From Fear to Fluency: Using Lawyer-to-Lawyer Learning in AI Adoption

Thanks. I'm really thrilled to be here and also thrilled to be in Chicago and not paying twelve dollars for a hotdog in Vegas.

Yeah. And it's particularly relevant because I've got a daughter starting college in August, and she's asking me for all sorts of advice, and I don't even know where to begin. But, you know, when I think about it now, for me, AI is my superpower. It makes me better, smarter, quicker.

It brings to life ideas that are turning around in my head and that I just didn't know how to maybe articulate the right way. It just I love working with it. But then I think about these kids who are in college or maybe even only, like, junior associates or so, you know, in the legal space. And if they're not gonna cut their teeth learning all of this stuff at the level of detail they can spot an error because AI does make lots of mistakes and I can catch them, who's going to catch them when I'm retired?

Right? And it's gonna come down to our educational approach, it's gonna come down to the way we train people, but it's definitely something on my mind right now.

Yeah, so I'm not quite at the point, I would say, of quality control currently. What I'm more focused on is getting people comfortable to experiment with the technology and not be afraid to use it, especially lawyers. I mean, I'm not a lawyer, but I've spent over a decade now supporting them. And I understand how lawyers are trained to be skeptical and are expected to be perfect. So using AI when you know it can make mistakes must be terrifying. There's so much on the line.

And interestingly, in a corporate in house department, you'll have the full spectrum of folks, like some who are warriors and are using it for everything, and others who are, like, afraid to type, you know, into the copilot cursor area. And for me, I wanna bring all of them along. And so one of the ideas we recently had is spitting up a program we're calling lawyer to lawyer. And I'm taking my lawyer warriors who are really good at this stuff and matching them up with the lawyers who are more reticent about it.

Yes. I would absolutely say there's that concern about how do the regulators feel, you know, how it's being used. And there's this pressure because you've got regulators who wanna make sure that banks are safe, right, and well controlled. But then you've got shareholders who wanna bank to be as efficient as possible and increase margins. So there's this healthy tension, and lawyers are right in the middle of it.

Yeah. So this is really interesting. My AI experts are a group of lawyers from Poland, believe it or not, who are our center of excellence for contracts.

And they have been working with contracts, and they've really focused on standardizing, understanding the work itself, and they've just completely run towards AI. And they've become our experts where they're now creating prompts for us on all sorts of things. And it's a really interesting contrast because when you think about a center of excellence, it's typically a team of people that you say, we're gonna give you a playbook, and you follow that playbook. And if you deviate from that playbook, make sure you call us to, you know, that it's okay. But they've grown beyond that in the eight years, and they've really become very proficient. And it's so neat for me and for them to say, hey. You guys are our experts at something now, and we're gonna help the entire organization with the skills you've developed.

You know, for me, it's going to be feedback.

You know? It's not I know we all like to have these numerical measurements, and so do I. I'm a math and statistics, you know, major in college. But what it really comes down to is if I take ten people, and all ten walk away saying, I use it now, I try it now, that was great. I mean, to me, that's the best kind of output of all.

Playbooks are guidelines, procedures are step by steps. I've also grown up in operations, know, not being a lawyer, investment banking operations to be specific.

And so I completely appreciate an organization where you follow these ten steps to get x done. And while there is part of that in legal, we can't forget that legal is very judgment based. So and that's why I started, like, a playbook as a guideline. And if a lawyer is using a playbook, it's not to dictate, but to guide.

I've been in three different organisations in a legal department now and I would say playbooks are always there to different degrees of specificity and usage. But I'll tell you how I'm personally thinking about contracting.

You know, one of the things that I'm focused on right now in my role is how do I completely reimagine contracting on so many levels with AI and agents, and that's probably a whole other podcast.

But coming back to the playbooks, like, the way I'm thinking about contracting is if I've got, you know, fifty contracts with client a that I've had over the past ten years, I can write a playbook just for that client, quite frankly, using Microsoft Copilot, the corpus of documents. And then when something happens or is proposed, bump it up against that, like Copilot completely unleashes.

It eliminates the need to have outdated playbooks if you know how to use it the right way, and they can become living, breathing documents.

It's definitely possible and I talk about one tool because that's what I have at my disposal. There are plenty of tools out there now that could probably do it in a more sophisticated manner and I'm looking at them.

I'm probably gonna disappoint you with my response, honestly. My biggest use of AI right now is my writing of emails. And I'm a really good writer, but what it helps me do is refine my tone to the audience. So I know what I wanna say, and I can say it eloquently, but now I can say, I'm writing to the general counsel, and it knows the voice I should be using for the general counsel, or I'm presenting to the executive committee, or I'm talking to my team, and so I can start with my ideas and write a draft and then use Copilot to rewrite it so that it'll resonate better with my audience.

I think I've lost count but it's definitely five or more.

I would definitely say that every CLOC has a different feel. And I think as I've matured as a leader, I've taken away something different each time.

And I think the biggest growth area for me coming to CLOC over the years aside from, you know, better understanding legal operations is really appreciating the value that vendors can bring. I embrace the vendors whether I'm gonna buy a few or not because you're a wealth of information.

And so I just really have come to appreciate that exchange of ideas and thought leadership and so on. So it's just given me a very different perspective on a part of the ecosystem that I probably didn't have as much appreciation for that I should have.

Oh, I love Legal Week. Yeah.

Yes.

With AI?

You know, you asked me how am I using it in my day to day, and it's less so about my day to day as much as where I wanna take in house legal. And I think about how can I use AI to help lawyers do their jobs even better?

For me, it's not about how do I do it more efficiently and go from twenty lawyers to ten lawyers? Like, honestly, I don't think that's the smartest way to think about AI for the legal industry because there's so much work that's needs to be done. There's more demand than there is supply. So let's think about how do we be efficient, redeploy that capacity rather than shrink a department.

But putting that to the side, how can I help them do their jobs even better? And for me, it's about what are the various data sets around an organization that if I were able to pull them together and put them at the lawyer's fingertips would help them make better decisions, write better contracts, whether that be, you know, not the obvious ones like, you know, what are the laws and regulations that are changing and horizon scanning? We know we need that. But what's happened historically inside the organization?

What errors and losses have we had in the past because we agreed to a clause in a contract that we keep, you know, re agreeing to, and I'm not saying this has happened, but hypothetically, right, and we lose money over it because salespeople are trying to cut a deal, and the operations people can't execute on the contract.

So it's like, how do I pull together all of these pieces of data that sit across an organisation in such a way that they help lawyers give better advice?

Oh my gosh. I wish there was one piece of software that would do all of that for me, but that's not realistic. But, yeah, like for me, from a vendor perspective, I will walk the floor several times and, you know, scout out what's there to get ideas. And are there pieces of different platforms that I can string together, or is there something we can build ourselves?

I'm always on the hunt for, you know, what can help. But on top of that, you know, just me personally, I love the newbie legal ops person too. Like, I wanted to be a teacher when I was five years old and I never pursued that, but I absolutely love helping people develop and bringing them along. So I also just love the pure energy that's here.