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October 22, 2025 21 mins

In this 48th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the value of practical conversations about AI pricing, promoting wellness at conferences, and empowering change.

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Episode Transcript

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(00:00):
Welcome to Charting Change in Legal. I am Ari Kaplan. I'm an analyst who covers the legal

(00:10):
industry and I'm here with my co-host.
Caroline Hill. Hi everyone. I'm the editor in Chief of Legalite Insider. I'm a journalist
based in the UK. Great to see you Ari. It was always great to see you. I have to acknowledge
the fact that this is actually episode 48. Wow. We can take the big 5.0. I think for the

(00:30):
big 5.0 we're going to try to get some listeners. Maybe that. Well it's been a busy month.
It's been a certainly a busy few weeks since the last time we spoke. You and I have been
actively at various events trying to wrap up the rest of the year with some, I think some

(00:53):
perspectives on where we've been and where we're headed. How are things? Yeah. Well that
was a great segue intro. It's conference season. I don't know if it's ever not conference
season but it's conference season. It's never not. It's it's not. It's it's autumn conference
season and it's pretty intense. We've got legal geek coming up. You've got a lot of

(01:19):
user conferences and also I went to two conferences last week. One was a two day event which was
a kind of stayover thing which was high level CIOs, CIOs. It was called Visaville. They've
resurrected it for the first time. They last they last ran it in 2022 and then I also went

(01:39):
to in London a day event called London Law Expo which is run by net law media which is
the company behind the British British legal technology forum. It's a different type of
event because it's more for CIOs. It's more operational perhaps but yeah they were both great
and I mean we can dip in and out of depending on what talk for ages but we can come back to

(02:02):
it but it was just interesting. I think Expo was more techy which is great. There were some
great talks by Workday with CMS talking about how they're using Workday which was interesting
to have. I really love when you have the client perspective rather than just one perspective

(02:23):
and so the end user but then Visaville what was really interesting was how people focused
it was. You know you and I have talked about things like this many a time but the content
there was a heavy emphasis on networking and spending time with people they deliberately
built a lot of time to network but then the content was very much talking about I mean it's

(02:51):
not a surprise but change people leadership how to get the best out of people how to cope
with your day how to build stuff into your diary there was a talk from a guy Robo Donohue
from Garnor talking about the habits of leaders he was kind of riffing off the seven habits
of leaders book and he was saying seven habits not enough these days and he said that you

(03:17):
really need to create he was talking about a culture of empathy and he was talking about
being authentic he was talking about enabling people to be vulnerable about being able
to be vulnerable and creating a culture which where you really embrace failure rather
saying you embrace failure and then actually underneath it don't embrace failure there

(03:40):
was so much around the cultural piece that that and I think that's what people this senior
leaders really want to hear right now I don't know if that resonates with with anything
you've been hearing recently. Well I'm about to release several different
reports one that I just finished about law firm leaders at mid-size law firms another one

(04:01):
focused on how legal AI is being used what perspectives on there and I think that in addition
to what you just mentioned all of which are very important points there needs to be a
practical element to it because I don't know that leaders struggle with the concept of
allowing for failure but it's more about what what does that actually look like in practice

(04:25):
I feel like the practical side of a lot of theoretical issues are now very much part of
the conversation for example I just returned from relatively fast and I think one of the
it was great great event it always as always I have been I forget when the first relatively
fast I attended was but it was at least ten years ago and they just do a great job they

(04:45):
really embrace the community and they're always on the edge of lots of different issues I'm
lucky to get to speak about several things one of which is about some research that I did
about litigators at large firms but also general counselor on the world and pricing came
up like how are we using the conversations about how do you use AI in general or generative

(05:09):
AI or what do you think about agente AI was obviously part of the conversation but the big
announcements were about what are you paying for how are you paying for it so the practical
elements of should we build it in will it be built into this platform which was one of
the announcements and other companies started to also mention this is what we're doing

(05:32):
about pricing because while innovation and driving change with AI are all super important
topics to all the leaders that you and I are lucky to speak to who's paying for how do we
pay for what's the practical side of failure and how much failure is too much failure and
how much is enough that shows what our culture is those are really important questions and
when we sit down and talk to folks and when they sit down with their other leaders and

(05:58):
their constituents and stakeholders what it means really matters and so I think it's been
been an interesting evolution of the conversation
so that's fascinating so who is making the pricing announcements a relativity made a pricing
announcement about air and its subscriptions and then other vendors who provide relativity

(06:20):
to their clients made announcements about pricing so there were several things that we've
seen because it's interesting because the conversations around pricing I have a lot of
the time are around the end user and it comes back to the bill of hour and what it means
and clients getting involved and this is this is the vendors what being more transfer

(06:43):
well this is the question so you know the questions that we both get which are kind of twofold
is the end of the bill blower you know how do we value a particular project also the questions
that I'm getting are who's going to pay for this cost of this tool that I am now using is

(07:03):
it a pass through cost it was you know there was a time once where firms would regularly
bill for additional items like faxes or mail or research etc. research tools themselves
now lots of that's just built into overhead and that's what the conversation was more about
now and I'm just noticing that how are you going to pay for it let's let's remove some of

(07:28):
these conversations about pricing and let's just get to the benefits and the innovation
and driving change so it was a there were a lot of interesting conversations about that
and that was pretty big news in addition to all the great developments that are taking
place right the technology continues to develop and expand and offer the opportunities

(07:48):
for change but the practical side was really interesting to hear about yeah I love that I love
that and that's I think going back to the workday conversation you know with CMS and I'm
seeing in continuing that vein of big mainstream providers being very visible in the sector

(08:10):
that's been quite an interesting trend and and yeah there's those very practical conversations
which I'm trying to have more and more with people I have to say so I had a bit of a
busy fit over LinkedIn about people not being prepared to come you speak to people are
if you're a research and I'd love to come back to your AI research actually but you know

(08:32):
and you wouldn't dream of producing a report without speaking to people but because you know
it's a busy period and there's been lots of press releases and you know so I'm really stressing
the need to have those conversations you know to really speak to be careful about not just
producing a ton of content without actually having the conversations including hopefully

(08:52):
with the end user you know to talk about these really important conversations about how
are you using it what are you finding you know because we're kind of done with those days
of hey Jenny oh yeah we're using it although still think there's a marketing going on.
Well there's also a spectrum of users that are quite experienced and those who are are you

(09:17):
know still at the very early stages I mean I'm lucky I'm going to go to the knowledge
management and innovation conference that Patrick need to Manico created or with Josh
Fireman if several years ago and they're gonna I'm sure these are going to come up you
know this sort of draws the innovation and knowledge management leaders from around the world

(09:38):
now in New York and so I'm looking forward to hearing not just the use cases because we
have been hearing about the use cases from the very top organizations for a couple of
years now but just to hear how that's proliferated among their teams and among their peers and
especially among people in the audience who aren't necessarily on the stage who are grappling

(10:01):
with different issues then those who have really figured it out and I love those kind of get
together because it's honest and sincere and really authentic.
I hosted a dinner last week I just say last week nearly killed me by the way so I went to
two conferences and hosted a dinner but they yeah the conversation around I had CIOs

(10:26):
around the dinner table it was really fun actually and it was talking we focused a lot on adoption
and the kind of next all the next questions around adoption what you know what's working
what's not working this to be honest there's still some conversations which are being
had again you know there's not it's not just all evolution and next thing it's still retreading

(10:49):
some of the stuff about where what are the strategies are you finding high adoption
amongst the seat more senior partners it's quite varied actually quite the conversations
I'm having there's one or two firms that are saying we've got really widespread adoption
including with the partners those are the firms that have spent a lot of time and effort

(11:09):
in training and been quite forceful perhaps maybe forceful is not the right word but they've
made a lot of effort you know but still a lot of firms are saying our seat our partners
it's just not for them I don't see this mass change you know in that sense but yeah having
those having those great honest you know sometimes on background conversations is proving

(11:35):
really helpful just to track and it's interesting because you know it's gone from very theoretical
to like you could use it the word practical you know it's gone from very theoretical to very
practical you know what's working and oh hey I've got this and this really worked in terms
of education and training and so that's really great to be able to do that sort of what prompt
did you use how did you iterate on that prompt how much time did it take what did you do with

(11:58):
that extra time that's another conversation is like what are people doing with the extra
time if you had an extra five hours in your day how would you spend it if you had an extra
one hour for just 30 minutes was that just like getting lunch or spending an extra time on
a break which isn't I should point out that's not necessarily a bad thing to take an extra
30 minutes for yourself you and I have been on the road a little bit whether it's locally or traveling

(12:20):
and the focus on wellness is really crucial when you're on these multiple day exercises you fly in
I mean I certainly know for myself I usually take a 6am or something super early to try to maximize
any kind of travel benefits the time where I am and then I'll sometimes take a late flight home

(12:41):
to also maximize the day almost like a vacation except it isn't and it's really important I
remember sitting at dinner at an event and I was sitting next to someone and it was getting
kind of late you know dessert hadn't come out yet but we were we had a great day it was just a great
great event but I said to him what time do you think you're going back to the hotel and he's like well
if you I'll go back whenever you go back and I thought okay and I just stood up and he laughed and

(13:06):
we both just said thank you to everyone and wasn't abrupt or anything people were chatting so
wasn't as much of them missing us was just an issue of just trying to leave so we could get some sleep
we also both had to prepare for something for the next day and it was just really funny I think people
need to try to know them their own strengths and weaknesses of those kinds of things as best they can

(13:27):
I also people know that I run at a lot of these events I try to encourage others to run and so
if I'm going to get up at 6.30 or 6.30 or 5.30 on one of those days you really need to
you need to just focus on some sleep some rest and make sure that you're maximizing by being
you know your best self at these things which is what I do are I know you do I know I go to bed

(13:52):
at a sensible time not no I did not do that at this weekend I don't do that anyone night and
stay out late every night and I'm much too old for it and by Sunday when it was my friend's birthday
I was like a razzle everyone's like what's wrong with you I was just to touch my eyebrow I need
to just get a grip and get some balance because you're right you know you can't you can't be

(14:17):
everywhere all the time I feel I lawyers talk about FOMO you know so I'm the best strategies people
have around technology adoption is FOMO well I can relate to that because I have FOMO and I just
don't want to leave but but well being keeps coming up so so two things I've hosted I actually know one

(14:38):
thing I hosted and one thing I spoke to to a firm they stressed well being in terms of the benefits
of this new technology different technologies different but both genate genate in the genate
is based they're talking about this the ROI being giving people back time to enable them one example

(14:58):
given was to get home and put their children to bed I am a big cynic about all of this you know I
I love the idea of this I love the idea that we're going to be giving people back time and that
we're going to be using that to focus on our kids I don't know why I'm really cynical I just think
is that going to actually last or is it just going to be with because we do what we do it's just

(15:21):
going to be taken up with with more work and how do you protect against that culturally because
that is that is a big shift it's not just tech that is like how do you affect that I mean I'm not
doubting actually I have to say so one of the firms I spoke to it's a UK firm brown Jacobson I
spoke to their CEO Abbey Ewan who I like very much and who I respect very much and she said that

(15:44):
there's been a well-being uplift through their adoption of Legora which so and I'm not doubting it
so but it's just curious as to how you maintain that you know long term when there's this culture
and this work ethic in law firms that has made them become the hugely successful enterprises that
they are right so yeah I'm just curious I think is a great thing if we can keep if we can make it

(16:08):
loss I need to do more of that there is a there is a fundamental base on which that needs to be built
and that's being optimally productive so I'm always talking about a book called Atomic Habits
by James Clear I think it's an amazing book I think it's very in easy read but the point of if you

(16:29):
had more time would you use it productively is there critical issue because sometimes I'll get
it all have a deadline and then I'll get an extension and then I still won't do the thing until the
very last minute or until later and it frustrates me that I haven't really just optimize that extra time
or that I didn't even optimize the time in the first place and so it's the same issue now if

(16:51):
technology gives us extra time and we didn't use the time well in the first place needing the extra
time to accomplish what we're trying to do there's a flaw there in the system that technology is not
saving it's very much our own performance and the productivity that we inject into our work so I

(17:12):
think it's really critical that we address that in a very easy way there are lots of ways that you can
do that but I think that that's a component that needs to be discussed in addition to the fact that
there's there may be this extra time which I guess comes back to you know makes sense when you think
we're whispering oh we started we started whispering I'm saving energy I'm

(17:37):
optimizing super productive when I'm quieter I very much more productive I mean very much here is
the visibly that I explained something the content because how do you create a great culture how
do you create an authentic empathetic culture how do you so teaching these leaders how to do things

(18:00):
which we've not really necessarily some people have but I had to think about too much right like it's
been been a pro I think it's been pro a progressive thing so from the days when I practiced I don't think
that leaders would have spent that much time thinking about how to have an authentic and empathetic
culture I think they would have spent a lot of time working out how to make more money how to cross

(18:21):
cell which was a perennial challenge you know how do we you know do more for our clients how do
but I think this there's been a change you know in leadership and types of priorities and perhaps
that's what will help translate into that end goal of how do we create a better quality of life
for people perhaps yeah I mean I think there are the the the crux of what we're discussing here is

(18:50):
really you can't create an organization that is driving change and building on top of what you've done
to achieve remarkable innovations unless the foundational issues of culture and leadership and

(19:10):
time management and trust are are at that at the core it's not unlike why the clients are choosing
to work with certain organizations they feel like they know them they appreciate them they can
empathize with their situation they will find the solutions that matter most to them and I think
that's that reflects really interesting progress from the conversations we had in the last 47

(19:35):
episodes to now I feel like we're really coming full circle in some respects and trying to
peel back several layers at once so that we can see what needs to happen and the organizations that
have done that and are now kind of solidly building to achieve something better is is impressive

(19:55):
and I'm excited to see where we're headed with that yeah well maybe we should go back and listen to
our first ever episode and see what we were talking about I have just found a plan for episode 50
we will listen to the very first one and we will critique ourselves and we'll be like wow why
will we talk about what was it we didn't even mention AI one time it's I think we probably just

(20:17):
laughed I remember just an absolute hysterics like for what I want to just highlight something just
just for fun that I am going to be at the Association of Corporate Council Annual Meeting next week
and I will be hosting a run sponsored by Level Legal and we will be running up the Rocky steps

(20:37):
and doing the rocky pose from Rocky one and so I think that it's in Philadelphia obviously and I
just thought it was such a fun idea that Joe Black came up with and I'm excited for it so I have
an addition to going to KM and I so it's a busy week next week but I just think that's so fun
and I'm looking forward to it and we can share it with we'll have all kinds of pictures and head

(21:00):
band and yeah yeah it'll be it'll be a lot of fun on the music you're gonna have the music I guess
somebody will on their phone have some music and it will just be a bunch of very dynamic in House
lawyers running up the Rocky steps and I will share that with our audience of one the next the
next time we are on John Hill it just the time just flies by it's really a privilege every single

(21:26):
chance we get to catch up and I appreciate very much like was that have a great week thanks everyone
thanks everyone
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