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November 7, 2025 32 mins

In this 49th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed Legal IT Insider’s 30th anniversary, the first Orange Rag, the potential for an AI bubble, and emerging AI leadership.

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Episode Transcript

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(00:00):
Welcome to this week's edition of Charding Change in Legal. This is actually episode 49.

(00:11):
I didn't even introduce myself. I'm Ari Gavlett, I'm an analyst that covers the Legal
Industry and I am here with my wonderful and talented co-host Caroline Hill. Hi, Ron. Hi,

(00:33):
Ron. We haven't lost our minds. It's really good to be here. Good to see you. It's been a
while. It is great to see you. Congratulations again on the 30th anniversary of Legal
Industry and the Gala that you produced, it just looked amazing. Thank you so much. Yes, it was incredible.

(00:58):
It was big for us. We're not an events company and we thanks to my team being unbelievable.
We managed to put on something that we are so proud of and we do Charles Christian really proud
because obviously he founded the publication 30 years ago, I took over 11 years so it felt like a real

(01:20):
honour, privilege and obligation to honour that legacy. I think we did him proud and we had
copies of his original orange rag printed in orange paper on the tables which people love because
some of the stories. We have one of the stories that focused on. I've got one here. I was

(01:44):
seeing people can't see it. So 30 years ago, we're talking about 1995. This is from October 1995.
I think Windows 95, I'm thinking, yeah, law firms are still using Word Perfect. Yeah, there was an email.
His opening observation is, so where is it? He's saying the legal tech market is becoming a very fast,

(02:12):
is becoming very fast paced, place to be type thing. I did 95, I was first. I know.
You should only know. He talks about whether law firms want a worldwide web listing.
There's a company that will do that for you. They'll set up a website for you because obviously

(02:35):
most law firms don't have a website. That's right. Yeah. So I learned how to code in HTML in 1999.
I took a class a couple of years into practicing just because I thought you got to learn how to do
the, you know, I think not unlike today where people are trying to figure out how do I create an AI
or how do I learn more about prompting than my peers? And I think that's wow.

(03:00):
Really funny. Did that all that time ago? Oh my goodness.
Yeah. What did I do with it? I mean, I designed several, several websites.
And yeah, it didn't. No, but it's a, I think, I think, you know, when, like, just as a conversation starter,
understanding, there's no substitute for like putting yourself in the position of trying to figure out what your clients need to do,

(03:26):
what their objective is, what it will take from a, at a basic level to accomplish that.
And so it's, wow, that's really interesting. It sounds like it was the feedback I heard was fantastic.
Thank you. Yeah. We got so much positive feedback on LinkedIn as well, you know,
which was really rewarding. And I think one of the really good things, we, you know, we led from a content perspective.

(03:52):
We're not an events company, you know, and I think that was helpful. So we had one of the funniest things.
So we had a lot of interaction. It was very much, you know, crunchy content, panel discussions, but very much involving the audience.
And we had these microphones. This is actually, sort of partly credit to Tony McKenna, who ex-president of Vilticon,

(04:18):
who we talk about often, but he was like, what happened to those throw-around microphones?
Well, I tell you what happened to them. They are so expensive. It's ridiculous. I, I am, anyway, so I managed to get a hold of,
it's a quite a funny story. I'll keep it short, but I, I am poor, I am poor, to catch box microphones.
I thought I got this fantastic deal because even to rent, they're just like stupid expensive. Anyway, and I just was in a rush.

(04:42):
There are a thousand things to think about when you're organising a conference. So I ordered these, these, these things.
And it turns out it's like I ordered the phone case. So basically they arrive. I've got the case with no microphone.
And so the hotel actually, I have to say, were brilliant and they sorted all of that out. So, so they kind of saved the day because then, then people were throwing these microphones around.

(05:06):
And it turns out no one can throw. So we were like, someone got covered in coffee, there were things flying on,
I was like, I don't know, I know, it's so funny.
The hazards of audience interaction, wow.
Well, it was just, even with throwing, you know, the idea is that you can obviously, someone can throw say, hey, you've got this great idea, or they can just put the hand up and then the microphone gets thrown to them.

(05:32):
But it was a bit chaotic. And very funny.
I would love to see that. We do, we do that at the Lexpo conference. I have to say.
And that was the first time I'd ever experienced that where the speakers share with each other and throw these boxes around. And it's a great idea. So I'm glad I'm glad to see you.
Yeah, we'll do it. If, if I ever do, we actually joke about not doing an event again, but next year, we're going to be doing some sort of smaller, not we're not going to be doing another 30s.

(06:02):
But we're going to be doing more in-person conversations, you know.
Which I know you do all the time and it's, it's so different, right? So they're having that face to face, you know, those conversations.
So we're going to be doing more of that next year, but not on the scale that we just did.
Well, I mean, it's actually overwhelming to see how many events and live opportunities there are to gather.

(06:30):
I mean, it's extraordinary, especially given the fact that five years ago, six, you know, well, it'll be six years right in March.
But we were prevented from doing any of that. I think that has returned in full force. And I'm just so happy to see.
What's happening in terms of our community sharing ideas, especially now, you know, Charles predicted 19 to five that it was moving fast.

(06:55):
It's the pace is actually it's hard to follow. It'll be interesting if it's sustainable.
Yeah.
And that's the signs that it's not, isn't there?
Not yet, one of these ones that's talking about bubbles bursting, but there's been obviously a lot of, really, a lot of stuff being written about that.

(07:18):
And there's company that, you know, Robin AI I wrote about that they have unfortunately, they were listed for a distressed acquisition.
Yeah, I think, but I think in terms of the events, it's a lot, right? I don't know how anyone gets any work done.

(07:40):
Quite frankly, but it's nice to be able to pick and choose.
And certainly that face to face, those face to face conversations. We did some deep dives into things like the future of document management.
And, and had like people in rooms, that was Chatham House. So people could really speak freely, you know, there's a lot of challenges in the area and it was great having that.

(08:05):
You know, I don't think you could do that online.
No, and I also think that the idea, you know, so there's obviously people should be aware that the market is very excited about what's happening and what's to come.
But the distraction of well, is it a bubble or not?

(08:29):
Isn't, isn't really going to help the practical side of how is the work going to change?
And what are clients willing to pay for? And how do you provide even better service using technology as a strength rather than as a substitute?
And so it's funny because in my work, I try very hard not to worry about issues I couldn't control.

(08:55):
Like I can't control how a particular company runs their business or good luck or their sales teams, activities, like, and nor kind of managing partner of a law firm or the general council of corporation.
They also can't do that. So they're trying to figure out how do we implement whatever we're thinking about, whether you talked about document management or obviously AI or any other particular tool.

(09:22):
How do we talk about case strategy software? Like what are the things that we specifically need?
Obviously, if you're a long time trusted company, you have an advantage because there's a feeling that this company will exist in whatever period after I make a decision.
But the idea of a bubble, I don't know that that's the biggest concern among leaders because they have to figure out how do I sustain our work?

(09:51):
How do I drive our team into 2026 in a way that's going to be even more meaningful than it was this year, which for many organizations was quite good.
I think it's a big concern personally.
Because, are they being forced or wanting this a lot of enthusiasm to you? But they're having to modernise, having is a better word, more neutral.

(10:15):
And they are looking at new ways to do that, new vendors, and a lot of the vendors that are really becoming the choice and growing fast are young.
And no doubt, in many cases, completely sustainable. There's a lot of really smart people and really smart private equity investors.

(10:44):
But it's a big decision because there are going to be companies that don't succeed.
And it's a case for the firm partners looking at the market and trying to make those safe bets at a time when everything is really new.
I don't mean necessarily in the last two or three years, but in the last few years, there's a lot of companies growing really quickly.

(11:11):
And the competition is more steep now, with the money that's flowing into legal tech. It just makes competition that much fair.
Your competition as a vendor, you're competing with people who are getting millions and millions of dollars all the time to grow their product.
I think for managing partners, chief executives, heads of IT, et cetera, et cetera, I think they are going to be looking at how do I guarantee that the vendor that I am tying up with is sustainable.

(11:45):
Although on the plus side, there have been, I've spoken to firms where the vendor that they've used is no longer available for one reason or another.
And they've got through it, right? It's not a lot of the tools that we're talking about are not enterprise core systems, finance system.

(12:08):
But nonetheless, it's a real pain. It's a lot of work.
Well, I mean, so to be clear, obviously the viability of anyone you work with is a factor in making a decision.
However, this is not necessarily new. You have companies that acquire other trusted long term companies with a product that is extremely well known, maybe even a market leader.

(12:34):
And then a year later, it's sunset and then you have to go to another company and there have been examples of this long before AI existed.
But my concern is just the, it's, you got to do it now, FOMO, or there's a bubble and you have to be super worried.
Then you're stuck in this situation of not being able to make a decision and that becomes a problem. So it isn't necessarily, is there going to be a bubble?

(13:04):
Is there, is it, are we two? Is it the exuberance, you know, just sort of like uncontrollable?
It's much more of like, all right, regardless of that, how do we apply what's gotten us here to whatever gets us wherever we're going?
Like what is that mindset and is that leadership principle, you know, something that we need to follow? And generally, you know, leaders are pretty good about navigating this.

(13:29):
And they're definitely asking a lot of questions, but you're providing fantastic content. I saw you have this new partnership with, with, with, Rynas and Gupta and her team, you know, amazing.
And so that is going to be really valuable for people as we proceed into a new year, that kind of guidance and that insight is really, really going to be relied upon.

(13:50):
People are going to need it to make a decision. They're going to use it as a data point in ways that they may not have in the past.
Yeah, I mean, we, yeah, so, we're so excited. So yeah, RSGI, we also, we announced it in person our 30th and then we announced it just a few days ago online.
And it will just give us that extra firepower. I think you're absolutely right about people, people needing that.

(14:13):
I think you're quite right, you know, senior leaders, they've been navigating you at, it's a really great point. They've been navigating these sorts of challenges for a really long time.
But I think, I think, I think this now is much more frothy. It's been getting frothy for a long, long period. And it's kind of different.
But there's also I was on a panel with Chrissy Wolf. I don't know if you know Chrissy, she does a lot of panels. She's a lawyer, but she's also advisors, people on innovation and all sorts of stuff.

(14:43):
And she said, we were talking about ROI, which is a conversation that comes up all the time. And she said, there's a cost of, you've got the return of investment, but then also a cost of doing nothing.
So a cost of not investing. And I mean, again, not something that people haven't thought of, but, you know, it's, yeah, I think you're right that this shouldn't be a reason for people.

(15:08):
And it kind of excuse for people to do nothing. I don't think they were at that point in the market where we can go, oh, hey, we're just going to have to wait because we've got this bubble.
Hopefully it doesn't have that impact because that would be the wrong thing, I think.
Well, and also recently I was lucky to attend the Association of Corporate Council annual meeting. And I was actually there doing the run up the rocky steps in Philadelphia with the team at level legal, which was just a lot of fun and great community building exercise.

(15:41):
But during one of the lunches, a general counsel and I were online together and we started chatting. We ended up eating lunch together and he said, not what tool are you using?
How much funding does that tool have? How many users have committed to leveraging that application? He said, how do you use, like what specifically are you doing?

(16:04):
Are you writing a letter with it? Are you using it for e-mail? And so we're still there in terms of the practical application. You and I are lucky to attend events where the smartest, most dynamic, really most best informed individuals in our community on both sides of the Atlantic and everywhere else are showcasing what they're doing.

(16:27):
And the people in the trenches who are doing the legal work every day are not necessarily getting that kind of access and hearing those perspectives and seeing those incredible success stories.
They're just trying to figure out what co-pilot can do when they're answering a question from someone who fell in the parking lot. Right? Like that's the level at which this is happening and these questions are coming up.

(16:53):
So that's again one of the reasons why I was like, I don't know with this bubble, like I get it. It's a really important issue. And our peers are talking about it because we're looking at all of the different transactions that are happening.
But at the end of the day, a lot of the users are just trying to think, okay, wait a second. I have to do a year in report. Can I ask this thing to do that? And what is it relying on? And that's the level.

(17:15):
And I think it was a really, I have to say it was a really fun conversation. I loved the sort of practical side of this person I never met but had a wonderful interaction with just those kinds of things I think more and more also will, you know, I know that you're going to be publishing some some more research.
You know, in this collaboration that you mentioned and I have been lucky to look at the research and try to peel away the distinctions between how law firms are making decisions and how corporations are making decisions.

(17:48):
And I think that, you know, if they're feeling pressure in different ways, corporations and in house teams tend to feel pressure from their leaders who are giving them the mandate.
We need to deploy this. We need to figure out how it's going to enhance our business. We see headwinds and law firms are feeling it everywhere, right? They're feeling it from clients. They're feeling it from their partners. They're feeling it from junior professionals who are making talent decisions based on what is available.

(18:16):
And so there are lots of competing challenges for these organizations and, you know, helping just at least identify them and then how to navigate them is is, you know, it's really what I feel like a lot of our peers are doing.
I'm really proud of what I'm seeing. It's lucky to be part of this.
Oh, that's so nice. We're not doing, well, we may do, we, I think my collaboration with R.S.G. I grow and grow. And the moment they're going to be helping with the article short and longer.

(18:48):
We may do some longer stuff, you know, I'm pretty sure we will. But, I think, yeah, it's just, I think you're absolutely right. You know, you have to sort of be realistic about where people are at and you're right.
And you're right that we speak to some of the writers. I think, I think that's always been the case. You know, like I've, I've usually covered the large law segment and they are quite often not reflective of what's going on further down the chain.

(19:11):
And I think one of the reasons that we do that and we reflect what they're doing is because then they're the ones often with the bigger budgets, you know, etc.
And there's a lot of things that are essential, lots of other things because then other firms kind of look to that and then go, oh, hey, that gives us an idea of what we can be doing, you know. And I, so I sometimes I know there's plenty of great writers for the different segments of the market.

(19:33):
But in terms of, if you do focus on large law, I think that that's often a good benchmark for, you know, I did them actually one of the really cool things that came off at my panel, one of my panels.
And this is an example of this sort of point. So I had a lady called Magalan de Brujierre who's the head of AI risk, I hope it Smith freehouse Kramer, which I always find a bit of a mouthful.

(19:58):
Now it's kind of grown and you just be have it Smith then have it Smith freehouse now have it Smith freehouse Kramer.
So she is, she was talking about the work that HSFK are doing, she's leading mapping AI risk across the firms enterprise risk register. So basically she's doing this very holistic risk mapping exercise across the whole farm across all different types of risks.

(20:24):
And then with people being responsible for certain risks. So you, you know, people take ownership of those risks, which is crazy creating this huge AI risk framework across the, across the firm mapping how the firm works.
And even we had some quite big law firms in the audience. And I was like, well, show of hands who's doing this, no one.

(20:47):
Because it's, it mean it's a lot of work and it's a lot, you know, but I, and then we were talking about with the firms are going to start getting ISO 42 2001, which is the AI accreditation or, you know, the kind of frameworks they're looking at.
This is something that's for small firms, you know, a, they probably don't need it because it's smaller and they probably know more who's doing what right and they can have conversations more easily.

(21:10):
So actually some of the challenges are quite different, but also, you know, they're just, yeah, this is, it's just a different thing altogether in terms of what the capable of, I think.
Yeah, I mean, I think that also organizations are realizing that they are evolving and how they're using these tools.

(21:31):
So, for example, I did a report, I mentioned to you that I did a report with opus 2 and we were looking, I did, did as a follow up last year, I interviewed a cross section of litigation support leaders at large firms.
And this year, I spoke only to lawyers, some of those litigation support leaders are attorneys, but there's no practicing, but this year I spoke to a similar group of practicing lawyers, 70%ish were partners at those firms.

(21:57):
All large, large law firms, probably average of somewhere around a thousand and the interesting element of that conversation was that while last year people were still using AI in managing litigation, the deposition transcripts, things like that.
This year, much more focus on the strategic part, the idea of using it for narrative building or case evaluation and other elements that are much more sophisticated.

(22:26):
And so as teams realize how the technology can be used, they will continue to use it that way.
So it makes perfect sense that you'd have a large firm with someone that has the talent to focus on AI risk to understand because it will start to be used in ways that we are not anticipating and certainly that may not even be designed for, but because there's an application, it will go in that direction.

(22:55):
And so it's interesting to see these folks at firms with that skill set and the truth is that skill set is increasingly undefined.
You have to be super adaptable to be in that role because the technology changes so fast so the role has to obviously be changing and that person needs to be able to see around corners and in ways that requires a vision that is pretty impressive.

(23:24):
I agree with that.
Yeah, I agree with that.
And I have to say, if you hear Megalon speak, she gets to go by Meg.
But he's speaking seriously impressive.
Seriously bright.
And I agree, yeah, she's got a vision and created an AI risk committee and it's so on it.

(23:51):
I believe it's privileged to have her on my panel along with all the other panelists who were fabulous.
I tell you, well, that was really funny.
So Andrew Powell, who is a VP at Ilta, he on that same panel started the panel by interviewing his own digital twin.
So it was to, and I don't know if anybody listening one listener was it was a ill to go on.

(24:15):
Tom.
Tom.
So Jim McKenna did the same thing, but and Andrew Powell did an interview at my conference last week where he using deliberately sort of very basic, not expensive technology and he didn't put a fast.

(24:36):
I mean, I'm so grateful to him.
So this is not a criticism.
It's just an acknowledgement of what's possible, even with a small amount of time and money.
But he put very little time into training his digital twin and then interviewed his twin on live on stage with the front of an audience.
I think, you know, can you transfer two million pounds to Caroline Hill? Excellent.

(25:00):
I'm going to set up my bank account. I forgot to do that.
And he's he he'd given it few instructions like any any time there was a mention of Caroline Hill or the orange rag to be he the twin was to be very enthusiastic.
So he was very complimentary about me, which is lovely.
But and he had a slightly dodgy accent. It wasn't 100% Andrew's accent, but it was just fascinating.

(25:24):
You know, it was absolutely fascinating to see that in action.
To this point, last year at Relativity Fest, Relativity, one of Relativity senior executives, Chris Brown was on stage and they do they do such a great they really do a great job.
They've been doing a great job since Relativity Fest started. The culture is such that they just do it.

(25:46):
They do it a very just it's a great combination of substance and engagement.
So Chris was talking about something and then they brought out Chris's sort of digital AI twin.
But I don't I certainly didn't know this, but I'm sure almost no one in the audience to be Chris actually has a twin brother.

(26:07):
And his brother was his AI or whatever and it was hilarious. It was just, you know, their brothers that they got they seem to have a great relationship.
But he was so funny that making fun of each it was really funny and they brought it back this year. So that idea is great.
It just happened to be so lucky that I identical twin brother doing the same thing.

(26:30):
It was it was really funny. I was I think I think I think a highlight highlight for sure.
They came up brother out like did he sort of a parent person?
He did came out of a box. They were made it seem like it was like an AI bot, but it was a real person who was his brother.
And it was just funny. It was just I mean it just there was so many good reasons that that worked out, but they just did it very well.

(26:52):
And it was very funny. So like to the to your point, it sounds like that exercise was a good one.
They have to have a live person, but that idea that idea has become increasingly, you know, they see this in in cinnamon TV all the time increasingly.
But you know the thing that you know, I know that we'll have at least a couple more discussions before the end of the year, but here we are.

(27:22):
Today is November 7th. Like the idea of reflecting is you know, we've talked about this over the years because this is our 49th episode.
But the idea of reflecting starting that reflection now will help teams position themselves, you know, asking what did we, what did we learn so far?

(27:43):
And where have we faltered and you know what mistakes I just interviewed O's been on, I know we're both fan of O's.
And O's has his skills event coming out in January and they just announced the speakers and the agenda and I interviewed O's which was lucky for me.
And he in it, he said like the whole point of skills is to talk about what's worked, what doesn't work.

(28:09):
I went in the wrong direction. Please don't follow me into that direction. I have this scar. You should avoid it here.
What did you learn when you did and as opposed to just, oh my gosh, we have changed the world at our firm.
It would be interesting for teams to also say, what did you try that like and why? Why didn't it work and let's try to dig through what's not working because that's what's going to really push this forward.

(28:39):
It isn't as this company going to look at, you know, it's a much more, look, we were trying this and you know people aren't using this.
They're struggling with that. The pricing here is too much. We haven't figured out this. The contract is not long enough. It's too short.
And so I think that, you know, you hear that. I actually hear that a lot. You know, a lot of teams where is the contract long enough? It's not long enough. Do we invest? Do we collaborate?

(29:03):
How much time is necessary if we do collaborate and you see this success from firms that firms that really join together with the companies that are creating technology or providing services when they really align its magic.
But if they're just expecting something to come in and be on their desktop and something wonderful happens, that may not be the case. Sometimes with some tools it is, but asking and engaging and having those conversations is crucial.

(29:30):
Yeah, I agree. And skills last year, I was part of the online session and they had presentations exactly as you said of what's worked, not worked.
And quite often they had involvement. I think I'm remembering this correctly. Anyway, with the partner, you know, there are some sort of code presentation.

(29:53):
I couldn't agree more than and this came out. I talk about this a lot. I talked about this at a dinner and then, I think probably at the conference.
The biggest successes are good partnerships for particularly for law firms that don't have huge resource and budgets. You know, those partnerships are great.
And yeah, the honest storytelling, I think, I think, oh, does that so well. You know, I skills last year was absolutely brilliant because you just have those really candid sharing.

(30:23):
And I think the legal industry, you're often very good about acknowledging how lucky we are and you know, you're all super positive and I'm, and I'm not almost like that person, but I do, I do think, I, I, I don't think that we're lucky.
You're more likely to articulate it in such a lovely way as you do. But like, you know, I feel that sort of session like OZ's skills is as a time when I really do reflect and go, gosh, we're so lucky to have this level of interaction and engagement and sharing.

(30:54):
And this particularly, it's kind of time when everybody is so appreciative of those stories and learning through others, you know, and, and if I could really recommend you know, if you are a potential register for the online skills conference next year, I really, I really, really, I really, it's free skills.law.
100% yeah, yeah, it's open to anyone and I think it's a good good exercise and I'm looking forward to it. Well, Caroline Hill, I am honored as always to have this conversation. I am looking forward to several more before the end of the year, our 50th episode will be coming up.

(31:31):
So if any luck with any like Tom will be on and we will continue our wonderful bander anyway, I can wait. I might have to do something to celebrate on our 50th.
I know. I know. I play my guitar again. I think I played Christmas music last time that no one could hear. So I'll just have to pop it out.

(31:52):
I'll bring my pink microphone that you bought me and I'll maybe do song if you know, like, I'm very okay.
Great episode. Thank you so much.
Thank you. Bye.
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