 Hello and welcome to this episode of The Security Angle. I'm your host Shelly Kramer, managing director and principal analyst here at theCUBE Research. Today, as usual, I'm joined by my co-host, fellow analyst, brilliant engineer, wonderful human being Joe Peterson. Joe, welcome. Always nice to see you. Thank you for the glowing intro. And today we are joined by Jason Thomas. Jason is the CIO of a law firm by the name of Cole Scott Cassain. And they happen to be one of the AM Law 200 firms and Florida's largest law firm. And we are going to have a conversation today about how to balance productivity gains and how to think about what you need to think about when you're getting ready to embrace AI for law firms. Jason, welcome. It's great to have you. Thanks, Shelly. Thanks, Joe. Good to be here. Absolutely. So, okay, before we dive into our conversation, let's set the table a little bit. And what we're going to talk about specifically today with Jason is Microsoft Co-Pilot for Microsoft 365. It's an enterprise-grade Gen AI Assistant part of the Microsoft application suite. And of course, it's designed to enhance user productivity. The AI Assistant works in conjunction with Microsoft Teams, Outlook, SharePoint, all the things. And I won't say it's important to note as we talk about AI powered solutions. There is a per user subscription for Co-Pilot in addition to a Microsoft Enterprise license. So, if you're inspired by this conversation to check it out, know that there are some costs involved. So, Jason, I want to start with what is the favorite thing about these conversations for me? I always ask our guests to share a little bit about their career backstory. We all sometimes take interesting paths to the place where we end up at this particular moment in time. And sometimes there's some surprising things that we've done over the course of our career. So, Joe and I always learn something new about our guests when I ask this question. So, how about you share with us a little bit about your career journey? Yeah, I made a lot of quote-unquote moves through college. I've been probably through three different colleges and programs because I couldn't quite find a good fit for what I thought that I wanted to do. And back then, there was no program for what I want to do. So, you know, I started with some, I think I started with pre-med and then went to computer engineering, then the computer science, and then I end up with the degree in business administration. So, we all take our different paths, I guess. And I end up with a, I applied for a job out of Craigslist back in the day and actually got the job. Believe it or not, can you imagine getting the job to Craigslist? Well, I mean, back in the day, that's not such an unusual thing. Yeah, that was a thing. Now, 10 years into that job, I found out later that the only reason why I was hired, because my English was better than the person they were interviewing for the job. So, I was like, okay, well, that's fine. That's hilarious. You know, I will share that in the journey, you know, and I have, I have 18 year old high school seniors who are getting ready to go to college. And this is not my first rodeo. They have too much older sisters. But one of the conversations I have with them is like, don't stress yourself out too much about trying to figure out what you want to be today, because most of us reinvent ourselves, right? Sometimes we reinvent ourselves throughout our college years. Sometimes it's after that. When I was in college, I would have bet any amount of money that I was going to end up being an attorney. I had worked as a paralegal for about 10 years. I had an amazing mentor who owned a law firm, who encouraged me, and I went to college. I resisted being a polysine major because I really, I knew enough about life to know that things sometimes don't work out, and I really couldn't see what I would do with that. But I ended up majoring in communications, which is a great major for lawyers and, or, you know, hopeful potential lawyers. And by the time I graduated, it just, I realized, well, I actually got a job at the small law firm, a big law firm, rather tested it out, and it wasn't what I wanted to do. And somehow I made a U-turn into advertising and marketing. So we all kind of kind of go our own ways here, and you never know what the next turn is going to be, do you? Yeah. So you've been the CIO of Cole Scott and Cassane for the better part of the last decade, and it's safe to say you've seen a few things. Joe and I both love the fact that in your LinkedIn headline, you say, we've been doing AI before that was a thing. Can you share with us a little bit as we launch into the show a little bit about your firm's journey on the AI train? Sure. So I say that because obviously what everyone, because there's AI now, I think it's generative AI, but from the from the back end for administrative functions, we've been using that for years in terms of automating cash receipts and a lot of billing slash processes. And now in the last couple of years, has it even been two years? I guess it's been a year and a half where Genevieve has really taken off. And now that's where everyone considers AI just what you see in ChatGPT, but that's not all on AI. That's right. It's been around as part of business process automation for a very long time. A very long time. But we're seeing now commercially and kind of I'll call it user-facing is very different from what everyone thinks the definition of AI is. That's a true story. So when you think about co-pilot Jason and how it empowers lawyers and their teams, what is your thinking on the business value that law firms like yours could realize beyond the some of the automation that you just talked about with mundane tasks? Something as simple as with co-pilot we're testing internally even just simple responses to emails where we kind of have to think about what we want to say whereas we can you know figure or prompt the other side this is what I want to say but I'm exactly sure the best way to say it. They help me out there and very simple things on that end to full-blown that we don't on our side I wouldn't say we use a ton of Excel or PowerPoint AI but for the lawyers at least but in this this there's a lot of flexibility and option there to just present something graphically so talking about is one thing showing data and showing information is another thing so I think it offers a lot for flexibility and options for lawyers say hey maybe I shouldn't talk about it let me let me present it in a different way that makes sense to the audience so that's that's where I see it now if you want my hot take right now do you want the hottest hot take? Yes! I think co-pilot is going to crush most of what's out there in the legal AI space that's an opinion that's just just my take because of how I think it's just because every day that I use co-pilot or every other day I log in I was like huh this is just new this is different this is something that to do and they don't even announce it anymore they're moving so fast I think I just think Microsoft has the money in the R&D to to build it out so quickly that look I'm happy for all these startups and you know people in in the AI startup space and and all that and getting investments to do whatever but I don't think they can match the speed. Well I think there's another part I think there's another part of this equation Jason and it's simply that you know well first of all Microsoft was very quick to the gen AI race right and there's no doubting that the other thing I will say that I just got back from Enterprise Connect in Orlando big industry event. I said a couple of folks in that last week yeah okay but the thing about it is I want to make sure that everybody knows we're talking about Microsoft co-pilot because every vendor on the planet now has named something co-pilot co-pilot co-pilot and so it can be very confusing um but that was one of the things I encountered at Enterprise Connect lots of co-pilots but that's a really good point that there's lots of co-pilots but back to what Jason was saying Jason don't don't you think that this is a rich environment for your ecosystem to develop? It is but who's going to do it the fastest? First of all I think the first market was first to win yeah right in this space particularly. Well I think the other thing too though that where Microsoft has such an advantage is and this happened really before the the gen AI wave but Microsoft 365 is and all of the Microsoft products are so embedded across enterprises right yeah so I think that the company had a competitive advantage to begin with you know it's kind of like when we talk about when we talk about collaboration platforms and we compare Microsoft Teams and Google Meet and Cisco WebEx I mean the reality of it is and and I will say that plenty of Microsoft Teams users don't love the Teams interface but the reality of it yeah can't stand it yeah it's but it's enterprise-wide so you're gonna use it so I do think that that plays a role here you know yeah I mean in general like Slack versus Teams I wish I could go about Slack but at this point we know I mean we're we have to move forward and we've adopted Teams and I don't love the interface but this is where it's going and we'll hope and pray that it gets better from a UI UX perspective and it will it's just gonna take some time but Jason like my young engineers all send me messages on Teams and I'm like would you please send me an email I'm old and I'm old school I need to track the thing I need to track it and I can't track it in Teams they make me crazy young ins with their with their things that say yeah I think it's also maybe how your brain works too and and I will say that some of us use our email as a filing cabinet and and and I've used all of these I've Zoom and WebEx and Teams and everything else and of course all of these vendors want you to put every bit of the work that you do and the communications that you have and documents that you show everything into their platforms and sometimes that I mean that's certainly beneficial for them right because they want you to be all in sometimes searchability and findability and all that kind of thing can be challenging so I don't think it's so much that you're old because you're not and I'm older than you are so shut it but I think it is how our brains are wired sometimes and what works best for some doesn't always work best for others but do you think it's generational too perhaps yeah yeah I think it's an interface that you know they're just more accustomed to so again you can file the conversation yeah and set a reminder if you want right it's just a different way of doing it so it's not like rather than dragging and dropping into a folder of immediate tension or whatever you want to call it you can you can stuff in a team just yeah yeah okay sure enough all right so I'm going to quit talking about collaboration platforms and we're going to keep talking about security so about four weeks ago we noticed that Clifford Chance global law firm 34 offices across 23 countries and paltry 3,600 attorneys rolled out Microsoft 365 and Viva Suite at scale across its entire workforce so this is probably the biggest and the first um of international law firms to integrate co-pilot in a conversation discussing this rollout there's CTO a guy by the name of Clifford Chance um oh no I'm sorry a guy by the name of Paul Greenwood cited the availability of live transcripts via teams premium as being important as well as co-pilot summaries now for any of us you know using any of these platforms right now those the summaries and the transcripts are incredibly valuable um absolutely can't argue there he also stated that AI helps everyone stay on track with tasks and commitments that were made and so our question here is what how much of an impact do you think that Microsoft co-pilot will have especially in large law firms I mean I feel like you already answered this in terms of it's amazing but go ahead so so listen Clifford Chance right a lot of respect to them as a as a leader and my my thing um is are we trying I'm not trying to dog them or whatever are we trying to make a splash are we actually trying to do something one do you have appropriate policies in place two did we train folks on co-pilot or we just say here's your license and here you go I didn't say they did it like these are the things we have to consider like everyone wants the newest stuff and latest stuff and the hottest stuff um and AI is obviously very hot right now um so hot right now that they say in su langer um you've seen that me I'm sure with um so the question is if you if you don't have a really good uh change management slash training slash policy in place I've seen so much in the space where you know there was a huge huge huge excitement adoption and it was up here and then over the course of time it dropped what are we doing to make sure that people understand what is it that we're doing why are we doing it what is it being really used for as opposed to we're just um we're excited about this technology there's there's just so much to it there's this almost too much to it where folks can get overwhelmed just go back to the way they were doing things just because you know what this is too much really just ingest right now well it is it is learning something new it is it is as you said change management tell us a little bit about you know in the conversations that you have with your peers within the legal field what do you see on the adoption front so far when you see that it's something that people are diving in with both feet or is it something that people are taking a more measured approach what do you see in the industry I think everybody wants AI but they don't really know what that means really it's it's a buzzword and it's something that whether it's the colleagues are using the kids are using whatever it is that they're doing they want it to but then how does it apply to what I'm doing on a day-to-day day-to-day basis and that's our job on the technology side and adoption side to help them explain to them say this is really this is what it's going to do for you for a day-to-day basis as opposed to yeah you go home at night sure you can help the kid with your homework and all this other kind of stuff but you know let's talk about you know everyone's talking about it well let's talk about what is going to help how is it going to help you um on the business side and help you generate business generate revenue all that and that's that's our job to help them figure that out so do you think that's where people are right now having these internal conversations how is it going to help us how will it help our teams how are we going to get our arms right is that kind of where we are in the early stages of conversations generally speaking yeah I think that's one of the conversations and the second conversations I think clients are they're not necessarily demanding right now but they're curious and wondering what we're doing and they'd like to see what we're doing maybe where's the four years ago when um the you know term cloud was a thing everybody was anti-cloud now we're not putting anything cloud we're not doing that whatever whereas something has changed for sure when it came folks aren't asking if you use it folks aren't saying hey or clients aren't saying hey if you use it we don't want to work with you it's more well how are you using it just out of curiosity and what are you doing we'd like to know more the attitude and just the whole reception has changed that makes sense yeah it does make sense and you you know you brought up a couple really good points or at least that I keyed into Jason one was about education right and the other one was about productivity that helps you make money quicker faster right so um when we think about co-pilot and we think about e-discovery um how is it that people are lawyers and their teams using co-pilot for e-discovery um and then how are they you know how are cio's like yourself educating them on it and and is there really a gain in terms of productivity for using the tool so with our current e-discovery platforms or everything that's out there right now we have to or our lawyers have to manually upload the data right now everything's being ingested and automatically uploaded which is great except the question becomes do you want everything to be discoverable for one right great concept until we say wait a minute we have we have guard rails we have policies place when it comes to emails you know whether it's hey we only keep we have a retention policy of x number days or months and now we have to apply these same policies they are we can't just just outright just gather all the data this is great we have all this data we can you know discoverable uh i don't think we want that necessarily but we do but we have to put those same policies guard rails in place we can't just let everybody out you know out of the game say hey here it is yeah go for it yeah well how did you know where i was driving the bus that's exactly where i was driving the bus right um permissions and confidentiality and data labeling yeah so why are you doing all that you can learn the early stages so i'll leave that to clever chance to figure out and then let us you know give us give us the case studies and you know right here's what we did wrong but no but seriously uh yeah they've probably done that for months and so yeah uh yeah we just don't want to just let this stuff loose no matter how badly anyone wants it because compliance unfortunately uh compliance and securing all that that's that's the back of the lawyer's minds right it's not that they don't want it it's just not their job right so it's on us um from the it security jersey side to say hey the these are kind of card rails we've put into place and say hey just because uh we gather all this data you know remember you only have X number of days to save and follow emails after that you know this is our retention policy this isn't like freedom inside the United States like just put everything out there for anyone to find at any time right right and you're always worried about exfiltration yeah yeah yeah i mean everybody's worried about exfiltration right um and that's really kind of a good uh a good segue into my next question is that you know as we see Microsoft co-pilot starting to gain adoption in the legal field and you know we've been talking about e-discovery you know you think there's going to be i want to talk about data a little bit and data management so do you think there'll be a shift away from custodian centric data this is my data that i've created here's my folder whatever whatever to collaborative data here's a file that we can all work on together or content centric data um yeah shall we i think we've already seen that on our i hate to call it legacy e-discovery but that's what it's going to become become right with our current platforms is okay i have this i have this and then you know i think there's already questions about and and uh desire for collaboration well let's just i'm some shirt holes where i've moved back for it i think it's just this is just simply going to accelerate you that that process because they because before you can kind of say oh i don't know if i could do that everybody knows you can do that here you know there's there's no there's it's so easy now it will in fact it's so easy that it's you can make a mistake and put everything out there so i think it's harder now to secure it as opposed to not yeah secure because uh by default i think the e-discovery platforms right now have become very pessimistic in their approach so everything is locked down whereas copo i think we're still you know you know they try to put something stuff out there so fast that i don't know if security is really number one okay that makes me a little twitchy the reason i see that is because now not to pick a microsoft but you know now they're kind of upselling more security platforms and solutions on top of their current stuff that in my opinion probably should have there should have been more thought put into how we're going to secure this from the ground up as opposed to well everybody wants this and this is whatever the demand is and oh yeah we did think of that so let's put something on top of this and we'll sell you more yeah and so you can pay for the enterprise instance and then you can pay for the copilot instance and then you can pay for the security or more security yeah no i i do have to say that i'm not a fan of that i mean i really i'm looking for security to be foundational into anything that i'm using across the board and i want people to be thinking about security as they're building the damn thing so yeah you know shelly there's there's and it still goes on there's you ever notice on the free platforms you don't get sso or mfa right i mean it's ridiculous yeah well when it's free and you're the product though so like listen upsell me on your other features but security is not a feature yeah it's an expectation right but you know i mean we've all even consumers we're all consumers right and even consumers without it backgrounds have gotten smarter and are starting to expect that which is awesome mm-hmm you know i'm at the sweeping generalization i'm just saying as three people who focus a lot in the realm of cyber security i you know far too many people are paying zero attention to the dangers that they're navigating but i mean i love your i love your sunny outlet show i mean if i'm buying a car right now um i shouldn't have to pay more for the key that locks the door when i walk off after a little longer or i mean come yeah i'm with you come on i mean if you want to charge you for heated seats like allegedly bmw is going for a subscription fee that's fine i mean i can get over i can get over that i think i can get over it and by the way i would pay for that subscription hashtag hot cross buns yeah all they love that is table stakes for every driving experience today one of the biggest things when i brought my well interesting life when i bought my deal was like can i get bmw when i was like can i get autos like in a remote start like now i'll pay more for the you know remote start like we can't do it and if you go third party it boys you're watching like oh yeah i'm like car in the winter they're like nope now it could be a different thing now this is 2018 yeah but maybe there's different things but you know there's certain things that i understand that i should or have to pay for for luxuries yeah security is not a luxury but it's it's foundational it's expected and and even if your end user and your customers don't expect it you know i feel like the industry should expect it and require it you know i mean it's just don't count on your consumers to know what's no way we know what's important when we're building this stuff so build it from a foundation of security and go from there and it's really not you know it's not rocket science good so we were talking earlier about ecosystem and i'm starting to see things labeled works with co-pilot already i'm seeing them labeled that way so my understanding is that co-pilot will scan the legal software that it's coupled with to automatically read various types of documents handwritten items pdfs find all the deadlines or appointments that are included question to you is do you anticipate a vendor collaboration explosion with co-pilot in the legal field and if yes is there really going to be value to it do i anticipate a vendor participation yes they have no choice number two is there a value for them for a little while but like i said at the beginning of this conversation unless there's a very niche very specific place in legal for for these yeah plot problems i think co-pilot is going to really crush a lot a lot if they don't play if they don't just jump in like i don't wish for that i don't mean wrong but i think that they're just they've got the money the r&d the name the coverage in terms of they have everybody they have everything yeah well and again that usage adoption throughout the enterprise of microsoft products is i mean that's you know we're all griping about teams but you know i was thinking you know i was just saying you know when i'm looking at ai platforms now and this is probably now becoming more um legacy type licensing we'll say hey so how much for your platform it's oh we we charge by number of employees or by number but you don't have to do that with co-pilot right i want to give it to a hundred attorneys or a hundred employees no problem microsoft doesn't you know say oh i'm sorry you have you know 1500 employees you got a flash for everybody i was like well how many of these 1500 people you think is going to use it i know they're not here and so they're they're kind of putting themselves in a bad spot just from that licensing model low yeah plus it's up front right you can't go monthly you can't go monthly it's up front okay let's expand i love you i'm not doing that deal i'm not i am just not doing that deal because you know what fine then i'll keep giving co-pilot to people until it gets better and better and better and then i'm not gonna i'm not gonna use your platform unless there's something really compelling i think as co-pilot is uh tweaked and whatever and the api if there's an api i think there is uh i'm not sure uh what the deals but as as we can continue to tune it then what do i need other platforms for yeah you're gonna have to give me something to buy into otherwise i'm not paying for 1500 employees yeah there's no value there i have to justify that expense in that you know investment we'll call it investment but you know if i get 30 adoption then where happened the other 70% well it was a licensing fee so i hadn't do it running here that's more than a little expensive yeah so jason as we wrap the show i want to circle back and just ask you for you know we are blazing new trails here um and i know that it's a big job to be trying to get arms around things like you know ai throughout the enterprise and the costs associated with that and the training all that sort of thing and of course the security risks um but what is your best advice for someone in the legal field who may be watching or listening who's thinking about this but hasn't yet gone down this path what what is your best advice to them where did we start what do we worry about so here i saw an interview with mark cuban um a few months ago on uh cnbc or something basically i'll put it like that what he said is either you're gonna get on the ai train or your and the ones that do are going to be successful the ones who don't will not be successful i'm not saying uh mark cuban is the god of you know technology and whatever but he's got a little bit under his belt at least he's made a few billion i think and i mean he understands it and that's my that's my take to my college stuff you you have to do it you adapt or die yeah and i think ai is is in such high demand and and there's so much interest that you have no choice but to otherwise i think you're gonna get left behind at the dust and somebody else will um take over so i agree with you um but my question is like so i'm thinking about this and i'm cio i'm a cto i'm a siso one of these things the i think that first of all you need to have a seat at the table as we're talking about these things obviously i mean but this is like a senior leadership board level conversation how are we going to do this how are we going to spur adoption how are we going to provide ongoing training what's our ai strategy you know all of those what are our guard rails how are we dealing with compliance how you know it our legal team needs to be a part of this conversation you know all those things i think sometimes it can be sort of overwhelming to think about all of those things but is the best you know what's great is just so much education out there right now and paid even and look uh harvard has one mit one has one cornell has one worton has one they all have ai in business it's just not a technical course it's you know a very business oriented strategic course if you know nothing right now you don't know where to go i'm taking a course yeah and most of them are free by the way many of them are free many of them free and if you want to go really out there i mean they might be three thousand dollars uh for a six or seven week course i think you're from would be more than happy if you saw the show interesting issues hey this i think where the firm needs to go where the company needs to go i just need a little more information you know what the experts are saying or you know what's out there to come and help figure out what direction we should go i don't can't see a good good leadership team that's going to say no to that yeah that's pennies so so best advice is to dig in to uh to accept the fact that this is the path forward even though it can be a little scary um take every opportunity that you can to learn more and and you know i think that this is also an important part i think that we are now in the time where continuous learning is a business imperative it's a career imperative it's an individual impaired you know what i'm saying like we all have to cut and you know i'm i'm that same geek that i was in you know sixth grade loving reading every book i could get my hands on or whatever but you know my point is this is a bit of a career advice that i give my 18 year olds is that you know we are as humans many times not crazy about change but i think learning to embrace change and really understanding that all of us i don't care how what age we are or where we are in our career roles or positions or anything else it's that that continuous learning that is going to be i think the important for all of us you know shelly it's funny and joe uh how much we complain about our end users about how they're so again slash not open to change but we can't be those same people and yet we are those same people who are not always open to change that funny and that works yeah well i will say i'm kind of i've always been an outlier on that front i love change i operate well in a state of chaos and sometimes you just get what you get from a wiring standpoint so this this whole these these times even going back for the last 10 or 20 years that that has served me well but i do i do agree that this is not this is not a fad this is not something that you can kind of ignore you know we've i've talked about this before you know i remember i remember we're all old enough to have lived through you know the the rise of the web and the internet and how that changed the way we we interact and the way we do business and everything and i'll never forget years and years ago when i was in my late 20s you know one of my bosses proudly saying i don't use email that's stupid i'm never going to use email to communicate you know and i remember thinking yeah we you're not going to go far with that attitude i don't care that you're the CEO because what it says is that you don't really understand the transformation that's happening right now and you're not going to be a part of it yeah so well jason thomas cio of coal scott and casane florida's largest law firm amazing conversation thank you so much for sharing your insights with joe peterson and i today it has been truly a pleasure and you know what we're going to circle back with you and we're going to i know you're going to be paying attention to what's going on at clipper chance and so we're going to come back to this conversation and you know maybe what we'll talk about is the lessons that clipper chance learned that we don't want to repeat the mistakes along the way that we don't want to repeat yeah i love tranches i i respect them highly for this big big big move and i love it it is it's a big man of course we wish them all the success in the only way that you learn what works and what doesn't work is sometimes to just dive right on in so with that again thank you so much for joining us you both have been awesome and again jay so we're gonna we're gonna be having you on the show again and and doing another catch up here in i don't know four six months and see what's changed awesome thank you all right thanks for a view thanks for our viewing and listening audience be sure and hit that subscribe button and we'll see you back here next week