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September 22, 2025 21 mins

In this 47th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed Legal IT Insider's 30th anniversary, reimagining billable work, anticipating disruption, and providing value.

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Episode Transcript

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(00:00):
Welcome to Chatting Change in Legal. I'm one of your co-host, Caroline Hill, and I'm joined by my

(00:06):
esteemed colleague. Ari Kaplan. I'm an analyst who covers the legal industry. Caroline,
wonderful to see you. Great to speak today. Wonderful to see, Ari. Wonderful to see you.
Yeah, so busy times. I feel like we've got a nice little cadence towards this autumn. You know,
we're come out of the summer and it's great to speak to you again so soon. How are things?

(00:29):
Like busy times. I feel everyone seems to be back fully in the swing after summer or be it that,
you know, feels like summer was whatever it goes. I feel like for what summer was in terms of
activity, people preparing for different events, the fall seems to be an acceleration of that.
And you know, this period, September, through, I guess, November, all over the world,

(00:54):
it's just fascinating to me. And every time I talk to somebody about a new event that they're not
sure will work, seems to just be even more successful than they could have anticipated. So there's
there's real, there's real interest. There are lots of issues that people are working through. And
of course, when I'm talking about things and events, I really try to find the issues on the margins

(01:18):
that are not as familiar if they're such a thing, like, you know, just use cases or I think there's
a lot of topics that people have been digging into, you know, the implications of these things,
how to prepare or how to plan or what it means for your role or what your role could do to

(01:41):
elevate the role of others is a topic that I think is more nuanced and really important to cover.
We are in full swing, so we're hosting its legal IT Insiders 30th anniversary coming up. So we,
on the 30th of October, are hosting an event ourselves, so we're not an events company and don't

(02:02):
have any plans to be. But we are hosting a day and afternoon session for IT directors, talking
about security and AI, talking about data management and also talking about DMS, like just three panels.
It's, I have to say, it's taking over my life. It's so busy right now. But it's what we're trying to do is

(02:23):
make it really interactive so that it's real conversations. We've got panels, but we're, we're bringing
back that real audience interaction. We're trying to find a throw around microphone again. You know,
do you remember those things? They were really popular. Well, I haven't to those. Maybe I'll have
to be honest. But Bero uses them at Lexpo and it's called like a mic box or something. It's a

(02:43):
soft box that you can put a microphone in. And when the audience has questions, we toss it to each other.
And it's a lot of fun and extremely effective. So I highly encourage you so that yes.
I did not know. So we're getting, we're bringing back the mic box because we want to make it really

(03:03):
interactive. You know, people's time is precious. So we're full swing planning, you know, doing panel
sessions and planning and we've got, got a competition for the biggest innovation. Actually,
this is kind of duplug. If anyone is listening to this and you haven't filled in our innovation,
if you haven't filled in our competition on the biggest innovation in legal in the last 30 years,

(03:26):
fell it in because we're going to be judging the competition over the next few weeks.
The biggest innovation in the last 30 years. Yeah, so impact on legal tech, but it's in visual format.
So it's a picture. We're going to create a picture book. So we've had some really funny entries. So
like people are using AI to create pictures. It's going to be a lot of fun and we're printing it out
for our event on the 30th. And so it's, what is the biggest innovation in your opinion to have

(03:52):
impact on the legal tech sector in the last 30 years, in visual form, creator, like an image, it might be,
like people have come up with all kinds of stuff and we're going to print out the winners.
I'm going to create it to hand out at the conference. So it's just going to be, it's just,
all of this. So we've actually known like legalite insider. We, we've, it's very serious, but also
we've got to have some fun, right? Like so, so we've got all sorts of stuff happening. We're printing out

(04:16):
the very first issue of the legalite of legalite insider from 1995 to hand out to people at the
conference, which is, and some of it's going to be very emotional. We've also got a surprise of
someone who's coming to the drinks party to to hand out an award. So this all kind of, it's all going on.
What were the topics that were covered in that issue in 1995? Oh my goodness, it's amazing. So it's,

(04:40):
it's, the internet was new, right? So there was a lot of like YouTube could have a website for law
firms and at the time firms were like, no, we think it's, no, that's not for us.
I took an HTML coding class in 1999, I remember thinking that you should know how to do that.

(05:03):
I'd never really mastered it, but I remember, I remember thinking it was important. I also would like
to submit something for your greatest innovation for 30s. I'm just going to tell you what I think it is.
I think it is the removal of the hyphen from email and e-discovery and e-commerce and e-visiveness.
There you go. I just want to throw it out there. I said it. Can you please? For all the listeners. Yeah, I was,

(05:28):
met that because we're judging it. All of our panelists, the panelists who were judging this and
they may not know this yet. Anyway, they're judging it in our panel prep. So yeah, you need to submit
a picture of that. Yeah, just like a cutting of the hyphen. I think that's going to be incredible.

(05:49):
Anyway, yeah, so I think that, I think that, you know, as we power through the end of the year, I always
find that people have this tendency to ineffectively make new years resolutions. But I'm usually thinking
of the beginning of the year, kind of at the end of the third quarter, beginning of the fourth quarter,

(06:09):
because it takes time to put things into place. And if you think you're starting the year
in January and that something is going to materialize in January, as a result of that landing,
I'm at least have experienced this, that, you know, that's a mistake. The better thing to do is to proactively
think, let me put this into place. I just had a call this morning and someone said, we were talking

(06:32):
about something for October and they say, well, we're thinking about maybe December. And I thought,
of course, you are like, right, like it makes perfect sense to give a little time. So this time of
year, I'm often thinking about strategic areas of opportunity for next year, as opposed to what's
going to happen to me. I mean, there are obviously things that are taking place this year, but I also

(06:54):
think that it's important for people to consider these issues proactively. Do you know what's such a
pleasure about having had these conversations with you for so long? I remember being here this
time last year. I'm talking about this. And it knows a pleasure rather than, you know, and I wonder,
do you, I mean, because you're super organized and super, I have a t-shirt with giant, oh, super.

(07:20):
I know you think about these. Have you gone back to this time last year when you, we have this similar
conversation? Have you gone back to those objectives and worked out how much of them you fulfilled?
Or, or no, because I would never be capable of doing that because I'm not-
No, but it's less complicated than that. It's not so much, did I accomplish? I set out in September,
on September 22nd to do X, on September 22nd, the following year, did I do X? It's more like,

(07:47):
I want to do certain things next year. Have I done them? So I think the answer there is absolutely
yes. And I just, I just think that most people, many people, I certainly didn't think that you needed
it as much lead time to plan projects or to connect with folks or to order all of a sudden develop

(08:11):
a consensus on something. And the truth is you do. So at this time of year, people are,
are generally focused on pushing toward the end as opposed to setting the foundation for the beginning.
And so when you think of it that way, I just think like you've been talking about your wonderful
event on the 30th of October, not of September. And I think it's important that people realize

(08:36):
this has been going on and being planned for a long, long time. And obviously it's a milestone.
So that milestone has been expected to arrive. So congratulations, very exciting.
Thank you so much. Yeah, no, I love it. And I think you are absolutely right about planning ahead.
The other thing I think is really important. We've been running to stand still for a long time.

(08:58):
Like everybody's so busy, like it's boring to even say you're busy. I'm trying to avoid saying I'm busy
when I'm someone says, "How are you?" Everyone goes, "Oh, so busy." And I'm trying really hard not to be
that person anymore. I'm like, "Let's just take that as red, we're all busy." But so, I feel like
I'm always thinking about what I haven't done. Like I constantly, "I didn't think to say,

(09:21):
"I did." But I was preparing the orange rag, which is out on Wednesday as it comes out,
orange rag newsletter comes out every month, what comes out 10 times a year. And I was looking
through loads of stories. And in all of them, I've had a conversation with the people and had a dive
into what it is that they're doing. Their Deloitte's partnered with Lagora, had a conversation with them.

(09:44):
And I'm thinking it's really important to remind ourselves of what we have done. I'm constantly
thinking about what I haven't done, but actually it's been a busy year. I think it maybe is time to start,
it's not time to slow down yet. But it's time to maybe also think, "What have I achieved?"
And I've just got to give ourselves a bit of credit as well.

(10:05):
At the end of every year, we would be asked to do some type of self-evaluation memo
when I practiced. And I practiced for nearly nine years, but that was from 97 to 2006. So it was a
while back. But I still remember that. And I still remember taking that time to think about

(10:26):
what I've done. You could probably go through your buildings if you were methodical about also
highlighting non-billable time and other time that maybe outside the framework of what you're
compensated for or to understand that. But that's a good exercise. I think just the quiet time of thinking.

(10:48):
As a swimmer, I have that. I swim twice a week. And I often, well, but you can't do anything with it,
because there's no place to write it down. And then by the time I get out of the water,
I've basically forgotten it because I'm onto something else. So I think that's a challenge.
And as a runner, those are all moments. I remember there was a period where people were

(11:10):
advocating for crayons in the shower because you could like write down. I have a great idea.
And you'd write it down on the wall or something on the floor on the bottle. I don't know. I never had them,
but I think that that's that quiet time, even if you were like walking. Sometimes I would do that. I
would walk and then have my phone. And I can dictate some thoughts and ideas as we can get closer to

(11:33):
the end of the year. There's something to that. And in fact, there's something to that because
more and more of the root work that you do, we're all kind of trying to figure out how to
eliminate that. I think people are proactively trying to evaluate what is it that I do and

(11:53):
which pieces of it can I discard and have something else do it quicker and more effectively.
And they're for me time to think. So I feel like there will be a lot more time for that in the next
year or two. What about, so you're talking about things doing being being done more quickly and,

(12:14):
so I know it's interesting. The other thing that I think people will be reflecting on is the progress
in terms of what tech can do and what their job is going to look like. I think this is going to be a
period of reflection soon. And I know it's interesting. There's been some reports,
doesn't there, about technology and the impact on jobs. And I think, you see, you know, more about

(12:37):
this than the me actually, but I think you were saying that it was funding that legal, it was jobs in
jeopardy and legal was not one of those jobs in jeopardy. Yeah, the USA today I saw an article and
it just talked about the fact that it almost had a bit of a misunderstanding of what happens in
the legal profession. It said knowledge workers are in jeopardy, but then it said paralegals or legal

(13:06):
assistance may be threatened in terms of the longevity of their career, but lawyers won't. As if there's
some distinction of very, and then it used the example of going into court, which also reflected
a misunderstanding of the fact that lots of people do something other than go to court. And it was a

(13:26):
very interesting observation that I don't think really captured what what the legal profession is
now and how it operates. And I'm not suggesting that it was incorrect in that, you know, that the
laws are not safe and your job is in jeopardy. I just thought it's a much deeper conversation,

(13:48):
and that look requires a lot more analysis and that each of us knows what it is that we do. And I
actually have recently done some research speaking specifically to trial lawyers who are
incredibly experienced advocates and some of them were under the misimpression that they were,

(14:10):
in fact, not as secure because technology is changing and the environment is changing and
and it was a actually a fun conversation to have with them because it's easier to replicate the
experience of one year writing a memo than it is of 30 years of complex advocacy. That is a very,

(14:36):
very hard. I just think they were at risk in terms of the advocacy that from tech.
I just think that that's the least being on your feet in court right now is that you know,
there's not a worry. Yeah, I just think that they are less familiar with all the tools available,
so they just see tools disrupting and so that disruption will happen and it will level across

(15:00):
all disciplines, but that's not necessarily the case. So it's really interesting. So as people,
and I put myself through this exact exercise, as people start to think about what may change,
they should spend time thinking about what they do and where they're focusing and

(15:22):
sometimes acknowledging that and then adapting is your greatest defense to whatever
evolution happens to bring. And I think that's a really important discussion that we're not
necessarily having and one of those kind of on the margins conversations, which is not in any way

(15:43):
couched as what's threatening, where should there be fear? These words are constantly used,
and I think it's much more about evaluating and being thoughtful and where you're providing value.
That's a great conversation. That conversation needs to be had more, needs to be a greater consideration

(16:07):
and it's something that we've addressed for a long time, but when you're thinking about the
specific tasks or work or accomplishments, as you mentioned, think about what you've done as
opposed to what you've missed, when you think about that, think about which of those things that
you've done have been most valuable. Can you lean into that and allow for the natural progression

(16:34):
of eliminating some of the things that you do to take place? And again, I'm almost speaking from
a personal standpoint because much of what I do is creating content that connects to buyers to
sellers. And so as I'm trying to facilitate those conversations or create those connections,
I'm also thinking, it's probably a piece of this that maybe I won't be able to do soon,

(16:59):
whatever that soon means. And so what does that mean in terms of my time and where can I provide
more value? And I think people who are thinking about that are going to give themselves an advantage.
Yeah, but that USA Today piece is the fact that you've seen that, I mean, I totally agree
wholeheartedly. It's really great points about value, strategy and leaning in.

(17:21):
And then just some of the USA Today, there's all this slightly skirmundery pieces or just
journalism where they haven't really necessarily asked the questions. And I think this is for me,
you know, as we come to the end of the year, it is really important for all of us to just sort of

(17:43):
do our job properly. Like one of my current book burs is, you know, press releases being sent out
and people like not doing their jobs in terms of actually asking the questions and engaging. And I
feel like, you know, we're quite far down the line, the journalism is not new. But like, we need
to just be wary about the stuff that we're putting out, you know, and it needs to be your type of,

(18:06):
you don't crush yourself as a journalist, you know, you're an analyst and that's a great place to be
because you're having these conversations with people and you're putting out great research. And,
you know, but I always thought you're putting your arm there. But yeah, but so, but, you know,
we, I think it's beholden on everybody to just be a little careful, you know, about what we're,

(18:27):
it's what we're spreading because it's like whether it be, is your job in fit, you know, you,
you fear, you know, is your job in danger like those, those trial lawyers who are thinking their jobs
are in danger, you know, it's beholden on everybody to be responsible. It always has been, but, you know,
let's, let's just remind ourselves of that. We are responsible for putting out accurate information

(18:48):
on the basis of conversations, hopefully, not just press releases. You can tell this is my bug
that Ariane, this isn't your bug. Well, no, but you make, you make a good point about a kind of this
line between provocative and productive. And that tends to be a challenge. You know, we want people to
read what we write, but we also want people to react in a way that's going to provide at least I

(19:15):
do, you know, I want them to benefit from what I'm trying to convey. And, you know, I have a,
in my, you discovery, unfiltered report, I always ask the question, what matters most when you're working
with a vendor or a law firm, like, what are the qualities that matter most to you? And, you know,
they're always about a partnership or responsiveness or, you know, quality of work and being proactive,

(19:40):
knowing my business, things like that. But there are elements in there, you know, I also ask the
question, you know, what makes you switch? What keeps something sticky? But why do you move? And it's
not necessarily to say, oh, your, your clients may move. It's more like, this is why people move.
And you should be informed so that you can avoid all the issues that drive people to move. And that

(20:09):
will likely, you know, help your team be better and be more responsive, but also recognizing,
you know, help your team recognize the strength of that client relationship is paramount.
And in addition, obviously, let's assume baseline is great work, but that relationship matters
and anything you do should build it as opposed to dilute it in some way.

(20:32):
Yeah, we're very so far, which was, we're just really thoughtful.
Imagine, imagine two other people who are chatting with each other are more thoughtful.
Can you imagine by the end of the actual year, like,
it's like, I'm going to send you a handwritten note right now. That's how thoughtful I feel.
I think it's going to be a busy period. I think that we're going to have a lot more to reflect on.

(20:55):
And I think it'll be interesting. Yeah, I think I'm going to stop preparing, Arif,
in the end of the year now. I'm going to be your, you've been in a, I've got a, I've got a
double bag right here. I'm packing. I, you know, I'm getting ready. One carry on one check bag. I'm in it.
Let's do it. Well, it's a big week for you. So I have to say,
happy rush, Hoshana. And it's so, so I know it's your new year.

(21:19):
Are you gonna, you're gonna take any time out? No, I will be out. I will be with my family,
which I'm lucky to, you know, to spend time with. And obviously wishing you all good things,
wishing our listeners all good things. And as always, a privilege to chat with you. Thank you.
With these things. Thank you.
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