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.

Jason on LinkedIn

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.

Welcome to Talk Technology with Atlas, the show

that plugs you into the important topics and trends for

technology leaders, all through a unique independent school

lens. We'll hear stories from technology directors and other

special guests from the independent school community,

and provide you with focused learning and deep dive topics.

Kevin Warenda, TLIS: Hello and welcome to Talking Technology

with Atlas. I'm Kevin Warenda, Director of Information

Technology Services at the Hoshka School in Lakeville,

Connecticut, and I'm Bill Stites, the Director of

Technology at Montclair Kimberly Academy in Montclair, New

Jersey,

and I'm Hiram Cuevas, the Director of

Information Systems and Academic Technology at St. Christopher

School in Richmond, Virginia.

Kevin Warenda, TLIS: Welcome back, gentlemen. I just got back

from 10 days spending in an RV with my family, well rested, as

you might imagine. I don't know how many people can actually say

they've been well rested after 10 days with their family in an

RV, but I give you credit for saying it. That's awesome. I had

my dog, so I had the therapy animal with me. I guess is the

best way to say

Bill Stites, TLIS: it.

Kevin Warenda, TLIS: Now, I would like to take the

opportunity just to express gratitude to my team. I don't

know if you guys experience this too, but I'm lucky enough to

have a team of folks. I'm not the only IT person at the school

or a team of six, so I have five really great folks that are back

at school, which really allows me to be away and disconnect.

They handle things. I had very few emails I had to respond to,

or things I had to take care of. So, just a thank you to my whole

team at the Hatcher School who allows me to actually get away

and get some rest. Either of you have that experience now or in

the past? So this year is the first time in quite a while that

I've taken some like extended time off, and yeah, when you can

fully and completely disconnect, particularly during the summer,

most people think you know when they're in school they're like,

"Oh, have a great summer, enjoy your time, and not realizing the

amount of work that goes on in the summer. So for your ability

to

Bill Stites, TLIS: get away and actually feel like you're away

really does speak to the quality of the teams that we put

together. So I'm equally thankful when I have that

opportunity here as well.

Yeah, this summer I actually did not take the

amount of time off I should have taken because I'm banking it.

I'm banking some of this time because I'm a new grandfather.

Nothing quite like it, and so when I need to take a day to go

for a visit, I'm going to take a day and go for my visit, which

is why you work hard during the summer sometimes.

Bill Stites, TLIS: Exactly.

Kevin Warenda, TLIS: Yeah, good for you, Hiram. Congratulations.

Well, speaking of working hard, we've got a great guest today.

Jason Epstein is director of technology at the Berkshire

School, which, in full disclosure, is right up the

street from my school, Hatcher School. Although, Jason, I don't

think we get together as much as we should. But why don't you

take a minute, introduce yourself to the listeners, tell

us about yourself.

Jason Epstein, TLIS: Absolutely. Thanks for having me here.

First, I'm really excited to talk with y'all and see what

happens. I am a 30-year tech veteran here started in a small

startup school in California, and I've kind of made my way

around getting over to the East Coast, and now here in the very

bottom corner of Massachusetts, a lovely area called the

Berkshires, hence the school name. I think now is a really

unique time for us as technology leaders, and so it's been a

really amazing last few years. I think since the pandemic, that

it's really pushed me in ways that I didn't know I was going

to be pushed before in this career. But hearkens me back to

being able to be adaptive to whatever came. Happily, my wife

works here at the school as well, so we're kind of all in.

My daughter is now a graduate, and our two cats are the local

mousers for the campus. So we are 100% Berkshire through and

through, and love sharing that with whoever will listen.

Bill Stites, TLIS: One thing I want to point out very quickly,

and I know this is an auditory podcast. This is fair warning

for Kevin because I want him to look around the squares. Each

one of us, myself, Jason, and Hiram, we all have 30 plus

years, and what do we all have in common? The gray beard, the

bald head. So, Kevin, it's coming for you. I know Hiram's

done a little work with AI to kind of put together what your

future may look like, but it's coming.

Kevin, Bill's already made a voodoo doll of

you. Been putting lead pins in your head. It

Kevin Warenda, TLIS: is striking. I was looking at the

screen and thinking to myself, "Wow, yeah, I have the glasses,

but other than that, it's like I don't even know who I'm talking

to on the screen. They all look the same.

Bill Stites, TLIS: Jason, I do have a quick starter question

for you. Actually, you mentioned how close you are to Kevin. Can

you tell us like a little bit about the school for those that

might not know, like where you're located, the size of the

school, your grades that you serve, what your team looks

like, so on and so forth, just so people can get that feel for

who we're talking to and what you're representing. Sure. So

Berkshire School has been here since the early 1900s. It's a

wonderful school nestled into the base of a mountain. Once you

become familiar with Berkshire, you realize we use the term

"under the mountain" a lot, which I absolutely love. We have

entrances on campus to the Appalachian Trail, we're a

boarding school that we do have some day students, population of

about 430,

Jason Epstein, TLIS: give or take, depending year to year,

grades nine through 12. We have a number of countries

represented as well as kids from all over the U.S. it's a

wonderful population, really diverse. And the thing that I

love most about Berkshire is, first and foremost, it's about

people. We walk that walk and talk that talk, and it makes me

really proud to be a part of this school.

Kevin Warenda, TLIS: You're an independent boarding school now,

but that was not always the case. I was actually saying

before the podcast started, you're the kind of guy that's

just been ever present to me throughout my career as well.

I'm approaching 30 years as well, and I remember way back

you and I were both, I think, at public school districts in

Massachusetts. We were part of the Massachusetts Educational

Technology Directors Association, which then became

the Cosen Chapter for Massachusetts. I think we

actually both served on the board of that at slightly

different times, so you're someone who has actually been

ever present throughout my career. But I know you started;

you had some public school experience too. To maybe talk

about that journey, similar to my own, where we kind of made it

to independent and boarding schools. Talk about that

transition for a moment, if you would.

Jason Epstein, TLIS: So started out, I was actually at an

independent day school for about nine years, and that's where I

cut my teeth on everything. My wife, after we got married, we

moved out to North Carolina, and that's where I hit public

schools for a little while. I wanted to get a taste of that,

and so my first two years, I was a social studies teacher in a

middle school, after that they realized I knew a lot more about

tech, and they moved me over to become the integrator for that

school. As the what was that term? As the crow flies, or

whatever. As the bird goes south, I went north, ended up at

a small private school in Pennsylvania, as more of kind of

a stepping stone up to Worcester Academy, which is when we met. I

was working as CIO at Worcester Academy for about six years, had

an amazing experience there, and really tried to get involved

with statewide groups. Meta being the first one that I

joined, as well as Mass Q, and I had been involved with ISTE

since my very first days as well, I plodded around Worcester

for a little while and had an opportunity back in North

Carolina. We hopped down there, and when that opportunity slowed

down, I moved back up here to the Berkshire School. I think

Kevin, you might feel the same way. I don't know, but it's

tough being here in the very end of Massachusetts, if you will,

because a lot of the schools and everything is geolocated close

to the Boston area. It's a three-hour drive, so I don't get

out there all that frequently. Get to conferences and whatnot.

I would really love it to figure out a way to get us here on the

western side together more, because Kevin, like you and I,

have been connected for a number of years, but I don't think I

know the people in my geographic area as well as I should. And I

think that's something that probably a lot

Kevin Warenda, TLIS: of larger states could probably benefit

is how do we connect geographically without having to

take a major hiatus? You know, I can't just drive in less than an

hour over to Boston to go to a one-day conference, like it

becomes a real challenge. Now that my daughter's in college, I

have some other opportunity to get out. I'm not worried about

one of her parents not being home for her, but at the same

token, three hours back and forth for a four-hour conference

is not realistic. Yeah, well, I know Atlas is doing some

regional meetups this year. I think maybe we'll have an

opportunity. We can organize our own. I think that's best part

about this community. As you mentioned, you were doing a lot

statewide in Massachusetts. I felt the same way. I was in a

public school district in Massachusetts for nine years,

and the opportunities to connect with other directors. I was

always searching for that. ISTE was a bit too large for me, and

that's what I love about Atlas. And similar to what you said

about the independent boarding school world, coming to Ashkes

for me was great. The community is so much more connected. I

think maybe because some of the schools are smaller, but

definitely opportunity to explore connecting. And we

encourage all our listeners find those regional meetups, create

your own. I know Bill, you often talk about the New Jersey

Association. I know there's something down in Virginia too,

right, Hiram? That there's all these opportunities in these

different organizations. Atlas is a great national

organization, and certainly the conference is, you know,

multi-day conference is worth traveling to. But you're right;

those smaller opportunities for PD and connection, if you have

to travel more time than it takes. To actually participate,

sometimes that's a little tough. So maybe we'll see if we can put

something together.

Bill Stites, TLIS: I'm up here in northern New Jersey. I'm

right next to New York City. I take advantage of a lot of stuff

that the New York State Association does, because

they've always been open and welcoming to people from other

states going in. Whether that was attending their events,

going up to the NEET conference at Mohank, which I talked about

at nauseam, in terms of just what a great conference that is.

But even like getting on their Slack channel and doing that, I

found that cross state lines, particularly when we got on the

podcast earlier, said you're at that intersection of like New

York, Massachusetts, and Connecticut. Jumping around the

region doesn't necessarily just need to be within the state.

Beauty of independent schools. We're not bound by having to

participate with the other schools in our state because of

that. You can kind of mix and mash and go around those things.

That's what I would encourage you to do because it's been

great for me where I am right here next to New York City.

Yeah, that's a great idea. I don't know why I almost had the

state lines in my head for some reason as a geophont. It's your

public school background. That's what that is. That's a public

school background. There, yes. Got to get more of that

independent vibe. You know, just going out and doing your own

thing. I mean, that's what Hiram does. You know, he just he bebop

around.

Kevin Warenda, TLIS: Jason, you talked about kind of the

evolution of your career, and I know a topic near and dear to

you. You write about this. You talk about this. The evolving

role of the tech director. We've touched on this a number of

times on this podcast. Actually, I was lucky enough to fill in

for Bill on a recent episode where Denise was actually the

host, and it was Barbara Cohen from Brandeis Marin. We got on

this topic. Hiram and Denise actually were asking her what

makes a school person, and so I think this might be an extension

of that conversation because we got to this place where we're

going to talking about school people are problem solvers,

right? Not problem creators. We're always looking to help out

and add one more thing. I think the technology director role

seems to be the epitome of that, right? We take on all these

things. So maybe share with our listeners your thinking, your

reflection on the evolution of the tech director role, how many

hats we now wear, and where we're going with that,

Kevin. I'd like to add to that, Jason. As a

boarding school, that's a dimension that both you and

Kevin share that Bill and I do not really understand, and it's

important for our listeners to understand that 24/7 environment

that you all are coming from.

Jason Epstein, TLIS: Really good point, Hiram and Kevin. I'll

start with you, and I'll kind of blend in the boarding school

part. Back when I started this, you know, when we all started

this, tech was really about okay, can we turn on a computer?

Can we get kids using Word or PowerPoint in a classroom? Do a

presentation. Okay, they're using technology. That was the

extent of it. And then as time went, it started getting into

audio, video, and then started getting into kids producing

podcasts. And our skill set had to keep growing. Some schools,

like the public schools, have district level tech offices that

send people out when the back end doesn't work, we get into

more independent schools, and I find personally most people

we're managing our stuff in house. Though some do bring in

outside vendors to kind of manage their back end. I'm lucky

enough to have a fantastic network administrator. He's been

my right arm since I got here. He's been at the school for

about 20 years now. He's retiring soon. It's making me a

little nervous. If you're a network administrator looking

for a really great, quiet, beautiful area, hit me up on

LinkedIn. We're going to be starting to work towards looking

to facilitate that change. But who knows? One of my other

teammates might want to jump up into that position, which is the

other thing that we'll talk about at some point: is our

teams and how we organize and utilize those teams to become so

great that it's not dependent on any one person to go. I digress.

Moving back towards the role of the tech director, it started

out. It was just tech. How do you use computers? Do you do the

back end? Do you do the front end? But then it started getting

into cybersecurity. And so, do you in house it? Do you outhouse

it? Do you use one person to kind of be your person and then

connect with contractors? They're umpteen different ways.

Now we're talking about professional development, we

talk about how do we train our students. We talk about policy.

These are all things that are kind of coming together. What I

realized is the plate, the person, the tech director, the

CIO, whatever your title is. There's a gajillion of them. Our

plate has stayed the same size, but stuff keeps piling on,

piling on, and it's very infrequent that we get to

offboard something, whether it's because somebody really likes

doing something or using a certain tool, and they're not

ready to get rid of it, so we can't offboard or move away from

certain software or other applications. It could be.

Remember, you know VCRs started going away, but we didn't have

VCRs in every classroom anymore, and they were getting harder and

harder to find. So, how do you transition people away from

technology that's being sunsetted when you bring the

boarding school aspect into it? Now we're talking about software

that needs to help record locations where students are at

any given time, we need to be able to have certain reporting.

We want to get into a student when a day in class, when are

they not in class, when are they at the health center, when are

they going away for a weekend with their parents? If you're a

school like ours that has day students as well, when are they

getting to campus? When are they leaving campus for the night?

It's 24/7, and that's something important. In fact, I live on

campus, so if something happens, I'm kind of on call 24/7. At

least I don't have to commute to handle that. I can handle most

everything from home because I can connect into the network. So

it's been a really interesting ride. I think it's really

important that our positions are around the executive leadership

table, whatever your school may call it. You should have a

direct conduit to your head of school. You shouldn't be two,

three people down the hierarchy tree. And I think leading with

technology is really important to give people that perspective

because let's face it, nothing can be done, nothing functions

without technology anymore.

I said the day I retire is the day toilets get networked

because I got to draw a line somewhere. That's my line, my

personal line is that I just can't do that, but the reality

of it is, everything has a network drop, or everything

needs wireless, or whatever the case may be. It's something that

we need to keep abreast of, and we need to keep our school

administration abreast of as well. Jason, I just warn you:

never go to Japan

Bill Stites, TLIS: because friends of mine have got toilets

that are from Japan, and I would assume they're networked at this

point. You sit down next to them, and there's like a keypad

that you can press that controls different things. So it's

coming, my friend. So I just warn you on that. One of the

things that you mentioned that I would like to just let our

audience know a little bit more about, because I think it's

always helpful, is you mentioned your staff. What does your

department look like in terms of the size and the different

positions that you've got to support that 24/7 nature that

you've got there at the school from an IT perspective and from

an ed tech perspective? What's that look like? Believe it or

not, there's only four of us. We've got myself. I have a

network administrator. I have a hardware software administrator

deals with all school issue technology, and I've got someone

who does kind of first level, first tier help on the fly. And

she's also audio visual manager. She edits a lot of video. She

manages our theater and other locations that

Jason Epstein, TLIS: have built in AV as opposed to something

that's coming with the teacher to a given space. That's pretty

much who we are as four of us. But there are also other people

around campus who have tasks, have jobs, have parts of their

careers that connect back to us. So we've got our registrar, but

she really also manages most of Veracross RSIS. I do some of the

back end stuff when it comes to re-enrollment and swapping

stuff, but she really does the day-to-day academics in the SIS.

We have someone in our college counseling office who handles

Naviance through and through. I really don't have to touch that,

we have people in the advancement office who are

focused on our databases. There, we offer them technical support,

but for the most part, they're managing their own data. So

we've got people in these other offices. I've got someone who

actually shares an IT office with my network administrator,

but he's really on campus safety and does a lot of the safety

infrastructure stuff, so cameras, door locks, entry

stuff. Now working towards a visitor center, and he's got all

those different pieces in his belt. But most people will see

him as an IT person. We have one person who's a part-time ed tech

coordinator. He does a lot of the PD works with different

teachers on how to do things in their different classes, but

right now it's still a part-time job, and he technically reports

to the dean of academics. Him and I have a great relationship.

We meet to make sure that everything flows. Something I

should say when I'm talking about this team and how it

extends out beyond IT is something that our school has

worked really hard toward is when anything that has

technology related to it is being brought into the school.

There's a bit of a gatekeep that has to go through my office so

we can make sure that it's going to work not only with our

current systems but also the way that it might have security

issues. So something. Working a lot on cybersecurity, looking at

vendors, making sure they have their SOC two reports, make sure

they have trust centers, and so we're working to try and find

the right way to garner all this data and all this information,

and to make sure that people are staying safe, that people are

using the tools that are right for the environment, and really

trying to create an ecosystem that achieves two things. It

needs to achieve great things for students. First and

foremost, are students getting the tools and training that they

need to be the best functioning human beings they can be when

they leave our school? Part A. Part B is are the tools that

we're using and the things that we're bringing in safe. Are they

allowing our students to work in a safe environment? Are we

making sure all our information and personal data is safe in any

number of different ways? And so, someone needs to kind of be

the spearhead. And my office

Kevin Warenda, TLIS: has done that. Our office has been that

spearhead. I'm really proud of what we've accomplished. And

what's striking to me, all these functions exist throughout all

of our schools. We're all different in terms of who and

how and the structure, right? All these things still have to

be done. It's just whether or not you have the resources to do

that centrally, whether that's distributed. It almost strikes

me that the IT role has really become more like the

collaborator in chief, right, or a mediator. Like we have to

understand and see all these pieces, and then recognize

whether it's within our own departmental purview or whether

we're actually collaborating across department with someone

else who might be doing that. But the functions are all the

same, and they've all grown just the same. We all have to do all

these things. Boarding schools, in particular, have additional

items, right? That we have to handle, like you said, with the

24/7 or the fact that we're providing internet service to

faculty homes that may live on campus too. Those are some added

pieces, certainly for boarding schools. But all these things

are the same in terms of the school needing to provide or

support it. Just the way in which we go about that's

different. So, what's your experience been throughout your

career and serving as that role in terms of that collaborator

and having to kind of work across departments, break down

silos to really effectively manage and be that traffic cop

or central clearinghouse for the understanding and to be managing

those risks that maybe aren't being handled within the

departments. What's your experience been there in that

collaboration?

Jason Epstein, TLIS: It's been an interesting experience in my

years in the different schools. First and foremost, I always

needed to ingratiate myself into more the faculty side than the

staff side. Happily, because I've taught in the classroom and

I've been kind of a core subject teacher. Being able to talk like

a teacher has helped so much. Now, it's not always the easiest

thing to do because, depending on your school, some people see

technology as the people behind the curtain, so they don't see

you as forward facing, and so that's something sometimes you

have to fight for. The other thing is sometimes the title,

and it's going to sound silly because the title is just words.

But being a director of technology is seen different

than being a CIO. Is seen different than being a dean of

technology. So one of the things I write about on LinkedIn, one

of the things I talk about when I can get a platform is the fact

that I think this position needs to have a title that is

universal, one that can encompass, because I think if

people see that, then whoever's under you should fit, like you

said, Kevin, should fit what the school is about, what the

school's resources are, what the school's needs are, but you need

to have that one person who can be that collaborator in chief,

that mediator, that translator. I can't tell you how much of my

career has been spent translating what people think

they hear to what it actually is when it comes to technology,

especially technology change. I think if we can get to that

point where school leaders are seeing our position as one

essential at the top echelon of leadership, but two that our job

transcends one box. I try and explain our position as we are

an umbrella that encompasses a whole lot of stuff. Sometimes

directly with our people on our teams, sometimes indirectly

working with other offices, whether it's on the staff or the

faculty side, department chairs, maybe a teacher who wants to do

something out of the box and needs some coaching and needs

some support-it all falls under this really, really big

umbrella. And I found my best tool in all of it is to know

what is happening, to know what is going on in all aspects. In

my school, including at the board level, I really try and

make it a point that I run the technology for the board

meeting. But part of that is making sure that I am a face and

that I am seen, but also that I'm hearing. I don't say a word

during these meetings short of hello and goodbye, but

understanding directions that the school is going in

understanding what people's fears and trepidations are.

Allow me to make better decisions as part of the school

leadership.

So, Jason, let's tease this out a little bit

more. You've piqued my interest. I'd be curious what would be

your ideal org structure, recognizing that it may not be

the setup that you would need at Berkshire, but let's take an

Atlas approach. What would that ideal org structure look like?

What title do you think you might give said person? The

skill sets that you're talking about are very broad.

Jason Epstein, TLIS: You're absolutely correct. If it came

to org structure, I think our position-we'll put the title

just on the side for right now-needs to be right under the

head of school. When people start getting put under business

leaders, start getting put under academic leaders, whatever the

case may be, even sometimes being put under an assistant or

associate head of school breaks the chain and the realization

that what we're doing has direct impact across the board. So I

think that's first and foremost. Title I prefer again in my

little world. I like the idea of CIO because it's known beyond

the education frame, but also because I think it lends itself

to some cachet. When you have a C-level position, there's some

cachet with it. Not only within the school, but also as you're

migrating around, meeting others, and trying to figure out

who are my peers, we get to things like this, and we can

figure it out. That's where my vision stops because I think it

is absolutely dependent on the school and what their goals are

set forth by both the head and the CIO to fill in. It may not

be the best choice to have a network administrator in house.

You may want to have a company manage your infrastructure that

has the resources to do what you need to do. But you know what?

Having somebody who, because you're a one-to-one school,

maybe you're an Apple school, understands these platforms

better. Maybe you don't film as much as the next school. Maybe

you don't need someone who's going to be not only an audio

video manager, but have the ability to professionally edit

your school stuff. Maybe that falls into your communications

department, so you don't need that kind of person. You know,

you could be like my school where we've got one certified

Apple repair group about 20 to 30 minutes from the school, so

within that window, that's who we go for repairs. If you're

located somewhere where there's not someone, you might need to

get someone certified and your school certified to be able to

fix apples, because otherwise you're mailing everything out. I

mean, there's so many different permutations. Cybersecurity. I'm

a big fan of outsourcing because there's no way I can afford

someone at the level that I would like, and if I did put all

that money into getting one person for 40 hours, that same

money spent is probably getting me a company to manage that's

there 24/7, 365. Again, personal preference on that, but that's

where your school needs to understand where its priorities

are. I think it's a work in progress. But I've gotten as far

as our position, and frankly, it's a large umbrella, and the

plate is over full. I mean, now with AI coming into the mix, is

a whole other batch of things we need to worry about. But unless

we're given the time, because we have a team that could support

the ongoing operations, sometimes that stuff's going to

fall through the cracks.

So, Jason, I find myself having to have more

conversations now with legal, especially when it comes to

things like terms of service and some of the DPAs that we're

starting to engage with. There are resources out there. Does

Berkshire have its own in-house attorney, or do you have to go

out? That's actually a question for each of you because I know

some schools have their own attorneys, their own counsel on

their staff.

Jason Epstein, TLIS: We do not have that, though. I do send a

lot of things to legal to go over, especially on the policy

end of things, I think it's going to be a work in progress.

But with the amount of PII that is generated at a school, I

think it's really important to make sure you're doing what you

can. I know I go around and I do information training with all of

my different departments as I can about how to deal with not

only physical data but. Digital data, it takes time and it takes

thinking. We have a written information security plan that I

had legal go over to make sure I was asking the right things and

making sure that we were headed down the right path. And every

year we have to go through and make sure we get our eyes dotted

and tees crossed for cybersecurity to make sure we

can get our insurance, our cyber insurance in place, and trying

to stay ahead of that. So it is definitely a challenge and

expensive at times because you're engaging the legal. But

the reality of it is, I think more of us are going to get hit

when one of our vendors gets hit than our own data. Personal

choice. I'm seeing way more hits on things like Canvas. You know,

well that threw a lot of us for a loop that we're still trying

to climb out of. Third party risk is just enormous. It takes

a big part of my job every day trying to get information and

making sure people are doing what they need to do on their

end to make sure I can say we're doing our due diligence on our

end.

Yeah, which doesn't include any sub

processors that third party vendor is utilizing.

Jason Epstein, TLIS: Exactly. I've read more terms of service

than I ever care to admit.

Bill Stites, TLIS: Yeah, terms of service should be a four

letter word at this point. I think it's definitely

like love, right?

Bill Stites, TLIS: It's unbelievable. How has studying

for taking and receiving the T list impacted you, either

personally, professionally, within the context of the

school? What were your motivations there, and what have

the benefits been for you? I went back and forth on whether

or not I should do it, and part of me realized that you know

because TLIS is through Atlas, and this is a group I've really

come to use as kind of my first team offense

Jason Epstein, TLIS: and defense, that getting certified

within the Atlas paradigm was a good thing to do, and as I

studied for it, I realized where my own weaknesses are, which is

not a bad thing. Understanding where you can grow is what

really separates the good from the great. If you think, "Oh,

I've got this, you're done before you start, because our

environment is changing faster than any of us can learn or

change, and so understanding at least where your starting point

is is a huge win. I did the studying, I passed, and was able

to put the little icon in my email signature, and that's all

great and dandy. But what it does is it aligns me and sets me

in with a pool of other people like me who have done this, and

I think having that group, whether physical or digital, is

tremendously important. I look for that when I look at someone

who I'm connecting with through Atlas. I look for that insignia,

and it doesn't mean I'm writing people off who don't have it.

What it means is, I know they understand that they've walked

the walk already, and that gives me something to start from. It

gives me a starting point. Again, they may just be like,

you know, what this is not my cup of tea, and that's fine. And

they're still perfectly incredible at what they're

doing. I haven't met anybody, at least yet that I've wanted to

write off, but there are people who I'm like, okay, you have not

dealt with X or Y or Z, and that's okay. But I'm looking for

this resource for whatever reason. So I think the effort,

the time, the expense to get that certification is really

important because our careers are all fluid. When I go to the

next school, if I go to another school, it's getting late in my

career. Having that and being able to say like I am certified,

I think goes a long way in the independent school circle. And

if a school doesn't know about Atlas, that's also something

that raises some red flags

Kevin Warenda, TLIS: or other things. Yeah, I had my own

motivations for taking the T list, and one of those is to

contribute to something that could actually help us with

succession planning. You've been talking about just the evolution

of this job, especially in independent schools, as I've

learned, having come from public K 12 as well as higher ed. This

is a different animal. There are many things that rhyme, but

there are some very unique things about the culture and the

independent nature of the schools. So, what I value, not

necessarily for myself in having it, but in that it exists, is it

is a good metric to say this person has demonstrated a level

of expertise across all the domains necessary to do this

job, and so for a school that otherwise doesn't have a way to

evaluate a candidate, this is a great barometer for that too.

How are you thinking about succession planning? Or as you

said, you're getting late in your career, perhaps. Maybe

you'll make a move. Maybe you'll stay. But at some point, we're

all going to leave. How are you?

Jason Epstein, TLIS: Thinking about talent development or

succession planning, and what comes after you. It's a great

question. Something I believe in. I call it the hydro model.

Is that when one head gets cut off, two can pop up in its

place. So I really try and cross train and encourage my team to

cross train on everything that's possible, including what I do.

Now there are pieces that are more appropriate for X or Y or

Z, but for the most part, I really want what we do to be. I

want the curtain to be removed. I want people to see what we do,

know what we do, and I want to teach people what we do within

my team. Super important. So two years ago, I brought in a

software app that allows us to document everything, everything,

everything, and that's something that all of my team has

directives to do. Is that when we do a task, whether it's

something we do every day and it's like rote at this point, or

it's something new, we document it, and even if we document it

in another platform, making sure we're linked over, making sure

we're connected, is really, really important. So, for

instance, as I mentioned, my network administrator is

leaving. I'm looking at my hardware software guy to be his

potential successor, and so knowing that that individual

knows what the network admin does and how to do it is really

important. So there's time set aside every week to get those

two talking, get those two sharing. I bring in my other

teammates, and when I'm working on something like, here's what

I'm doing. You know, I'm sharing this Google Doc with you, or I'm

sharing this document so you understand what I'm working on

right now. You know, when it comes to budget time, I don't do

that in a vacuum. Okay, these are reoccurring costs. Do we

still need them? Why are we using them? What can you tell me

about them? Should someone else know about them.dot.dot.so? for

succession, we all have to have the humility to say we are all

replaceable. Period. That's a given fact. If that's the given

fact, how are we going to leave our position for the next person

that comes in? And for me, if someone's coming in blind,

they're going to have the documents to help them see

almost immediately, but also they'll have the people to talk

to, they're going to have a team. Rarely, I have heard of

it. I have not seen it. Where a whole team walks, like, all

right, we're done. We've done our thing. We're all moving on

to something else. I have not seen that. So when I have left

the place, or one of my team members have left the place,

there has been not only a breadcrumb trail of paper or

digital, but there's also a breadcrumb trail of people. So

someone is coming in, and they have the human resources as well

as the documentation to hopefully give a solid

transition.

There are a lot of nuggets in there that I'm taking

back with me. The

Bill Stites, TLIS: breadcrumb tour of people, love that.

What's interesting, Jason, that you bring up, and it's something

that I struggle with at our school often, is the idea of

cross training. You know, I think is incredibly important

because right now I'm in a situation where there's really

four of us that are working year round, that are at the front of

the IT side of things. I've got people that kind of split roles

between, but there's really four of us. I'm in right now. My

assistant director's in. One of my lead techs is actually out on

vacation, and one of my others, he's okay, but he was in an

accident, so he's recovering from that at this point. But the

problem is, two of those people are prime like JAF

administrators. So now there's stuff that needs to go on where

I was in terms of planning vacation schedules. I was

covered, but now because I'm in this position where I've got

somebody who's unexpectedly out, we're trying to balance those

things. And it's interesting. You can document things, you can

cross train as best as possible, but the level to which you do

that is always interesting because you need to strike that

balance. One of the things that we've talked about here, you

know, maybe there are too many cooks in the kitchen. Like we've

got this recipe, but everyone's kind of putting it together a

little different. So when you get that final finished product,

it was like tastes the same, but it's not exactly the same. So

how do we deal with those things and we clean those things up?

And that's where some of the cruff can develop some of those

things. So I think as much as we work to cross drain, there's

also got to be this balance of documentation and knowledge

transfer when those people come back and step in to make sure

that we're all aligned. Because what I find myself doing at

times is looking and saying, "All right, what was missed?

What wasn't? How do we need to do that to avoid doubling up on

the work? So I, my only point here is striking that balance

and trying to figure that out and how hard that is,

particularly.

Jason Epstein, TLIS: When you are a small staff, as you are,

how do you strike that balance? How do you find that equilibrium

to make sure that things move ahead and do so consistently?

When I figure that out, Bill, you will be the first to know.

Thank you. I appreciate it. I got to be honest. Striking

balance has never been a strong suit of mine, and I'm definitely

someone who, if I see a gap, I've got to fill it. It's my

department. I've got to take the lead, and that's great. But the

older we get, the slower we get. The more that gets put on the

plate, it gets harder to do that. You can't take it all on

yourselves, and that's my hardest thing. I try very hard

when I go home to be able to go home and only be on call for

those things that I would venture to say are emergent. You

know, my phone goes to Do Not Disturb, and the head of school

and the CFO can get me if they need me. My team can get me if

they need me, but I really want to time out for a while. And I

think that is the other half of what you were talking about. Is

that we've got all these things that we need to get done, and we

have to find balance. But part of finding that balance is being

able to turn off and really re-energize. A hard lesson I'm

learning is how to look at something and say, "Okay, this

is not emergent. This can hold. The school's not going to burn

down. Any of these things, it's not going to happen. I need to

be able to say that in my own head. Say, you know what? It's

just going to have to wait. And so, like when you have someone

out who it's a surprise, you got to look at okay, what's falling

through the cracks and what's okay to fall through the cracks

to come back. What am I bookmarking for later? And like

I said, I can't say I'm good at it. I can't say I'm you know the

balance thing is my strong suit, but it's something I'm aware of

at least. So I think it's important to have it in your

mind. But it's going to be really individual to each school

because we have to understand what risk can we absorb, what

things can be put on simmer, if you will, until we get the

important stuff ironed out.

Kevin Warenda, TLIS: I appreciate that lens. I think

that's practical advice for all of us. I've had to adopt that

mentality myself. Right when something comes in, you know

everything's on fire according to the person that's bringing it

to you. So I think first: is anyone in danger as a result of

this, or is there a real substantive risk to the school

that needs to be addressed? And if the answer is no to either of

those, I can pause, or I can delegate, or I can come back to

it. So I think that's real practical advice you have there,

and the right way to handle it, based on how much is on our

plate. Are there any topics or anything that you hoped we'd ask

about, or something you wanted to talk about, this would be an

opportunity to bring those up now.

Jason Epstein, TLIS: I've really appreciated this call, this

podcast, this discussion. It's you know talking with people who

I greatly respect helps to put things in perspective, and I

have the advantage of being able to see you and see the head nods

and to see smiles and points and to get that validation, and I

think that's one thing. Like if anybody leaves here with

anything, the reality of it is technology and technology

leadership is generally a thankless position. We're not

going to get that validation all the time, and it's not

intentional. You know, I always laugh and say, people when they

come to my office, they don't come just to say hi. The first

words before hi are, "I've got a problem. That's who we are.

That's what we do. People look to us to fix. That doesn't mean

they're not grateful, but when we can look towards each other,

that's where the validation should come when your peers can

say to you, "I was really good, or "I wish I would have thought

of that, or "I'm doing the same thing. I'm having great success.

Keep it up. Any of those things, which is why another reason I

talk about wanting to have some sort of level where we know

those of us in this leadership position can look to each other,

but also have some consistency across the board at it, so that

we know we're there for each other. We have that level of

symmetry amongst ourselves. People are grateful, but we're

also grateful for each other, we have each other. Listening to

these podcasts, participating in the podcast, have all been ways

for me to get that validation without needing a

Kevin Warenda, TLIS: hat on the back and a thank you. It's

listening to someone do a podcast and say, "You know what?

Yeah, that's right. Yeah, that's how I feel. Oh, someone else is

in my shoes. Well, thank you for saying yes. This podcast only

happens because members of the community are willing to share

their stories. Bill will find other ways to hear himself talk.

I'm sure if we didn't have

Bill Stites, TLIS: it. All right, Kevin, it's great. Thanks

for that. I appreciate it. Am I fit again? The culture yet,

Bill. You're slotting it perfectly.

Kevin Warenda, TLIS: You point out an important thing that

maybe we all learned. Like there are people that are grateful,

and I'll actually share. I started this episode by just

extending a word of gratitude to my team for you know allowing me

to be able to go away on vacation and not have to really

worry about things here. I know you feel similar. I'll wrap by

also taking the opportunity to say, I recently had an

experience of gratitude from a department. We've been working

on a multi-year project to replace our financial systems,

and this has been somewhat of a labor of love. And actually, the

majority of the business office has turned over in that time. So

I'm actually the only one who's been through the project start

to finish, and I wasn't expecting thanks. This is my

job. This is what I was doing, and I put the effort into it.

But just before I left for vacation, I actually our

director of finance Hannah had asked me to come over. She had

something for me in the office, and totally unexpected, she had

some cards that she had actually filled out, and all the business

office staff had actually handwritten notes of thanks for

just helping through the transition and being a resource

from them, and they had some gifts for me too. So, in my 11

years at Hodge, because that's the first time I had anyone

really appreciate me in that respect. So I just publicly want

to call out thanks to them for being such great partners. You

know, they did the majority of work. I was there to help

support, but this was their platform change, and there were

a lot of moving pieces, and they handled that with grace. And you

know the community is going through a tough transition, and

they're the ones that get the feedback for how that functions

in the field, not me. So, but it was nice to get that. Thanks.

So, as you say, it often goes maybe unsaid, but there are

folks who do appreciate what we do because we touch so many

departments and activities of the school. So again, thank you

for being willing to come on and share your story. I often like

to ask folks to kind of wrap the session if there's any kind of

resource, a podcast, a book, or something that you feel is a

resource you'd love to share with the community. Is there

anything in your playlist right now that you'd say listen to

this or you need to read?

Jason Epstein, TLIS: Please don't take this as a cop out.

But if you go to my LinkedIn, I've been kind of highlighting

some books I've been reading right now, and I would highly

recommend going through that. I mean, I've been reading books on

leadership, on working with kids, on obstacles, how

obstacles can encourage innovation. Some really great

stuff out there, and so check that out. Connect to me. Talk to

me. I'm happy to share. But the one thing I would say is, no

matter what resource you get, spread the resources out to a

variety of topics. Don't just read tech leadership books.

There's stuff out there, and we work with kids. We work with

adults. We work with vendors. We have all these different venues

that we have to be knowledgeable in. So I would highly recommend

get as much enjoy it and be as well rounded as you can be.

Kevin Warenda, TLIS: Jason, thank you so much for being

willing to share your story on the podcast. Encourage all the

listeners to connect with you on LinkedIn. I've been reading some

of your posts. I think you're doing a great job there. So,

just thanks for being willing to contribute your expertise and

your story to community, and we will see you next time.

Jason Epstein, TLIS: Thanks for having me. This has been a

blast.

This has been Talk Technology with Atlas, produced

by the Association of Technology Leaders in Independent Schools.

For more information about Atlas and Atlas membership. Please

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