August 5, 2025 • 15 mins
I spoke with Donna Frugoli, the Lead Application Support Analyst at Seyfarth Shaw, Julia Montgomery, the Director of Practice Enablement at King & Spalding, and Carlos Rodriguez, the CEO & CISO at CA2Security. The three are contributors to a new book titled "Lessons in Leadership," published by the International Legal Technology Association. We discussed the lessons they shared in the book, the power of relationship-building in a hybrid environment, best practices for demonstrating intellectual curiosity, and how strategic planning and team building affect the success of an initiative.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:01):
Welcome to Reinventing Professionals,a podcast hosted by industry analyst
Ari Kaplan, which shares ideas,guidance, and perspectives from market
leaders shaping the next generationof legal and professional services.
This is Ari Kaplan and I'm speakingtoday with Donna Fr the Lead Application
(00:24):
support Analyst at Seyfarth Shaw.
Julia Montgomery, the Director ofPractice Enablement at King and
Spalding and Carlos Rodriguez,the CEO and CSO at C two Security.
The three are contributors to a newbook called Lessons in Leadership,
published by the InternationalLegal Technology Association.
(00:45):
Donna, Julia, Carlos, great to see you.
Thanks for having us.
Yeah, thanks.
Sorry.
Thank you.
Donna, tell us about your background andthe lesson that you shared in the book.
Certainly.
So I started my career as a highschool English teacher, and that's
what I thought I was going to be.
I went to school for it.
I loved it.
(01:05):
I loved everything about it.
And then life happened and I was no longera teacher and through out my life, the
relationships that I've had with othershave helped me get to where I am now.
And I didn't really know they werehelping me at the time because
they would give me a suggestion.
They would offer me a applicationfor a particular role.
(01:28):
They'd say, you'd be really great at this.
And that feedback fromthose that were around me.
Is what got me to think that yes,I can be a leader, yes, I can be in
these leadership roles and do it.
It's what got me to be co-chair for IltaCon this year was those individuals around
me who saw something me that I didn'tnecessarily see, and then afterwards
(01:53):
came back and said, yes, see, you did it.
And shared my successin all of those things.
So I didn't know along the way thatthose relationships that I was making
with others were going to be soimpactful for where I was in my career.
And many of those individuals arelifelong friends because of it.
(02:13):
I really feel that the lesson I'mtrying to communicate is, find your
people and find your community.
And not only take those suggestionsfrom others, but be that person
for those that are around you.
Once you're where you want tobe, look back and see what you
can do to help others in the sameway that they had helped you.
(02:37):
Julia, tell us about your backgroundand the lesson that you shared.
Of course.
Thanks.
I've been in legal for more than 30 years.
I've worked in law firms and then wasconsultant to law firms and then crossed
over to the legal tech vendor side.
So have seen it fromall the different sides.
And now I'm back in-houseat King and Spalding.
My focus is on change management in legal,and it's a very exciting time if you're
(03:01):
a change manager in legal, and thatis connected to the lesson that I wrote
about in the book the art of Not Knowing.
It's really about the how wesometimes undervalue intellectual
curiosity or a beginner's mindset.
And I say undervalue, and I don't thinkthat's intentional always, but things
move so fast in legal tech, where weneed to get more done, we have three
(03:22):
projects going at the same time, and weneed to make decisions and then execute.
So oftentimes we lose that moment wherewe pause and ask meaningful questions.
We assume that we know what lawyers wantor we assume we know what would be useful.
But I've learned that it's reallyimportant to not assume and instead
(03:42):
to just pause as if you've neverheard about any of this before.
A beginner's mind.
And ask questions.
That can be a delicate balance.
Sometimes questions can feel threateningto folks who don't have answers for them,
but they can be a phenomenally usefultool for teasing out things that were not
considered or hidden for some reason andensure success in a more complete way.
(04:07):
Oftentimes when we think about leadership,the image that conjures up for most
people is someone who's confidentand can answer all the questions.
But I was really lucky to have amentor early in my career when I was
feeling a lot of pressure as I wasjust starting out to come over prepared
to meetings and be able to quicklyanswer questions with confidence.
And her coaching as a mentor to mewas that it's much more powerful she
(04:32):
found to be the person in the roomwho's asking good questions instead
of just having all the answers.
So as my career progressed and I became aconsultant, that certainly served me well.
And as a change manager, it really is atthe root of all of the work that we do.
Why are we doing this?
What problem are we seeking to solve?
(04:52):
Are there other waysto solve this problem?
And how we explored those?
How do we determinethis was the right path?
And so as a leader now myself,which is still weird to think of
myself as that, but here I am.
It definitely has become part andparcel of my leadership style.
Not only do I practice intellectualcuriosity when my folks bring ideas
(05:14):
forward, but I really ask them todo the same with me just because I
say something don't assume that'sa great idea and let's go do it.
Question me, ask me questionsand challenge me to think about
things in ways I haven't before.
And that's more important now than everin the age of disruption that we're in.
Carlos, tell us about your backgroundand the lesson that you shared.
(05:38):
Thank you . So I went to school forcomputer engineer in Venezuela, south
America, and I remember my firstassignment as a intern was to wire
this warehouse for an American company.
When I was doing that, I run into theAmerican engineers, setting up a router.
And if you've never seen a router.
(06:00):
It's a black screen with linesand it looked like the matrix,
and that just caught my attention.
I asked the engineers what are you doing?
And so they explained we'resitting at A VPN between here
and somewhere in the US to talk.
Technology here connecting.
And so that was it for me.
(06:20):
I needed to connect things togetherand then learn to secure them.
So went through the ranks on differentindustries from health and positions,
from help desk to when I got my firstmanagerial job at my first law firm at
Nixon Pruit, and that changed everything'cause you are trained to be a great
(06:45):
engineer, but you can't reboot people so Ihad to like, learn a lot about leadership.
I left legal around 2012.
And I've been back for the lastfew years as a fractional chief
Information security officer fordifferent law firms of different sizes.
In 2012, we saw the industry startingto go through this transition about
(07:11):
clients pushing for more security.
I was also an officer at Ilta backthen, talked to the team and said,
are you guys dealing with this?
Yes, so that gave birth tolegal tech which is still going.
Now the challenge was that at thetime, I went through the whole period
of building it and right when itlaunched, I knew I was sleeping legal.
(07:36):
And so the entry in the book thatI wrote it's called lessons Learned
through the Legal Self Journey.
I thought it would be aboutthe lessons that learned about
legal psych and that's it.
And it was, I started writing about.
Legacy.
That was a legacy that I left behind.
At the end of the article, itwasn't about building succession,
(08:00):
it was about connecting the strategyto the needs of of the business
or in this case of the industry.
I talk about connection.
That's been my theme,is connecting things.
Understanding the strategic needsof the organization, of the firm,
or in this case of ilta connectedto the industry and building a plan.
(08:25):
But also because I knew I wasleaving, I had to make sure that.
Strong team was in place and I had themindset of the volunteer that we are
serving first to build that longevity.
And so that the theme of my career as aleader, because every place I've left.
(08:50):
First when I joined or start as aleader, I immediately identify who the
leaders within my team are and buildthem and coach them and get them ready
for the next level, and then I leave.
And nobody knew that I left.
In many cases, they're still there inthose companies where we work together.
And that's something that I'm proud ofbeing able to enable and empower people
(09:13):
to grow and to lead and to add theirown thing to be long lasting problems.
Donna, what's changed aboutrelationship building that readers
should incorporate into their work?
Remote working is the biggest changer.
You don't have the just run intosomebody at the coffee wall or
(09:35):
the water cooler is it used to be.
You really have to be intentionalabout having conversations.
When I first started working remotely,I'd only pick up the phone and talk to
someone if I needed something from them.
Or I need you to do something for me, or,responding to something they asked me.
And it had to be very intentionalto just have conversations about
(09:57):
how are you, what are your goals?
What do you want to dowhat's your next step?
And really make them feel like you wantto know that and wanna help them with
it and not be just checking a box andsaying, oh, I've asked you what your
five year plan is, but really engage withthose that you work with and find out
(10:18):
about them and make the time to do it.
Because when we're all in theoffice together, it was easy.
You've had lunch together, you.
Went and took a walk outside for a break.
Now you don't have that whenyou're all in your remote location.
I think that's the biggestthing that has changed and.
It really had to be learned.
It was not something thatcame natural to me, at least.
(10:41):
It was something that I, at the beginning,I had a little item on my calendar,
call this person and just talk to them.
How silly it may sound, but , it hadbuild that habit so that you would do it.
Julie, why is intellectual curiosity somuch more valuable in the current climate?
(11:02):
Everything's changed, and thingsthat we were certain about before.
Certainly not certain any longer.
I was reading the Accenture Pulse ofChange Index which survey CIOs across
Professional Services works and theyestimate that the rate of change has
increased about 183% over the last fouryears in that kind of an environment.
(11:22):
We feel a lot of urgency to move fastbecause things are changing and it's
really easy to assume and execute.
So this idea of intellectualcuriosity, building in timelines
for our projects, a moment to pauseand explore and to brainstorm.
We talk a lot in legal these days aboutinnovation, but sometimes it feels like
(11:42):
innovation theater where we're just buyingthe latest solution and deploying it.
And this urgency and the disruptionhappening can lead us to short
change those periods where weexplore together and brainstorm and
ensure that we're bringing differentperspectives to the table to make
intentional, reasoned decisions thatwill deliver value for our customers
(12:05):
and for the firms that we support.
Carlos, how does strong strategicplanning and team building affect
the success of an initiative?
It's super important because inmy field, I can't tell a managing
partner or any partner, we need to besecure 'cause they're gonna ask why.
(12:26):
Because you're gonna get a virus.
That's not an answer.
You have to provide a strategic directionon why this will impact the firm and
a PO and their clients positively.
So working with Delta, I was an officer,so I had access to the strategic
objectives, and I've done this inevery company I go to even today.
So I took the strategicobjectives of iTime and put them
(12:50):
on a table on the far right.
Then on the left, I had anothercolumn when I walked back to it.
So objective one, there is amapping, an objective for the program
that's gonna help realize that.
And then that led me to have goodconversations with the board and the
staff leadership and the industry aboutwhy we thought this was a needed thing.
(13:14):
And it applies today in your day to day.
And then again by connecting.
That you could also then connectthe team to their purpose.
'cause then I was able to talk upand down and across the leadership
scale clearly, and everybodyunderstood what we were talking about
(13:34):
and that's how we gained support.
Everybody was collaborating, veryimportant to be able to speak Terms and
the firm's business terms and objectives.
How can attendees at the upcomingILTA conference this year execute
on the lesson that you've shared?
(13:56):
Talk to people.
Come out of your comfort zone, walk upto someone you don't know, introduce
yourself and learn their story.
It's amazing how open andwilling to share everyone is.
You just need to step up andask for the conversation.
The book in microcosm is a phenomenalexample of what ILTA does best.
It facilitates personal growth andprofessional growth through learning from
(14:20):
peers, and there's no better opportunityto do that other than buying the book,
but no better opportunity than ILTACON.
So, attend a session that is alittle outside your comfort zone
or there are lots of folks in theindustry who I follow on LinkedIn.
Go and find that person andthen there'll be a Q&A section.
You can ask them questions and you canalways stay later and connect with those
thought leaders or folks that you wantto build relationships with and connect
(14:43):
in person and do it with intention.
When I go to conference, I go to thethings that I need to understand to
talk to the partners and to the CIOs.
That's very important to get out ofyour comfort zone and explore those
areas that are about the business.
You have to be industry savvy.
(15:04):
You have to understand how law firms work.
Go out, meet people, go to sessionsthat you don't think you need, but
you really do, and and have fun.
This is Ari Kaplan speaking withDonna Fr the Lead Application
support Analyst at Seyfarth Shaw.
Julia Montgomery, the Director ofPractice Enablement at King and
(15:25):
Spalding and Carlos Rodriguez, theCEO and CSO at CA two Security.
The three are contributors to a newbook called Lessons and Leadership
published by the InternationalLegal Technology Association.
Thank you all so very much.
It's been a privilege and bestof luck with the new book.
Thank you, Ari.
Thanks, Ari.
Thank you guys.
(15:46):
Thank you for listening to theReinventing Professionals Podcast.
Visit reinventing professionals.com orari kaplan advisors.com to learn more.
Welcome to Reinventing Professionals,a podcast hosted by industry analyst
Ari Kaplan, which shares ideas,guidance, and perspectives from market
leaders shaping the next generationof legal and professional services.
This is Ari Kaplan and I'm speakingtoday with Donna Fr the Lead Application
(00:24):
support Analyst at Seyfarth Shaw.
Julia Montgomery, the Director ofPractice Enablement at King and
Spalding and Carlos Rodriguez,the CEO and CSO at C two Security.
The three are contributors to a newbook called Lessons in Leadership,
published by the InternationalLegal Technology Association.
(00:45):
Donna, Julia, Carlos, great to see you.
Thanks for having us.
Yeah, thanks.
Sorry.
Thank you.
Donna, tell us about your background andthe lesson that you shared in the book.
Certainly.
So I started my career as a highschool English teacher, and that's
what I thought I was going to be.
I went to school for it.
I loved it.
(01:05):
I loved everything about it.
And then life happened and I was no longera teacher and through out my life, the
relationships that I've had with othershave helped me get to where I am now.
And I didn't really know they werehelping me at the time because
they would give me a suggestion.
They would offer me a applicationfor a particular role.
(01:28):
They'd say, you'd be really great at this.
And that feedback fromthose that were around me.
Is what got me to think that yes,I can be a leader, yes, I can be in
these leadership roles and do it.
It's what got me to be co-chair for IltaCon this year was those individuals around
me who saw something me that I didn'tnecessarily see, and then afterwards
(01:53):
came back and said, yes, see, you did it.
And shared my successin all of those things.
So I didn't know along the way thatthose relationships that I was making
with others were going to be soimpactful for where I was in my career.
And many of those individuals arelifelong friends because of it.
(02:13):
I really feel that the lesson I'mtrying to communicate is, find your
people and find your community.
And not only take those suggestionsfrom others, but be that person
for those that are around you.
Once you're where you want tobe, look back and see what you
can do to help others in the sameway that they had helped you.
(02:37):
Julia, tell us about your backgroundand the lesson that you shared.
Of course.
Thanks.
I've been in legal for more than 30 years.
I've worked in law firms and then wasconsultant to law firms and then crossed
over to the legal tech vendor side.
So have seen it fromall the different sides.
And now I'm back in-houseat King and Spalding.
My focus is on change management in legal,and it's a very exciting time if you're
(03:01):
a change manager in legal, and thatis connected to the lesson that I wrote
about in the book the art of Not Knowing.
It's really about the how wesometimes undervalue intellectual
curiosity or a beginner's mindset.
And I say undervalue, and I don't thinkthat's intentional always, but things
move so fast in legal tech, where weneed to get more done, we have three
(03:22):
projects going at the same time, and weneed to make decisions and then execute.
So oftentimes we lose that moment wherewe pause and ask meaningful questions.
We assume that we know what lawyers wantor we assume we know what would be useful.
But I've learned that it's reallyimportant to not assume and instead
(03:42):
to just pause as if you've neverheard about any of this before.
A beginner's mind.
And ask questions.
That can be a delicate balance.
Sometimes questions can feel threateningto folks who don't have answers for them,
but they can be a phenomenally usefultool for teasing out things that were not
considered or hidden for some reason andensure success in a more complete way.
(04:07):
Oftentimes when we think about leadership,the image that conjures up for most
people is someone who's confidentand can answer all the questions.
But I was really lucky to have amentor early in my career when I was
feeling a lot of pressure as I wasjust starting out to come over prepared
to meetings and be able to quicklyanswer questions with confidence.
And her coaching as a mentor to mewas that it's much more powerful she
(04:32):
found to be the person in the roomwho's asking good questions instead
of just having all the answers.
So as my career progressed and I became aconsultant, that certainly served me well.
And as a change manager, it really is atthe root of all of the work that we do.
Why are we doing this?
What problem are we seeking to solve?
(04:52):
Are there other waysto solve this problem?
And how we explored those?
How do we determinethis was the right path?
And so as a leader now myself,which is still weird to think of
myself as that, but here I am.
It definitely has become part andparcel of my leadership style.
Not only do I practice intellectualcuriosity when my folks bring ideas
(05:14):
forward, but I really ask them todo the same with me just because I
say something don't assume that'sa great idea and let's go do it.
Question me, ask me questionsand challenge me to think about
things in ways I haven't before.
And that's more important now than everin the age of disruption that we're in.
Carlos, tell us about your backgroundand the lesson that you shared.
(05:38):
Thank you . So I went to school forcomputer engineer in Venezuela, south
America, and I remember my firstassignment as a intern was to wire
this warehouse for an American company.
When I was doing that, I run into theAmerican engineers, setting up a router.
And if you've never seen a router.
(06:00):
It's a black screen with linesand it looked like the matrix,
and that just caught my attention.
I asked the engineers what are you doing?
And so they explained we'resitting at A VPN between here
and somewhere in the US to talk.
Technology here connecting.
And so that was it for me.
(06:20):
I needed to connect things togetherand then learn to secure them.
So went through the ranks on differentindustries from health and positions,
from help desk to when I got my firstmanagerial job at my first law firm at
Nixon Pruit, and that changed everything'cause you are trained to be a great
(06:45):
engineer, but you can't reboot people so Ihad to like, learn a lot about leadership.
I left legal around 2012.
And I've been back for the lastfew years as a fractional chief
Information security officer fordifferent law firms of different sizes.
In 2012, we saw the industry startingto go through this transition about
(07:11):
clients pushing for more security.
I was also an officer at Ilta backthen, talked to the team and said,
are you guys dealing with this?
Yes, so that gave birth tolegal tech which is still going.
Now the challenge was that at thetime, I went through the whole period
of building it and right when itlaunched, I knew I was sleeping legal.
(07:36):
And so the entry in the book thatI wrote it's called lessons Learned
through the Legal Self Journey.
I thought it would be aboutthe lessons that learned about
legal psych and that's it.
And it was, I started writing about.
Legacy.
That was a legacy that I left behind.
At the end of the article, itwasn't about building succession,
(08:00):
it was about connecting the strategyto the needs of of the business
or in this case of the industry.
I talk about connection.
That's been my theme,is connecting things.
Understanding the strategic needsof the organization, of the firm,
or in this case of ilta connectedto the industry and building a plan.
(08:25):
But also because I knew I wasleaving, I had to make sure that.
Strong team was in place and I had themindset of the volunteer that we are
serving first to build that longevity.
And so that the theme of my career as aleader, because every place I've left.
(08:50):
First when I joined or start as aleader, I immediately identify who the
leaders within my team are and buildthem and coach them and get them ready
for the next level, and then I leave.
And nobody knew that I left.
In many cases, they're still there inthose companies where we work together.
And that's something that I'm proud ofbeing able to enable and empower people
(09:13):
to grow and to lead and to add theirown thing to be long lasting problems.
Donna, what's changed aboutrelationship building that readers
should incorporate into their work?
Remote working is the biggest changer.
You don't have the just run intosomebody at the coffee wall or
(09:35):
the water cooler is it used to be.
You really have to be intentionalabout having conversations.
When I first started working remotely,I'd only pick up the phone and talk to
someone if I needed something from them.
Or I need you to do something for me, or,responding to something they asked me.
And it had to be very intentionalto just have conversations about
(09:57):
how are you, what are your goals?
What do you want to dowhat's your next step?
And really make them feel like you wantto know that and wanna help them with
it and not be just checking a box andsaying, oh, I've asked you what your
five year plan is, but really engage withthose that you work with and find out
(10:18):
about them and make the time to do it.
Because when we're all in theoffice together, it was easy.
You've had lunch together, you.
Went and took a walk outside for a break.
Now you don't have that whenyou're all in your remote location.
I think that's the biggestthing that has changed and.
It really had to be learned.
It was not something thatcame natural to me, at least.
(10:41):
It was something that I, at the beginning,I had a little item on my calendar,
call this person and just talk to them.
How silly it may sound, but , it hadbuild that habit so that you would do it.
Julie, why is intellectual curiosity somuch more valuable in the current climate?
(11:02):
Everything's changed, and thingsthat we were certain about before.
Certainly not certain any longer.
I was reading the Accenture Pulse ofChange Index which survey CIOs across
Professional Services works and theyestimate that the rate of change has
increased about 183% over the last fouryears in that kind of an environment.
(11:22):
We feel a lot of urgency to move fastbecause things are changing and it's
really easy to assume and execute.
So this idea of intellectualcuriosity, building in timelines
for our projects, a moment to pauseand explore and to brainstorm.
We talk a lot in legal these days aboutinnovation, but sometimes it feels like
(11:42):
innovation theater where we're just buyingthe latest solution and deploying it.
And this urgency and the disruptionhappening can lead us to short
change those periods where weexplore together and brainstorm and
ensure that we're bringing differentperspectives to the table to make
intentional, reasoned decisions thatwill deliver value for our customers
(12:05):
and for the firms that we support.
Carlos, how does strong strategicplanning and team building affect
the success of an initiative?
It's super important because inmy field, I can't tell a managing
partner or any partner, we need to besecure 'cause they're gonna ask why.
(12:26):
Because you're gonna get a virus.
That's not an answer.
You have to provide a strategic directionon why this will impact the firm and
a PO and their clients positively.
So working with Delta, I was an officer,so I had access to the strategic
objectives, and I've done this inevery company I go to even today.
So I took the strategicobjectives of iTime and put them
(12:50):
on a table on the far right.
Then on the left, I had anothercolumn when I walked back to it.
So objective one, there is amapping, an objective for the program
that's gonna help realize that.
And then that led me to have goodconversations with the board and the
staff leadership and the industry aboutwhy we thought this was a needed thing.
(13:14):
And it applies today in your day to day.
And then again by connecting.
That you could also then connectthe team to their purpose.
'cause then I was able to talk upand down and across the leadership
scale clearly, and everybodyunderstood what we were talking about
(13:34):
and that's how we gained support.
Everybody was collaborating, veryimportant to be able to speak Terms and
the firm's business terms and objectives.
How can attendees at the upcomingILTA conference this year execute
on the lesson that you've shared?
(13:56):
Talk to people.
Come out of your comfort zone, walk upto someone you don't know, introduce
yourself and learn their story.
It's amazing how open andwilling to share everyone is.
You just need to step up andask for the conversation.
The book in microcosm is a phenomenalexample of what ILTA does best.
It facilitates personal growth andprofessional growth through learning from
(14:20):
peers, and there's no better opportunityto do that other than buying the book,
but no better opportunity than ILTACON.
So, attend a session that is alittle outside your comfort zone
or there are lots of folks in theindustry who I follow on LinkedIn.
Go and find that person andthen there'll be a Q&A section.
You can ask them questions and you canalways stay later and connect with those
thought leaders or folks that you wantto build relationships with and connect
(14:43):
in person and do it with intention.
When I go to conference, I go to thethings that I need to understand to
talk to the partners and to the CIOs.
That's very important to get out ofyour comfort zone and explore those
areas that are about the business.
You have to be industry savvy.
(15:04):
You have to understand how law firms work.
Go out, meet people, go to sessionsthat you don't think you need, but
you really do, and and have fun.
This is Ari Kaplan speaking withDonna Fr the Lead Application
support Analyst at Seyfarth Shaw.
Julia Montgomery, the Director ofPractice Enablement at King and
(15:25):
Spalding and Carlos Rodriguez, theCEO and CSO at CA two Security.
The three are contributors to a newbook called Lessons and Leadership
published by the InternationalLegal Technology Association.
Thank you all so very much.
It's been a privilege and bestof luck with the new book.
Thank you, Ari.
Thanks, Ari.
Thank you guys.
(15:46):
Thank you for listening to theReinventing Professionals Podcast.
Visit reinventing professionals.com orari kaplan advisors.com to learn more.
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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!