AI ROI For In‑House Lawyers

What if your legal team could deliver core work ten times faster without sacrificing quality?

 In this conversation, Richard Nicholas and Steve Cunningham of Simple Academy reveal how "you plus AI" transforms everyday legal tasks into structured, high-quality outputs through practical workflows rather than magic buttons.

 Discover the AI performance matrix that maps your work into clear competencies and repeatable workflows. Learn how to assign AI the heavy cognitive lifting whilst you retain judgement and legal responsibility. The result? Consistent quality, faster cycles, and more time for strategy.

 Drawing on his experience, Steve challenges the "turkey problem" - the dangerous belief that tomorrow will resemble yesterday and demonstrates why AI can handle far more than summaries. He maps a critical market shift called AI insourcing: as cognitive power becomes abundant, organisations will pull routine work in-house. The lawyers who thrive will run end-to-end workflows and translate business goals into reliable, AI-accelerated processes.

 Ready to move from curiosity to capability?  Join Richard and Steve as they look at how to deal with the “turkey problem” for in house lawyers. 

Transcript

Setting The Stakes For AI In Law

Richard Nicholas 0:08

Okay, so if you're an in-house lawyer and faced with AI, you have probably got quite a few questions in terms of how you might govern AI, the sorts of issues you might have in terms of implementing it in your business a nd in this series of webinars, I'm speaking to experts in a number of different fields about AI and their experience so we can bring that to you. And here, I've got an expert, particularly in getting businesses to implement AI and actually to understand it within wider teams. So particular expert in the training of AI, and that is Steve from the Simple Academy. So Steve, welcome to the podcast. I feel like I've known both you and the Simple Academy for some time now, but for those who don't know you, I wonder if you could give a bit of background about yourself and how you got into AI in the first place.

Steve Cunningham 1:05

Yeah, well, as you know, I always start off my story with I was a lawyer for exactly one week, which is a true story. I think I'm the world's shortest tenured lawyer. Nobody has fact-checked me on that yet, so I'll continue to claim it. Then went on to run a marketing agency for a decade and then created an e-learning business called "Read It for Me", which ultimately was up-ended by AI in November of 2022. Content production became very inexpensive and widely available. And so it really had an enormous impact on our business. Luckily, we were able to see it coming, and we pivoted into helping organisations start to adopt generative AI because we were using it in that business. And so we're just showing people here's how we're using it and as it turns out, there was a large appetite for that, and we turned that into our next act, which is helping organisations generate what we call AI ROI, which is how do you help your organisation become more productive, be more efficient, and ultimately generate more profit by using AI. And of course, there's a million details to how that gets done, but that's ultimately what we help organisations do, is productively adopt generative AI across the entire organisation.

Richard Nicholas 2:30

Excellent! No, thank you. And I can see that's the real killer application, really, isn't it? Making sure that you've got the return on investment. Now I know for in-house lawyers who may be listening to this and might be wondering, you know, how or even if, AI can help with their job. I know you've got a fantastic tool that can show exactly that, which I think the performance matrix. Is that right? Yes.

The Performance Matrix Explained

Steve Cunningham 2:57

Yeah, Yeah. So obviously the first question that people ask is how can it be useful in my role? They want to know how can I do my job faster and easier. And so we produced a tool, which is itself an AI workflow that shows for any role that exists, here are all the different areas in which AI can be useful. So we deconstruct the role into its competencies, like those would be things that would show up in a job description. Like this role is responsible for like an in-house lawyer, might be responsible for contract management, risk management, regulatory compliance, employment and labor law, and so on. And then beneath all those are all of the tasks and deliverables that get done within that responsibility. So, you know, for regulatory compliance, like a compliance obligations tracker, an annual compliance calendar, and just things that would typically need to be done by somebody in the organisation on a regular basis. And so then we help folks use AI to make those things go faster and easier. So it's actually really straightforward from an implementation point of view, but it's just the trick in getting organisations to be productive with it, to show them here are all the areas in which it can be useful. And once they get the hang of how to interact with the AI, which is actually really straightforward as well. It's, you know, we're off to the races and we get that AI ROI. So we like to say is that for the most part, this is a behavior change issue. The technology works, it helps people do their jobs faster and easier by orders of magnitude, and it's gonna be a really good time for the organisations that adopt it at scale inside their companies.

Toolkit, Tasks, And Behavior Change

Richard Nicholas 4:45

No, I can and I appreciate obviously anyone listening to this won't be able to see albeit what I will do is I'll put an example of that perhaps in the show notes, because I did that myself for my own own role, and I have to say, I found it slightly scary that AI knows so much about what I do on a regular basis, so it understands the sort of contractor issues, the data protection issues, the sort of DPIAs, onboarding of clients, that sort of thing. And I'm sure the in-house lawyers will find the same sort of level of detail in terms of the things that AI knows about you and sorts of things AI can do for you. And they I know you've described that before as a toolkit that people can take away and and use. And I've also heard you describe a little bit the turkey problem. I think this is from the book "The Black Swan". Is that something you could give us a bit more about the Turkey problem?

Seeing Your Role Mapped By AI

The Turkey Problem And Blind Spots

Steve Cunningham 5:49

Yeah, so for 10 years of my life, maybe more, my job was to read a business book every single day, summarise what I learned, and send it off to our executive clients around the world. And one of the books that I read was a book called "The Black Swan" and it talks about the fact that we live in this world that's highly unpredictable. Most of the things that shape in society and our businesses and our personal lives are events that come out of nowhere, that we can't see coming, a nd how do you live in a world like that? Like it's a really difficult thing to think about. And so one of the chapters in the book introduces what the author calls the turkey problem. And then the turkey problem goes something like this, the turkey wakes up in the morning, it is predictably fed by a farmer. This farmer seemingly cares quite a bit about the turkey because it lets it go play with his friends all day, makes sure that it has a roof over its head at night and that pattern just repeats itself over and over, and over again until finally the turkey concludes, well, I guess this is what being a turkey must be like. And so, one day, usually around, you know, we say here in the US, Thanksgiving or whatever, wherever holiday where maybe a turkey might end up on your table, usually a day that day, that pattern changes. The farmer comes out, does not feed that turkey breakfast, but grabs it by the neck, and in an instant, things have changed. And so, the turkey problem in AI goes like this. Ok, fine, usually this is after we demonstrate here's how AI can do a specific part of your role. It's like one use case demonstration. And so usually people will think, ok, fine, it can it can do that thing, but clearly it can't do insert whatever you think the AI can't do here. And what we have been able to prove over and over and over again is that if so, when we produce this toolkit, it's like 81 different ways that AI can be useful in your your role, and it typically covers almost everything that you do. So we said it, we say to people if it's on your screen right now, if it's in one of these 81 different things, you plus AI can do that job or deliverable 10 times faster with no decrease in quality and usually an increase in quality. And so, we kind of deconstruct it and show them how that is true. And a couple of things worth pointing out is like you plus AI, this is not, we are not yet, maybe, maybe never in a world where it's going to be just AI. You don't press a button and the thing happens. It's a process that you go through with the AI. So it's you plus AI, which usually makes people feel a little bit more comfortable, despite what you might see on social media, the vast majority of AI use cases requires a human being in the loop, and we're nowhere near autonomous AI doing all the work. Secondly, as we demonstrate when we use these workflows, the idea is that you can do the thing 10 times faster. So that's kind of the second part of that statement. Nobody has a qualm with that, it's clearly faster in orders of magnitude. So we get over that hump. Where people typically have a problem is when we say it's no decrease in quality. And the reason why there's no decrease in quality is because the workflows are basically step-by-step instructions. It's you plus AI, and AI is just doing a lot of the cognitive work in that workflow. You are now the editor, you are now the quality assurance person in this process. And so it is actually impossible for you to turn in a piece of work that is at a lower quality than you would have done it manually, unless you purposely turn in lower quality work, so that would be that's why that part is true. And then consistently over time, the AI is getting exponentially better. So, in more and more of those deliverables, it will be true either today or soon in the future that it will be an increase in quality over the vast majority of the population. So that's sort of like if there's only one statement you can leave people with for me, it would be that it's like you plus AI can do the work 10 times faster with no decrease in quality and usually an increase in quality. That is just true, so and we got thousands and thousands of case studies to back up that idea.

Richard Nicholas 10:14

I know, I've certainly seen that for myself in my own work. It's something that I know some of the AI vendors that are selling AI legal services, that's something that they focus on, the sort of cheap the doing things faster, doing things cheaper, in particular. But I know you've got a, you bring an extra element to the equation as well about sort of how this can also prepare you for sort of your future role, whether you're a lawyer or not a lawyer, and it how it allows you to actually carry out sort of performance experiments and actually to learn new skills as you as you develop. Is that that's right?

You Plus AI: Speed And Quality

Steve Cunningham 11:01

Yeah, so if you think of this concept of what is the best way to learn something, it's always by doing it. So we learn mostly through the doing of new things, and thus the best way to learn how to do something new with AI is to do it with AI. And so the best way to do that is with what we call an AI workflow. So the same tool that will help you do your current things faster and easier with AI. So let's just say I have not been, you know, I've been in law for a week, as I said, I was in marketing, n ow we're in the the AI training business. But let's just say I wanted to go off and on a tangent and become a project manager for some reason. The best way for me to learn how to become a project manager would be to run workflows that do project management work because it's deconstructing the process and a step-by-step. I'm doing the work, I'm participating in the work. And by the end of 20 minutes, I've actually done the work rather than going off and taking a weekend long course and never doing anything with the information. And one of the things that has been, that is going to be increasingly true, and there have been studies done around this, is that a person equipped with a like a non-expert in a field, equipped with a good AI workflow, will produce near expert level work in any field. And so what that means is that the core meta skill that people will need in the future is not subject matter expertise. It's going to be the productive use of these AI workflows. And so for those who can peer a little bit into the future, starting to take over other responsibilities in an organisation, mostly end-to-end workflows, that typically you would not have expertise in, subject matter expertise, that is going to be the new power source in an organisation. Whoever knows how to run those workflows or those processes from end to end, usually which will cross different functional areas of a business, will be the ones that have the power. The people who have the power will be the people who run the workflows and processes across those dimensions. It's a little bit abstract to think about. Certainly in an audio format, it's tough to get across. But your ability to learn how to do new things with AI in new functional areas is going to be the key superpower that people will need to have in this new economy.

Richard Nicholas 13:45

And that's really the thing I love about the training that you provide. I've spent a long time learning to be a lawyer. I've learned, I think I'm pretty good at it. I don't want to be a button pusher, just pushing out some sort of automation. And I think the thing that you really show in your training is how to use AI with the skills you have, and I know you've managed to condense various bits of work into various processes from your marketing days into a tool, for instance. And I, from what I've picked up from you, I've learned to create workflows in law to research legislation, to look at data transfers, to do things that are in my day-to-day work and actually do that better, and also to be able to do things I couldn't do before. And I think that's really phenomenal. And I'm very conscious as I'm speaking here, it sounds like, I'm going, I'm looking to sell something here. There is no sale, I should say, in this workshop, although there is an offer which I know you've very kindly made a scholarship to people on this, who are listening to this. And we'll put a we'll put a link to that in the in the show notes. I don't know if you want to say a little bit about the the scholarship itself.

Steve Cunningham 15:10

Yeah, you want me to explain what the scholarship ? Yeah, so you know, we're committed to being in the space for the next decade. And so, we have found that the best way to build something sustainable over the long run is to provide a massive amount of value to folks up front. So one of our core trainings is this AI workflow black belt training, which takes people from novice to advanced in AI workflow building in less than eight workshops and ultimately we found that to be the best first step for anybody in their AI journey. We would typically sell this on the open market for $4,000 dollars per person. We've created a scholarship program for the first person in any organisation who wants to become what we would consider the AI champion inside their company. We're making this workflow training available for free. So just go to the the link that are, I think will be in the show notes and if you're the first person in your organisation to show up there, you will have unlocked the training for free.

Learning New Skills Through Workflows

Richard Nicholas 16:19

No, thank you, Steve. I think that's a fantastic offer. And if anyone's interested in that, just do look for that, or if you can't find it for any reason, just look on my LinkedIn. I'll put a link to that there. So, I think there's some fascinating, you gave a fascinating view of the future there in terms of the way things might go forward in terms of across different disciplines. I mean, any thoughts from yourself in terms of looking to the future and what you might, what you think this might mean for the future of work, where you see work, where you see AI going, particularly for you know, external lawyers like myself or in-house lawyers, do you think there's a change to how that that dynamic might work?

From Lawyer To Workflow Operator

Steve Cunningham 17:08

Yeah, absolutely. There's a term that we coined called AI insourcing. And basically what AI has done, like in every revolution, there's the industrial revolution, there's the internet revolution, there's the PC revolution, it's made some form of previously scarce thing abundant. And in this case, we're making the, its cognitive power in any domain freely available to anybody. So there's this subject matter expertise that has become less and less important and is going to continue to become less and less important over time. So previously, most, and I still for the most part today, most professional services firms make money by having subject matter experts and billing those people out at hourly rates, usually three times at three times whatever they're being paid, is usually how most professional service firms work, you know, give or take, order of magnitude. But previously, that was scarce knowledge that is no longer scarce, and any person who knows how to reasonably well put together an AI workflow can get work done, as I said earlier, at a near expert level. So only a really small portion of your subject matter expertise is going to be valuable in the future. Almost all of it is no longer valuable. And so what is going to happen is organisations are going to figure out how to do contract reviews with AI. They're going to figure out how to do all, you know, many of the things that'll show up in the deliverables that if you ran, you know, an IP risk exposure report. Like somebody with a workflow to do these things can just do them internally at a company. And the work that'll be left will either be much less work for professional services firms or new kind of work. So there's no world in which you in the next 12 to 24 months are doing the exact same work that you're doing today. Much of it is going to shift in-house to organisations. It's gonna be very disruptive. There's like, I think the professional services firm worldwide market is something like $6.3 trillion dollars a year. It's large and it's going to be massively disrupted over the next 12 to 24 months. So there are, of course, things you can do to protect yourself and to get ahead of it but none none of it looks like ignoring AI.

Richard Nicholas 19:48

Excellent. No, so it sounds very much like as lawyers, we need to learn new skills to really sort of show our worth, show what we're still bringing to the table. And I think that's something that I'm looking to do with these sorts of webinars. So thank you very much, Steve. Really appreciate it your your time today. And thank you so much for the very generous offer and which I'll put in the show notes and as I say on my LinkedIn as well. So if you're interested in learning more about using AI and creating workflows and the sorts of things and how this might be relevant to your role then I would say do take Steve up on his offer. I have found his training to be fantastically useful so I would recommend that to anyone, so thank you very much Steve all it remains for me to say is thank you very much again for coming and I hope that we will speak again very soon.

Steve Cunningham 20:51

Yeah thanks for having me always a pleasure to talk to you.

Richard Nicholas 20:54

Thanks very much