May 5, 2026 • 13 mins
Virtual legal assistant programs take years to get right. We started with one in 2018. Now we run 40 across our firm.
If you're trying to scale without burning out your lawyers, this is the conversation. Real structure, real mistakes, real results from our firm.
Kelley walks through the reporting structure shift that fixed our two-team problem, the culture work behind our remote legal team, and the law firm efficiency math that makes it pay off.
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---
📄 CHAPTERS
0:00 - Virtual Legal Assistant Team: From 1 Person to 40 in Seven Years
2:19 - The Reporting Structure That Created a Two-Team Problem
3:32 - Why Each Virtual Legal Assistant Now Reports to a Department Manager
5:11 - Building One Team Culture: Christmas Cards, Cameras, and Daily Lightnings
8:09 - Every Function Except Lawyer: QA, IT, Intake, Web Dev, and More
11:13 - The Cebu Trip: Why We Fly to The Philippines Every Year
----------------------
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
think the overarching goal here, right,if I'm a law firm owner and I'm
thinking about, well, do I need to explorethis is creating efficiencies
for your most valuable assets, right.
If you run a law firm,your lawyers are the ones
that need to doso much of the heavy lifting.
And if you can add supportresources to them,
you are creating efficiencies everywhere,which is translating into profitability
(00:21):
for the firm.
Well, hello and welcome to the Sterlingfamily Law Show.
I'm Jeff Hughes, I'm your co-host,along with Tyler Dolph as well.
And we have a guest, Kelly Shaw, who isthe director of operations in our firm.
And Kelly has worn just about every hatin our firm, with the exception of lawyer.
And she is our second or third longestserving teammates.
(00:44):
So Kelly, welcome back.
And I asked you tocome on today to talk about
how you have built a structurefor managing our offshore teammates.
So if you can just help us understandthe volume of teammates, the number of
teammates we have that are not herein the United States, and the history
of how we used to work with themand how we've changed that for the better.
(01:06):
I think there's some real goodinformation there to share.
Yeah, well,thank you so much for having me back.
Yes, I could certainly talkabout our offshore team.
That team is exclusivelylocated in the Philippines.
They're spreadall throughout the Philippines.
And there's about.
I believe there's about 40 teammembers on that team now.
(01:28):
And so, yeah, just to talk a little bitabout how they are
structured now versuswhen we first started utilizing the team,
I think we've been utilizing individualsin the Philippines.
Gosh, it's got to be like five years now.
Well, actually, we went back to 2018is whenever I started working with Eden,
(01:49):
who was helping with our sales processand kind of auditing kind of our process
and what we were doing.
So that was our first one,and it has grown from one
seven years agoto where we at, we're at today.
Can I just interject quicklyif you are thinking about this?
We have found that these teammembers are incredible humans,
(02:11):
very dedicated to the cause,very easy to train and open to.
To doingwhatever is needed to help the firm.
Thank you.
Tyler was great.
I heard you refer to them as offshore.
That's actually a termwe don't really use a lot internally, so.
But for identifying it for our listeners,that's why you did that.
So talk to thatbecause there's I'll let you take over
(02:32):
from your explain kind of the processthat we've developed over the years.
Yeah.
So originally, as you mentioned,and you brought up Eden.
So Eden was one of our original teammembers there.
So she actually then went onto kind of oversee that whole team.
She was responsible for training,for hiring, for recruiting.
And regardless of what teamthat an individual was supporting,
(02:56):
they all kind of reported up through her.
She did all of the coaching,the one on one, like all of that.
As that team began to grow.
That obviously was not a verysustainable structure, not just because
it was very difficult to for one managerto know and train ten different functions.
(03:17):
There's many more now, but also because itinadvertently kind of created a two team
structure, right?
Like we had this offshore teamthat kind of was their own.
And then we had our onshore teamand that that just didn't have the culture
that wasn't supporting the culturethat we that we were striving for here.
(03:39):
So I think about 3 or 4 years agonow, we made the transition
to have each of those team membersjust report directly to
the manager of the teamthat they're working for.
So for if you're on our QA team,if you're doing QA for the legal team,
you're in the legal team.
If you're doing QA for the intake team,you're in the intake lens.
(04:01):
That allowed for those team membersto really feel part of the team
that they were supporting.
They know.
They know those individuals now.
They're better connected to the processesthat the team is executing.
They have inputs.
They do the trainingwith those team members.
They're engaged in the variousactivities that that team might do.
(04:23):
You know, I know intake is verythey're very engaged with each other.
They do a lot of types ofteam building, even virtually.
So, you know, to your point about,you know,
I'll speak a little bit tohow do we make this feel like one team.
We are pretty intense.
We're very intentionalabout including everyone.
(04:44):
Right?
Like they're in management meetings.
They're in lightness.
You know, Elton's for those of youthat aren't for maybe familiar,
every team in the firm has these standinglightens each week for that team.
So they're in all of those meetings.
In addition,the managers are doing one on one meetings
with them, just like they're doingwith their state side individuals.
(05:05):
So there's really nota distinction anymore
in terms of what one team is doing versusthe other, That's a huge best practice
that we've learned over the years, is thatit should feel like a single team, not
oh well, you're offshore, you're on shore, you're whatever.
It's like, no, you're part of the team.
You're doing this thing,and we're all lined on the goal.
(05:29):
And that, you know, that comes downeven to like a Christmas party, right?
Like we do a virtual versionof our Christmas party
for to facilitate our offshore team, tomake sure that they're feeling included.
I send Christmas cards to the Philippineteam members every year.
I put pictures togetherand handwritten notes to send to them.
I have to do it like next weekin order for it to get there in time.
(05:49):
But so it's just little things like that.
I mean, I know we've donelike after our social events
just to make it really feel like,like we're one team.
So that I think, is if you are consideringutilizing offshore team members,
making sure that they actually feel likepart of the team is is huge,
and you'll see the difference inhow they engage with your clients
(06:11):
and how they engagewith your internal teammates like they
they are part of the family.
So you also didn't mention that they workthe same hours as we work here.
Right.
And because our teammates here inthe US are frankly, spread out among,
what, 5 or 6 statesand all over Illinois, in Wisconsin.
(06:31):
So we'realmost exclusively virtual already.
So adding in these teammatesfrom the Philippines
who speak English tremendously well,it doesn't feel any different.
I don't even think of them any differentas some as a US based teammate.
On that topic real quick, I think if youif you aren't a firm that has like
(06:52):
we are very virtual, everybody's virtual.
Like you were just sayinghe was even in the States,
even if you're not set upthat way, if you start to have team
members that are in other countries,wherever they may be,
you have to really dedicateand be intentional
about the camera stuff like there.
(07:14):
It is just a part of our culture.
Now. Anytime you jump into a meeting,your your camera is on
and if your camera is not on,it's like it is. It's frankly weird.
Like, are you in a bad spot?
Are you okay? Are you sick?
Like, we're worried about youif your camera is not on.
And I just thinkthat's important to call out
because I think people underestimatehow important that is.
And having that face to face interactionwhen you're virtual,
(07:36):
it's hugely It's extremely important.
And that's something we've actuallymandated across the firm over the years.
I know so many meetings.
When we first started switching over tothis was like,
hey, put your camera on,we expect to have a camera on.
So there's a lotthat happens in connection with people
whenever you can, like lookyou in the like each other in the face,
talk to if you would.
(07:57):
Kelly I want to build a little bit moreand kind of double tap on.
Each Philippine teammate is on a teamand they report up
just like anyone else on that team.
Talk about the numberof different functions and teams,
because I think a lot of peopledon't appreciate that.
It's not just answering the phone, it'sin every department other than lawyer.
(08:19):
We have teammatesthat are in the Philippines.
So talk talk about all those differentfunctions.
Sure. Yeah.
See if I can remember themall off the top of my head.
I'll start with the ones I workwith closely the closest.
So our to start echo.
He supports our ticketing system.
So anytime you put in a ticket intoSalesforce saying I'm struggling
or I have an issue ormy email is not working,
(08:40):
I got locked out, that's going to echo.
And so he's doing that correspondence,he's following back up, he's
jumping on a Google meet with youto to troubleshoot and get through that.
Our web developerYuri, he's also in the Philippines.
So he works very closely with us.
Also with rocket clicks. Right.
So he works pretty seamlessly,you know, in that remote environment
(09:02):
doing all of those items.
We also have a fair amount of team membersthat are on our QA.
So they're listening to phone callson our intake team
and literally shaping itlike giving a score, saying
either you miss the markor you nailed it based off of your script.
Similar for the attorneys.
(09:23):
So there's a individualsthat will review consultations.
We do have a proven processfor our consultations.
So they're doing giving a scoreof how well newer attorneys
are adhering to that process.
We also have individuals that are workingas a more traditional personal assistant.
(09:43):
So helping some of our team leaderskind of stay organized,
helping them with small projectsthey may be working on,
whether that's Sterling Day or,you know, other projects.
They might be doing project work for me,but they work closely with Katie,
or they're Katie'sdirect personal assistant.
So those team members,we've got quite a few of them
that are kind of sitting in that utilityrole, like they're they're supporting
(10:06):
their supporting the leaders in the firm.
We also have a couple of what we've dubbedas a virtual legal assistant.
So kind of this hybrid between a paralegaland an assistant,
they will they'll do some drafting,but they're reaching out to the courts.
They're scheduling thingsthey're client facing.
So they're having interactionswith clients.
(10:26):
Just trying to think of any otherWhat you have
e-filing, they do e-filing as well rightThank you.
Yep. E-Filing.
So they state those courtcommunications to the clients.
They're doing intake.
So the first time a client will call usthey're answering the phone.
So we're that's a high level of trustthat we're going to go to put our
(10:48):
you know, the people that we're tryingto, you know, help and serve in our.
And we have the data that backsit up, right.
They're doing a tremendous jobin doing that.
I think the overarching goal here, right,if I'm a law firm owner
and I'm thinking about, well,do I need to explore
this is creating efficienciesfor your most valuable assets, right.
(11:09):
If you run a law firm,your lawyers are the ones
that need to doso much of the heavy lifting.
And if you can add supportresources to them,
you are creating efficiencies everywhere,which is translating into profitability
for the firm.
And last thing I want to close with Kellyis that your investment,
our team's investmentin our team in the Philippines is you
you went over there this last year, right?
(11:33):
And you put togethera 2 or 3 day event on an island.
And I know Jeff Kurlanddid that last year.
I'm on deck, I believe, to go in 26.
So talk to about thata little bit on the the investment
that requires to get everyone togetherand then go over there and spend
time just with each other.
Yes, I mean it.
(11:53):
It's an awesome tripand I'm excited for you to go.
But it's the goal of it is just give givethat team an opportunity to get together
and just be with each other.
They spend they put a lot of workinto putting that event together.
So like last year we went to,we went to Cebu.
And so I had a planning committeethat they really took.
(12:17):
They took care of all of the details.
They found the resort,they coordinated the food,
they coordinated getting everyone,40 of us to each of those locations.
And that's I mean, the point ofit is like, we want them to feel they want
we want to give them the opportunityto engage and be together,
just like we prioritizethat state side here with Sterling Day.
(12:39):
So I love thatthe firm has made that investment.
And the fact that we now sendsomeone from,
you know, the states over to goand do that with them.
It just makes them feel likelike they are
valued and they they are so valued here.
And we just love havingthat additional interaction with them.
And it was just some of these peopleI've been working with for 5 or 6 years.
(13:02):
And to finally see them, not with a screenbetween us was just really, really fun.
And yeah,it was just a really engaging weekend.
And you always kind ofwonder it will it be different
when you finally meet someone in person?
And it was like, you don't skip a beat.
It's like, hey, remember that conversationwe had last week, right?
(13:22):
Like every it does.
There's nothing awkward about it, right?
Because they are just partof everything that we do.
There's no there isno this them two different teams,
everybody is very much working together.
Tremendous.
Well,thank you again for coming on and explain
the processthat you've developed over the years.
It was really helpful.
(13:43):
Yeah. Thank you so much for having me.
think the overarching goal here, right,if I'm a law firm owner and I'm
thinking about, well, do I need to explorethis is creating efficiencies
for your most valuable assets, right.
If you run a law firm,your lawyers are the ones
that need to doso much of the heavy lifting.
And if you can add supportresources to them,
you are creating efficiencies everywhere,which is translating into profitability
(00:21):
for the firm.
Well, hello and welcome to the Sterlingfamily Law Show.
I'm Jeff Hughes, I'm your co-host,along with Tyler Dolph as well.
And we have a guest, Kelly Shaw, who isthe director of operations in our firm.
And Kelly has worn just about every hatin our firm, with the exception of lawyer.
And she is our second or third longestserving teammates.
(00:44):
So Kelly, welcome back.
And I asked you tocome on today to talk about
how you have built a structurefor managing our offshore teammates.
So if you can just help us understandthe volume of teammates, the number of
teammates we have that are not herein the United States, and the history
of how we used to work with themand how we've changed that for the better.
(01:06):
I think there's some real goodinformation there to share.
Yeah, well,thank you so much for having me back.
Yes, I could certainly talkabout our offshore team.
That team is exclusivelylocated in the Philippines.
They're spreadall throughout the Philippines.
And there's about.
I believe there's about 40 teammembers on that team now.
(01:28):
And so, yeah, just to talk a little bitabout how they are
structured now versuswhen we first started utilizing the team,
I think we've been utilizing individualsin the Philippines.
Gosh, it's got to be like five years now.
Well, actually, we went back to 2018is whenever I started working with Eden,
(01:49):
who was helping with our sales processand kind of auditing kind of our process
and what we were doing.
So that was our first one,and it has grown from one
seven years agoto where we at, we're at today.
Can I just interject quicklyif you are thinking about this?
We have found that these teammembers are incredible humans,
(02:11):
very dedicated to the cause,very easy to train and open to.
To doingwhatever is needed to help the firm.
Thank you.
Tyler was great.
I heard you refer to them as offshore.
That's actually a termwe don't really use a lot internally, so.
But for identifying it for our listeners,that's why you did that.
So talk to thatbecause there's I'll let you take over
(02:32):
from your explain kind of the processthat we've developed over the years.
Yeah.
So originally, as you mentioned,and you brought up Eden.
So Eden was one of our original teammembers there.
So she actually then went onto kind of oversee that whole team.
She was responsible for training,for hiring, for recruiting.
And regardless of what teamthat an individual was supporting,
(02:56):
they all kind of reported up through her.
She did all of the coaching,the one on one, like all of that.
As that team began to grow.
That obviously was not a verysustainable structure, not just because
it was very difficult to for one managerto know and train ten different functions.
(03:17):
There's many more now, but also because itinadvertently kind of created a two team
structure, right?
Like we had this offshore teamthat kind of was their own.
And then we had our onshore teamand that that just didn't have the culture
that wasn't supporting the culturethat we that we were striving for here.
(03:39):
So I think about 3 or 4 years agonow, we made the transition
to have each of those team membersjust report directly to
the manager of the teamthat they're working for.
So for if you're on our QA team,if you're doing QA for the legal team,
you're in the legal team.
If you're doing QA for the intake team,you're in the intake lens.
(04:01):
That allowed for those team membersto really feel part of the team
that they were supporting.
They know.
They know those individuals now.
They're better connected to the processesthat the team is executing.
They have inputs.
They do the trainingwith those team members.
They're engaged in the variousactivities that that team might do.
(04:23):
You know, I know intake is verythey're very engaged with each other.
They do a lot of types ofteam building, even virtually.
So, you know, to your point about,you know,
I'll speak a little bit tohow do we make this feel like one team.
We are pretty intense.
We're very intentionalabout including everyone.
(04:44):
Right?
Like they're in management meetings.
They're in lightness.
You know, Elton's for those of youthat aren't for maybe familiar,
every team in the firm has these standinglightens each week for that team.
So they're in all of those meetings.
In addition,the managers are doing one on one meetings
with them, just like they're doingwith their state side individuals.
(05:05):
So there's really nota distinction anymore
in terms of what one team is doing versusthe other, That's a huge best practice
that we've learned over the years, is thatit should feel like a single team, not
oh well, you're offshore, you're on shore, you're whatever.
It's like, no, you're part of the team.
You're doing this thing,and we're all lined on the goal.
(05:29):
And that, you know, that comes downeven to like a Christmas party, right?
Like we do a virtual versionof our Christmas party
for to facilitate our offshore team, tomake sure that they're feeling included.
I send Christmas cards to the Philippineteam members every year.
I put pictures togetherand handwritten notes to send to them.
I have to do it like next weekin order for it to get there in time.
(05:49):
But so it's just little things like that.
I mean, I know we've donelike after our social events
just to make it really feel like,like we're one team.
So that I think, is if you are consideringutilizing offshore team members,
making sure that they actually feel likepart of the team is is huge,
and you'll see the difference inhow they engage with your clients
(06:11):
and how they engagewith your internal teammates like they
they are part of the family.
So you also didn't mention that they workthe same hours as we work here.
Right.
And because our teammates here inthe US are frankly, spread out among,
what, 5 or 6 statesand all over Illinois, in Wisconsin.
(06:31):
So we'realmost exclusively virtual already.
So adding in these teammatesfrom the Philippines
who speak English tremendously well,it doesn't feel any different.
I don't even think of them any differentas some as a US based teammate.
On that topic real quick, I think if youif you aren't a firm that has like
(06:52):
we are very virtual, everybody's virtual.
Like you were just sayinghe was even in the States,
even if you're not set upthat way, if you start to have team
members that are in other countries,wherever they may be,
you have to really dedicateand be intentional
about the camera stuff like there.
(07:14):
It is just a part of our culture.
Now. Anytime you jump into a meeting,your your camera is on
and if your camera is not on,it's like it is. It's frankly weird.
Like, are you in a bad spot?
Are you okay? Are you sick?
Like, we're worried about youif your camera is not on.
And I just thinkthat's important to call out
because I think people underestimatehow important that is.
And having that face to face interactionwhen you're virtual,
(07:36):
it's hugely It's extremely important.
And that's something we've actuallymandated across the firm over the years.
I know so many meetings.
When we first started switching over tothis was like,
hey, put your camera on,we expect to have a camera on.
So there's a lotthat happens in connection with people
whenever you can, like lookyou in the like each other in the face,
talk to if you would.
(07:57):
Kelly I want to build a little bit moreand kind of double tap on.
Each Philippine teammate is on a teamand they report up
just like anyone else on that team.
Talk about the numberof different functions and teams,
because I think a lot of peopledon't appreciate that.
It's not just answering the phone, it'sin every department other than lawyer.
(08:19):
We have teammatesthat are in the Philippines.
So talk talk about all those differentfunctions.
Sure. Yeah.
See if I can remember themall off the top of my head.
I'll start with the ones I workwith closely the closest.
So our to start echo.
He supports our ticketing system.
So anytime you put in a ticket intoSalesforce saying I'm struggling
or I have an issue ormy email is not working,
(08:40):
I got locked out, that's going to echo.
And so he's doing that correspondence,he's following back up, he's
jumping on a Google meet with youto to troubleshoot and get through that.
Our web developerYuri, he's also in the Philippines.
So he works very closely with us.
Also with rocket clicks. Right.
So he works pretty seamlessly,you know, in that remote environment
(09:02):
doing all of those items.
We also have a fair amount of team membersthat are on our QA.
So they're listening to phone callson our intake team
and literally shaping itlike giving a score, saying
either you miss the markor you nailed it based off of your script.
Similar for the attorneys.
(09:23):
So there's a individualsthat will review consultations.
We do have a proven processfor our consultations.
So they're doing giving a scoreof how well newer attorneys
are adhering to that process.
We also have individuals that are workingas a more traditional personal assistant.
(09:43):
So helping some of our team leaderskind of stay organized,
helping them with small projectsthey may be working on,
whether that's Sterling Day or,you know, other projects.
They might be doing project work for me,but they work closely with Katie,
or they're Katie'sdirect personal assistant.
So those team members,we've got quite a few of them
that are kind of sitting in that utilityrole, like they're they're supporting
(10:06):
their supporting the leaders in the firm.
We also have a couple of what we've dubbedas a virtual legal assistant.
So kind of this hybrid between a paralegaland an assistant,
they will they'll do some drafting,but they're reaching out to the courts.
They're scheduling thingsthey're client facing.
So they're having interactionswith clients.
(10:26):
Just trying to think of any otherWhat you have
e-filing, they do e-filing as well rightThank you.
Yep. E-Filing.
So they state those courtcommunications to the clients.
They're doing intake.
So the first time a client will call usthey're answering the phone.
So we're that's a high level of trustthat we're going to go to put our
(10:48):
you know, the people that we're tryingto, you know, help and serve in our.
And we have the data that backsit up, right.
They're doing a tremendous jobin doing that.
I think the overarching goal here, right,if I'm a law firm owner
and I'm thinking about, well,do I need to explore
this is creating efficienciesfor your most valuable assets, right.
(11:09):
If you run a law firm,your lawyers are the ones
that need to doso much of the heavy lifting.
And if you can add supportresources to them,
you are creating efficiencies everywhere,which is translating into profitability
for the firm.
And last thing I want to close with Kellyis that your investment,
our team's investmentin our team in the Philippines is you
you went over there this last year, right?
(11:33):
And you put togethera 2 or 3 day event on an island.
And I know Jeff Kurlanddid that last year.
I'm on deck, I believe, to go in 26.
So talk to about thata little bit on the the investment
that requires to get everyone togetherand then go over there and spend
time just with each other.
Yes, I mean it.
(11:53):
It's an awesome tripand I'm excited for you to go.
But it's the goal of it is just give givethat team an opportunity to get together
and just be with each other.
They spend they put a lot of workinto putting that event together.
So like last year we went to,we went to Cebu.
And so I had a planning committeethat they really took.
(12:17):
They took care of all of the details.
They found the resort,they coordinated the food,
they coordinated getting everyone,40 of us to each of those locations.
And that's I mean, the point ofit is like, we want them to feel they want
we want to give them the opportunityto engage and be together,
just like we prioritizethat state side here with Sterling Day.
(12:39):
So I love thatthe firm has made that investment.
And the fact that we now sendsomeone from,
you know, the states over to goand do that with them.
It just makes them feel likelike they are
valued and they they are so valued here.
And we just love havingthat additional interaction with them.
And it was just some of these peopleI've been working with for 5 or 6 years.
(13:02):
And to finally see them, not with a screenbetween us was just really, really fun.
And yeah,it was just a really engaging weekend.
And you always kind ofwonder it will it be different
when you finally meet someone in person?
And it was like, you don't skip a beat.
It's like, hey, remember that conversationwe had last week, right?
(13:22):
Like every it does.
There's nothing awkward about it, right?
Because they are just partof everything that we do.
There's no there isno this them two different teams,
everybody is very much working together.
Tremendous.
Well,thank you again for coming on and explain
the processthat you've developed over the years.
It was really helpful.
(13:43):
Yeah. Thank you so much for having me.
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If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Hey Jonas!
Hey Jonas! The official Jonas Brothers podcast. Hosted by Kevin, Joe, and Nick Jonas. It’s the Jonas Brothers you know... musicians, actors, and well, yes, brothers. Now, they’re sharing another side of themselves in the playful, intimate, and irreverent way only they can. Spend time with the Jonas Brothers here and stay a little bit longer for deep conversations like never before.
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.