Cybersecurity Resilience And Seamless Succession Planning with Jason Epstein, TLIS
Presented by:
In this episode, Jason Epstein, TLIS, from the Berkshire School unpacks the evolving, around-the-clock responsibilities of technology leadership in a boarding school setting. Listen in to learn practical strategies for cross-training small IT teams, managing third-party vendor risks, and maintaining work-life balance amid relentless operational demands.
Berkshire School — The independent boarding school located in Massachusetts where guest Jason Epstein currently serves as the director of technology.
ISTE — The International Society for Technology in Education, an organization Epstein has been involved with since his early days in education.
MassCUE — The Massachusetts organization for computer-using educators, mentioned as a key regional networking group for technology professionals.
Veracross — The student information system utilized at the Berkshire School and managed day-to-day by their registrar.
Naviance — A college counseling platform managed independently by the school's college counseling office.
Canvas — A learning management system cited during a discussion about the importance of evaluating third-party cybersecurity vulnerabilities.
Transcript
Peter Frank:
Welcome to Talk Technology with Atlas, the show
Peter Frank:
that plugs you into the important topics and trends for
Peter Frank:
technology leaders, all through a unique independent school
Peter Frank:
lens. We'll hear stories from technology directors and other
Peter Frank:
special guests from the independent school community,
Peter Frank:
and provide you with focused learning and deep dive topics.
Peter Frank:
Kevin Warenda, TLIS: Hello and welcome to Talking Technology
Peter Frank:
with Atlas. I'm Kevin Warenda, Director of Information
Peter Frank:
Technology Services at the Hoshka School in Lakeville,
Peter Frank:
Connecticut, and I'm Bill Stites, the Director of
Peter Frank:
Technology at Montclair Kimberly Academy in Montclair, New
Peter Frank:
Jersey,
Hiram Cuevas:
and I'm Hiram Cuevas, the Director of
Hiram Cuevas:
Information Systems and Academic Technology at St. Christopher
Hiram Cuevas:
School in Richmond, Virginia.
Hiram Cuevas:
Kevin Warenda, TLIS: Welcome back, gentlemen. I just got back
Hiram Cuevas:
from 10 days spending in an RV with my family, well rested, as
Hiram Cuevas:
you might imagine. I don't know how many people can actually say
Hiram Cuevas:
they've been well rested after 10 days with their family in an
Hiram Cuevas:
RV, but I give you credit for saying it. That's awesome. I had
Hiram Cuevas:
my dog, so I had the therapy animal with me. I guess is the
Hiram Cuevas:
best way to say
Hiram Cuevas:
Bill Stites, TLIS: it.
Hiram Cuevas:
Kevin Warenda, TLIS: Now, I would like to take the
Hiram Cuevas:
opportunity just to express gratitude to my team. I don't
Hiram Cuevas:
know if you guys experience this too, but I'm lucky enough to
Hiram Cuevas:
have a team of folks. I'm not the only IT person at the school
Hiram Cuevas:
or a team of six, so I have five really great folks that are back
Hiram Cuevas:
at school, which really allows me to be away and disconnect.
Hiram Cuevas:
They handle things. I had very few emails I had to respond to,
Hiram Cuevas:
or things I had to take care of. So, just a thank you to my whole
Hiram Cuevas:
team at the Hatcher School who allows me to actually get away
Hiram Cuevas:
and get some rest. Either of you have that experience now or in
Hiram Cuevas:
the past? So this year is the first time in quite a while that
Hiram Cuevas:
I've taken some like extended time off, and yeah, when you can
Hiram Cuevas:
fully and completely disconnect, particularly during the summer,
Hiram Cuevas:
most people think you know when they're in school they're like,
Hiram Cuevas:
"Oh, have a great summer, enjoy your time, and not realizing the
Hiram Cuevas:
amount of work that goes on in the summer. So for your ability
Hiram Cuevas:
to
Hiram Cuevas:
Bill Stites, TLIS: get away and actually feel like you're away
Hiram Cuevas:
really does speak to the quality of the teams that we put
Hiram Cuevas:
together. So I'm equally thankful when I have that
Hiram Cuevas:
opportunity here as well.
Hiram Cuevas:
Yeah, this summer I actually did not take the
Hiram Cuevas:
amount of time off I should have taken because I'm banking it.
Hiram Cuevas:
I'm banking some of this time because I'm a new grandfather.
Hiram Cuevas:
Nothing quite like it, and so when I need to take a day to go
Hiram Cuevas:
for a visit, I'm going to take a day and go for my visit, which
Hiram Cuevas:
is why you work hard during the summer sometimes.
Hiram Cuevas:
Bill Stites, TLIS: Exactly.
Hiram Cuevas:
Kevin Warenda, TLIS: Yeah, good for you, Hiram. Congratulations.
Hiram Cuevas:
Well, speaking of working hard, we've got a great guest today.
Hiram Cuevas:
Jason Epstein is director of technology at the Berkshire
Hiram Cuevas:
School, which, in full disclosure, is right up the
Hiram Cuevas:
street from my school, Hatcher School. Although, Jason, I don't
Hiram Cuevas:
think we get together as much as we should. But why don't you
Hiram Cuevas:
take a minute, introduce yourself to the listeners, tell
Hiram Cuevas:
us about yourself.
Hiram Cuevas:
Jason Epstein, TLIS: Absolutely. Thanks for having me here.
Hiram Cuevas:
First, I'm really excited to talk with y'all and see what
Hiram Cuevas:
happens. I am a 30-year tech veteran here started in a small
Hiram Cuevas:
startup school in California, and I've kind of made my way
Hiram Cuevas:
around getting over to the East Coast, and now here in the very
Hiram Cuevas:
bottom corner of Massachusetts, a lovely area called the
Hiram Cuevas:
Berkshires, hence the school name. I think now is a really
Hiram Cuevas:
unique time for us as technology leaders, and so it's been a
Hiram Cuevas:
really amazing last few years. I think since the pandemic, that
Hiram Cuevas:
it's really pushed me in ways that I didn't know I was going
Hiram Cuevas:
to be pushed before in this career. But hearkens me back to
Hiram Cuevas:
being able to be adaptive to whatever came. Happily, my wife
Hiram Cuevas:
works here at the school as well, so we're kind of all in.
Hiram Cuevas:
My daughter is now a graduate, and our two cats are the local
Hiram Cuevas:
mousers for the campus. So we are 100% Berkshire through and
Hiram Cuevas:
through, and love sharing that with whoever will listen.
Hiram Cuevas:
Bill Stites, TLIS: One thing I want to point out very quickly,
Hiram Cuevas:
and I know this is an auditory podcast. This is fair warning
Hiram Cuevas:
for Kevin because I want him to look around the squares. Each
Hiram Cuevas:
one of us, myself, Jason, and Hiram, we all have 30 plus
Hiram Cuevas:
years, and what do we all have in common? The gray beard, the
Hiram Cuevas:
bald head. So, Kevin, it's coming for you. I know Hiram's
Hiram Cuevas:
done a little work with AI to kind of put together what your
Hiram Cuevas:
future may look like, but it's coming.
Hiram Cuevas:
Kevin, Bill's already made a voodoo doll of
Hiram Cuevas:
you. Been putting lead pins in your head. It
Hiram Cuevas:
Kevin Warenda, TLIS: is striking. I was looking at the
Hiram Cuevas:
screen and thinking to myself, "Wow, yeah, I have the glasses,
Hiram Cuevas:
but other than that, it's like I don't even know who I'm talking
Hiram Cuevas:
to on the screen. They all look the same.
Hiram Cuevas:
Bill Stites, TLIS: Jason, I do have a quick starter question
Hiram Cuevas:
for you. Actually, you mentioned how close you are to Kevin. Can
Hiram Cuevas:
you tell us like a little bit about the school for those that
Hiram Cuevas:
might not know, like where you're located, the size of the
Hiram Cuevas:
school, your grades that you serve, what your team looks
Hiram Cuevas:
like, so on and so forth, just so people can get that feel for
Hiram Cuevas:
who we're talking to and what you're representing. Sure. So
Hiram Cuevas:
Berkshire School has been here since the early 1900s. It's a
Hiram Cuevas:
wonderful school nestled into the base of a mountain. Once you
Hiram Cuevas:
become familiar with Berkshire, you realize we use the term
Hiram Cuevas:
"under the mountain" a lot, which I absolutely love. We have
Hiram Cuevas:
entrances on campus to the Appalachian Trail, we're a
Hiram Cuevas:
boarding school that we do have some day students, population of
Hiram Cuevas:
about 430,
Hiram Cuevas:
Jason Epstein, TLIS: give or take, depending year to year,
Hiram Cuevas:
grades nine through 12. We have a number of countries
Hiram Cuevas:
represented as well as kids from all over the U.S. it's a
Hiram Cuevas:
wonderful population, really diverse. And the thing that I
Hiram Cuevas:
love most about Berkshire is, first and foremost, it's about
Hiram Cuevas:
people. We walk that walk and talk that talk, and it makes me
Hiram Cuevas:
really proud to be a part of this school.
Hiram Cuevas:
Kevin Warenda, TLIS: You're an independent boarding school now,
Hiram Cuevas:
but that was not always the case. I was actually saying
Hiram Cuevas:
before the podcast started, you're the kind of guy that's
Hiram Cuevas:
just been ever present to me throughout my career as well.
Hiram Cuevas:
I'm approaching 30 years as well, and I remember way back
Hiram Cuevas:
you and I were both, I think, at public school districts in
Hiram Cuevas:
Massachusetts. We were part of the Massachusetts Educational
Hiram Cuevas:
Technology Directors Association, which then became
Hiram Cuevas:
the Cosen Chapter for Massachusetts. I think we
Hiram Cuevas:
actually both served on the board of that at slightly
Hiram Cuevas:
different times, so you're someone who has actually been
Hiram Cuevas:
ever present throughout my career. But I know you started;
Hiram Cuevas:
you had some public school experience too. To maybe talk
Hiram Cuevas:
about that journey, similar to my own, where we kind of made it
Hiram Cuevas:
to independent and boarding schools. Talk about that
Hiram Cuevas:
transition for a moment, if you would.
Hiram Cuevas:
Jason Epstein, TLIS: So started out, I was actually at an
Hiram Cuevas:
independent day school for about nine years, and that's where I
Hiram Cuevas:
cut my teeth on everything. My wife, after we got married, we
Hiram Cuevas:
moved out to North Carolina, and that's where I hit public
Hiram Cuevas:
schools for a little while. I wanted to get a taste of that,
Hiram Cuevas:
and so my first two years, I was a social studies teacher in a
Hiram Cuevas:
middle school, after that they realized I knew a lot more about
Hiram Cuevas:
tech, and they moved me over to become the integrator for that
Hiram Cuevas:
school. As the what was that term? As the crow flies, or
Hiram Cuevas:
whatever. As the bird goes south, I went north, ended up at
Hiram Cuevas:
a small private school in Pennsylvania, as more of kind of
Hiram Cuevas:
a stepping stone up to Worcester Academy, which is when we met. I
Hiram Cuevas:
was working as CIO at Worcester Academy for about six years, had
Hiram Cuevas:
an amazing experience there, and really tried to get involved
Hiram Cuevas:
with statewide groups. Meta being the first one that I
Hiram Cuevas:
joined, as well as Mass Q, and I had been involved with ISTE
Hiram Cuevas:
since my very first days as well, I plodded around Worcester
Hiram Cuevas:
for a little while and had an opportunity back in North
Hiram Cuevas:
Carolina. We hopped down there, and when that opportunity slowed
Hiram Cuevas:
down, I moved back up here to the Berkshire School. I think
Hiram Cuevas:
Kevin, you might feel the same way. I don't know, but it's
Hiram Cuevas:
tough being here in the very end of Massachusetts, if you will,
Hiram Cuevas:
because a lot of the schools and everything is geolocated close
Hiram Cuevas:
to the Boston area. It's a three-hour drive, so I don't get
Hiram Cuevas:
out there all that frequently. Get to conferences and whatnot.
Hiram Cuevas:
I would really love it to figure out a way to get us here on the
Hiram Cuevas:
western side together more, because Kevin, like you and I,
Hiram Cuevas:
have been connected for a number of years, but I don't think I
Hiram Cuevas:
know the people in my geographic area as well as I should. And I
Hiram Cuevas:
think that's something that probably a lot
Hiram Cuevas:
Kevin Warenda, TLIS: of larger states could probably benefit
from:
is how do we connect geographically without having to
from:
take a major hiatus? You know, I can't just drive in less than an
from:
hour over to Boston to go to a one-day conference, like it
from:
becomes a real challenge. Now that my daughter's in college, I
from:
have some other opportunity to get out. I'm not worried about
from:
one of her parents not being home for her, but at the same
from:
token, three hours back and forth for a four-hour conference
from:
is not realistic. Yeah, well, I know Atlas is doing some
from:
regional meetups this year. I think maybe we'll have an
from:
opportunity. We can organize our own. I think that's best part
from:
about this community. As you mentioned, you were doing a lot
from:
statewide in Massachusetts. I felt the same way. I was in a
from:
public school district in Massachusetts for nine years,
from:
and the opportunities to connect with other directors. I was
from:
always searching for that. ISTE was a bit too large for me, and
from:
that's what I love about Atlas. And similar to what you said
from:
about the independent boarding school world, coming to Ashkes
from:
for me was great. The community is so much more connected. I
from:
think maybe because some of the schools are smaller, but
from:
definitely opportunity to explore connecting. And we
from:
encourage all our listeners find those regional meetups, create
from:
your own. I know Bill, you often talk about the New Jersey
from:
Association. I know there's something down in Virginia too,
from:
right, Hiram? That there's all these opportunities in these
from:
different organizations. Atlas is a great national
from:
organization, and certainly the conference is, you know,
from:
multi-day conference is worth traveling to. But you're right;
from:
those smaller opportunities for PD and connection, if you have
from:
to travel more time than it takes. To actually participate,
from:
sometimes that's a little tough. So maybe we'll see if we can put
from:
something together.
from:
Bill Stites, TLIS: I'm up here in northern New Jersey. I'm
from:
right next to New York City. I take advantage of a lot of stuff
from:
that the New York State Association does, because
from:
they've always been open and welcoming to people from other
from:
states going in. Whether that was attending their events,
from:
going up to the NEET conference at Mohank, which I talked about
from:
at nauseam, in terms of just what a great conference that is.
from:
But even like getting on their Slack channel and doing that, I
from:
found that cross state lines, particularly when we got on the
from:
podcast earlier, said you're at that intersection of like New
from:
York, Massachusetts, and Connecticut. Jumping around the
from:
region doesn't necessarily just need to be within the state.
from:
Beauty of independent schools. We're not bound by having to
from:
participate with the other schools in our state because of
from:
that. You can kind of mix and mash and go around those things.
from:
That's what I would encourage you to do because it's been
from:
great for me where I am right here next to New York City.
from:
Yeah, that's a great idea. I don't know why I almost had the
from:
state lines in my head for some reason as a geophont. It's your
from:
public school background. That's what that is. That's a public
from:
school background. There, yes. Got to get more of that
from:
independent vibe. You know, just going out and doing your own
from:
thing. I mean, that's what Hiram does. You know, he just he bebop
from:
around.
from:
Kevin Warenda, TLIS: Jason, you talked about kind of the
from:
evolution of your career, and I know a topic near and dear to
from:
you. You write about this. You talk about this. The evolving
from:
role of the tech director. We've touched on this a number of
from:
times on this podcast. Actually, I was lucky enough to fill in
from:
for Bill on a recent episode where Denise was actually the
from:
host, and it was Barbara Cohen from Brandeis Marin. We got on
from:
this topic. Hiram and Denise actually were asking her what
from:
makes a school person, and so I think this might be an extension
from:
of that conversation because we got to this place where we're
from:
going to talking about school people are problem solvers,
from:
right? Not problem creators. We're always looking to help out
from:
and add one more thing. I think the technology director role
from:
seems to be the epitome of that, right? We take on all these
from:
things. So maybe share with our listeners your thinking, your
from:
reflection on the evolution of the tech director role, how many
from:
hats we now wear, and where we're going with that,
Hiram Cuevas:
Kevin. I'd like to add to that, Jason. As a
Hiram Cuevas:
boarding school, that's a dimension that both you and
Hiram Cuevas:
Kevin share that Bill and I do not really understand, and it's
Hiram Cuevas:
important for our listeners to understand that 24/7 environment
Hiram Cuevas:
that you all are coming from.
Hiram Cuevas:
Jason Epstein, TLIS: Really good point, Hiram and Kevin. I'll
Hiram Cuevas:
start with you, and I'll kind of blend in the boarding school
Hiram Cuevas:
part. Back when I started this, you know, when we all started
Hiram Cuevas:
this, tech was really about okay, can we turn on a computer?
Hiram Cuevas:
Can we get kids using Word or PowerPoint in a classroom? Do a
Hiram Cuevas:
presentation. Okay, they're using technology. That was the
Hiram Cuevas:
extent of it. And then as time went, it started getting into
Hiram Cuevas:
audio, video, and then started getting into kids producing
Hiram Cuevas:
podcasts. And our skill set had to keep growing. Some schools,
Hiram Cuevas:
like the public schools, have district level tech offices that
Hiram Cuevas:
send people out when the back end doesn't work, we get into
Hiram Cuevas:
more independent schools, and I find personally most people
Hiram Cuevas:
we're managing our stuff in house. Though some do bring in
Hiram Cuevas:
outside vendors to kind of manage their back end. I'm lucky
Hiram Cuevas:
enough to have a fantastic network administrator. He's been
Hiram Cuevas:
my right arm since I got here. He's been at the school for
Hiram Cuevas:
about 20 years now. He's retiring soon. It's making me a
Hiram Cuevas:
little nervous. If you're a network administrator looking
Hiram Cuevas:
for a really great, quiet, beautiful area, hit me up on
Hiram Cuevas:
LinkedIn. We're going to be starting to work towards looking
Hiram Cuevas:
to facilitate that change. But who knows? One of my other
Hiram Cuevas:
teammates might want to jump up into that position, which is the
Hiram Cuevas:
other thing that we'll talk about at some point: is our
Hiram Cuevas:
teams and how we organize and utilize those teams to become so
Hiram Cuevas:
great that it's not dependent on any one person to go. I digress.
Hiram Cuevas:
Moving back towards the role of the tech director, it started
Hiram Cuevas:
out. It was just tech. How do you use computers? Do you do the
Hiram Cuevas:
back end? Do you do the front end? But then it started getting
Hiram Cuevas:
into cybersecurity. And so, do you in house it? Do you outhouse
Hiram Cuevas:
it? Do you use one person to kind of be your person and then
Hiram Cuevas:
connect with contractors? They're umpteen different ways.
Hiram Cuevas:
Now we're talking about professional development, we
Hiram Cuevas:
talk about how do we train our students. We talk about policy.
Hiram Cuevas:
These are all things that are kind of coming together. What I
Hiram Cuevas:
realized is the plate, the person, the tech director, the
Hiram Cuevas:
CIO, whatever your title is. There's a gajillion of them. Our
Hiram Cuevas:
plate has stayed the same size, but stuff keeps piling on,
Hiram Cuevas:
piling on, and it's very infrequent that we get to
Hiram Cuevas:
offboard something, whether it's because somebody really likes
Hiram Cuevas:
doing something or using a certain tool, and they're not
Hiram Cuevas:
ready to get rid of it, so we can't offboard or move away from
Hiram Cuevas:
certain software or other applications. It could be.
Hiram Cuevas:
Remember, you know VCRs started going away, but we didn't have
Hiram Cuevas:
VCRs in every classroom anymore, and they were getting harder and
Hiram Cuevas:
harder to find. So, how do you transition people away from
Hiram Cuevas:
technology that's being sunsetted when you bring the
Hiram Cuevas:
boarding school aspect into it? Now we're talking about software
Hiram Cuevas:
that needs to help record locations where students are at
Hiram Cuevas:
any given time, we need to be able to have certain reporting.
Hiram Cuevas:
We want to get into a student when a day in class, when are
Hiram Cuevas:
they not in class, when are they at the health center, when are
Hiram Cuevas:
they going away for a weekend with their parents? If you're a
Hiram Cuevas:
school like ours that has day students as well, when are they
Hiram Cuevas:
getting to campus? When are they leaving campus for the night?
Hiram Cuevas:
It's 24/7, and that's something important. In fact, I live on
Hiram Cuevas:
campus, so if something happens, I'm kind of on call 24/7. At
Hiram Cuevas:
least I don't have to commute to handle that. I can handle most
Hiram Cuevas:
everything from home because I can connect into the network. So
Hiram Cuevas:
it's been a really interesting ride. I think it's really
Hiram Cuevas:
important that our positions are around the executive leadership
Hiram Cuevas:
table, whatever your school may call it. You should have a
Hiram Cuevas:
direct conduit to your head of school. You shouldn't be two,
Hiram Cuevas:
three people down the hierarchy tree. And I think leading with
Hiram Cuevas:
technology is really important to give people that perspective
Hiram Cuevas:
because let's face it, nothing can be done, nothing functions
Hiram Cuevas:
without technology anymore.
Hiram Cuevas:
I said the day I retire is the day toilets get networked
Hiram Cuevas:
because I got to draw a line somewhere. That's my line, my
Hiram Cuevas:
personal line is that I just can't do that, but the reality
Hiram Cuevas:
of it is, everything has a network drop, or everything
Hiram Cuevas:
needs wireless, or whatever the case may be. It's something that
Hiram Cuevas:
we need to keep abreast of, and we need to keep our school
Hiram Cuevas:
administration abreast of as well. Jason, I just warn you:
Hiram Cuevas:
never go to Japan
Hiram Cuevas:
Bill Stites, TLIS: because friends of mine have got toilets
Hiram Cuevas:
that are from Japan, and I would assume they're networked at this
Hiram Cuevas:
point. You sit down next to them, and there's like a keypad
Hiram Cuevas:
that you can press that controls different things. So it's
Hiram Cuevas:
coming, my friend. So I just warn you on that. One of the
Hiram Cuevas:
things that you mentioned that I would like to just let our
Hiram Cuevas:
audience know a little bit more about, because I think it's
Hiram Cuevas:
always helpful, is you mentioned your staff. What does your
Hiram Cuevas:
department look like in terms of the size and the different
Hiram Cuevas:
positions that you've got to support that 24/7 nature that
Hiram Cuevas:
you've got there at the school from an IT perspective and from
Hiram Cuevas:
an ed tech perspective? What's that look like? Believe it or
Hiram Cuevas:
not, there's only four of us. We've got myself. I have a
Hiram Cuevas:
network administrator. I have a hardware software administrator
Hiram Cuevas:
deals with all school issue technology, and I've got someone
Hiram Cuevas:
who does kind of first level, first tier help on the fly. And
Hiram Cuevas:
she's also audio visual manager. She edits a lot of video. She
Hiram Cuevas:
manages our theater and other locations that
Hiram Cuevas:
Jason Epstein, TLIS: have built in AV as opposed to something
Hiram Cuevas:
that's coming with the teacher to a given space. That's pretty
Hiram Cuevas:
much who we are as four of us. But there are also other people
Hiram Cuevas:
around campus who have tasks, have jobs, have parts of their
Hiram Cuevas:
careers that connect back to us. So we've got our registrar, but
Hiram Cuevas:
she really also manages most of Veracross RSIS. I do some of the
Hiram Cuevas:
back end stuff when it comes to re-enrollment and swapping
Hiram Cuevas:
stuff, but she really does the day-to-day academics in the SIS.
Hiram Cuevas:
We have someone in our college counseling office who handles
Hiram Cuevas:
Naviance through and through. I really don't have to touch that,
Hiram Cuevas:
we have people in the advancement office who are
Hiram Cuevas:
focused on our databases. There, we offer them technical support,
Hiram Cuevas:
but for the most part, they're managing their own data. So
Hiram Cuevas:
we've got people in these other offices. I've got someone who
Hiram Cuevas:
actually shares an IT office with my network administrator,
Hiram Cuevas:
but he's really on campus safety and does a lot of the safety
Hiram Cuevas:
infrastructure stuff, so cameras, door locks, entry
Hiram Cuevas:
stuff. Now working towards a visitor center, and he's got all
Hiram Cuevas:
those different pieces in his belt. But most people will see
Hiram Cuevas:
him as an IT person. We have one person who's a part-time ed tech
Hiram Cuevas:
coordinator. He does a lot of the PD works with different
Hiram Cuevas:
teachers on how to do things in their different classes, but
Hiram Cuevas:
right now it's still a part-time job, and he technically reports
Hiram Cuevas:
to the dean of academics. Him and I have a great relationship.
Hiram Cuevas:
We meet to make sure that everything flows. Something I
Hiram Cuevas:
should say when I'm talking about this team and how it
Hiram Cuevas:
extends out beyond IT is something that our school has
Hiram Cuevas:
worked really hard toward is when anything that has
Hiram Cuevas:
technology related to it is being brought into the school.
Hiram Cuevas:
There's a bit of a gatekeep that has to go through my office so
Hiram Cuevas:
we can make sure that it's going to work not only with our
Hiram Cuevas:
current systems but also the way that it might have security
Hiram Cuevas:
issues. So something. Working a lot on cybersecurity, looking at
Hiram Cuevas:
vendors, making sure they have their SOC two reports, make sure
Hiram Cuevas:
they have trust centers, and so we're working to try and find
Hiram Cuevas:
the right way to garner all this data and all this information,
Hiram Cuevas:
and to make sure that people are staying safe, that people are
Hiram Cuevas:
using the tools that are right for the environment, and really
Hiram Cuevas:
trying to create an ecosystem that achieves two things. It
Hiram Cuevas:
needs to achieve great things for students. First and
Hiram Cuevas:
foremost, are students getting the tools and training that they
Hiram Cuevas:
need to be the best functioning human beings they can be when
Hiram Cuevas:
they leave our school? Part A. Part B is are the tools that
Hiram Cuevas:
we're using and the things that we're bringing in safe. Are they
Hiram Cuevas:
allowing our students to work in a safe environment? Are we
Hiram Cuevas:
making sure all our information and personal data is safe in any
Hiram Cuevas:
number of different ways? And so, someone needs to kind of be
Hiram Cuevas:
the spearhead. And my office
Hiram Cuevas:
Kevin Warenda, TLIS: has done that. Our office has been that
Hiram Cuevas:
spearhead. I'm really proud of what we've accomplished. And
Hiram Cuevas:
what's striking to me, all these functions exist throughout all
Hiram Cuevas:
of our schools. We're all different in terms of who and
Hiram Cuevas:
how and the structure, right? All these things still have to
Hiram Cuevas:
be done. It's just whether or not you have the resources to do
Hiram Cuevas:
that centrally, whether that's distributed. It almost strikes
Hiram Cuevas:
me that the IT role has really become more like the
Hiram Cuevas:
collaborator in chief, right, or a mediator. Like we have to
Hiram Cuevas:
understand and see all these pieces, and then recognize
Hiram Cuevas:
whether it's within our own departmental purview or whether
Hiram Cuevas:
we're actually collaborating across department with someone
Hiram Cuevas:
else who might be doing that. But the functions are all the
Hiram Cuevas:
same, and they've all grown just the same. We all have to do all
Hiram Cuevas:
these things. Boarding schools, in particular, have additional
Hiram Cuevas:
items, right? That we have to handle, like you said, with the
Hiram Cuevas:
24/7 or the fact that we're providing internet service to
Hiram Cuevas:
faculty homes that may live on campus too. Those are some added
Hiram Cuevas:
pieces, certainly for boarding schools. But all these things
Hiram Cuevas:
are the same in terms of the school needing to provide or
Hiram Cuevas:
support it. Just the way in which we go about that's
Hiram Cuevas:
different. So, what's your experience been throughout your
Hiram Cuevas:
career and serving as that role in terms of that collaborator
Hiram Cuevas:
and having to kind of work across departments, break down
Hiram Cuevas:
silos to really effectively manage and be that traffic cop
Hiram Cuevas:
or central clearinghouse for the understanding and to be managing
Hiram Cuevas:
those risks that maybe aren't being handled within the
Hiram Cuevas:
departments. What's your experience been there in that
Hiram Cuevas:
collaboration?
Hiram Cuevas:
Jason Epstein, TLIS: It's been an interesting experience in my
Hiram Cuevas:
years in the different schools. First and foremost, I always
Hiram Cuevas:
needed to ingratiate myself into more the faculty side than the
Hiram Cuevas:
staff side. Happily, because I've taught in the classroom and
Hiram Cuevas:
I've been kind of a core subject teacher. Being able to talk like
Hiram Cuevas:
a teacher has helped so much. Now, it's not always the easiest
Hiram Cuevas:
thing to do because, depending on your school, some people see
Hiram Cuevas:
technology as the people behind the curtain, so they don't see
Hiram Cuevas:
you as forward facing, and so that's something sometimes you
Hiram Cuevas:
have to fight for. The other thing is sometimes the title,
Hiram Cuevas:
and it's going to sound silly because the title is just words.
Hiram Cuevas:
But being a director of technology is seen different
Hiram Cuevas:
than being a CIO. Is seen different than being a dean of
Hiram Cuevas:
technology. So one of the things I write about on LinkedIn, one
Hiram Cuevas:
of the things I talk about when I can get a platform is the fact
Hiram Cuevas:
that I think this position needs to have a title that is
Hiram Cuevas:
universal, one that can encompass, because I think if
Hiram Cuevas:
people see that, then whoever's under you should fit, like you
Hiram Cuevas:
said, Kevin, should fit what the school is about, what the
Hiram Cuevas:
school's resources are, what the school's needs are, but you need
Hiram Cuevas:
to have that one person who can be that collaborator in chief,
Hiram Cuevas:
that mediator, that translator. I can't tell you how much of my
Hiram Cuevas:
career has been spent translating what people think
Hiram Cuevas:
they hear to what it actually is when it comes to technology,
Hiram Cuevas:
especially technology change. I think if we can get to that
Hiram Cuevas:
point where school leaders are seeing our position as one
Hiram Cuevas:
essential at the top echelon of leadership, but two that our job
Hiram Cuevas:
transcends one box. I try and explain our position as we are
Hiram Cuevas:
an umbrella that encompasses a whole lot of stuff. Sometimes
Hiram Cuevas:
directly with our people on our teams, sometimes indirectly
Hiram Cuevas:
working with other offices, whether it's on the staff or the
Hiram Cuevas:
faculty side, department chairs, maybe a teacher who wants to do
Hiram Cuevas:
something out of the box and needs some coaching and needs
Hiram Cuevas:
some support-it all falls under this really, really big
Hiram Cuevas:
umbrella. And I found my best tool in all of it is to know
Hiram Cuevas:
what is happening, to know what is going on in all aspects. In
Hiram Cuevas:
my school, including at the board level, I really try and
Hiram Cuevas:
make it a point that I run the technology for the board
Hiram Cuevas:
meeting. But part of that is making sure that I am a face and
Hiram Cuevas:
that I am seen, but also that I'm hearing. I don't say a word
Hiram Cuevas:
during these meetings short of hello and goodbye, but
Hiram Cuevas:
understanding directions that the school is going in
Hiram Cuevas:
understanding what people's fears and trepidations are.
Hiram Cuevas:
Allow me to make better decisions as part of the school
Hiram Cuevas:
leadership.
Hiram Cuevas:
So, Jason, let's tease this out a little bit
Hiram Cuevas:
more. You've piqued my interest. I'd be curious what would be
Hiram Cuevas:
your ideal org structure, recognizing that it may not be
Hiram Cuevas:
the setup that you would need at Berkshire, but let's take an
Hiram Cuevas:
Atlas approach. What would that ideal org structure look like?
Hiram Cuevas:
What title do you think you might give said person? The
Hiram Cuevas:
skill sets that you're talking about are very broad.
Hiram Cuevas:
Jason Epstein, TLIS: You're absolutely correct. If it came
Hiram Cuevas:
to org structure, I think our position-we'll put the title
Hiram Cuevas:
just on the side for right now-needs to be right under the
Hiram Cuevas:
head of school. When people start getting put under business
Hiram Cuevas:
leaders, start getting put under academic leaders, whatever the
Hiram Cuevas:
case may be, even sometimes being put under an assistant or
Hiram Cuevas:
associate head of school breaks the chain and the realization
Hiram Cuevas:
that what we're doing has direct impact across the board. So I
Hiram Cuevas:
think that's first and foremost. Title I prefer again in my
Hiram Cuevas:
little world. I like the idea of CIO because it's known beyond
Hiram Cuevas:
the education frame, but also because I think it lends itself
Hiram Cuevas:
to some cachet. When you have a C-level position, there's some
Hiram Cuevas:
cachet with it. Not only within the school, but also as you're
Hiram Cuevas:
migrating around, meeting others, and trying to figure out
Hiram Cuevas:
who are my peers, we get to things like this, and we can
Hiram Cuevas:
figure it out. That's where my vision stops because I think it
Hiram Cuevas:
is absolutely dependent on the school and what their goals are
Hiram Cuevas:
set forth by both the head and the CIO to fill in. It may not
Hiram Cuevas:
be the best choice to have a network administrator in house.
Hiram Cuevas:
You may want to have a company manage your infrastructure that
Hiram Cuevas:
has the resources to do what you need to do. But you know what?
Hiram Cuevas:
Having somebody who, because you're a one-to-one school,
Hiram Cuevas:
maybe you're an Apple school, understands these platforms
Hiram Cuevas:
better. Maybe you don't film as much as the next school. Maybe
Hiram Cuevas:
you don't need someone who's going to be not only an audio
Hiram Cuevas:
video manager, but have the ability to professionally edit
Hiram Cuevas:
your school stuff. Maybe that falls into your communications
Hiram Cuevas:
department, so you don't need that kind of person. You know,
Hiram Cuevas:
you could be like my school where we've got one certified
Hiram Cuevas:
Apple repair group about 20 to 30 minutes from the school, so
Hiram Cuevas:
within that window, that's who we go for repairs. If you're
Hiram Cuevas:
located somewhere where there's not someone, you might need to
Hiram Cuevas:
get someone certified and your school certified to be able to
Hiram Cuevas:
fix apples, because otherwise you're mailing everything out. I
Hiram Cuevas:
mean, there's so many different permutations. Cybersecurity. I'm
Hiram Cuevas:
a big fan of outsourcing because there's no way I can afford
Hiram Cuevas:
someone at the level that I would like, and if I did put all
Hiram Cuevas:
that money into getting one person for 40 hours, that same
Hiram Cuevas:
money spent is probably getting me a company to manage that's
Hiram Cuevas:
there 24/7, 365. Again, personal preference on that, but that's
Hiram Cuevas:
where your school needs to understand where its priorities
Hiram Cuevas:
are. I think it's a work in progress. But I've gotten as far
Hiram Cuevas:
as our position, and frankly, it's a large umbrella, and the
Hiram Cuevas:
plate is over full. I mean, now with AI coming into the mix, is
Hiram Cuevas:
a whole other batch of things we need to worry about. But unless
Hiram Cuevas:
we're given the time, because we have a team that could support
Hiram Cuevas:
the ongoing operations, sometimes that stuff's going to
Hiram Cuevas:
fall through the cracks.
Hiram Cuevas:
So, Jason, I find myself having to have more
Hiram Cuevas:
conversations now with legal, especially when it comes to
Hiram Cuevas:
things like terms of service and some of the DPAs that we're
Hiram Cuevas:
starting to engage with. There are resources out there. Does
Hiram Cuevas:
Berkshire have its own in-house attorney, or do you have to go
Hiram Cuevas:
out? That's actually a question for each of you because I know
Hiram Cuevas:
some schools have their own attorneys, their own counsel on
Hiram Cuevas:
their staff.
Hiram Cuevas:
Jason Epstein, TLIS: We do not have that, though. I do send a
Hiram Cuevas:
lot of things to legal to go over, especially on the policy
Hiram Cuevas:
end of things, I think it's going to be a work in progress.
Hiram Cuevas:
But with the amount of PII that is generated at a school, I
Hiram Cuevas:
think it's really important to make sure you're doing what you
Hiram Cuevas:
can. I know I go around and I do information training with all of
Hiram Cuevas:
my different departments as I can about how to deal with not
Hiram Cuevas:
only physical data but. Digital data, it takes time and it takes
Hiram Cuevas:
thinking. We have a written information security plan that I
Hiram Cuevas:
had legal go over to make sure I was asking the right things and
Hiram Cuevas:
making sure that we were headed down the right path. And every
Hiram Cuevas:
year we have to go through and make sure we get our eyes dotted
Hiram Cuevas:
and tees crossed for cybersecurity to make sure we
Hiram Cuevas:
can get our insurance, our cyber insurance in place, and trying
Hiram Cuevas:
to stay ahead of that. So it is definitely a challenge and
Hiram Cuevas:
expensive at times because you're engaging the legal. But
Hiram Cuevas:
the reality of it is, I think more of us are going to get hit
Hiram Cuevas:
when one of our vendors gets hit than our own data. Personal
Hiram Cuevas:
choice. I'm seeing way more hits on things like Canvas. You know,
Hiram Cuevas:
well that threw a lot of us for a loop that we're still trying
Hiram Cuevas:
to climb out of. Third party risk is just enormous. It takes
Hiram Cuevas:
a big part of my job every day trying to get information and
Hiram Cuevas:
making sure people are doing what they need to do on their
Hiram Cuevas:
end to make sure I can say we're doing our due diligence on our
Hiram Cuevas:
end.
Hiram Cuevas:
Yeah, which doesn't include any sub
Hiram Cuevas:
processors that third party vendor is utilizing.
Hiram Cuevas:
Jason Epstein, TLIS: Exactly. I've read more terms of service
Hiram Cuevas:
than I ever care to admit.
Hiram Cuevas:
Bill Stites, TLIS: Yeah, terms of service should be a four
Hiram Cuevas:
letter word at this point. I think it's definitely
Hiram Cuevas:
like love, right?
Hiram Cuevas:
Bill Stites, TLIS: It's unbelievable. How has studying
Hiram Cuevas:
for taking and receiving the T list impacted you, either
Hiram Cuevas:
personally, professionally, within the context of the
Hiram Cuevas:
school? What were your motivations there, and what have
Hiram Cuevas:
the benefits been for you? I went back and forth on whether
Hiram Cuevas:
or not I should do it, and part of me realized that you know
Hiram Cuevas:
because TLIS is through Atlas, and this is a group I've really
Hiram Cuevas:
come to use as kind of my first team offense
Hiram Cuevas:
Jason Epstein, TLIS: and defense, that getting certified
Hiram Cuevas:
within the Atlas paradigm was a good thing to do, and as I
Hiram Cuevas:
studied for it, I realized where my own weaknesses are, which is
Hiram Cuevas:
not a bad thing. Understanding where you can grow is what
Hiram Cuevas:
really separates the good from the great. If you think, "Oh,
Hiram Cuevas:
I've got this, you're done before you start, because our
Hiram Cuevas:
environment is changing faster than any of us can learn or
Hiram Cuevas:
change, and so understanding at least where your starting point
Hiram Cuevas:
is is a huge win. I did the studying, I passed, and was able
Hiram Cuevas:
to put the little icon in my email signature, and that's all
Hiram Cuevas:
great and dandy. But what it does is it aligns me and sets me
Hiram Cuevas:
in with a pool of other people like me who have done this, and
Hiram Cuevas:
I think having that group, whether physical or digital, is
Hiram Cuevas:
tremendously important. I look for that when I look at someone
Hiram Cuevas:
who I'm connecting with through Atlas. I look for that insignia,
Hiram Cuevas:
and it doesn't mean I'm writing people off who don't have it.
Hiram Cuevas:
What it means is, I know they understand that they've walked
Hiram Cuevas:
the walk already, and that gives me something to start from. It
Hiram Cuevas:
gives me a starting point. Again, they may just be like,
Hiram Cuevas:
you know, what this is not my cup of tea, and that's fine. And
Hiram Cuevas:
they're still perfectly incredible at what they're
Hiram Cuevas:
doing. I haven't met anybody, at least yet that I've wanted to
Hiram Cuevas:
write off, but there are people who I'm like, okay, you have not
Hiram Cuevas:
dealt with X or Y or Z, and that's okay. But I'm looking for
Hiram Cuevas:
this resource for whatever reason. So I think the effort,
Hiram Cuevas:
the time, the expense to get that certification is really
Hiram Cuevas:
important because our careers are all fluid. When I go to the
Hiram Cuevas:
next school, if I go to another school, it's getting late in my
Hiram Cuevas:
career. Having that and being able to say like I am certified,
Hiram Cuevas:
I think goes a long way in the independent school circle. And
Hiram Cuevas:
if a school doesn't know about Atlas, that's also something
Hiram Cuevas:
that raises some red flags
Hiram Cuevas:
Kevin Warenda, TLIS: or other things. Yeah, I had my own
Hiram Cuevas:
motivations for taking the T list, and one of those is to
Hiram Cuevas:
contribute to something that could actually help us with
Hiram Cuevas:
succession planning. You've been talking about just the evolution
Hiram Cuevas:
of this job, especially in independent schools, as I've
Hiram Cuevas:
learned, having come from public K 12 as well as higher ed. This
Hiram Cuevas:
is a different animal. There are many things that rhyme, but
Hiram Cuevas:
there are some very unique things about the culture and the
Hiram Cuevas:
independent nature of the schools. So, what I value, not
Hiram Cuevas:
necessarily for myself in having it, but in that it exists, is it
Hiram Cuevas:
is a good metric to say this person has demonstrated a level
Hiram Cuevas:
of expertise across all the domains necessary to do this
Hiram Cuevas:
job, and so for a school that otherwise doesn't have a way to
Hiram Cuevas:
evaluate a candidate, this is a great barometer for that too.
Hiram Cuevas:
How are you thinking about succession planning? Or as you
Hiram Cuevas:
said, you're getting late in your career, perhaps. Maybe
Hiram Cuevas:
you'll make a move. Maybe you'll stay. But at some point, we're
Hiram Cuevas:
all going to leave. How are you?
Hiram Cuevas:
Jason Epstein, TLIS: Thinking about talent development or
Hiram Cuevas:
succession planning, and what comes after you. It's a great
Hiram Cuevas:
question. Something I believe in. I call it the hydro model.
Hiram Cuevas:
Is that when one head gets cut off, two can pop up in its
Hiram Cuevas:
place. So I really try and cross train and encourage my team to
Hiram Cuevas:
cross train on everything that's possible, including what I do.
Hiram Cuevas:
Now there are pieces that are more appropriate for X or Y or
Hiram Cuevas:
Z, but for the most part, I really want what we do to be. I
Hiram Cuevas:
want the curtain to be removed. I want people to see what we do,
Hiram Cuevas:
know what we do, and I want to teach people what we do within
Hiram Cuevas:
my team. Super important. So two years ago, I brought in a
Hiram Cuevas:
software app that allows us to document everything, everything,
Hiram Cuevas:
everything, and that's something that all of my team has
Hiram Cuevas:
directives to do. Is that when we do a task, whether it's
Hiram Cuevas:
something we do every day and it's like rote at this point, or
Hiram Cuevas:
it's something new, we document it, and even if we document it
Hiram Cuevas:
in another platform, making sure we're linked over, making sure
Hiram Cuevas:
we're connected, is really, really important. So, for
Hiram Cuevas:
instance, as I mentioned, my network administrator is
Hiram Cuevas:
leaving. I'm looking at my hardware software guy to be his
Hiram Cuevas:
potential successor, and so knowing that that individual
Hiram Cuevas:
knows what the network admin does and how to do it is really
Hiram Cuevas:
important. So there's time set aside every week to get those
Hiram Cuevas:
two talking, get those two sharing. I bring in my other
Hiram Cuevas:
teammates, and when I'm working on something like, here's what
Hiram Cuevas:
I'm doing. You know, I'm sharing this Google Doc with you, or I'm
Hiram Cuevas:
sharing this document so you understand what I'm working on
Hiram Cuevas:
right now. You know, when it comes to budget time, I don't do
Hiram Cuevas:
that in a vacuum. Okay, these are reoccurring costs. Do we
Hiram Cuevas:
still need them? Why are we using them? What can you tell me
Hiram Cuevas:
about them? Should someone else know about them.dot.dot.so? for
Hiram Cuevas:
succession, we all have to have the humility to say we are all
Hiram Cuevas:
replaceable. Period. That's a given fact. If that's the given
Hiram Cuevas:
fact, how are we going to leave our position for the next person
Hiram Cuevas:
that comes in? And for me, if someone's coming in blind,
Hiram Cuevas:
they're going to have the documents to help them see
Hiram Cuevas:
almost immediately, but also they'll have the people to talk
Hiram Cuevas:
to, they're going to have a team. Rarely, I have heard of
Hiram Cuevas:
it. I have not seen it. Where a whole team walks, like, all
Hiram Cuevas:
right, we're done. We've done our thing. We're all moving on
Hiram Cuevas:
to something else. I have not seen that. So when I have left
Hiram Cuevas:
the place, or one of my team members have left the place,
Hiram Cuevas:
there has been not only a breadcrumb trail of paper or
Hiram Cuevas:
digital, but there's also a breadcrumb trail of people. So
Hiram Cuevas:
someone is coming in, and they have the human resources as well
Hiram Cuevas:
as the documentation to hopefully give a solid
Hiram Cuevas:
transition.
Hiram Cuevas:
There are a lot of nuggets in there that I'm taking
Hiram Cuevas:
back with me. The
Hiram Cuevas:
Bill Stites, TLIS: breadcrumb tour of people, love that.
Hiram Cuevas:
What's interesting, Jason, that you bring up, and it's something
Hiram Cuevas:
that I struggle with at our school often, is the idea of
Hiram Cuevas:
cross training. You know, I think is incredibly important
Hiram Cuevas:
because right now I'm in a situation where there's really
Hiram Cuevas:
four of us that are working year round, that are at the front of
Hiram Cuevas:
the IT side of things. I've got people that kind of split roles
Hiram Cuevas:
between, but there's really four of us. I'm in right now. My
Hiram Cuevas:
assistant director's in. One of my lead techs is actually out on
Hiram Cuevas:
vacation, and one of my others, he's okay, but he was in an
Hiram Cuevas:
accident, so he's recovering from that at this point. But the
Hiram Cuevas:
problem is, two of those people are prime like JAF
Hiram Cuevas:
administrators. So now there's stuff that needs to go on where
Hiram Cuevas:
I was in terms of planning vacation schedules. I was
Hiram Cuevas:
covered, but now because I'm in this position where I've got
Hiram Cuevas:
somebody who's unexpectedly out, we're trying to balance those
Hiram Cuevas:
things. And it's interesting. You can document things, you can
Hiram Cuevas:
cross train as best as possible, but the level to which you do
Hiram Cuevas:
that is always interesting because you need to strike that
Hiram Cuevas:
balance. One of the things that we've talked about here, you
Hiram Cuevas:
know, maybe there are too many cooks in the kitchen. Like we've
Hiram Cuevas:
got this recipe, but everyone's kind of putting it together a
Hiram Cuevas:
little different. So when you get that final finished product,
Hiram Cuevas:
it was like tastes the same, but it's not exactly the same. So
Hiram Cuevas:
how do we deal with those things and we clean those things up?
Hiram Cuevas:
And that's where some of the cruff can develop some of those
Hiram Cuevas:
things. So I think as much as we work to cross drain, there's
Hiram Cuevas:
also got to be this balance of documentation and knowledge
Hiram Cuevas:
transfer when those people come back and step in to make sure
Hiram Cuevas:
that we're all aligned. Because what I find myself doing at
Hiram Cuevas:
times is looking and saying, "All right, what was missed?
Hiram Cuevas:
What wasn't? How do we need to do that to avoid doubling up on
Hiram Cuevas:
the work? So I, my only point here is striking that balance
Hiram Cuevas:
and trying to figure that out and how hard that is,
Hiram Cuevas:
particularly.
Hiram Cuevas:
Jason Epstein, TLIS: When you are a small staff, as you are,
Hiram Cuevas:
how do you strike that balance? How do you find that equilibrium
Hiram Cuevas:
to make sure that things move ahead and do so consistently?
Hiram Cuevas:
When I figure that out, Bill, you will be the first to know.
Hiram Cuevas:
Thank you. I appreciate it. I got to be honest. Striking
Hiram Cuevas:
balance has never been a strong suit of mine, and I'm definitely
Hiram Cuevas:
someone who, if I see a gap, I've got to fill it. It's my
Hiram Cuevas:
department. I've got to take the lead, and that's great. But the
Hiram Cuevas:
older we get, the slower we get. The more that gets put on the
Hiram Cuevas:
plate, it gets harder to do that. You can't take it all on
Hiram Cuevas:
yourselves, and that's my hardest thing. I try very hard
Hiram Cuevas:
when I go home to be able to go home and only be on call for
Hiram Cuevas:
those things that I would venture to say are emergent. You
Hiram Cuevas:
know, my phone goes to Do Not Disturb, and the head of school
Hiram Cuevas:
and the CFO can get me if they need me. My team can get me if
Hiram Cuevas:
they need me, but I really want to time out for a while. And I
Hiram Cuevas:
think that is the other half of what you were talking about. Is
Hiram Cuevas:
that we've got all these things that we need to get done, and we
Hiram Cuevas:
have to find balance. But part of finding that balance is being
Hiram Cuevas:
able to turn off and really re-energize. A hard lesson I'm
Hiram Cuevas:
learning is how to look at something and say, "Okay, this
Hiram Cuevas:
is not emergent. This can hold. The school's not going to burn
Hiram Cuevas:
down. Any of these things, it's not going to happen. I need to
Hiram Cuevas:
be able to say that in my own head. Say, you know what? It's
Hiram Cuevas:
just going to have to wait. And so, like when you have someone
Hiram Cuevas:
out who it's a surprise, you got to look at okay, what's falling
Hiram Cuevas:
through the cracks and what's okay to fall through the cracks
Hiram Cuevas:
to come back. What am I bookmarking for later? And like
Hiram Cuevas:
I said, I can't say I'm good at it. I can't say I'm you know the
Hiram Cuevas:
balance thing is my strong suit, but it's something I'm aware of
Hiram Cuevas:
at least. So I think it's important to have it in your
Hiram Cuevas:
mind. But it's going to be really individual to each school
Hiram Cuevas:
because we have to understand what risk can we absorb, what
Hiram Cuevas:
things can be put on simmer, if you will, until we get the
Hiram Cuevas:
important stuff ironed out.
Hiram Cuevas:
Kevin Warenda, TLIS: I appreciate that lens. I think
Hiram Cuevas:
that's practical advice for all of us. I've had to adopt that
Hiram Cuevas:
mentality myself. Right when something comes in, you know
Hiram Cuevas:
everything's on fire according to the person that's bringing it
Hiram Cuevas:
to you. So I think first: is anyone in danger as a result of
Hiram Cuevas:
this, or is there a real substantive risk to the school
Hiram Cuevas:
that needs to be addressed? And if the answer is no to either of
Hiram Cuevas:
those, I can pause, or I can delegate, or I can come back to
Hiram Cuevas:
it. So I think that's real practical advice you have there,
Hiram Cuevas:
and the right way to handle it, based on how much is on our
Hiram Cuevas:
plate. Are there any topics or anything that you hoped we'd ask
Hiram Cuevas:
about, or something you wanted to talk about, this would be an
Hiram Cuevas:
opportunity to bring those up now.
Hiram Cuevas:
Jason Epstein, TLIS: I've really appreciated this call, this
Hiram Cuevas:
podcast, this discussion. It's you know talking with people who
Hiram Cuevas:
I greatly respect helps to put things in perspective, and I
Hiram Cuevas:
have the advantage of being able to see you and see the head nods
Hiram Cuevas:
and to see smiles and points and to get that validation, and I
Hiram Cuevas:
think that's one thing. Like if anybody leaves here with
Hiram Cuevas:
anything, the reality of it is technology and technology
Hiram Cuevas:
leadership is generally a thankless position. We're not
Hiram Cuevas:
going to get that validation all the time, and it's not
Hiram Cuevas:
intentional. You know, I always laugh and say, people when they
Hiram Cuevas:
come to my office, they don't come just to say hi. The first
Hiram Cuevas:
words before hi are, "I've got a problem. That's who we are.
Hiram Cuevas:
That's what we do. People look to us to fix. That doesn't mean
Hiram Cuevas:
they're not grateful, but when we can look towards each other,
Hiram Cuevas:
that's where the validation should come when your peers can
Hiram Cuevas:
say to you, "I was really good, or "I wish I would have thought
Hiram Cuevas:
of that, or "I'm doing the same thing. I'm having great success.
Hiram Cuevas:
Keep it up. Any of those things, which is why another reason I
Hiram Cuevas:
talk about wanting to have some sort of level where we know
Hiram Cuevas:
those of us in this leadership position can look to each other,
Hiram Cuevas:
but also have some consistency across the board at it, so that
Hiram Cuevas:
we know we're there for each other. We have that level of
Hiram Cuevas:
symmetry amongst ourselves. People are grateful, but we're
Hiram Cuevas:
also grateful for each other, we have each other. Listening to
Hiram Cuevas:
these podcasts, participating in the podcast, have all been ways
Hiram Cuevas:
for me to get that validation without needing a
Hiram Cuevas:
Kevin Warenda, TLIS: hat on the back and a thank you. It's
Hiram Cuevas:
listening to someone do a podcast and say, "You know what?
Hiram Cuevas:
Yeah, that's right. Yeah, that's how I feel. Oh, someone else is
Hiram Cuevas:
in my shoes. Well, thank you for saying yes. This podcast only
Hiram Cuevas:
happens because members of the community are willing to share
Hiram Cuevas:
their stories. Bill will find other ways to hear himself talk.
Hiram Cuevas:
I'm sure if we didn't have
Hiram Cuevas:
Bill Stites, TLIS: it. All right, Kevin, it's great. Thanks
Hiram Cuevas:
for that. I appreciate it. Am I fit again? The culture yet,
Hiram Cuevas:
Bill. You're slotting it perfectly.
Hiram Cuevas:
Kevin Warenda, TLIS: You point out an important thing that
Hiram Cuevas:
maybe we all learned. Like there are people that are grateful,
Hiram Cuevas:
and I'll actually share. I started this episode by just
Hiram Cuevas:
extending a word of gratitude to my team for you know allowing me
Hiram Cuevas:
to be able to go away on vacation and not have to really
Hiram Cuevas:
worry about things here. I know you feel similar. I'll wrap by
Hiram Cuevas:
also taking the opportunity to say, I recently had an
Hiram Cuevas:
experience of gratitude from a department. We've been working
Hiram Cuevas:
on a multi-year project to replace our financial systems,
Hiram Cuevas:
and this has been somewhat of a labor of love. And actually, the
Hiram Cuevas:
majority of the business office has turned over in that time. So
Hiram Cuevas:
I'm actually the only one who's been through the project start
Hiram Cuevas:
to finish, and I wasn't expecting thanks. This is my
Hiram Cuevas:
job. This is what I was doing, and I put the effort into it.
Hiram Cuevas:
But just before I left for vacation, I actually our
Hiram Cuevas:
director of finance Hannah had asked me to come over. She had
Hiram Cuevas:
something for me in the office, and totally unexpected, she had
Hiram Cuevas:
some cards that she had actually filled out, and all the business
Hiram Cuevas:
office staff had actually handwritten notes of thanks for
Hiram Cuevas:
just helping through the transition and being a resource
Hiram Cuevas:
from them, and they had some gifts for me too. So, in my 11
Hiram Cuevas:
years at Hodge, because that's the first time I had anyone
Hiram Cuevas:
really appreciate me in that respect. So I just publicly want
Hiram Cuevas:
to call out thanks to them for being such great partners. You
Hiram Cuevas:
know, they did the majority of work. I was there to help
Hiram Cuevas:
support, but this was their platform change, and there were
Hiram Cuevas:
a lot of moving pieces, and they handled that with grace. And you
Hiram Cuevas:
know the community is going through a tough transition, and
Hiram Cuevas:
they're the ones that get the feedback for how that functions
Hiram Cuevas:
in the field, not me. So, but it was nice to get that. Thanks.
Hiram Cuevas:
So, as you say, it often goes maybe unsaid, but there are
Hiram Cuevas:
folks who do appreciate what we do because we touch so many
Hiram Cuevas:
departments and activities of the school. So again, thank you
Hiram Cuevas:
for being willing to come on and share your story. I often like
Hiram Cuevas:
to ask folks to kind of wrap the session if there's any kind of
Hiram Cuevas:
resource, a podcast, a book, or something that you feel is a
Hiram Cuevas:
resource you'd love to share with the community. Is there
Hiram Cuevas:
anything in your playlist right now that you'd say listen to
Hiram Cuevas:
this or you need to read?
Hiram Cuevas:
Jason Epstein, TLIS: Please don't take this as a cop out.
Hiram Cuevas:
But if you go to my LinkedIn, I've been kind of highlighting
Hiram Cuevas:
some books I've been reading right now, and I would highly
Hiram Cuevas:
recommend going through that. I mean, I've been reading books on
Hiram Cuevas:
leadership, on working with kids, on obstacles, how
Hiram Cuevas:
obstacles can encourage innovation. Some really great
Hiram Cuevas:
stuff out there, and so check that out. Connect to me. Talk to
Hiram Cuevas:
me. I'm happy to share. But the one thing I would say is, no
Hiram Cuevas:
matter what resource you get, spread the resources out to a
Hiram Cuevas:
variety of topics. Don't just read tech leadership books.
Hiram Cuevas:
There's stuff out there, and we work with kids. We work with
Hiram Cuevas:
adults. We work with vendors. We have all these different venues
Hiram Cuevas:
that we have to be knowledgeable in. So I would highly recommend
Hiram Cuevas:
get as much enjoy it and be as well rounded as you can be.
Hiram Cuevas:
Kevin Warenda, TLIS: Jason, thank you so much for being
Hiram Cuevas:
willing to share your story on the podcast. Encourage all the
Hiram Cuevas:
listeners to connect with you on LinkedIn. I've been reading some
Hiram Cuevas:
of your posts. I think you're doing a great job there. So,
Hiram Cuevas:
just thanks for being willing to contribute your expertise and
Hiram Cuevas:
your story to community, and we will see you next time.
Hiram Cuevas:
Jason Epstein, TLIS: Thanks for having me. This has been a
Hiram Cuevas:
blast.
Peter Frank:
This has been Talk Technology with Atlas, produced
Peter Frank:
by the Association of Technology Leaders in Independent Schools.
Peter Frank:
For more information about Atlas and Atlas membership. Please
Peter Frank:
visit theatlas.org. If you enjoyed this discussion, please
Peter Frank:
subscribe, leave a review, and share this podcast with your
Peter Frank:
colleagues in the independent school community. Thank you for
Peter Frank:
listening.