Mastering Contract Processes and Empowering Your Intuition with Lucy Bassli

you can contract May 16, 2023

This is the full transcript of You Can Contract's episode featuring Lucy Bassli, founder and principal at InnoLaw Group, former Assistant General Counsel at Microsoft, as well as a legal writer and LinkedIn thought leader.

Lucy talks with Laura Frederick about her transition from her first job in a bankruptcy boutique to working in-house at Microsoft to starting her own consultancy. She discusses the importance of trusting your instincts and judgment when it comes to contracts, as well as learning to find a compromise in negotiations. Lucy also touches on combining the substantive, creative stuff of contracts with automation and efficiencies.

Please note: this is an automatically generated transcript. Please allow for some imperfections.

Laura Frederick: Hi, this is Laura Frederick. Welcome to this episode. Today I'm talking with Lucy Baslli, founder and principal at In a Law Group. This episode includes some really interesting discussion around how to learn to trust your gut and how moving towards a better process allows you to do more of the fun with contracts. Let's start the show.

Laura Frederick: Lucy, it's so great to have you. Thank you for being on the podcast.

Lucy Bassli: Thank you for having me. So excited to talk about our favorite subject.

Laura Frederick: Exactly. We could do this all day long. And we do sometimes. We'll just sit and talk contracts other times. So It's great to record it because you have so much wisdom to share and you've had such an interesting journey with contracts. So I'm real excited to get into this conversation.

Why don't we start. Tell me a little bit about you and what you're doing.

Lucy Bassli: Sure, absolutely. Like you, I came from the world of commercial contracting and I spent the bulk of my career in-house. I was at Microsoft for 13 plus years doing contracts and then figuring out how to do them faster and more of them quicker and better.

And then about five years ago left to start my own consultancy. And so we work now with corporate law departments to help them become more efficient in doing their contracting.

Laura Frederick: Did you ever expect to be doing contracts before you went to law school? Did you know anything about contracts before that?

Lucy Bassli: Before law school, I knew nothing about law school, nothing about lawyering. I just knew I wanted to be a lawyer. I watched Ally McBeal and LA Law. My skirts aren't that short, but I thought something like that sounds cool. And then I started law school and that was a big bucket of ice water.

Laura Frederick: I think the same for me too. I'm not too into the case law thing and really didn't like that part of it and trying to learn through cases. I know some people love it. It wasn't for me.

Lucy Bassli: No, not my thing at all. And then, so I quickly learned, okay, I'm not gonna be a litigator even though I saw those shows growing up, but I gravitated immediately to the commercial side of it, or I guess contracts. And then I also stayed away from anything that had its own code because my philosophy was why I learn that even though my first job out of law school was with a corporate bankruptcy boutique. So you never know. But no it wasn't necessarily a love for contracts during law school, but I knew I'd end up working in it. I just didn't really know what that meant.

Laura Frederick: Exactly. And so you graduate law school and then you're moving on to your first jobs. You said you started in a bankruptcy boutique?

Lucy Bassli: Oh my God. This is here's a life lesson of the you never know what's gonna happen. So I had [00:03:00] a job with Baker and McKenzie coming out of law school. I did the third year thing of coasting and enjoying my life very well. That was all back in the heyday when we were getting raises during the third year and getting letters in the mail like, Hey, now your new salary is this. It was crazy town. But then life changed things and we ended up relocating between right after I graduated to Seattle. One of the few places Baker McKenzie doesn't have an office back then. Baker McKenzie was the biggest firm in the world and it didn't have an office in Seattle. I had to pull every possible name I've ever met who was a lawyer.

None of my family by the way. I don't come from lawyers. And it turns out that the best connection I had was a big partner in the commercial bankruptcy practice at one of the big firms who knew all the other commercial bankruptcy lawyers around the country, and hooked me up with a bankruptcy boutique.

So yeah, day one was not at all what I was thinking or expecting it all. And there I was.

Laura Frederick: So how did it go from there to eventually work in contracts?

Lucy Bassli: It actually is pretty logical now that I understand it. Being in the middle of it, of course, was a complete whirlwind. Because we did commercial bankruptcy, we were on the creditor side and one of the biggest creditors back in circa 2000, 2001, when the dot com bust happened was Microsoft who had of course commercial contracts with a bunch of companies who all crashed and went out of business. We were on the creditor side and a lot of what we had to do was look at their contracts.

That's how I got to know Microsoft as a corporate law department entity. They got to know me and needed help with things. And some of those things were contracts, and I had looked at a lot of their license agreements during the bankruptcies and that kind of made its way into, hey, we've got this opening and hey, would you be interested? And it is doing contracts all day long job. And I said, absolutely, yes, thank you. That's how I got into contracts.

Laura Frederick: That's so cool. Did you have a particular mentor or anybody, either in your law firm or once you got to Microsoft? That's one of the things I've noticed is some people learn from a really great [00:05:00] mentor and other people don't. And they just have to piece it together themselves.

Lucy Bassli: Yeah. I would say I had a really great mentor as a commercial bankruptcy lawyer who also was great at commercial contracting within the context of a bankruptcy.

I did have a great mentor when it came to just doing procurement contracts. I started those as at the firm I went to then next. I went to Davis Wright Tremaine with again, this great mentor, but that's where I started doing more contracts. I would lean on that mentor a little bit, but I would say I learned the most once I got in-house. I think even when I was at the firm, what I was doing was still smallish and focused, but once I got in-house and realized, oh, I'm just doing this. Double checking. There's nobody with a red pen coming behind me, double billing the client for double checking.

There's not, none of that is it's suddenly, oh my God, I get to decide this cap on liability? Me? So that I remember very crisply, one of the first big purchasing procurement big deals I did was the big hardware provider to Microsoft, which they buy lot of laptops. And this cap came up and I was, 5 billion? Like somehow that number came in. I don't know. And I remember that feeling like it was yesterday. Who? I get to? And that's a feeling a lot of us get when you're a commercial lawyer because there weren't people like you going, here's what's normal, here's what's standard.

There weren't technologies out there, like some of the ones we know that can tell me what's standard and what's normal. It really is you and then you're walking down the hall and you're, or if you have a mentor at that point. I did have somebody I can ask, but I would say that day-to-day learnings were very much on the job, actually learning from opposing counsel also quite a bit. Not because I'm like, yeah, I should trust you. That's five millions good thanks or whatever, but really oh, that tactic they did, or how to negotiate is almost another beast. So yes I did have a good mentor, but it wasn't the kind of mentor that I would run to on a deal by deal basis at all. So the deal work, I was learning as I went.

Laura Frederick: Even if you have that me, because I was in law firms for nine years, almost exclusively commercial contracts. So I started with franchise, moved into tech, but because it was so many years in law firms just doing contracts, I had lots of great mentoring, but then when I moved in house, I was clueless.

Lucy Bassli: I knew my contract stuff as outside counsel, but it's such a different job when you go in the house. You're figuring it all out and everyone's busy. So that makes a lot of sense. Yeah, that's right.

Laura Frederick: Now you're learning, you're figuring it out on your own. Is there something when you look back, or you're looking at lawyers or law students who are trying to figure out contracts on their own, do you have any particular advice for them about how to learn contracts, how to acquire the skills of contracting?

Lucy Bassli: Yeah first of all, there's resources now which just didn't exist. So spend the time. You'll save yourself so much time if you spend a little bit of time now learning and gathering that [00:08:00] information. So there is now helpful hands-on practical guidance that really just didn't exist before. So that's one, use those resources.

I would say the other one is if it doesn't make sense and you think there's a better way, go with your gut. Test it. Ask. Get validation. Get confirmation. That's a good use actually of a mentor. That's a good use of the resources is really just to validate.

You are learning your own craft a little bit. Here's the secret. No two contracts would ever be the same if two different lawyers did them, at the end of the day, Laura and I can get this exact same contract at the exact same company from the exact same third party. We will end up with two different contracts. That's a fact. Neither one is right or wrong. That's the other fact. So you're probably okay going with what makes sense to you in the context of the business that you're now a part of. So I think that's the one thing I would love people to feel a little bit more confident. It's hard cause you think there's an answer. There's guidance. There's training. There's [00:09:00] good things to look and learn from. But you are going to make that final call on your own and you've gotta feel good about it. That's really gaining that internal confidence is from trial and error. And by error by the way, I don't mean you're gonna do a contract and then five years later you've taken down the whole company with your terrible contract.

That rarely happens if at all. And none of us get those in our lifetime. That's like literally what makes the news. You're gonna watch, read back what happened in Enron. Maybe there's somewhere a terrible contract. But that's usually not what the business we deal with. We really are dealing in a pragmatic world where the business is trying to get done and your job is to provide useful legal advice that gets the business done.

So it's got, it has to make sense. And by the way, the world's on the paper. If they don't make sense to you, they don't make sense. It's not you. It's not you're not too dumb to understand it. Whoever wrote it did a pretty bad lawyering job of over complicating unnecessarily. And that is just something unfortunately we have to undo in our profession.

So please, you go with this. That's what you were trained in law school is actually to use your analytical skills. If it doesn't make sense, there's a reason.

Laura Frederick: There were so many great gems you just said, and I wanted to go back to a couple of them. So one of 'em, which I love, is that two different lawyers will do a contract differently.

Lucy Bassli: Even if we have a playbook, our contracts will end up different. And I think one of the things I see is people get so attached to their model clauses, so attached to their playbook, which I get in some ways, like I love playbooks to make it easier. Oh, here's grant-back license language, I can go grab it. It's been approved. I don't have to go to IP lawyers. That purpose. Great. Or suggested language. Yep. But I think a lot of people just are scared to deviate and they think, as you said, that's the answer. And I think that's the challenge with all this contract training out there. And everybody, including me, is talking about here are best practices, here are ways to do things, but we have to make sure they also hear this is just one way. There's lots of ways

That's right. And I think that fear of deviation, that's not okay. We're paid to think. We're paid to be analytical. If you're not gonna deviate from a playbook, I'm gonna outsource that. You shouldn't be doing it. If you are so stuck to a playbook as a practicing in-house attorney a couple years in, I'm not saying on your first couple of years, if you're a couple of years in and you are still living and breathing by a playbook, I will be the first one to tell a corporate law department that's probably something they can outsource. If the playbook is that black and white. Yeah, I wanna spend half the resources. Lawyers are expensive resources. When we go in house, we're still expensive. We're on the upper end of what is paid to employees. So we need to earn our keep. And that means using your brain, using the analytical side. You can't live and die by a playbook. That's just I always push back on those. And I love building playbooks. We do them all the time. We do them for the purpose of efficiencies, enabling a law department, or enable business professionals outside the legal department because it's just not something lawyers should spend their time on if it's that playbook, if it's that crisp and black and white. Gotta use our skills.

And another thing you said was about there being no right answer. And this, I swear, the reason I know so much about contracts is because I believed there was, and if only I studied it all, if only I had the right content, the right resources, I would know it all. I wouldn't feel so anxious all the time. I wouldn't worry I was making mistakes all the time and doing a bad job for my clients. And I just had this, I don't know exactly what it is. It's the self-doubt. There's so many elements to it.

It's scary. You're putting your name on something and you're saying, this is good for the company and what we're here to tell anybody who's listening is somebody else can read that and disagree. That doesn't make you wrong, but they can read it and disagree. There's nothing more frustrating than somebody looking back at a contract in January, "oh, who agreed to this?" I did, but you know what? You have no idea what the context was. Maybe this was the last thing that we were working on after an eight month bloody battle in the ring to get to this and you just had to horse trade.

Yeah, that's right. Everybody, sometimes you just horse trade. You give up something had nothing to do with something else, and they give up something had nothing to do with, and you're like, all right. Exactly. That happens. That happens all the time. So never judge a bad contract. I say, if you're gonna go good or bad, look at the writing. How many notwithstanding the foregoings did you see? One is too many. Yeah, that makes a bad contract in my book. Yeah. Not the actual deal. Cause the deal probably made sense at the time in that context. Are we having a CFO breathing down your neck? Guess what? You're gonna make some different decisions than if you had all the time in the world. So anyway there's a lot that goes in it and people have to understand that's why it is a bit of an art form and all the training and guidance out there is guidance. It is not black letter law.

Laura Frederick: Exactly. There was an issue that came up in one of the posts on LinkedIn talking about a particular issue in an indemnity.

And I was like, okay, I've been thinking about this. I think of it this way. Is that right? Is there another way to think of it? And what I loved was we had so many different answers. I think there was like a hundred comments and all these genius lawyers, like lawyers who I respect who I consider at least as if not a lot better than me, and they all had different answers and different reasons and different strategies. Yeah. And it was such a great reminder. Some of them were like, oh, it's black and white, it's yes or no. And then others are like, yeah, it's completely black and white, but the opposite of what you think. That's where I think lawyers who are learning, who are figuring out contracts, who think there's an answer out there, and if they just learn it, they'll know. First just understand it's a lifelong process. We're always getting better. We're always improving because we're forgetting all the time.

If I don't work on an area for a little while, I come back to it and I have to start over because I've forgotten all the details.

Lucy Bassli: Oh yeah just the company the relationship between limits of liability and indemnity is enough to make my head spin every time. Fresh. Every time. Like now what? Hold on. Oh yeah. Oh wait. They all did insurance also. Oh, and there's warranty. Oh wait. That's right. That all plays in here. And suddenly you're like starting over every time. So that's why the guidance is good because it keeps you be able to quickly refresh and then you have to apply to your particular situation. That's all. That's what we learned for three years in law school. It's applying. Applying logic and reason and law to a situation. And every contract's its own situation. It just is. Yeah. Even templates. At the end of the day, you're gonna give and take and you're gonna win and lose. The one thing one of my mentors did tell me that I love we ended up duking out is negotiation. It was actually, it was in a commercial bankruptcy context. But the point is it was a negotiation, which is what every contract is. And it took all day. It was a mess. Came home, I was like, oh my God, the other side's really mad at me. And I was like, a year and a half out outta school. So this was all very fresh, but I was thrown in. So it was a boutique small firm. Long story short, my 70+ year old mentor is " You piss off the other side? Yeah, you're a little mad. That's probably a good deal. If anybody walks away too happy, it can't be a good deal." And I was like, there's something to it. You gotta give a little, if you walk away totally happy. I would double check number one. Or the other side really did give away the farm. That was the best lesson for my mentor.

Laura Frederick: It's really understanding that again, there's no right answer, but it's also, the deals go back and forth, you give some you give on others, and it just plays out how it plays out.

The other truth that I learned is I fight so hard for some provisions. I've done this so many times in my career, like I have to have a limit of liability. It has to be capped, absolute, no exceptions. And the other side's no, we need exceptions. We need this. And then we have to give, and then a year later, we are the ones who need to access more than the limit of liability, and we're taking advantage of those exceptions.

Yeah. And I think, thank God I didn't get that one. Because you just never know how these contracts play out and we play on probabilities, like most vendors approach it it this way, but not every time. It often vendors don't have it that way. So I think for me, I love the comfort of knowing there is no right answer.

That even if I look at model clauses, those are just one perspective, one approach to risk, and there's so much freedom in a way to operate within the confines of the contract world. That to me, it's such a great practice area for people who are creative, who want autonomy, who want to own their stuff. They don't just want to follow a code as you said. It's such a great practice area for all of that, and I think that's why I love it and probably why you do.

Lucy Bassli: Oh, absolutely. I love it. And then I look at it from that angle, knowing all that creative stuff that can happen. That's what I want lawyers to spend their time on. So what I love to do is figure out all the stuff that you don't need to spend your time on. I want you to duke out and battle in your brain how the limits of liability cap works with the indemnity [00:18:00] obligations and the exceptions and exclusions. That yes, spend your time on. Please don't spend your time on whether the governing law can be California or New York. Yeah, have option A, have option B, and that's where being pragmatic, being efficient, that's what I ended up loving in the contract negotiations.

After I've done enough of them, I was like, oh. Each one I do, I should do the next one faster. And that became to me, the game that I like to play and focused my practice on. And then able to really say, okay, but now I'm gonna spend my time on just this stuff that I think is gonna really add value.

And I think too many lawyers, again, the fear of letting go of even any part of the contract holds them up. Spend your time wisely. That's the fun stuff. That's why we will go to law school. We don't go to law school to, oh, California. No, I really wanna do Texas. No, I really like New York. I don't know. Let's have another call about it. Stop. That's the madness we need to stop and focus on this other stuff. That's where the brainy work comes in. But yeah, that's I think why we like contracts. It's the brainy puzzle.

Laura Frederick: It is, and I love the puzzle analogy. To me that was always it, the puzzle with creative writing, that's what it's all about.

Lucy Bassli: It's and that's interesting cause what I end up doing is working on efficiencies and that automation and there's a lot of talk around contract management technologies and, automation and CLM, all these buzzwords, which is fine, great, good.

There's a place for them and a use for them. But that art of what goes inside the four corners. Let's preserve that and make people really good at that substantively. Let's remove what they shouldn't be spending their time on to automate and all that good stuff. But I think we're at a nice intersection point right now with all the work that you're doing, educating on the substantive, really substantive stuff, and then automation and efficiencies.

But those two don't live in the same place because it's an art. It's like you said, it's the creativity. Helping evolve in this area? I think there's a dynamic duo aspect where we want lawyers to realize there is that substantive part, but you can't scale and do every part of every contract with that depth of substance and creativity.

You can't, you'll break because we know when you're in house, it's just an ongoing, continuous tidal wave. It's a constant coming of contracts. So going in, you gotta become a little more efficient.

 It's the exact opposite of the law firm. Spend a little more time, do it perfect. Spend a little more time. It's the exact opposite.

So you have to have the skills and available and the playbook and the access to substance information to make you quicker. And then you have to have the enablement infrastructure to move it out off your desk as fast as possible. I think it's a fun space. It's gonna continue to evolve. Technology contracts will continue to grow in volume.

Laura Frederick: Exactly.

Contracts are never gonna go away. We can't be replaced by ChatGPT there's too much nuance, there's too much detail there. I think we're gonna be the last ones to go when it comes to the lawyers we replace.

Lucy Bassli: I'm surprised we went this long without mentioning ChatGPT. Good for us. I think we just that deserves some sort of reward.

Laura Frederick:  Yeah. So I think we're toward the end of the episode. So tell me, you were talking about what I'm training on, which is more substantive, but you are training on how the process works and how you can become more efficient. And you as a contract, lawyer, or professional, you need to understand both of these sides. So how can people learn from you? What resources are available? 

Lucy Bassli: Oh, thanks so much for that question. Yeah, Laura. It's obviously I have a book and that's always an easy place to start. More books, multiple books. I do. And we have a workbook because what we realized is this is a different part of the muscle that most corporate in-house lawyers don't know they need exercise. They haven't been trained on this stuff at all either. And by this stuff, it is the process. It's the operating efficiency. So if you think about a contract and what's inside the four corners, super important. There's substantive content. But how those four corners travel across the company.

Why they come to your law department when they come. What do you do with them once they get there? Not just once you finish what's inside the four corners. Where they go next. You use electronic signature, by the way. How do you find them? Where? Do you know where you store all your contracts? Can you find that beautiful piece of art that you just spent five months negotiating easily? Can you extract information from it? So it's all that stuff around the four corners that really, I think, sends a sign to the business that you get it. You're not just here to do a good contract, but you're here to get that contract done as quickly as possible while protecting the company.

That's what we focus on. That what I help train as lawyers to think about the contracting, not the contract negotiation, but yeah, the contract has a life before it comes to the legal. It's been talked about. It's been planned in people's heads or on spreadsheets or PowerPoints, or even in a Word doc.

Then it comes to Legal and then stuff happens to it when you're done.

Laura Frederick: Yeah. And so it, that's what we focus on and help automate where it makes sense, but really just process redesign, workflow. and Yeah. It can make all the difference.  I mean it's for me, once I got to the point of having process and better work design, the anxiety goes down because you wanna focus on the contract and do the legal stuff, and instead you're worrying about, okay, is this signature authority? All that kind of extra stuff. So I'm so glad we're both here, covering different sides of the contracts. And I really appreciate you coming on the show and it's been great to see you and I'm sure we'll be talking more.

Lucy Bassli: Thanks for having me, Laura. My favorite topic. Thanks. Bye. Bye.

Laura Frederick: Thanks for tuning into this episode. If you'd like to learn more about How to Contract's training programs, check out our website You can sign up for our weekly newsletter, which includes links to these episodes as well as contract tips, upcoming events, and other offers.

Lucy Bassli: Happy contracting.

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