Preparing In-house Counsel for the AI Age — The Cleanup Crew Renaissance

How can in-house counsel prepare for the compliance, governance, and litigation challenges of the AI era? 

In the latest episode of Mintz On Air: Practical Policies, host Jen Rubin is joined by Ginny Johnson, a partner at Outside General Counsel LLP, for the second part of their conversation about how AI is changing the skills and competencies for board members and in-house counsel. 

Their discussion explores: 

• The "cleanup crew renaissance" and how in house counsel need to prepare for AI’s creation of legal risk
• How AI may reshape legal training and the traditional apprenticeship model, and the dual importance of adopting technology but embracing human collaboration
• Some practical considerations for how in house teams can harness their superpower of enterprise-wide knowledge to better utilize AI to deliver legal services

In the first part of this two-part series, Jen sits down with Ginny Johnson to discuss Board Member Competencies for the AI World. Together, they examine how AI is transforming the boardroom and what today's directors need to know to navigate emerging opportunities and risks.

Practical Policies — The Cleanup Crew Renaissance Transcript

Jen Rubin (JR): Welcome to Mintz On Air: Practical Policies. Today’s topic: The Cleanup Crew Renaissance, how in-house counsel might prepare for what’s to come in the AI world. I’m Jen Rubin, a Member in the Mintz Employment Group with the San Diego–based Bicoastal Employment Practice, representing management, executives, and corporate boards, and I enjoy providing creative solutions to workplace problems.

Thank you for joining our podcast. If you’ve not tuned in to our previous episodes and would like to access our content, visit us at the Insights Center at Mintz.com, or find us on Spotify.

Today we are continuing our conversation with Ginny Johnson about how AI is impacting the competencies needed for organizational leadership. Along those lines, we have more to discuss about competencies needed for in-house counsel — how those competencies will change, how AI is impacting those competencies, and what in-house counsel might do to help prepare for what’s to come.

Ginny knows a thing or two about general counsel, chief legal officers, and corporate law departments. Ginny just joined Outside General Counsel LLP as a partner. OGC is an innovative platform that combines the practicality and efficiency of in-house counsel with the sophistication of big law. It’s composed entirely of former chief legal officers, general counsel, and senior in-house attorneys. Ginny’s practice with OGC will focus on fractional CLO and GC engagements and strategic advisory work across industries. Ginny will serve as a member of two of the firm’s practice groups: the corporate and finance practice and artificial intelligence, cybersecurity, and privacy. Ginny recently published a paper titled “500 Conversations: One Legal Executive’s Bird’s-Eye View of the Current Legal Services Market (And Ancillary Musings).” I found this paper insightful and thoughtful, and I thought it was an ideal time to do an episode with Ginny to talk about some of these issues. If you joined us for the first installment, you heard us discussing competencies for board members. Today we’re going to be talking about in-house counsel. So, Ginny, welcome back.

Ginny Johnson (GJ): Thanks so much. Happy to be here.

JR: Listeners who tuned in to the previous episode know that Ginny and I discussed the ways AI is changing board member competencies. In other words, what skills do boards need in their members in order to utilize the corporate board as a significant corporate asset? Today’s episode pivots to how the skill sets needed for in-house counsel are changing as a result of AI’s profound impact on our business and personal landscape.

What Is the “Cleanup Crew Renaissance,” and How Will AI Transform Legal Risk?

JR: Ginny, I’d like to explore some of these topics you discussed in your paper about those charged with organizational governance — I’m looking at you, in-house counsel — and the things they need to do to change or think about changing, or how they can focus on some core competencies for the future.

Let’s start, Ginny, with your conclusion that AI is going to cause what you call a “cleanup crew renaissance,” where the lack of regulation and uniformity and predictability that comes with the anything-goes mindset that’s being created with AI is also creating new, required skill sets — people with the proverbial brooms and mops who are going to figure out how to make all of this work in the future. What does this mean for our profession?

GJ: We’ll get into how we think the skills in-house lawyers and all lawyers will need to have in the AI age are changing and evolving, and what that is going to mean for success as a practitioner. To start out, I used the phrase “cleanup crew renaissance” because I believe that in a few years we are going to see a significant increase in some of the things that are already happening, whether it is securities and disclosure claims around AI privilege disputes, around discoverability of AI chats and prompts, and the risk writ large that is being created by what I’ll call “ungoverned usage of AI.” I’m bullish on a lot of aspects of AI, I’m a proponent, I’m an evangelist. But I also think we need to be clear about what we don’t know, and put up appropriate guardrails to protect our organizations and ourselves from undue risk in extracting the opportunities we can gain from use of AI.

“Cleanup crew renaissance” is a nod to what I believe is going to be a wave of litigation or discovery disputes around what you can get, how much you can get, and whether things are privileged in terms of how AI is being used today in a lot of shadow ways.

“Cleanup crew renaissance” is a nod to what I believe is going to be a wave of litigation or discovery disputes around what you can get, how much you can get, and whether things are privileged in terms of how AI is being used today in a lot of shadow ways. I think it is undeniable that AI tools and applications are being used by a vast number of people, both inside their workplaces and for personal use. And for sure, not all of those uses are known to the employer, or have been shared or subject to policies, procedures, or training that would provide a line of sight for the legal department or IT to know when and how this is happening.

Then, fast forward and you get into a dispute, a shareholder litigation, a contract dispute, an employment matter — it could be anything — and the plaintiff’s bar will be knocking on your doors for the entire history of chat logs. You may be able to assert privilege where there was a lawyer in the loop and it was arguably in connection with or in anticipation of a dispute or a work product. But I think there’s an avalanche of things happening on a daily basis where there’s not a lawyer in the loop, it’s not in anticipation of litigation.

The other big thing I think about a lot is that with AI, we’re talking to our computers and our phones in a way that has never been the case until very recently. So, yes, there’s been risk with email, of course — and that changed the game with respect to discovery when we moved from paper documents to email. This is a whole new level of that risk in the sense that people are very vulnerable when they’re interacting with their own AI apps and using them as a thought partner and not directing it as correspondence to another human being, but rather talking to ourselves about solutions to problems or generating ideas or whatever the case may be. The guard is down when people are using these tools, and people are not thinking about whether what they’re saying is something they’re going to be okay with ending up on the front page of The New York Times.

How Can In-House Counsel Prepare for AI Compliance, Litigation, and Governance Challenges?

JR: Corporations look to their in-house counsel, their law departments, for guidance for legal issues, but also for how the business should be run within these legal guardrails. This feels a little bit like the phrase “you’re building the airplane as you’re flying it.” How do you give that advice when you don’t actually know where this is going to end up? This was another of the points you made in your paper about the cleanup crew renaissance. How do you prepare for something when you don’t know what something is going to look like down the road? What is some advice for folks who are in-house now who are thinking about how to address this? How do they educate themselves?

A superpower for in-house lawyers is to be able to connect the dots, synthesize information, and provide better enterprise advice in terms of those collective risks.

GJ: This goes to the heart of why I think being an in-house lawyer is an amazing role. I’ve always said to the teams I’ve managed in-house that one of the most unique and fun things about being in the legal department is, unlike any other function, you get a bird’s eye view of what’s going on across the entire enterprise and externally. So you’re scanning the horizon for regulatory changes, geopolitical threats, competitor risks, IP, everything — but you’re doing that in the context of working closely with finance, HR, IT, sales, and marketing. You’re seeing all of their problems in a way that most other functional leaders don’t see. A superpower for in-house lawyers is to be able to connect the dots, synthesize information, and provide better enterprise advice in terms of those collective risks. That also involves not knowing what is coming.

The uncomfortable part for many lawyers and legal professionals is that the apprenticeship model and law schools have trained us to try to always be correct, to strive for excellence in every answer. So having to be transparent with your stakeholders about the fact that you don’t know how this is going to play out, you don’t know the answer, can be uncomfortable for many lawyers. The strongest lawyers and advisors I’ve worked with are people who have grown into not feeling like that is a limitation, but owning it to say, “I don’t know, but I’ll go research, figure it out, talk to my peers, come up with a credible assessment of what I think is coming.”

But in that sense, AI isn’t really so new. Whether it’s cybersecurity or other emerging threats that have come onto the landscape in the last 20 years, it’s often the case that we can’t say with precision what’s going to happen or how it’s going to play out. So my answer to “how do you grapple with that as an in-house lawyer?” is having strong relationships with your colleagues to facilitate ongoing communication. If you’re a legal department that people don’t want to come to because they think the answer is going to always be “no,” or if you’re just dispensing academic answers and not helping get things done — then you’re not going to have the level of trust and cooperation and collaboration required to iterate on these risks. It’s not about knowing what’s coming, or getting it 100% right. It’s about being a lawyer or a legal team who wants to be fully immersed and embedded in the operations so you can truly be a partner to anticipate the risks together and figure out collectively, for the benefit of the company, what is the best course of action.

How Will AI Change Legal Training and the Traditional Apprenticeship Model?

JR: A thing I think you lose when you move away from the apprenticeship model, which I think is probably going to happen as we move forward, there’s that thinking and creativity challenge. If you deputize thinking to something like AI, you’re not exercising those brain connections, which can then fail to lead to the creativity because you’re not being curious. I’m a strong believer in this as somebody who’s in a private law practice — the fact that I can go to another human who has judgment and experience and ask them, what do you think about this? You can draw on that to reach your own conclusions. How do we teach this to individuals coming up through the ranks as we move forward? How do we retain that teaching skill set?

How do we need to modify the apprenticeship model for the next generation for our profession to be successful?

GJ: I think this is one of the biggest challenges that law firm partners, general counsel, and law schools need to proactively start figuring out together. How do we need to modify the apprenticeship model for the next generation for our profession to be successful? It’s a two-way street in the sense that there’s a lot of chatter about how young people and law students and emerging lawyers are going to know their output is incorrect or know the substantive skills to be a good advisor if they weren’t taught in the same way previous generations were. Meaning sitting in offices until two o’clock in the morning watching a partner revise using a pencil. But I think there’s an equal or greater burden on us as senior supervisors to embrace innovation in the way we teach and mentor and coach, and not dig in our heels and say it has to be this way because that’s what we did 20 years ago. We need more senior people to become proficient with tools so they can credibly talk about and understand what new entrants into the profession are seeing and how they’re navigating their assignments.

And there might be a thing we need to do — and this is antithetical to running a business and trying always to do better and make more revenue — but we might need to slow down on purpose. Could you automate entire workflows that are going to rip out time and cost from a process? Yes, and there will be a great deal of pressure to keep doing that for the sake of efficiencies and the bottom line. But are there going to be times where it makes more sense to say, we’re going to do it the old-school way, and that’s because if we spend a year with this new class of first-year associates teaching them in a more deep-dive way, to make sure that the legal reasoning and writing ability and advocacy skills will be imparted effectively, then maybe that’s what we need to do. I have heard anecdotes from a few private practice lawyers who are experimenting with how to do this. For example, by staffing associates on matters not to be billed to the client but solely for the sake of the learning experience. I think we’re going to see more of that; I think we need to.

How Can the AI Era Bring New Career Advantages for Lawyers?

JR: We talked about junior people and senior people, but I want to talk about the mid-level career in-house lawyer. One of the things you say in your paper, and it’s a very blunt statement, quote, “your compensation trajectory will track how far you sit from replaceable process and how close you sit to accountable judgment.” What is your advice, Ginny, for in-house career lawyers under these circumstances as this whole paradigm is shifting?

If you are someone who is embracing using technology to augment your ability to think even more strategically, holistically, and get more done faster, then you’re going to still have a lot of pathways in this profession

GJ: If you are someone who is embracing using technology to augment your ability to think even more strategically, holistically, and get more done faster, then you’re going to still have a lot of pathways in this profession because what clients need is sound judgment and the ability to problem-solve — things that can’t simply be outsourced to a machine. On the other hand, if you’re someone who’s outsourcing the obligation of thinking through a problem because you’re just relying on an AI output, clients aren’t going to pay for that anymore.

JR: Wise words indeed.

Wrap-up

JR: Ginny Johnson, thank you so much for spending two episodes with me. I want my audience to know there are many more interesting and valuable takeaways from Ginny’s paper that we can’t possibly cover in just two episodes. I picked out two I found especially fascinating, but I really recommend the paper to all of you. 

Watching these things unfold around us, maybe we’ll do a follow-up episode in a couple of years. We’ll look back and see how much of this we were correct about, and how many of these things we said were misses. I think it’s all really interesting and I enjoy talking about it. So, Ginny, thank you so much.

GJ: I’m willing to be wrong in a few years if we reconvene and some of my predictions were way off-base. That’s entirely possible. But I really appreciate the podcast. I’m a listener and a fan and I love how passionate you are about these topics. Thank you so much for including me.

JR: For more information about our practices at Mintz and our other thought leadership, visit us at the Insights Center at Mintz.com, or you can look for our Mintz On Air: Practical Policies podcast on Spotify. Again, I’m Jen Rubin. Thanks for joining.

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