, and only by trying it out do you discover that.

When I was in a law firm, I was just helping on M&A, I remember multiple people asked me, what the favorite and least part, favorite part of my jobs is in every single time I said my least favorite is M&A. I did not like playing that support role at all. It was boring and it was hard to see the value in it. But then I just needed to see the bigger picture, and then it became one of the most favorite parts of my job. And so you just never know until you seek out everything from different perspectives.

And the other thing I liked better about commercial was the clients, because I had a specialty even early on. I liked to work with clients that didn't have in-house lawyers. I didn't like working with lawyers in house as much because it felt like they didn't need me as much, they weren't as dependent on me. And there was something really fulfilling having someone dependent on me and me helping them. It made me feel better.

Laura Frederick: So, it's almost like a psychological analysis to see where we get pulled toward with our contract career. Yeah. I can totally see that.

One of the really interesting things about your career is this shift from patent law to contracting. Do you have any advice for perhaps other patent lawyers or people who are in that space and maybe not doing a lot of contracts, things that you learned along the way that might help someone?

Shaun Sethna: Sure. In terms of specific to somebody in that kind of background, I'd say it probably makes sense to start with a natural transition. Like for example, start working on licensing agreements or asset purchases involving the sale of patents or things like that. Because that will, you're starting with subject matter that you're familiar with.

You don't have to start learning something brand new and you'll see that there's really nothing too magical about it They're just words on a page that that patent lawyers should already be comfortable with the idea of words on a page. And they're much like a patent application read and a patent claims read.

You're working on trying to be precise with your language to accomplish what you need to accomplish, which is the exact same skill that you need when you're drafting patent claims. The word choice may be different, the style may be different, but it's that same mindset. And so I would say start with something like that.

And then you will start to get more comfortable and then you'll realize, okay now, yes, that background was helpful, but going from a patent licensing agreement to any other kind of commercial contract at that point is not that big of a jump. Whereas if you try to go straight from drafting patent applications all day to negotiating SLAs in a cloud platform or something, that might be difficult.

I'm not saying you can't do it, but it might be difficult. But if you take some interim steps to create a natural transition for yourself, then it'll feel much, much easier. You'll be a little bit more confident.

Laura Frederick: I think that's fantastic advice and so important because a lot of lawyers and professionals I see start with some subject matter expertise and they, even if it's not patent lawyer going into transactional work, it could be supply chain buyer who suddenly is starting to work with contracts and focusing on the fact that you already know what you're talking about.

Shaun Sethna: I love what you said about there's really no magic to it. It really isn't, even though it feels magical to me because I love it, but at the end of the day, the work itself is just writing words. And most of us, especially in a business context, even if you didn't go to law school, you didn't get trained on legal writing per se. If I keep going with the supply chain folks, they're writing specifications, they're writing statements of work. They can understand it. Keep pushing yourself to do more, especially if you have the opportunity to dive in. And I always love this where I could jump into a role where I was clueless, but everybody knew I was clueless and it was okay that I was clueless.

That's the best because if you have that opportunity, you don't have to feel that imposter syndrome. You don't have to feel that anxiety that you're letting everybody down cause you don't know what you're talking about. Because everybody knows you don't know what you're talking about. They're okay. They're ready to help you learn.

Laura Frederick: Yeah, and it sounds like you've had that experience as well. It's somewhere where you were coming in and they knew you didn't know this work, but they encouraged you anyway.

Shaun Sethna: Absolutely. Yes. And I've certainly taken that on as a manager now. I've hired people who haven't had contract experience before, even though this was the primary contract's role, knowing that yes, people can figure it out.

And if they're the type of person who likes learning new things and writes, then that's probably somebody that you can turn into a pretty good contracts lawyer pretty soon.

Laura Frederick: For those folks that you're training, and this is because that's another part of this whole podcast. As a manager, how are you helping them learn contracts? What's your approach to that?

Shaun Sethna:  One thing — I don't do it so much in this job, I'm the only lawyer here — but in my last job where it was for 10 years, one of the key things was every company has their templates usually.

And so start with, a couple of the most frequently used templates and it would help if somebody takes the time to annotate all of them to say, okay, this is what this clause does. It's, we often get pushed back for this reason. If that happens and here's a fallback clause and go through.

I'm not saying every single line, the people who have been working with those templates for a while know what are. 10, 15 issues that are gonna come up and just explain what that's gonna happen and what are you gonna do. So I think that's definitely one big thing.

The other big thing that I recommend that I've done before is to try to give people samples of agreements that in theory should be polar opposites from each other. And then compare them and see, and when I first started, we were definitely in the camp of every NDA is a very serious negotiation no matter what.

We had two one-way NDAs. One if you're the discloser, one if you're the receiving party. And they were very, very different from each other. But then you realize if you compare this one to this in theory that should be the universe of issues that are likely to come up. And so one thing that I did was I just ran a redline comparing the two, and so it was right there and used that to explain, okay, these are the different types of issues that come up. Here is the concern. Here's what our receiving party might worry about. Here's what a disclosing party might worry about.

Here are some potential compromises and do that. And I found that kind of tool was really helpful.

Laura Frederick: I like that a lot. Yeah, that's great.

Shaun Sethna: And then it was much more complicated and yet less user-friendly, but I did also try to dig out past M&A deals that we've done and start with our purchase and sale agreement.

And basically, create three versions of it. One is the final agreement. The other one is what was like if we did the first draft, what was our first draft. And the other was what was their first, the counterparty's first revisions back to us. Sometimes issues come up later in the process, but usually, that's the universe of issues. And so by doing those comparisons, you can see, okay, what are the universe of issues and compared to the final to see, okay, what are some good compromises to resolve those issues? The work is already there. If you just take some time to just find the right documents and explain, okay, this is how you could use them.

Just simple steps like that can really make a big difference to let people study on their own and try to get up to speed.

Laura Frederick: The thing I like about it is it's not theoretical. It's not generally indemnification, blah, blah, blah, blah, blah. It washes right over us as opposed to here's indemnification and this specific deal with this specific parties and this is what they decided. Because then you're teaching context, you're teaching specifics, which is everything. And I'm such an advocate that like model clauses are great, playbooks are. But they're guides. They're information for us. Once in a while, playbooks will have hard, fast rules. We don't do X, but most of the time we shouldn't be looking at playbooks as the rule and we can't deviate because the real world doesn't work like that. We often have to deviate.

Shaun Sethna: Right. It's an issue to consider. Here are some things that you, here are some potential solutions. This is why it's important, and this should help you with your thinking. It's not a copy-and-pasting or hard rule exercise.

Laura Frederick:  One other thing I wanna ask you about as a manager is the imposter syndrome. And we talked a little bit about this. We both have experienced it. I certainly did way longer than I should have, but such is life.

When you're acting as a manager of people learning and you know they're facing those issues, did you discover any particular techniques or ways you can support them to help them with that particular challenge?

Shaun Sethna: I can tell you what I've done. I don't know if it helped because nobody came out and said, Hey, I was suffering from imposter syndrome and you made it all go away. But I do think these are the types of things that I recommend. First is, honesty and transparency, and vulnerability.

At the right time, I would tell each new person that I was working with, this was my own journey with imposter syndrome. This happened to me, it almost derailed my entire career. It's important to me that people talk about it because that's the only way that, that we can prevent it from happening or stop it in its course.

The second thing would be to let them know you're expecting them to screw things up. That it would be weird if they didn't and if somebody's consistently doing perfect work, that means I'm not giving them enough challenging work to do and say it however many different ways you can to let them know that you want them to make mistakes, that is how they're going to learn. So they don't feel that trepidation of always being afraid to make mistakes, it's something that they're expecting and that I'm expecting of them. And then the third would be to give specific feedback, good and bad, to let them know the things that should be changed and why.

Or if they're not meeting expectations in one area, then be honest with them about that, to say, "Hey, I'm here to help you, but I am concerned that this is a recurring issue. What can we do to improve that." But also good feedback needs to be specific as well.

Because if you have kinda constructive feedback and then you just say, "But overall this was good," most are gonna feel, "Are they just saying that? Do they really mean that? They listened to all these nine things that they wanted me to do differently, but why are they still saying it's good?"

But no, you have to take the time to say, Hey, I thought this was good for these reasons. It was very well organized. I noticed that you fixed this time the mistakes that you had been doing the past time, and that was really good. And if you give them that level of specificity, they're more likely to internalize it and believe it.

And then you can have a more cooperative relationship where they feel, okay, yes, you know what Shaun says is really what he's thinking about me. He's not holding back. I feel comfortable now.

Laura Frederick: I think back to my early career and I actually found a performance review. It was really interesting. And they did a fantastic job because, as you said, they spent the time really talking about these are your strengths, these are areas for improvement.

And because they spent so much time, I didn't feel like they were lying, like they really think I suck because there was so much substance to what they thought I did well, and that was just so valuable.

The listeners, if they want to find more about you, I know you're still super active on LinkedIn. And maybe tell 'em a little bit about to find you and get in touch with you. Obviously at TechGC, they'll see you there.

Shaun Sethna: Yeah, absolutely. So yes, I'm still nowhere near the dedication that you have, Laura, but I try to post almost every workday on LinkedIn.

So definitely feel free to check out my profile on the post, et cetera, if you think there's something I can help you. I can't pretend to say that I respond to every message that I get, but I do think that when I get a message if it's something that I feel I can help with I will respond.

And so don't ever feel shy about sending me a message. It's not gonna annoy me. But then, yes, to the extent any of the people listening are TechGC members or are in the future, feel free to connect with me that way. I'll be at some of the events and happy to chat with anybody in person if you happen to see me. So yeah, I think those are the main ways.

Laura Frederick: Thank you so much for being on, and I really appreciate your time and all this great advice. I appreciate it. Thank you for having me on, Laura. It's always great chatting with you. Yeah, you too. Okay, bye.

You Can Contract is a podcast and a YouTube show that shares stories and advice about learning contracts in the real world. Follow us on YouTube, Apple Podcasts, Google Podcasts, and Spotify.

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