All Episodes

September 12, 2025 24 mins

In this 46th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed budgeting, purchasing, and piloting in legal tech, measuring ROI and value, and building community.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome to charting change in legal. I'm Ari Kaplan and analyst who covers the legal industry and I'm here with my cohost

(00:10):
Caroline Hill Hi everyone. I am editor in chief of legal IT insiders great to be here with you. I usually have all you.
I'm well and looking forward to this conversation been a busy few weeks since we last spoke about Iltecon and exciting that we are kind of you know in the momentum driven period toward the end of the year is as strange as that sounds it's kind of exciting. It's been a fast one it seems.

(00:44):
It's really it's gone crazy fast I keep teasing that we're going to hear my right carry any minute now.
I will I would just remember in the summer seeing back to school things and then you're right I guess the holidays will be here.
The holidays there are lots of holidays over the next few months but the holidays will be here and easy busy season though right this is the season when everybody so so you have I mean the summer wasn't sleepy I found the summer to be super busy and obviously we have Iltecon on which you and I.

(01:13):
Talk about and still I feel like there's so much going on there that there's still reflections from that that sort of have similar around my head in terms of conversations that I've had with people and I think they'll be reflecting on those in the next couple of months I think it's it's one of those great times when you can take away some of that learning and discovery and then start putting it into practice is not maybe as easy as that but and then it's but it's this it was not a question.

(01:43):
Quite a bit this really feels like it's ramped up you know that the number of conferences and the number of you know just trying to get hold of people people are just busy well I'm going to go with topic number one for today and I think that one of the interesting observations that I have made over the last few weeks I've been lucky to be completing some research so I'm regularly interviewing someone for something and the interesting observation I will say is that I ask about.

(02:13):
Ask about costs and budgeting and purchasing and piloting and I'm not sure at this time last year as many people were focused on including in their budget various emerging tools or budgets for implementation or maybe individuals who will either add to their role or have someone new and as we approach the end of the year there's a lot of.

(02:42):
A lot more of that it seems happening in the fall of 2025 than there was in the fall of 2024 when people were still uncertain waiting when the technology landscape was crowded but not as crowded so there weren't as many conversations and I'm just thinking that there's a lot of activity happening now in preparation for.

(03:06):
Announcements my senses that will be made let's say at legal week or at some of the other events that will take place in the first and second quarter of 2026.
Yeah I agree agree and actually you know it took me a while to the income sort of back in you know it feels like eight years ago now but.
It's almost a month.

(03:26):
I believe it.
I spoke to Tony McKenna who at the time was president and we reflected back on number one in the Tony McKenna fan club right here.
I'm a wonderful wonderful individual great leader can't say enough nice things about Tony so go on but I just I had to say that because I just think so highly of him.
I think that's so great.
Yeah so if he was fabulous and we reflected on some of the changes of the conversations of the G 100 200 which I wrote after it took me a while to be fair.

(03:57):
But so wrote after the conference and they were saying that you know there was tangible difference in the conversation in terms of you didn't want to overblow it and make out like everybody was way down the the adoption curve but but actually that the conversation had substantially changed this year to last year and very much in terms of you know real investment and not kind of waiting and not if but when.

(04:25):
Which was which was really interesting because we don't get to go to those conferences sorry those sessions the G 100 200 he said the 200 was particularly useful you know like real exchange information which I absolutely love about our industry.
But yeah he said does that tangible difference so I think you're right I think we're going to see some sort of announcements in the next few months.

(04:46):
Also I wonder if there's an element of that where there as you have more people and you're more inclusive you're getting a sense of a differing ability level of organizations very large organizations can take a chance on certain technologies and others really have to be more methodical.

(05:09):
However anyone who takes a chance has to be very thorough in their due diligence and making sure it integrates making sure that the security levels are appropriate because that's clearly the biggest issue here you know there is concern yes there's concern about the tools not working the tools being inaccurate but in the end there's concern about.

(05:33):
Data loss and privilege loss and there's just so many fundamental aspects of leveraging technology in legal especially that are of concern that you really need to manage those are in advance before taking the next step and that's a conversation that's come up I will say that I had my legal tech mafia breakfast this week and one of I.

(05:58):
I never really know what we're going to talk about people who asked me for an agenda and I start laughing and I'm hoping people show up and that they get a time to introduce themselves and we'll see where we go from there but.
Because of that the conversation very naturally tends to progress and this week it really was about our why and how you show a very real return and some metrics is actually great second topic but how do you show the value because people.

(06:27):
We're concerned about users let's say users was a metric and they were like I don't know what that means or time in a tool people said I don't know what time in a tool is does that equate to some sort of return or is that just.
You can use it in the future and it was a great conversation opinion here but there were lots of builders there buyers there on both sides of the corporate spectrum you know law firms in law departments and it just lots of people were very animated about that it wasn't what is the tool do how does it work how do I get people to use it is like how do I show.

(07:07):
That it was meaningful for us to invest the time and effort and money to bring it here and we had a very honest conversation about it wasn't wasn't bad of it all wasn't as if someone said we do this and we do this everyone was trying to get to a point of a fundamental metric that made the most sense for their organization.

(07:30):
I mean ROI is not been from the beginning right like it's been an ongoing conversation not not almost not combative either right because at the very beginning people were saying like we need to invest and then the ROI conversation early doors was really difficult because it was nothing was no kind of proof of concept in many cases and also it's like are you talking about ROI in the sense of the practice of law or the business of law what sort of technology sometimes with.

(07:59):
Business of law it's easier to show that ROI if you're talking about for example a gen AI tool and you might say if it's something like Ocg compliance and your.
So you can prove that by complying with the Cg rules better that you save or you claw back six percent of revenue you know those kind of arguments actually.
In different places it's been easier to have those conversations hasn't it like then some areas of practice of law but but actually interestingly recently i've been seeing.

(08:30):
There's been surveys out that focus on ROI in terms of time back for people which I have different views on that because there was one survey that if you actually really dug deep into the findings it showed quite low adoption in you know mainstream adoption of of gen AI tools.
But then it was like then it said oh and and all these people found that they got loads of time back from using the tools that they don't want necessarily using so I was like okay.

(08:58):
But then and then I'm doing a talk next week company with the company called strident and a UK law firm wedlach bell and actually they so strident help roll out gen AI tools they work with and they do specifically around co boiler and they have got some.
Really fascinating first hand stats around people getting time back and they focus on very much like the quality of life and you know perhaps you can go home earlier i'm always the cynical one i'm an excellent much like you know you.

(09:33):
So i'm always be like yeah sure that's going to happen but does that is that what we mean by ROI like can we can we can we count that quality of life I think that's beautiful and if we can do that i mean that is amazing does that qualifies ROI probably should be.
Whether it does to a lot of people I don't know but it's kind of cool.
The time capture question is a really interesting one right now because obviously you see very smart companies focused on using AI in time and billing and you know laurels a great example we talked about laurel before and that metric seems to make tremendous sense I can get you an extra.

(10:14):
15 minutes 30 minutes hour for every what at the firm times x and all of a sudden it's a massive revenue generator I completely get that it's a very easy thing to understand I can save you x amount of time.
At a base level that.
Has you know counter intuitive concerns about the business model I can use you can then use that time to provide even greater service and support amazing who wouldn't want that we can enhance your quality of life again amazing who wouldn't want that the.

(10:52):
Practice though I think that's a that's a core issue and people have asked me in my conversations with law firm business leaders so cfo's or c o's or executive directors or managing partners others who are trying to figure out what does this look like in a universe going forward you hear a lot about this and i'm confident we will continue to talk about what the.

(11:17):
Structural aspects of the business of law look like and those have been the first areas where generally I has kind of penetrated what's happening in law firm but.
It's a it's a great conversation and it does come up but it's a fairly uncertain.
Area at the moment that that has say you know a tool has saved me time as a metric well what.

(11:42):
What is actually the practical answer to that I think it's an interesting it's an interesting place that the firms fall into and they're trying to figure it out wrestling with and and and I wrote.
It's so fascinating like this week I wrote about look or and deloitte partnering and I interviewed them it's not out yet always give you the exclusive I.

(12:03):
Well that announcement that they partnered has been publicized they're very good at so it's not an exclusive is it is already public but I spoke to them and.
They're saying they're gonna blow up the whole model you know like actually i'm putting words in them if they probably didn't say that but you know like you know that change the whole way that.

(12:24):
Team this corporate teams are operating and you know everything's going to kind of turn on its head and i think it you know I think it probably will I think you need I think right now there's I think from speaking to lots of people like you do.
There's still that the change piece is frustrating right so there's the belief there's the investment but they the change is hard and that's not getting necessarily any easier because.

(12:51):
It takes resource it takes experience there's a lot of people being hired there's the people side of things which sometimes we forget to talk about not necessarily you and I but just the industry there's the people side of things which to actually delivering this stuff can be really hard and these these those sort of partnerships are super interesting because you're combining technology good technology.
With resource and experience in in in manage services and change and I think that's that's kind of interesting to sort of help get over what is still really a bit of a hump for people they got the belief they got the money they got the sometimes they got the ROI they got this stuff and then actually doing the do is really hard.

(13:33):
Well they're good there's going to be a lot of testing it I if you don't mind I'd love to just mention this because you mentioned LaGora so well I like I like them I you know I've met I met Max long before it was LaGora and he's been a visionary entrepreneur since I met him but I because I host these breakfast every other month I.

(13:57):
The pilot I tried something this this past breakfast which was I serve on the board of trustees for an organization that empowers the homeless in New Jersey and in the New York area and they are having a gala on September 24th and so as a board member I really wanted to make sure I could support it and so I offered sponsorships to the breakfast which gets a lot of his ability it was standing room only it was a good really a great event for for our breakfast.

(14:26):
To the community and I asked some companies if instead of giving me anything they donated to the apostles house and either bought some tickets to the gala or made a donation and we raised $6,000 and there were four companies deal a trust.
Harbor LaGora and Steno who each contributor equal amount and I was just so honored that they felt like that was just a great way to do you and do good right like to do a thing that we do anyway and for the community to really support another community and you know breakfast and food insecurity it like very consistent in terms of.

(15:08):
And I just those companies were immediate hey would anybody yes yes yes yes and you know it just wonderful community that that we have here in legal tech and legal services and I'm proud to be part of it I just wanted to share that because I just think it's such so powerful and believe me $6,000 means a lot to.
And I think it's a lot of people who are working to empower others in that way so great companies there well done you and well done them that is really awesome to.

(15:38):
Yeah well done then I send email they did they did the work and I'm really proud of it so let's let's I feel like there's another topic in terms of we'll have to get we're going to get a bell next.
Yeah we're going to have to get a bell David Hargan the dynamic leader relativity who I've been lucky to work with for many many years has this very funny we've done this thing where he has like yes and no buttons so if you agree or don't agree and I still have them in my closet because they he shipped them to me at one point we did the we did a session remotely during the pandemic instead of on stage and it was it was very funny it was like do you agree yes no and everyone sort of you know their buttons are bouncing it's very.

(16:19):
You and I in addition to our microphones that we don't really use because we've got to I forgot them and I'll come back in addition to the karaoke microphones we need to get a yes no up so a bell and yes no button we need to just have a whole bunch of.
Multi media we should have guesses of the courty come on we should have like a whole thing we get it as well yeah anyone.

(16:41):
Water I can't believe you said that that's ridiculous.
Who is listening this is the point in our discussion where people are like I'm out of here log out change those go to better show anyway I do think that that one of the things that I have noticed and I've

(17:05):
mentioned this you see this on LinkedIn all the time is that the legal industry I'm thinking about the virtual lunch community and all of these organizations supporting this initiative that I was trying to drive support for the legal community has created so many incredible

(17:26):
communities and pockets in house law firms paralegals like it's just it's really he discovery project managers you know there and they are regional there's a New York group is a Detroit group there's a London group it's amazing to me how many communities and I just wanted to encourage people to continue to do that I think it's every single I see things all the time and there are always people that show up I rarely and maybe it's because who would post this but I rarely see like

(17:55):
someone in a room with one other person like no one can you know it's it's it's really remarkable and it's inspiring like all of these things I see people trying things they're the new to the industry they've been doing it in the industry for 30 years they're retired and doing something they've changing the course of their careers and their people are interested in learning from other people and I just think that wherever you are in whatever country it's fascinating

(18:23):
and great to see so I just I just wanted to that sort of like like like public service in house and I think so are you always like say the nicest things and then I come in and just have to ruin it all but like
I think you're I so I want to agree the and I do agree with you and I absolutely love the sector and I love the sharing and I've said it many times you know we're so lucky including I mentioned earlier with the G 100 200

(18:51):
but there is a pocket of the biggest firms that don't necessarily want to share that's very professional since I have for those of you probably wiped out by my phone just one so there's a pocket of you know I think there is
this doesn't take away from what you're saying so there is and within the biggest funds they do so much good as well right there's within the biggest funds they they have so much pro bono and the those communities are amazing and the pro I'm not to take away from that actually so so actually I kind of maybe retract that I'm being horrible but

(19:23):
but like I do think that there's you know there's in the biggest law firms there's less sharing around the sort of stuff that gets shared amongst the sort of like slightly lower mid-tier stuff you know like
there are pockets of sharing and I love the community but I feel like it was it's quite interesting you know that the biggest firms they're not sharing as much and if you know it's important to notice right I think it's important at this moment in time to kind of make a note of that and just go hey I'm not encouraging anyone to go down that route and I believe that there's huge value and

(19:52):
and we've talked about the elder community and that non-sharing that you get but if I would actually encourage the bigger firms this is maybe where I'm going with this or encourage the bigger firms to continue sharing you know
you know like and continue being very much a part of the community and because of the huge value that everybody gets out of it but yeah no I think you're right I mean there's some lovely groups yeah it's good.

(20:17):
Well I think it also depends where you know for example Osborne Omram has an incredible community and skills and they do a tremendous amount of sharing I mean they're very candid with each other in a
in a in a way that doesn't compromise their firms initiatives or anything but he does speak to the largest firms on earth he and and shares that and provides it as a as a service in many ways so you're right it's not

(20:47):
100% transparency however you can really make important strategic decisions and initiatives based on some of that feedback even if that feedback only goes halfway down the surface you know
I do think that you don't need full transparency in order to create or at least to begin the conversation the lower you know the sort of the smaller you go in terms of the form size.

(21:13):
Osborne amazing job and I would encourage people to go down that route the G100 filter not so much like there was a visible like you know not wanting to over share that is fine but actually you
said you can share without you know it becoming a competitive disadvantage and actually you can turn it into an advantage I believe but in the way that Osborne those controls that very well you know they they have sort of I mean the G100

(21:39):
is a very controlled environment and sort of you know it's supposed to be beneficial for for the people within that room and they share only a certain amount and that's the same with
Osborne right so the is very strategic and but amazingly valuable in terms of the learning that comes out of it and also there are great where there are gaps my point is that we're even where there are gaps there are people who are

(22:04):
filling those gaps and so my message I hope is just ask a few people if they'd like to get together and share ideas and the result may surprise you.
And also think about from a you know hiring perspective like obviously the big firms they're always going to have that name right but people are looking now to the firms that are the most innovative and you know there's all the awards as the F.T.

(22:30):
Innovation Awards which they do such an amazing job you know they you people looking for those firms who are sharing their kind of cutting cutting edge innovations and that's that's just that you've got to share in order to do that and that's becoming something that you know from a hiring
perspective the really top people want to join those firms they're looking for not those sort of cookie got to are yeah we've done some staff or our knowledge they're looking for people that are really doing some cutting edge staff

(22:59):
so and the big firms have got the resource and they've got the ability you know and and sharing that stuff is super important in terms of recruitment I think.
And I actually am featuring Sarah Hybert as Shredley Ronin today on the virtual lunch during our series about knowledge re-imagined so with Atlas work by clear people so yeah I I'm really trying to facilitate those conversations and I feel lucky every time.

(23:22):
So I always I always say that even even I've been I said graduate law school in 1997 and I used to come home and tell my wife I was like you wouldn't believe the conversation I had today and all these years later I'm like I can't believe I have the conversation I had today so I wish that for others and Caroline Hill.
All right captain this is a highlight of my week or my every other week or the cadence that we're on but it's wonderful to see you again and I'm happy to have this conversation I look forward to many more I look forward to introducing the bell.

(23:51):
Yes no buttons and the bucket of water and just you know people can't even see it.
We'll have to do video now that'll be unfortunate for for folks to see me in the morning but I look forward to it and as always as always wonderful conversation thank you.
conversation. Thank you. Thank you.
Advertise With Us

Popular Podcasts

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

Cardiac Cowboys

Cardiac Cowboys

The heart was always off-limits to surgeons. Cutting into it spelled instant death for the patient. That is, until a ragtag group of doctors scattered across the Midwest and Texas decided to throw out the rule book. Working in makeshift laboratories and home garages, using medical devices made from scavenged machine parts and beer tubes, these men and women invented the field of open heart surgery. Odds are, someone you know is alive because of them. So why has history left them behind? Presented by Chris Pine, CARDIAC COWBOYS tells the gripping true story behind the birth of heart surgery, and the young, Greatest Generation doctors who made it happen. For years, they competed and feuded, racing to be the first, the best, and the most prolific. Some appeared on the cover of Time Magazine, operated on kings and advised presidents. Others ended up disgraced, penniless, and convicted of felonies. Together, they ignited a revolution in medicine, and changed the world.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.