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February 28, 2025 32 mins

In this 38th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed achieving work-life balance, building momentum in 2025, and preparing for Legalweek.

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Episode Transcript

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(00:00):
Welcome to Charting Change in Legal. I am one of your hosts, Caroline Hill, I'm the

(00:08):
editor of Legalite Insider and I'm joined here today by my very esteemed co-host.
Ari Kaplan. I'm an analyst who covers the legal industry and as always I look forward
to this conversation, Caroline. Nice to see you.
It is great to see you. So it's been so busy that you and I have been more ships in the
night than the usual. We got a ton of stuff to catch up on.

(00:30):
Yes, I should say that we missed our last call because I went to visit my son for a father
son weekend. So I don't know that it was so busy but it was wonderful and I was very happy
to do it and I went to a college basketball game and did a bunch of other stuff which was
a lot of fun and I'm glad to be here chatting with you but also glad that we skipped our

(00:53):
conversation for one week. But the idea of being busy or trying to balance is, you know,
is starting to come into more conversations now that we are entering the last month of
the first quarter of the year which seems incredible and also that we are approaching one
of the biggest conferences of the year. Legalink. So it's been an interesting adventure.

(01:18):
I am trying to reframe being busy in my brain so the temptation is or the
temptations are all the the risk is that you start to say being busy is a bad thing and I have
slightly fallen into that going oh I'm so busy, you know people go how are you? I'm so busy.
Everybody's doing it because this sector this year is going to match, you know, the number of

(01:41):
press releases I get every day has troubled I think and so I've been trying to reframe in my head
how to express being busy because if you say it to yourself in a really negative way then you feel
a bit hard done by right but so I've been trying to turn it into a positive thinking I'm busy
that's a great thing and also thinking about when I'm 90 and I look back on this period of my life

(02:07):
I'm just going to think wow that is incredible how did you do all that and I'll probably long for
I would long to come back and be that busy right so I'm just trying to I'm trying to put a positive
spin because otherwise the risk is that we all just go round to each other how are you? Oh I'm so busy
which is so you may remember this from practice like that's a very common conversation in a law firm

(02:29):
how are you doing I'm busy great because that means that things are going well you'll bill your
hours and everyone will be comfortable that I think it's a part of the profession I will say knowing
you and knowing your business and knowing your work I think it's a credit to legal IT insider and to
your visibility and talent that you're getting so much of this stuff so I agree enjoy it and I

(02:55):
you know honestly I see it a lot of it as an adventure and if I could highlight this as
Fridays tend to be very busy for me you know we do our calls on Friday mornings just so our one
listener knows it's usually on Friday morning but I actually designate all of my podcasts for
reinventing professionals on Friday afternoons and so I have all of these discussions scheduled I

(03:19):
usually have a guest on the virtual lunch on Fridays and so there's lots of interviewing happening
and it requires lots of questions and I have recently turned to chat GPT to say listen I'm going
to be interviewing this person this is their background and I have a format for my programs but sometimes I
miss that they you know so I'll maybe copy a bunch of stuff from LinkedIn and say can you just

(03:43):
what kind of questions you think would be helpful it's really really efficient and I do this
sometimes with the podcast not always with the questions because I asked the guests to send questions
so that it gives us a head start on what to talk about but when I summarize the episode or whatever
I also use it and I also use a tool now that eliminates all the filler words with the edit it's just

(04:07):
I've really increasingly found easy ways to maybe make the busyness more focused on the highest value
work as people have said but in practice I've really tried to do it. I love that I love that practicing
what we preach a little bit like but yeah it's so it's so good it's so good I know from my peers

(04:32):
you know the peers you know we do the Friday evening panel with Boba and Brogie and people
talk on the panel sometimes about how much they're using AI and the response has been mixed but some
of them really not that much almost on principle I use it for tons of stuff like I use it for headlines
I'm using it for suggestions on I don't know I mean so much stuff like I was like with organizing

(04:58):
organizing events with my with my colleagues you know I'll be like now we're doing this in this
region for this sort of thing who might you suggest you know who who in this particular role in
this particular region do you think we should invite and those are kind of things of mind blown

(05:19):
because you know otherwise you've got somebody who's having to go search for LinkedIn and obviously it's
not it's not gonna come back with a hundred percent but it's a really good starting point for all
kinds of things which take so much time you know like for people to find it is amazing. The busyness
also isn't really a function of organization most of the time I really I know I'm laughing myself

(05:41):
but and also kind of just taking action for example I am going to be next week in Florida for spring
training and also to visit my my some family and I thought you know what I'm going to do a breakfast
in Florida because I host these breakfast just to kind of build community and I had no location

(06:06):
I mentioned to some people yeah I'll probably do one and then I found a location and then I just
sent out a bunch of notes on LinkedIn and people say they're coming so I think action
creates momentum and that really can drive results but it requires some level of organization and

(06:28):
so every time I do feel busy and even overwhelmed I'll think all right let's step back break this down
like what are we talking about here is this make a call because if it's just make a call let me make a
call and if it's sent to emails 10 emails 50 like what does that look like and if that's the case can
I organize it into a spreadsheet or something and I think that that's more important than us feeling

(06:51):
busy and sometimes it's interesting don't you want to just say are you busy no I'm all set like I
have I have I have a team of people that are helping me and supporting my work I'm not really that
busy I'm you know thinking about my next opportunity and where I'm going it so I think it's um
yeah I really want to I agree with you about the organization so this is my ongoing forever and

(07:17):
during challenge which I'm putting a lot of effort into different strategies to be more organized
and using different bits of software to help with that you know and and and finally enough I just
got a full call looking through that with somebody who has a more objective eye and they're like well
why we used a sauna for past management which is great and my whole team keep it updated and then

(07:44):
you know when we're looking through like someone was like well why is that like that and I'm like I
don't know but you know there's always continuous from from improvement and then it's like well where
do you have your shed calendar where do you and just in my own personal you know tar I'm trying to
get trying to get better I'm actually going quite old school with a note pad I have to tell you

(08:05):
but anyway I'm trying to get better about writing everything down like even if it's an email you
don't like to sit you do so many things during the day I know I learned so much from you so much
better at the stuff but but like you know if I'm not careful I run chase around chase around my tail
and then achieve nothing in a morning if I'm not careful that's a quite an easy thing to happen
because I do like this this this this this this is the one I don't finish any of it so I'm just

(08:30):
that's my challenge to my my ority for this year is to get everything down listed however that might
be actually and then tick it off and tick it off so you got that feeling of satisfaction you know
that kind of rather than just going off done a thousand things what have I done I was just writing
about this the idea that over the years I have tried a notepad host it's writing on my iPad

(08:56):
setting voice reminders on my device in my office having my device connected to my calendar so
that it would read things to me which was super comical because I add a lot of things to my calendar
sometimes I listed as busy sometimes I listed as free so that people can book over it and I would
be on a call or recording a webinar or doing a podcast and my calendar would read something like

(09:22):
don't forget to my running shoes today and I'll think oh my gosh why and it would say it several times
so that I knew it and so I'm doing this webinar and there are all these people listening and it's
just like arey by milk you're gonna get in a lot of trouble if you do not purchase the yogurt and
it's just like and I'm like why am I leaving myself messages like that in the first place so

(09:44):
sometimes we get we overwhelm ourselves with the effort to try not to overwhelm ourselves and I
think that's that's pretty interesting which which also makes us you know even that much more fascinated
by you know the ability of people to be so accomplished you know we're in a profession where people
are incredibly productive and are are just impressive in their ability to produce high quality

(10:14):
content you mentioned Bob and Brogie on the huge fan of his and so he's a great example of that
and I think that there's just you know and I think part of it is just chipping away one step at a time
these do prepses listen we can have a whole episode of how great he is I'm he's great dad like

(10:34):
there are a lot of things of it like there are like hugely important things about his character that
that I recognize that there aren't aren't recognized publicly but I think as a person he's a great guy
and a wonderful mentor to many people in our space frankly so anyway the whole crew that whole crew is
I look I always look forward to seeing them at legal week which is coming up and good good

(10:58):
good public service announcement to folks to start planning because it's coming more quickly
than we realize also a random public service announcement for I think our listeners in the US
so I'm just going to mention that I learned recently that your TSA pre-check
expires so I'm just going to throw that out there I don't remember I don't know what minute of this

(11:23):
episode it is but I've just dropped a massive massive a lot of value what what oh TSA pre is like
this pre-approved line at the airport so it's not clear with the fingertips and the eye
you know the iris check it's not a biometric thing but it it allows you because you've been pre-approved

(11:44):
to get on a faster line right in generally in the airports and so I didn't realize that it expires
so now it's inspired and after I knew and it's more time consuming to travel without it so
I need to check whether you're new president that would have had any impact on my ability to do it

(12:06):
no I think for you it doesn't matter but for our our listener our listener in the US I think he's
he's really I like I like I know exactly who he is anyway um
what is your name he's been I'm gonna be busy so I think this week has been you know I do I do
think that there you have to be a bit careful that there's there's so much coming in it's a case of

(12:31):
also not just from an organizational point of view but from sorry I went from right back from
from conference to being busy but so and the a seamless jump uh just in the weeks ahead and then
running up to League of Week there's gonna be lots of press releases there's gonna be lots of
announcements that always is this this you know this this this period running up to the conference
will be busy for everybody so and I think it's just a question of you know all of us sort of having

(12:56):
to discern not you I don't know you're not so much on the news from but like having to discern
you know what what really deserves coverage like I think um there's a lot of there's a
continuation of a trend of just pushing out a lot of news there was a lot of very genuine
exciting news on the J&A iPhone you know there's a ton there's a ton of new products coming to market

(13:18):
um there's a ton of investment like this last this last month I'm most different the more
investment stories of you know all varying stages of companies obviously we had Harvey with like
300 million right down to new startups with small amounts of seed funding it's just been been
not the amount of press releases and I know I'm anticipating that that will just either continue

(13:41):
or ramp up in as we approach League of Week as obviously everyone starts to want to get their
news out there um I still change because obviously of the type of companies that we typically
just see us but we're probably going to start seeing some more you discovery I'm an announcement
so they run up to League of Week we haven't seen a huge amount of those in the last few weeks but
I expect that will probably start to ramp up um because League of Weeks typically still being quite

(14:06):
you discovery heavy um so so yeah that'd be interesting to see what we what starts to come up in
the next few weeks in terms of news about those companies I know that obviously warm up
all right yes I'm actually finishing my 2025 e discovery unfiltered research today and then I'll
have the number crunch of spent some time or the weekend I've really made a commitment to try to
have that report finished for legal week which is uh not what I've it's just it's just it's just

(14:32):
too voluminous a piece of research to have ready but I I'm planning to I've I've structured it in a
way that I will but I wanted to say I attended the uh Cornell panel discussion with O's Ben
Amrum Meredith Williams range Nikki Shaver and Scott Rexhafen and and and of course Matt who's at

(14:57):
at uh at Cornell and it was a great really interesting insightful discussion there sort of the
leaders of just sort of knowledge and innovation and it was it was great I'm actually I've been
planning to post something based on my takeaways because there were so many great takeaways about it

(15:19):
I just have it at time but because I'm busy uh no that's not even true I just have it at time but today
I that's my plan for at some point today so that that might be a late Friday afternoon post but they
were great and I'd love to promote what they were talking about and promote each of them because they
do a tremendous amount to share their knowledge with our industry I gave it talk for Scott twice

(15:43):
actually uh Cornell because like but but oh he's straight he has a class he had a class at Cornell so
and he did teach his um digital sorry um like he has a tech group believe people tell
kind of great which it was super super smart and so they talk to a couple of times I helped
to judge they they he gets them to find he gets them each of them to choose a tech company

(16:08):
that they want to present and and they want to do some research into and present their findings
across various different um areas that he sets them to look into and then they have to present and
then he kind of asked we asked questions about why they're interesting um and and and yeah he does
he does it is an amazing class so just to make sure that the study of the training the training there is

(16:29):
super relevant and and contemporary yeah yeah and I met some students and it was a great discussion
and some of them have come to my legal technopheobrickfist in New York which I welcome and so I didn't
thought of like inviting students I over the years that these things have grown from hey let's have

(16:52):
coffee me caroline and nicky black right it's just from from some friends getting together with coffee
to well let me tell some people let me ask some other people and all of a sudden it's it's just
outstanding really inspiring conversation with people who were just so smart really just doing
amazing things and then I think there's there seems to be more opportunity to have more of those

(17:16):
conversations which I feel like is helping the industry move faster legal has historically been a slow
and lagging in many ways and that's really changing and all of a sudden you're seeing
some of these companies like harbory being treated as high tech main tech as opposed to legal tech

(17:37):
however you want to distinguish it but you know and I think that's been described in the media
just as all of these interesting companies being broadly tech as opposed to narrowly legal tech
and we're having lots of conversations about that and deployment and in fact
I've heard more and more discussions about leveraging legal tech specifically for

(18:02):
compliance and other business issues that you know maybe go beyond maybe or more legal adjacent
and that's also legal research tools being created for populations that typically wouldn't
right not necessarily lawyers or legal professionals but people who need to understand

(18:23):
what the law is and how it affects them particularly these days as it's changing so quickly
there's going to be so much change this year this is going to be um I think no change at all
it's more it's a small little change
a little change it's like almost no change I would imagine nothing nothing nothing
nothing says yeah on a scale of zero to ten maybe a one yes oh but yeah so I think um you

(18:50):
we're going to see this morph you know we've got these big general type AI assistants um and I think
we're going to see so much change in all the types of technologies and the move towards the
genticae I but also I wrote about a very specific you know this um a general AI tool for
g diligence and you know that I think this year we're going to see some really interesting changes

(19:14):
in how firms are using this technology is going to be a lot more use cases the one thing I would say
which was which is interesting I'm I'm involved in um a conference next week where they are
working with with much smaller so the midsize law firms um and they did a survey which
I wrote wrote about this week talking about gen ai and how many of them these these are like firms of

(19:38):
you know much smaller than the ones that we normally work with so sort of around a hundred people
or sometimes less um and what were that there's really really deep server which is out next week
um this is a company called action set um so they do access practice management and they um
interviewed lots of lots of lots of leaders and it's amazing to see the difference you know like so

(20:01):
so that these these smaller firms that used to have they could be you know very high quality work but
they they used to have the edge in terms of like the quality of life which now that the big firms
post covid have got you know can enable home working they've they've kind of lost some of their edge
and then they don't have the tech resource and so a lot of them are not looking at AI at all um

(20:25):
and then not really you know they're not some of them very digitally enabled um so that was kind of
fascinating you know like in this this year that we're going to be focusing very heavily on the
largest firms and the biggest use cases but it's also important to remember that there's like a whole
strata of firms out there where you know they're going to have to really think about defining

(20:47):
themselves and really trying to work out a lot of the case it was the lead it's the lead ship if you
know like you have to bring a leadership on this journey of okay fine we've got to win more business
and we've got to retain talent they were most focused on talent you know retaining and
employing good people which is important but digital transformation was really low on the list of
priorities and um it's like well eventually that's going to bite and and I actually also do mid-size

(21:14):
firm research generally last year I did a report called the change makers trying to figure out
how firms are adapting and the real challenge you're right that there are many more firms of mid-size
and small-size than there are large and as the costs of developing and implementing gender

(21:35):
of AI drop and they are dropping there will be opportunities but the danger is that if you wait too
long at least to understand how it works to pilot to test to experiment you don't learn
what it's doing that will displace some of the lower value work that you're doing and you will find

(21:59):
yourself at a disadvantage down the road and that down the road point is coming more quickly than ever
the time horizons are so much shorter five years is now a year a year is now a month it's it's just
incredible and you just see this for every new version of these tools that come out how rapidly this
is changing also how interesting the competitive landscape is you have certain recognized names

(22:27):
and then lots of others and they're sort of going toe-to-toe in terms of new feature new use case
new firm new advocate and as that's happening if you're not paying attention or you're not
tactically trying to incorporate this somehow my fear is that those organizations fall behind

(22:51):
and then it becomes very hard to jump ahead i don't know that they need to make the kind of
investment that we're seeing from the largest firms and and the expertise and the talent
but certainly some level of use and determining where they might be able to gain an advantage as
opposed to weight to be at a disadvantage i still think that culturally the culture is the issue

(23:18):
and there's the cost which you are absolutely right you know that's a huge cost which
necessarily have to invest but but also it's the culture it's the mindset of you know we know
we know we know we know people when we we're all about relationships they're very much
relationship front and center and that's great right so how do you differentiate your service is

(23:40):
is a great relationship the people that people want to deal with but but they you know they
it feels like the culture is a massive barrier you know in terms of we don't really need all of
this technology they don't have that culture of curiosity that even if you're not paying money
even if you're not investing even if you're not really doing stuff like you need that culture of

(24:01):
curiosity of going okay we're now in a world where this is going to be really relevant and
it's going to help provide a better experience for our customers our clients you know if we even if
we do it just around the edges you know but actually they don't I think it's a massive challenge
in in in a lot of mid-sized firms that's sort of the leadership is really just not there and I think

(24:26):
that's a world danger someone needs to be the champion for conversation at a minimum participating
in conversations I'm not suggesting that you have to fly across the country and attend some event
in Silicon Valley because that is where things are happening but at least gather with your peers

(24:49):
and try to learn some best practices where have people made mistakes the benchmarking at this point
is so important and I understand as a as a opportunity to come full circle here in our conversation
people are busy and right and that is a challenge it's it's not a good enough excuse being busy

(25:12):
now is a short-term time issue it's it doesn't necessarily determine the quality of what you'll be
doing a year from now two years from now five years from now and so this idea of being nimble is
more important than ever and modeling that approach only happens when you're paying attention and

(25:38):
looking at what your peers are doing and even people you emulate firms that you aspire to be like
I think that for a for a moment in many ways the mid-sized firms were taking work from larger firms
because they could scale more quickly with technology they could provide a certain level of service

(25:58):
that they once weren't able to now they are but if the larger firms are now investing and evolving
and smaller firms or mid-sized firms are remaining stagnant then they lose that competitive edge
and so it's a it remains a challenge so when I hear that I'm always like I think it's really important

(26:18):
to these firms if they're not going to make the investment that they at least engage in the conversation
so that they're as informed as possible and can position and revisit their strategic plans and
yeah make adjustments and gain and gain energy from one another as well potentially there's a great
thing about this market you know I did a webinar yesterday and I wrapped up just by saying I

(26:40):
have great with a lot of people it's very engaged we were talking about this year like the
challenges and opportunities of this year so people from legal practice in it and we lose people
and I just was like I wrapped up just by just saying I'm really grateful to be in this industry where we
are all about knowledge sharing we are keen and willing to share our experiences with one

(27:06):
another which is unique and it's very special so you know I think that people should really take
advantage of that you know that culture which is not there if you take something like the private
equity sector you don't I know for a fact from speaking to people if you don't have competitors
sitting around going hey what are you doing they don't share you know like and so we are so lucky

(27:28):
that we are part of an industry where people do have that amazing knowledge sharing and I think that
this is the year to as you said to really take advantage of that any tips for people in preparing
for legal week that you would share before we go be organized I will tell people that I create a

(27:49):
calendar link for meetings and I send it to all the people I want to meet not because
I it's my schedule is so busy I just want to create an efficient way that I can guarantee I get to
meet that person and and give them the maximum flexibility and so I that's a tip that I think people

(28:10):
should use it's I have a paid version of calendar which isn't very expensive but I think even with a
free calendar you can do that just send your link but I organize it according to those days it's
specific to those days and I pay attention to when I'm doing something I have a run at 6 am on the
Wednesday at legal week and I'll be doing some other things but I encourage people to take advantage

(28:34):
of that organization because otherwise there's no way to manage it's not just legal week ilta
clock any of the events that people go to if you're going to go to their lexbo there you need to
be organized and schedule out when you can meet with people because otherwise you say you're
going to see them and you don't so I've had this conversation with other peers and some of them will

(28:59):
like calendar are you kidding me but I think if you send it to people that you want to meet and you
and it's you you make it clear gently that it's for them only that the risk with journalists is
so we've had it I've had this before where I share my calendar with one person and then I find
my and this happened the most recent conference last year like my diary started filling up with

(29:19):
meetings that were people that I don't want to see which is you know really kind of when it puts
me in an extremely embarrassing position you'd never want to turn around and say to somebody I
don't want to meet with you but it was kind of you know so yeah you have to be careful I think just to
make sure that that put is that person he used to tell him talent Lee and that person only but yeah

(29:42):
this is what this is what the managing part of my old firm used to call a high class problem nobody's
doing that with me and and maybe our other listener he he made that maybe a challenge it is not a
challenge for people passing around my calendar and booking me endlessly because I'm such an important
person it's usually just the fact that you go to these events most most of your peers if you're

(30:05):
traveling these circles are going to this particular event or the you know I know that there are
several events in the UK that you attend like your peers are going to them and you want to just
think proactively about finding 30 minutes to have a coffee and a face to face and I think I have found
that sometimes reaching out is is a catalyst for something even better and they may not even be

(30:32):
going and so I reach out broadly and many people are not going to be there or don't have the time
but the second best thing after a meeting is I'm not going to be there I don't have the time can
we set up a call the following week same value to me I'm happy to chat with that person I'd love

(30:53):
to see them on site but if I can't I'm happy to see them on zoom and I think that that being that
proactive with such a simple thing the county controversy makes no sense to me of people like don't
send a county do send a county I always think are we are we not interested in being efficient do you
have the time to send a thousand emails back and forth not to there's not going to have a two
for you know that two for me I walk on my dog oh what about will you dog be available and six now

(31:17):
six is not good I'm gonna have you know dinner it just okay let's never let's never meet we've
got so much interaction on email I feel like we've talked already so we're good thank you very much
you've been a great audience anyway well Cal I know I love this I have no idea what we talked about
today let's just recap we talked about being busy and then we talked about there's some money in AI

(31:42):
and we talked about legal week and we talked about being busy again and we talked about being
organized and we talked about how happy we were to see each other when we started and I am remain
happy and I look forward to you know having another conversation before legal week yeah and I look
forward to you know sharing other things that you know we've talked about but I hope I hope things

(32:05):
calm down for you and that people stuff sending you press releases I hope they're doing I'm so
happy I'm delighted to be busy I'm so grateful I'm so grateful great to see you thank you so much bye bye
time.
You
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