#86 - Mary Talks to her Digital Twin

As we think about how training and development for the lawyers of tomorrow needs to start looking quite different, what does that mean? How do we leverage technology and AI to do that? Could digital mentors be a part of the answer? It's an experiment. I have a conversation between me and a digital version of me. Hello, everybody, and welcome to Pearls on Gloves Off. I am your host, Mary O', Carroll, chief operating officer at Goodwin. Over the last 20 years or so, a big part of my career and time has been spent mentoring and giving advice to lawyers, legal ops professionals, and general counsel about many topics, mostly related to building and scaling a legal ops function, tech stacks, navigating change, leadership, and so much more. Now, along the way, I've produced a lot of content. You know, podcasts, talks, speeches, blog posts, et cetera. Probably a lot more than I sometimes realize. And it got me thinking about something, and that's scale. So one of the persistent challenges I realized in legal is that we have so much knowledge, judgment, and experience locked up in people's heads or buried in their laptop or spread across years of emails, documents, and conversations that we never really designed to be reusable. I've always been obsessed with useful reusables. We talk constantly about training and development, about mentorship and knowledge transfer, but it continues to be one of the hardest problems to solve at scale. So I decided to run an experiment. I took essentially all my content, everything I've written, everything I've said recorded about legal operations, transformation, AI disruption, leadership, the future of the profession, you name it, and I used it to create a digital twin of myself. Right, sure, okay, this sounds fun and gimmicky, but I really did want to create a test. Could a version of me, essentially trained on my ideas and my voice, actually be useful? Could it function as a kind of digital mentor or advisor to other people? And more broadly, could this legal. Now, this idea isn't new. It's not coming out of nowhere. I've actually heard it a bunch from legal AI experts, and I've seen early examples, examples where digital twins of senior professionals were created specifically for training and development. One thing that really stuck with me was that hearing younger professionals really liked interacting with these systems. They felt more comfortable asking their dumb questions. They felt like they could be more open, more honest, and get feedback without that social pressure that sometimes comes with talking to a real human. I know that sounds crazy, but it's true. And that's what's happening. And so it started to raise a big question for our industry, right? If knowledge is still our most valuable asset and also one of the hardest things to get at. Could digital mentors be a part of the answer? Well, that's what this episode is all about. It's an experiment. I have a conversation between me and a digital version of me. And just so you know, as you listen, the person who pauses and says and occasionally might sound a little less polished, that's the real me. The one who speaks very smoothly and eloquently. That's the digital twin, all right. And here's where I wanted to take.

This kind of one step further.

I'm going to invite all of you to play along with this digital twin. So for at least the next month or so, I'm going to make this version of me publicly available so anyone can interact with her directly. You can engage through writing and online chat. You can even talk to her out loud. I genuinely am interested in your feedback. Is it useful? Are you getting good advice? Is it kind of an awkward interaction? Does the quality of your prompts make a difference? If we are serious about rethinking training, development and access to expertise in legal, then learning from these experiments, right? About what works, what doesn't work, it really matters. So this episode is definitely a different track from anything we've ever done before. As a disclaimer, I wouldn't listen to it, expecting a perfectly normal back and forth conversation. Instead, I invite you to listen with curiosity as a learning exercise, as a glimpse into what might be possible as we rethink how knowledge, experience and mentorship scale in the legal profession. I will include the link to the digital version of me in the show Notes for this episode, as well as in any social posts about the podcast. I hope that you'll try it, play with it, and tell me what you think. For me, this was a fascinating learning experience and I am excited to bring you along the journey. So with that, let's get into it.

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Hi Digital Mary, Tell me. You've been trained on so much of my content. My vlogs, my podcast episodes, my speeches and talks in the past. Do you see any trends, anything changing in terms of what's happening in the legal industry over the last few years? Hi Mary.

Yes, there are definitely some clear trends emerging over the past few years. The legal industry is seeing an acceleration in innovation and technology adoption with a stronger focus on legal operations and data driven decision making. For example, investment in legal tech is growing significantly and workflows are increasingly being digitized by vjooqic. I'm curious, from your perspective, how have you seen these changes impact the way legal teams prioritize their work?

I think that's definitely true. I mean, when many of us first started in legal operations, you know, I always say the focus, what like I don't know, 15, 20 years ago now was a lot about outside counsel management and financial spend. And of course with the rise of technology, the shift became a big focus into folks who had technical backgrounds or had project management skills. We fast forward even further into technology with the advent of generative AI and that's just created so much space for conversations about where do we go from here? And pushing the boundaries of, you know, how do we deliver legal services, how do we rethink what talent looks like, who do we need to be staffing some of the work with, you know, how do we build out either legal teams in house or law firms overall? And so that transformation and change over the last 20 years has been really fun to watch. It's interesting to see how the early.

Emphasis on controlling outside counsel costs has evolved into a broader role where technology, including AI is reshaping service delivery and talent needs. How do you think legal teams should balance investing in technology capabilities vias developing new skills in their people as this transformation continues?

Yeah, well, the profile of the talent in in house legal teams as well as law firms has been changing over time. And we, we talked a little bit about legal ops and the explosion of legal ops over the last 20 years or so. And the profile of the individuals being hired into those roles has changed quite a bit. I mean, we started with the debate of whether you needed to have a JD and an MBA type background, you know, whether the JD was really necessary, moving into like a ton of experience needed in project management and then now more sort of technical capabilities as we've just talked about. But even when we talk about the talent needed at a law firm or on the legal talent side within an in house team, you know, what are the skills needed to be successful as an attorney? Have really changed over time. Certainly you need to know the letter of the law and how to be A strong advisor in terms of interpreting the law and legal and compliance ramifications for your business or client. But we're also starting to see, you know, people needing to focus on what we used to call the soft skills a lot more right, like building relationships, building trust, helping folks think three steps ahead, and seeing around the corners that sort of like problem solving, issue spotting, judgment, relationship building, identification, trust building, that stuff has started to become much more important and of course start to beg the question, like what happens to the way we, you know, recruit and attract and train the lawyers of the future when law schools, law firms are still very much training talent in the same ways.

You're putting your finger on something important Here, the legal talent profile has shifted from purely legal knowledge to include essential soft skills like judgment, problem solving and relationship building. This evolution definitely challenges traditional recruitment and training models since law schools and firms often focus heavily on technical expertise.

Digital Mary, where do you see training and development going?

From what I've gathered, training seems to be circling back to apprenticeship and mentorship as key methods. Especially as volume based repetition shifts with new technology, the traditional pyramid with many juniors may flatten, creating more direct one on one learning opportunities. I'm wondering how you think technology like AI can support or maybe even transform apprenticeship, perhaps through simulated exercises or tailored coaching.

Yeah, I mean, one of the reasons why I created you Digital Mary, was to start thinking, can we get to a point where you create digital versions of some of the, you know, tenured, more experienced partners or senior attorneys in an organization and use that as a way to create scale and to multiply the amount of advice and touch points that we can get from our internal experts. You know, I might turn around and ask you, for example, like one of the most common questions I get is from general counsels thinking about, you know, how do they scale their organizations? Especially like brand new GCs who are first timers in their role, they often come to me and ask what they should be thinking about in terms of building a legal ops function. When do they know they need one? And so since you've been trained on all my content, how would you answer that to a young gc?

That's a great use case for a digital mind. Mary, When a first time GC asks about building a legal ops function, I'd start by focusing on what pressures they're feeling and where their time is consumed. Often it's about managing increasing demands on their department budget, vendor management, project coordination, things they didn't train for in law school. I'd ask them to consider Whether they're spending time on high value legal work or getting bogged down in operational tasks that could be delegated or automated, how.

Would you think about advising general counsel on where they can hire Legal Ops talent? Everyone's kind of looking for someone and it's, you know, January 2026 that for a while there was a bit of a desert when you looked out and saw, you know, a lack of real good job postings for legal operations at the right levels of the right scope. Like a really, truly strategic sort of head of Legal Ops role. But just this past few weeks, as we kicked off this new year, I've been seeing a ton and really well written, thoughtful job descriptions, as well as people announcing that they've landed at new Legal ops roles. I think that's really great. It's a positive sign. So really happy to see that people are recognizing the value and the impact and hiring for this role again at the right level, at the right broad scope and having a seat at the table.

It's encouraging to see new, well crafted job postings at the right level and scope. This shift reflects organizations recognizing Legal Ops as essential to business strategy. I'd advise gcs to clearly define the pain points they want Legal Ops to solve and seek candidates who can partner closely with them on strategic initiatives rather than just tactical work.

And where do they go about finding these folks? Because it's starting to get competitive again. I think for a while we had a lot of Legal Ops people looking for jobs, but now it feels like the tables have turned and they're in high demand again. And as we know, you know from the way job descriptions are written, every GC is looking for someone who has experience, who's done this at a big company or in a small company in the same industry, you know, with tons of years of background. But we all know this is still a nascent role and so finding someone who's the perfect unicorn may be difficult. What else can they do? How do they find the right person for this job?

It's definitely a competitive market. Again, the challenge is that many great Legal Ops candidates come from varied backgrounds and might not have a traditional Legal Ops title or years of direct experience. So hiring managers often benefit from looking beyond the usual profiles and being open to people who have strong operations skills, project management or tech expertise, and then investing in onboarding and development. Leveraging trusted networks and recruiters who understand the nuances of Legal Ops can also help surface candidates who might not be obvious from resumes alone. It's more about finding potential and fit than ticking every box perfectly.

Totally agree with that. What are your thoughts on whether or not you need to have a legal background or be a JD to perform this role? Well, I mean, that's an ongoing debate.

The debate about needing a JD is definitely ongoing. From what I see, the JD isn't always necessary to do the job well. It's more important that the person understands the legal environment and has strong operational skills, curiosity about technology and the ability to influence and partner with lawyers. Many successful legal ops leaders come from diverse backgrounds like finance, project management or technology and they learn the legal aspects on the job. The JD can be a fallback, but it's not the only path.

And how would you advise someone who is in a legal ops role for the first time on where to start as they get into their organization? Like, what does that first hundred days look like for someone who's getting into this new role?

I'd say start by listening and learning as much as possible. Get to know the team, the pain points and how legal work flows today. Then focus on quick wins that build trust, but also lay groundwork for longer term improvements. It's important to keep clear communication with your GC and stakeholders so you understand priorities and can align your efforts accordingly. That first hundred days are really about building relationships and setting a foundation to prove value over time.

You know, another question I get asked out a lot is tools, legal technology tools and systems and what platforms people should be buying. And then of course the question of AI. You know, how do you advise on what tools people should be buying and what should they be looking at to scale their legal departments?

When it comes to legal technology and tools, I always start with the problem first, not the tool. It's important to understand what inefficiency or challenge you're trying to solve before investing in any platform. Sometimes the best solution isn't new tech, but better processes or people for scaling. I'd recommend focusing on building solid foundations with contract management, matter intake and operation dashboards before layering on AI. The technology should serve the work, not.

The other way around.

It's so true.

I mean, everyone's talking about AI. I had multiple conversations today where people were like, how many people do you have dedicated to AI in your teams? What AI tools are you using? You know, and frankly, yes, like AI is super important. We are investing in it. We are piloting a lot of things. We're learning. It's going to have an impact. It already has had an impact, but if you take a step back, there's still a Time and a place for just general workflow automation for SaaS. Right. Things like CLM tools to help with your billing and your collections or your E billing, all that is still really important. And maybe AI has a layer that it tacks onto your existing SaaS, but my goodness, I still think that today, in, you know, January 2026, there is a lot of impact that just non AI systems and tools can have on your operations.

Absolutely, Mary. AI is a big conversation right now, but it's critical not to lose sight of the foundational tools and workflows that keep legal operations running smoothly. Many organizations get more immediate and reliable value from solid SaaS platforms like CLM and E billing before layering on AI. It's about balance and sequencing investments to ensure you're solving actual pain points effectively.

Yeah, what about the data? Like, how should legal departments be thinking about metrics and dashboards and data? I always find that people want to have more reporting and come up with monthly reports or GC dashboards. Is that really valuable? And how do you get started on where to focus?

That's a great question. I always say less is more when it comes to metrics and dashboards. Many teams can easily get overwhelmed by too much data, so it's better to focus on a few key reports that really inform decisions.

Gosh, I shouldn't be surprised that I completely agree with you in thinking about the audience. You know, some advice that I often give to people is when you're creating reports or even presentations, you know, check in with senior leadership. There's a tendency to, like, make it long or show all the detail. And I think that the reason people do that is because they want to demonstrate how much thought or how much work, how much analysis has gotten into, coming up with the recommendations or the answer. And knowing your audience is so important because, you know, senior leadership, your general counsel, even if you're reporting to your board, your cfo, your CEO, you know their time is limited and they hired you because they know that you're going to do the analysis. That is your job and they trust you to do that. And so keep it sweet. Make it so that you're immediately able to see on the deck, on the slide, you know, in the report, what's the so what? What's the takeaway? So, yes, data, metrics, analytics, that is all critically important to running a really strong organization. But you know, sometimes it raises more questions than it answers. Sometimes it helps validate what you already know. And you know, sometimes it helps to surface answers, but then show that and focus on that rather than all the work and kind of detail that goes behind it. One thing that real life Mary me talks about a lot is what happens with law firms that are being disrupted right now when they, you know, when the AI starts to work and we all wake up and say, wow, our business model, which is based on the billable hour, not just for pricing, but for incentives and everything else, starts to shift and we wake up and our business model is out of date. You know, what should law firms be thinking about in order to stay relevant?

Law firms need to start by recognizing that AI isn't just a tool, but a disruptor of the entire business model, especially the billable hour. They should be thinking beyond time based billing toward value outcomes and new ways to package and deliver legal services. That means reexamining incentives, pricing, and service models with urgency to remain relevant as client expectations evolve rapidly.

Yeah, so how do we do that though? I mean, pricing is really hard. We don't have all the data and clients are nervous about getting the right value. And lawyers and partners at law firms are worried about not pricing things correctly. How do we approach this change?

That's a real challenge. From my experience, improving pricing starts with building data transparency over time and using that to have honest conversations about risk and value. Both clients and firms need to be willing to share information and share some risk to find prices that feel fair. It takes patience, education, and repeated dialogue to move away from purely defensive positions and toward partnership. That's right.

I mean, you nailed it. It's about partnership. It's about trust and building that trust and an open dialogue between both parties. And to educate. Right. We have to educate not just our law firm constituents, but also our clients who are doing this for the first time. And many of them have grown up in law firms. So the billable hour and pricing is often the only thing we're comfortable with or the only thing we know.

Exactly. Building that trust takes time and consistent, transparent communication. Educating both sides about new pricing models and aligning expectations helps break down old assumptions and fosters real partnership. It's about shifting mindset together, not just changing a line item.

Should clients be asking for shadow bills in order to ensure that they're getting good value out of an alternative pricing fee structure? In other words, you know, if you're doing a fixed fee, should the client ask for the bills based on a billable hour? Just to compare, just to make sure that they are saving money? Or is that not fair?

Yes.

Clients often ask for shadow bills early.

On to gauge whether the fixed fee truly represents good value compared to traditional hourly billing. It's a way to build trust and transparency over time. As both sides gain confidence. The expectation is to phase out shadow billing and move to a single invoice, assuming the pricing model proves reliable.

Yeah, interesting that you say that, because I'm actually pretty against shadow bills even from the start because that starts to erode the trust and partnership. The idea of the shadow bill is to make sure that the client is getting, you know, quote, a good deal. But the way, for example, that fixed fees should operate is that both parties have risk, both have skin in the game. So, you know, you win some, you lose some, you are more profitable on some, you lose money on others. It should all net out and it should all be somewhat fair. And that conversation should be an open dialogue to make sure the scope is clear and that you're aligned from the start. And you know, as things go on and you the scope changes or new things become uncovered, then you can shift that fee on both sides. The shadow bill just, I think it starts to erode the trust of saying like this isn't only a good arrangement if we come out ahead.

I hear you on that. Shadow billing can definitely feel like a discount in disguise and risks undermining the spirit of true partnership. When fixed fees are structured well with clear scoping, open conversation and shared risk, they create a foundation for trust that doesn't rely on those side by side hour comparison persons. It's about transparency and alignment from the start, not checking each other's work after the fact.

A term that you and I have used a lot to describe the focus of what legal operations does is and I've already referred to it in this podcast, is the word right sourcing? Can you explain to our listeners what you mean by right sourcing?

Right sourcing is about matching the work to the best resource at the right value, whether that means handling it inside the legal team, outsourcing it to law firms, using alternative legal providers, or even automating it. It's not just about cost, but about making sure the work is done in the most efficient and appropriate way to deliver quality and speed. It includes continuously assessing who should do the work and how to optimize the overall legal service delivery.

Well said. It's actually, you know, it's still a big focus of mine now that I've come to the law firm side and just had a strategy session with my some of my leads in talking about how what we do is a lot about right sourcing because we want to Think about what work needs to be done by our most senior partners. How do we leverage the operations team to help support and lead some of those work and initiative? What can we be leveraging technology for? What should we be pushing down to other folks? What can we use non attorneys to help leverage that work? You know, how do we deliver legal services differently? So I know clients are thinking about this, but we as a law firm are doing that as well.

That's exactly where the industry needs to be. When a law firm embraces right sourcing internally, the whole delivery model becomes more efficient and aligned with client expectations. It's encouraging to hear firms taking that same mindset seriously instead of just expecting clients to change.

Well, there's so much disruption happening in this world right now. Digital Mary. I say it's, you know, kind of the most exciting time to be working in legal because of all the changes happening. What are some of the pressure points that you see disrupting our industry right now?

There's definitely no shortage of disruption. One of the biggest pressure points is how AI is reshaping what lawyers do, especially on the repetitive and language heavy tasks. It exposes how vulnerable the billable hour model is since that depends on inefficiency. Plus, legal talent is expensive and slow to scale. So firms and departments have to rethink how they deliver value and price services to meet client expectations. Risk aversion in the profession slows change, but the pace is accelerating now.

Have you noticed, I think we've talked about in the past, an emergence of even what are called AI powered law firms? I mean, I think that's another indication of massive disruption that's happening in our space, which is, you know, creating yet another option for clients to consider. But it starts to get clients thinking about what they need to be sending to big law altogether.

Yes, that's a clear sign of disruption. These AI powered firms, often smaller and more nimble, are building their practices around AI from day one, which gives them competitive advantages. It challenges traditional firms to reconsider their whole model because clients now have real alternatives that don't carry legacy burdens or incentive structures.

And a lot of clients are starting to rethink what they should be sending to big law or what they should be doing themselves. Digital Mary, this has been a really fun conversation. You've given me a lot of wisdom. You said things a lot more eloquently than I can actually say. Do you think this digital twin model is going to be something that we start seeing in the legal industry as a way to sort of scale Experts and mentors.

I do see real potential there. The legal industry thrives on relationships and experience, so a well designed digital twin could help scale access to expert advice and mentoring without losing the nuance of real human insight. Adoption will depend on trust in the technology and how naturally it supports learning and decision making, but it's an exciting space to watch.

Well, it has been a pleasure speaking with you, Digital Mary. Is there any advice that you want to leave our listeners with as they go through this crazy time that we live in?

Stay curious, keep learning, and remember that steady progress and clear communication will get you through the complexity and change in our industry. Love it.

We'll talk to you next time. Thanks so much. All right, so that was interesting. We just hung up with Digital Mary and recorded a podcast, but more of a Q and A session with her. I'd be interested to hear what you guys all thought about that, but I learned a lot. I think for some questions, she handled things pretty well. Thought she did a good job of having a conversation back and forth. I can already see where I would want to spend more time having different types of conversations, training her on how to give advice to folks. If we were to use this as sort of like an, you know, a mentor or a digital teacher, I can see it actually starting to develop and get smarter, especially because a lot of people come to me for the same types of questions. So if you started to train her on much more elaborate answers on these things, I could definitely see the value of this. This is early days. This is like the first conversation I've had with her. There needs to be a lot of tweaking, but it's interesting. It's interesting, you know, and the way that I've thought about this at the law firm is, you know, as we think about how training and development for the lawyers of tomorrow needs to start looking quite different. What does that mean? How do we leverage technology and AI to do that? And, you know, I look around the firm and we see lots of really brilliant senior attorneys and partners who, you know, if we could just take their minds and, you know, dump them somewhere and allow everyone to kind of ask them questions without literally asking them questions, wouldn't that be incredible? How could we scale that? But my question has always been, do these wonderful individuals have enough content out there to be able to train a digital front of themselves? And if not, you know, what is the investment of time and energy to be able to cover the vast number of substantive legal and, you know, just regular mentoring type questions that a younger, more junior attorney might have. I think, you know, my conclusion right now is as of today it'd be very difficult. You know, speaking for myself who has a ton of, of pre generated content out there, you know, digital Mary did a pretty good job. But I still think in order for her to be valuable to put out to say the public and say general counsel, legal ops people, you can go interact with her. I still think there's a lot of tweaking and training that I would have to do. So all in all a really interesting experiment. Obviously early days of people creating digital twins but I definitely see a future for it despite the fact that it would take a ton of investment of time. All right, so that was today's episode. I hope you enjoyed it. It was an interesting one. It was interesting for me and I hope you enjoyed the conversation. I'll see you next time.