Transitioning into a new technology leadership role at an independent school presents unique challenges and opportunities. Two technology leaders share their insights on navigating these transitions, from establishing a vision and fostering team dynamics to managing change and building trust within the school community. This episode provides valuable guidance for current and aspiring technology leaders in independent schools.

Resources

• Ravenscroft School
• Marlborough School
• FolioCollaborative, flexible, paperless, cloud-based experience for managing and guiding professional growth and learning, and encouraging collaboration among faculty and staff
• Technology Leaders in Independent Schools (TLIS) certification, differentiating independent school technology leaders by identifying those with the appropriate skills and experience, as well as commitment to ongoing professional development, to manage with excellence their complex and ever-changing role
• Community-building resources from ATLIS
• Management Time: Who’s Got the Monkey?, article from Harvard Business Review

Phil, welcome to Talking Technology with ATLIS,

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.

And now please welcome your host. Kristina Lewellen,

Hello everyone, and welcome back to

talking technology with Atlas. I'm Kristina Lewellen, the

President and CEO of the Association of Technology

Leaders in Independent

Schools. And I am Bill Stites, the Director of

Technology at Montclair Kimberly Academy in Montclair, New

Jersey. Hello, Bill. How are you today? I'm freezing today. It's

cold. It is

cold. I mean, you are in New Jersey.

It's always cold in New Jersey. Well, we're just

cold people, maybe. But I mean, in general, it is

cold outside and it's windy and it cuts right through you to the

bone,

it really does. I am in Atlanta today, and

I am doing the final visit of our property in terms of our

planning for the annual conference. And I'm getting

excited, like I'm walking through the space, and I can

kind of feel the energy of the Atlas people being with us. And

I'm getting real excited about annual conference.

I'm very much looking forward to that we have

a large contingent coming down. It's going to be something that

we're very excited for, and can't wait to see everyone that

goes this year. It's always my highlight of the year.

So I almost hate to say this, but on my way

out the door this week, one of my daughters was home, and my

husband and we were talking about the fact that I'm coming

down to Atlanta, and I was talking about the fact that you

and Hiram are constantly on me about this whole zombie thing,

so they saw fit to turn on the first episode of Walking Dead.

And I will admit that it kind of sucked me in. I still don't know

what's happening. They would lean over and be like, This is

how you kill them, right? And it's very graphic, so I'm not

sure if I recommend this or not, and I'm not sure if I'll watch

episode two, but I did watch one. So yay, yay, yay. You.

Okay, yeah,

you. It's about the human stories. It's about the

drama that I really like. It has nothing to do with the genre

whatsoever. It's a drama based series that I think has

excellent acting and directing, and it's well worth watching.

The zombies just are out at bonuses.

Bonuses, they're disgusting, all right.

Well, that's all I got for the intro. So there you go. Oh, but

we are in Atlanta and looking forward to our conference

registration is going really well. Our vendor community so

supportive as always. So we're really looking forward to it.

Two faces. I am certain we'll be walking those halls. We welcome

to the pod today. Louis to low, who is the Chief Information

Officer at Ravenscroft school, and I also have with us, Matt

Norco, the Director of Technology at Mar rural school.

Guys, thank you so much for joining us on the pod. Glad to

have you both here. Awesome

to be here. Excited to chat with you all. And Matt,

yep, it's great to be here. Thanks for having us.

So part of why we wanted to bring you in,

you guys, is that both of you have made some interesting moves

in your career. We talk a lot on the podcast about the fact that

the first generation tech leaders at independent schools

are starting to look toward the end of their careers. You know,

they might not be stepping out quite yet. They might not be

retiring quite yet, but with that phase of their careers kind

of firmly in their sites, they're starting to have

conversations around succession planning, business continuity

planning, and I know that both of you gentlemen have made some

pretty impressive leaps in the last couple years, so I really

wanted to talk to you a little bit about how you thought about

that and what your leadership styles are like now that you're

in these top leadership positions for your schools. But

before we walk that path together, I'll give you guys

just a second to introduce yourselves and tell us a little

bit about your background, Louis, we'll go to you first.

Yeah, I've been working in it now for over 15

years, which is kind of crazy to think about that, because

originally graduated with my bachelor's degree in theater, so

I thought my life was going to turn out much more differently

than it has.

Now this is something that we have in

common, Louis, is that I'm a theater geek as well. I mean,

probably not as bad as you are, but we haven't even talked

wicked. That's where we should have started this conversation,

not with zombies, but with wicked. Yes.

And I feel like I've done my job as a theater

parent by converting my oldest to be completely obsessed with

defying gravity. And I think we've together, watched the

movie and maybe four or five times at home. Love it honestly,

working in it started out as I'm auditioning in New York, and

rather than working in food service, I'm going to work at

the help desk, because that's what I did during college. And

then as things slowly progressed, realized how much I

enjoyed the fact that. That technology is constantly

changing. It was an opportunity to connect with people in a way

that I enjoyed doing so because of my theater background, and

gratefully had some people along the way who saw leadership

potential in me and gave me a shot, even though my background

maybe made me the least likely candidate to be an IT leader and

really found my calling in independent schools. So

you've always been on the tech side

rather than the teaching side, which is kind of unusual among

your peers.

Yeah. And interestingly enough, my first

tech job in an independent school, my title was the

Director of Educational Technology. In an interview

process, I had to basically prepare a TED style talk for a

group of faculty and a technology initiative I wanted

to lead. And I thought to myself, all right, let me just

reflect on what impacted me the most as a student. Take my tech

background, try to merge those two things together, obviously,

with the theater kid energy into the space, and it was really

exhilarating. So it's been an awesome opportunity getting to

apply those tech things in the school space. Awesome.

And Matt, you most recently had been out

here in the cold on the East Coast, like Bill, and now you

are out in sunny California. So tell us a little bit about your

journey?

Yeah, absolutely. I think listening to Lewis, I

realized that my journey is probably the exact opposite,

literally in every respect. So I have a bachelor's in Business

and Information Systems, and just happened to see a job

posting for a tech role at a school from the newspaper. I

applied for this job back when it was a newspaper ad. And so

they were really little, it didn't have a lot. And I

remember going through the phone interviews and going for an on

site visit as a finalist, getting to the second interview

of the day with the division head and the assistant head at

the time. And they said, How do you feel about the teaching

part? And I'm like, How did nobody mention this yet? So I

sort of fell into a working at a school and then teaching, by

sure happenstance, and wound up teaching middle school and doing

academic tech integration work for 14 years. And I think for

me, it was more I was doing this work for a really long time, and

realized along the way, that rather than just be doing this

work, I wanted to help lead this work, and that's what led me to

go get a Master, is continue, sort of my academic journey, and

then ultimately transition from that school to other schools.

And now here, as you said, out in sunny California,

awesome. So one of the things I want to do

before we move into some of the reasons that we invited you here

is I've come to understand that different roles are called

different things at different schools. And so if I could ask

you to please describe what you are responsible for as the Chief

Information Officer at Ravenscroft, and then, of

course, we'll go to Matt. But every tech leader, the duties as

assigned is a little different for every school. So can you

describe for me, Lewis, what you're responsible for at your

school? In

my role right now, I am in charge of the IT side of

the house, which we call technical services so your rank

and file, help desk, techs and support personnel who are

awesome. I love my team. In addition, library services

currently falls under my purview, although that's

actually changing next year, with our Associate Head of

Academic Affairs coming on board, and that falling under

her, the registrar is a position, and all school

registrar is one that I brought under my purview a couple of

years ago and will remain here for now. In addition, our

director of Ed Tech and all of our STEM plus faculty fall

underneath my purview as well.

How about you, Matt, what does Director of

Technology mean to your school at Marlboro? Yeah,

so Mar rural is a little similar to Lewis's. So I

like to say everything that plugs in falls under tech here.

That means both the operational side of the tech house, the

educational side of the tech house, and then registrar,

mostly those pieces. This is like my fourth school, and so

that has looked so different at those different schools. It is

interesting to see how it plays out in different places. That's

exactly why I asked, because it's different

even for Bill and Hiram, just getting a sense of who's in

charge of what. All right, so my last question, and then I'll let

Bill jump in, is in terms of setting the groundwork. Tell us

a little bit about the nature of your schools. You both work at

fairly prominent schools, so a lot of folks probably know, but

like, what's the size of your team and what's your student

body look like? Ravenscroft,

it's a day school, pre K through 12th grade, and we

have about 12 150 students, give or take, depending on the point

of the year that we're in. We are on a really large campus.

Yes, it's 135 acres, 13 buildings. So there are a lot of

things that connect and have wires, as Matt alluded to

before, when he was talking about his role and the size of

our team. We have about five FTEs on the IT side of the

house, including myself, because I really put myself as like a co

FTE, with all the different parts of my team, we have about

five STEM faculty, registrars, Department of one. And the

library services team is a department of five as well.

We're

a department of five as well. We're a day school.

We're a seventh through 12th grade girls school with 530

students. We're an urban school, so we have, like, I don't know,

two acre campus, very compact. Everything's really squished

together, but a good FTE to student ratio on the tech side.

So Louis, I

actually have a question for you. And similarly,

Matt, I'd be curious as to your take on this if you think it

applies. So one of the conversations I had with Louis a

little while ago is when he came into this position, his title,

and Louis correct me if I'm wrong with CTO, and then you

moved over to CIO, the idea of what's in a name, and Christina

asked what all of our different responsibilities are. What was

the reason for your decision, the impetus for you wanting to

make that shift between the T and the i, and why did you see

or think that that was important? Yeah, that's

a great question. And I think because I came from

a corporate space before, my understanding of what CTO versus

CIO might have been very different than what schools

we're familiar with. Typically, if you're working in a company

that builds technology products, like, if you want to take

stereotypes, think of a company like Apple or HP or Lenovo or

whatever, the person who's in that CTO role is really driving

the product forward, really thinking about I'm building this

solution, or coordinating the team of people that builds the

solution. It's kind of an odd title in independent schools,

because oftentimes we're not building platforms and software

unless there's some sort of proprietary ed tech startup that

lives inside of school. And anyway, that's besides the

point, but a CIO really has oversight over the flow of data

through a school, manages the IT service arm of an organization,

and really possesses a lot of breadth of responsibility, and

not necessarily the depth that I typically associated with a CTO

around software development and product

and Matt, you went from a role as director to then

Chief Information and innovation and now back to a role of

director. What have those title shifts meant to you in terms of

when you were applying for these different types of jobs. Did

they carry any different emphasis or weight in your mind?

And how did you make the decision to make that change?

And are you looking to change that title, having had both in

your background? Yeah, you

know, I think it's like a really interesting

situation with title, because at the end of the day, the work

doesn't really change that much, right? But I think what I find,

especially kind of going back to kristina's question earlier,

like, as a director of technology, I have the core

things that I'm responsible for, but technology is so much bigger

than that, and so I'm liaising with all these departments, and

spend most of my time with the HR department, in admissions and

the business office, all these other spaces, as Louis said,

where the data is flowing Back and forth, and those are the

things that I'm doing all day. And so when you have a title

like director of technology, I think it automatically puts into

people's mind that you literally just do the things that plug in,

and you don't necessarily have something to do with the flow of

data or how things in your schools should be. And so I do

actually think that having those titles, like a chief information

officer or something of that nature, it gives a different

perception to the work that we do, and it's a little bit more

all encompassing than Director of Technology. Yeah, thank

you for that. I think that makes sense.

I mean, I made the same joke on a previous podcast when my title

changed, it was simply benchmarking around other

associations in the independent school space, but I still did

the same work the next day. It really didn't change anything

about the day to day. So I appreciate that perspective. All

right. So I want to ask you guys about You've each gone through

in the last couple of years a pretty significant job change,

leadership transition. So one of the things I'd love to spend

some time on is, how did you tackle that first school year?

How did you go about managing that as a leader, and from a

leadership perspective, the background and the context of

the conversation and part of why we wanted to have you on the pod

is that. When this year's data came out in the Atlas

compensation report, we are seeing a surprisingly high

number of respondents talking to us about a job change in the

next two years. So I don't want to overstate it or be

hyperbolic, but I do believe that we in our space are facing

a wave of transitions. There are a lot of tech leaders who have

some level of dissatisfaction at their current jobs and or

they're looking for more opportunity at a different

school. And so I think we're going to see a lot of job

changes in the next couple years. So the main thing I

really want to hit on with you guys is, how in the world did

you do it? You each, I believe, had to do a move, physical move.

And most tech leaders, when they take a new job, they have to

change locations. Rarely are you taking a job down the street.

You're generally moving to a different part of the country,

starting with a brand new team in a brand new school culture.

It has to be a bit overwhelming, so I'd love you to just sort of

reflect on that a little bit and tell us a little bit about how

you handled your first school year. This is the

third new school that I've been at, actually, and Louis and I

were talking one time a little bit earlier about the fact that

I've never actually taken over for a previous director. I've

filled roles where there hasn't been a director in each of the

last three schools that I've been at, and that makes for that

first year to be even more challenging, because there's no

roadmap, there's no transition time, there's no nice handoff

from one person to the next. And it's challenging, right? Because

you're hopefully walking into a space where you have a team, and

not just a department of one, but you have just your team

dynamics to figure out. You have your school culture to figure

out, then you have the actual bits of technology to figure

out. And for me, one of the things that's been most

important is figuring out where we are, whether or not there are

any expectations for where we need to go, and to figure out

whether or not there are opportunities to sort of quickly

get us into the right place. And I think that's one of the most

challenging things about coming into a school where there hasn't

been a tech director, is that a lot of things have just been

happening for the last couple of years without any sort of

direction. And so for me, it's a lot about figuring out what that

direction should be and then quickly actually making that

happen. And I think the old adage is, don't change anything

in your first year. And I have not followed that advice ever,

unfortunately.

Well, I think a lot of things happen even when

you're in the same spot that I was in, taking over for people

who were previously in the role, I know, my first independent

school technology leadership role, there was a director who

had left and had sort of a study done by an MSP that was very

popular regionally. You know, a report outlining, oh, these

things really need to be taken care of. These are the

opportunities for growth and things that you have to

remediate. And so there was a pretty clear charge in my first

technology role about what were priorities, things to look at,

and things to look at specifically aimed at change.

Because often, when you're coming into a new school, you're

being hired not just as the expert in the space, but as a

change agent. I found that to be the case when I moved back to

the east coast from the West Coast back in 2021 right after

COVID. I know when the job that I had opened up, it was

legitimately my dream technology job. I had very low expectations

that I'd have the opportunity to have a role like this so early

in my career, and was really grateful that Jason Ramsden, one

of the key people who was seminal to Atlas at the

beginning, was available for transition calls prior to

starting. Really kept me clued into where the bodies were

buried and some of the personalities that I'd be facing

and projects that he would have loved to have taken on if he was

going to continue on. And so that first year was really about

taking the posture of a scientist studying the

landscape. Matt, I agree with you. I know that our out of

school at the time was very leery about me making change,

but I am so type A that once I see something, I can't unsee it.

And there were definitely some opportunities for change,

especially when it came to optimizing data and analytics,

that I just couldn't resist that first year. And I think even

with the transition to a new Head of School this past year

who has a very different perspective when it comes to

innovation and technology, there's been opportunities to

kind of go back to that same space that I was in my first

year at Ravenscroft, and again, be a scientist, but also

continue to be that change agent to drive the school forward to

where it needs to be.

So one quick question for the both of you.

You know, because you both have left a school to come into a new

school. And Lewis, you mentioned Jason's willingness and ability

to have those calls to work through those different things.

And I think the joke is, is that, oh, it's a July 1 start

date. The start date, at least I've seen in a lot, not that

I've changed a lot, but you know, in talking to a lot of

people, is the start date is really once you agree to start

the job, but to the point it's a matter of trying to get up to

speed, because trying to come into a job like this, where

there is so much institutional knowledge, so much knowledge

that may or may not necessarily be documented well coming into

it, and that learning curve can be fairly steep when you're

starting. So thinking about how that is managed, I think, is

really important. So the question is actually for both of

you, in terms of, what did you do in your previous jobs before

leaving to set the person up that is following you for

success, and then what did you do with the school or with the

team or with the person for which you were coming in behind

at your new school. What did you do to make sure that you were

again set up for that same level of success that you would like

to have left for the person following you?

Yeah, is it like you kind of have to do two

jobs for half of a school year? Or at least your brain has to be

maybe in two places?

Yeah, definitely. So when I just left my school in

Massachusetts, I was lucky enough to have transition time

with my replacement, and so we didn't have a ton of time. We

had about a 10 day overlap. It allowed me time to sort of get

things in place for him, have some time to work through things

with him, get him set up for the coming school year, and then off

I went, but he and I have still been in contact, and it's been

six months. And so, I mean, that's something I would think

is a professional courtesy, but also, just as a tech person like

we know that the tech community is pretty communal, and so just

being there for people, I think, is obviously really helpful, and

that's definitely an aspect of things that that is helpful, as

Lewis said, like reaching out to Jason, knowing that he knows

certain things. Louis can text him today and it's been three

years, but Jason will respond. On my end, coming into a job

where there wasn't a person made that more difficult, as Lewis

said, I was hired to be a change agent, like I was hired for my

knowledge, for my ability to come in and just figure it out.

And unfortunately, that is sometimes what you have to do.

And for me, because I didn't have a tech person to be able to

talk to, like, obviously I could talk to my tech team about the

daily stuff, but that didn't necessarily help with the

direction of technology at the school or bigger decisions that

have been made. And so for me, it was just a lot of talking

with people. Unfortunately, it wasn't always on the tech side,

but it was every administrator on this campus. It was every

consultant that I could do, reaching out to my local area

like Jim is not too far away, so that's really helpful. And

understanding the landscape of like this geographic area and

like vendors that are available things like that. Obviously, if

you have somebody that you can reach out to, that's always

best, but you don't have to, like, you can make it work

without actually doing that. And that is, I think, the reason why

we do the work that we do. And Christina, you alluded earlier

the T list, like, there's reasons why we're in the places

that we're in, and so being able to just jump into a school and

make it happen. That's why we're hired.

Yeah, I completely agree Matt, and I think when I

thought about helping Bobby, who's at Athenian, where I was

at prior to Ravenscroft transition, the thing that came

to mind first is schools operate on this calendar, and the thing

that could really make or break an IT leaders. Initial

impression at a school is the way that they're able to get the

plane off the ground at the beginning of a school year and

land it at the end, and so really providing good

documentation resources, talking through those unique pieces of

what they look like at a particular school in transition

meetings was something that I prioritized. And I think

thankfully, again, thinking about the T list and those

domains when I was in my prior role, up until the point that I

made the decision to leave, I had tried to instill a lot of

structure, documentation, things about it, operations and Ed

Tech. So that way, when I was handing things off to the person

who was taking my place, that they had a set of resources they

could very easily navigate. And I would say that Jason really

did the same for me coming into Ravenscroft, it was immensely

helpful. I think the key sort of getting to what Matt was saying

about organizations having that trust and a tech leader to drive

the ship when they come on board. If you are transitioning

someone, it's important to give them a heads up so they can be

successful, but not lead with that just because this is the

way things have. Always been done that you shouldn't broach

changing it. I think sometimes a less seasoned it leader can say,

Oh, I just need to continue the momentum of this train so it

keeps going. But the reality is, tech in schools is constantly

changing. COVID showed us that. AI is showing us that, and if we

continue to rely simply on the way things were done in the

past, and I don't have this willingness to change moving

forward, even if we're going into a new role in a new school,

then we're not serving our communities in the way that we

should be.

So let's stop down on that, actually,

Louis, because I think that that's where I was sort of

heading next anyway. Is that okay? So year one, you are

observing, you are learning from, hopefully, the person who

had the job before you, and you're getting used to the

dynamics at your new school. So school year one is kind of

scientist mode, right? Cool. So how do you then begin to do

exactly what you're talking about, which is you've observed

for a year, and now you're going into your first summer leading

into your second school year. How do you begin to start

getting those change flywheels moving? To me, the

technology leader is only as good as the team that

is working for them. And so really taking a look at what

team members are doing on a day to day basis, balancing getting

in the weeds, not to micromanage people, but to build empathy,

and say like, Oh, our frontline help desk person is dealing with

X, Y and Z, how should their job description and responsibility

shift so that they're not just coming at supporting it from a

reactive place, but being proactive and strategic and

doing the same for all different roles in the team? You know that

means on the teaching side, observing people in class. How

are teachers using tech, those that are STEM faculty, and maybe

those who aren't. So that way you can say, Oh, we've had this

piece of AV going for a while, and these solutions in place,

but maybe we need to evolve, because it's limiting the

teaching in this way or that way. So finding that balance

between being very proximate to the community that you're

working with but also thinking at a high strategic level is

really important. I would say that's the first step.

Yeah. And I also think one of the things that's

particularly challenging about this work at a school,

especially in your first year, is that, you know, a lot of

this, to be clear, revolves around money. I can give you an

example. I started here in August. Well, budget meeting

started in November. So how much of a runway am I going to get

before I need to have my plans done for next July? So I don't

necessarily have the luxury of like, an entire school year

waiting to observe because then it's another whole summer of not

doing anything and then putting things in the budget for the

following year. And so to Lewis's point, like observing

what people are doing, where those pain points are, what some

other people's priorities are, and trying to put either a

return on ROI or a value on investment to the things that

we're doing is really helpful. I'll give you an example, like

for us, the phone system that we were using is just not right for

us. Not that I wanted to change the phone system within my first

year, but it just made a lot of sense for us to do it over

spring break. And so the amount of return that we're going to

see by doing that project over our spring break, which is eight

months into my tenure here, is going to be immense, because the

new system is going to allow us to do so much more stuff that we

actually can do, and reduce a lot of those pain points. End up

cheaper on the budget, a whole bunch of different things that

are definitely just where we need to be, at that strategic

level, that are just not currently there. It's

interesting

because it sounds like there's a little bit

of a journey in all of this, and whether you're a couple years

into your job, or like Bill, who's been around for several

decades, there's always this kind of cyclical nature, because

it's technology. It's not like you do a project once and then

you ride it out for the next 25 years. I mean, often, even

talking about phone systems, you know, if it was done five or six

years ago. It probably needs to be looked at again. In any

number of technology solutions always need that kind of

evaluation. So it's cyclical like that.

Not only that, I would also say, like some of the

projects are so long in their implementation. So, you know, we

have a blackboard renewal coming up, and we have to decide, do we

want to stick with Blackboard are going to look at something

else, and if we are going to look at something else, how much

of runway do we actually need? Because we're all in on one

product. So if we're going to look elsewhere, that's a 24

month implementation from beginning to end. And so even

just coming up with what contract you choose now to give

yourself the ability to make a transition. Question Two years

from now is something that you have to consider, and is like an

important piece in figuring out, even in your first year. Matt,

one quick question for you. So I find it very

interesting. You know, you came into a program where you had

there were staff there, but there wasn't leadership in place

for that. Coming into that type of environment, what has it been

like to try to re establish leadership in this area where

there's been either the status quo or this vacuum of that for

the time since you've been there so far?

Yeah, it's really hard. Like it's not something

that happens overnight. It's been, I think, two and a half

years since there's been a person in my role, and in two

and a half years, the culture of the organization can really

shift. And so the immediate sort of things that I know are that

my role is not necessarily regarded as like a thought

partner automatically. It's not that people have anything

against me, but because there hasn't been that person here,

they're not coming to me and my role and being that thought

partner before things show up. And so just last year, we had a

couple of softwares that other departments just adopted, and

they sort of showed up in August when I got here, and I'm like,

How did nobody know about this? Like, and so that's a

challenging thing to overcome that takes a lot of patience and

a lot of thoughtful work and a lot of outreach on my part,

again, because people aren't really used to it. So if I'm not

inserting myself in certain conversations, I'm not going to

be part of them. And then ultimately, we're the ones that

are sort of left supporting that work. And so it's beneficial for

the school, it's beneficial for me to make sure that I am

inserting myself into any and all conversations that can

happen. And

Louis, to the flip of that, you were following

someone who had a very large footprint, I think both probably

at Raven, given the time and tenure, and the fact, you know,

his wife was working there, and everything that went on at

Atlas. So there were big shoes to fill, and there was, I think,

a certain way in which things had been done, and a certain

expectation for the way the rhythm and flow of things. I had

the good fortune of actually being able to go out there for a

site visit. So I got to see the school first hand, and what that

was like, and see the immenseness of that. What was

that like, following someone like that and either again,

establishing yourself for who you are and your style of

leadership. Yeah,

I would say that it was both a blessing and a curse

to be 100% transparent. I think because Jason had built such

good will amongst the community when a lot of people were very

satisfied with the way that things were from a technology

perspective. I think some people thought, Oh, well, Lewis is

going to come in, and he must be capable of doing this job, and

so he'll just continue what Jason was doing. And it was

interesting when there were points and I said, Well, I might

approach that a little bit differently and having to really

justify myself and making a change. I remember probably the

first time that I really had to do that was when I pitched an

all school registrar role. Previously there was a registrar

in the Upper School. They just took care of that. Scheduling

was done at the division level. And when our Upper School

registrar was retiring, I said, given the fact that we are in a

pre K through 12 institution and that the person who sits in the

seat manages so much key academic data for the school,

what are we losing by having this function just live within a

single division, rather than looking at our school as a

whole? And you had a variety of reactions, you know, Lower

School administrators who thought, oh my gosh, like we're

dealing with stuff in kid land all day long. Please take

registrar stuff from us. It's a welcome change. And then you had

people on the upper school side who are like, well, we're a

little bit different than the middle and the Lower School and

so we want to make sure that our needs are being met, and don't

want it diluted by having this person be responsible for

scheduling as a whole. But when it came down to it really having

conversations with people in different spaces and showing

them the fact that if we're going to really be data driven

our decision making, it starts with our key data, which is in

the academic side of the house, then this change has to happen.

That's just one example of places where I've had say, I see

things differently. Here's some data that is informing a

hypothesis that I have, if we make this change, I believe that

we will be able to whatever the end of that sentence is, and

really taking the time to not end change when, like the person

is hired or the. Equipment is bought and say no, I'm not gonna

just say, all right, things are great now I'm gonna carry things

through to the support stage, and as people are experiencing

the pains of dealing with change that I've made support them and

bring them along the way has been key in having my leadership

style be received, and hopefully the way that it's intended to be

received. I

have a question for all three of you. I

did mention earlier that we've got a lot of our peers who are

considering a job change in the next two years. If a colleague

in our space calls you and says, I'm thinking about changing

jobs, how do I know if it's the right time? Do you have any

advice or guidance or lenses through which they can make that

decision?

I will say I think it depends on where the position

is, because you may know about the school like so if it's

something that is going on in the area, if it's something that

opens up regionally, you may have some personal experience

there, or people that you may know that are at the school that

you can reach out to. So I think those first hand or those first

hand adjacent, I don't wanna say second, but those close ties

that you may have with people that are either there or have

interacted with them, that you can reach out into a trusted

sense, I think, is incredibly important, because you'll also

see the way in which those schools and those organizations

interact, not only in their own space, but at the state level.

So How involved are they, like for us in New Jersey, How

involved are they at NJI s, do I see them participating? Do I see

them out there? Are they involved? Atlas, are they

involved in other areas? So to get a feel from that and

understand what's going on there. The other thing that I

always tell people to do is dig in on the website. And how much

can you find on the website that either speaks to the mission and

value of the schools? Because you want to make sure those are

aligned, that you're in alignment with those things,

more so than anything else. But the other thing, from an IT

perspective, is, how well is it represented on their public

facing website? Because I think that speaks a lot to what goes

on there and what that might be like, and you're going to be

able to get as much information as possible, kind of reconning

those public areas, in those public spaces where that might

be. And lastly, what I do with everyone, before we record the

podcast or before I speak to everyone, stalk them online, see

what's going on, via LinkedIn, via Twitter, who are the people

there, who are the players there, and get an idea of what

are they posting, what are they talking about, and equally as

much, what aren't they saying? Or are they not saying anything

at all, because then I think that tells a story as well. So

those would be some of the areas where I think I would jump in. I

think this is a really loaded question in many

respects, because if you're talking about moving on for

career progression, I think it's obviously a much more linear

path. But again, this is my fourth school, and I've been

through a few things. I think some of what Bill said was

really key to me, right? Like, if you see the school's mission

or culture not in alignment with your own, then that's a clear

sign that it's probably time to start looking I think also, if

you feel like you just need to put your head down and do your

work and get through the day, that's probably not where you

want to be. We all talk about the Independent Schools as being

such a warm and welcoming community where we all feel

appreciated and loved and known. And if you don't feel that way,

then I think probably there's something missing there, and I

know that's happened to me, where I like my job, but

something is not right there. And so I've known that okay, as

much as I like Job, I like the setting, I like the school, I

like my colleagues, it's still not the right fit for me. And so

it's time to move on, and I think that could be challenging,

and particularly if there's any sort of acrimony or animosity,

especially if you're serving on a leadership team, it might not

be all cakes and roses. Luckily, I've not really been in that

position, which is great. But leaving on good terms is

certainly a good thing. But also knowing when is time to go is

really important. And if there are a lot of jobs available,

that's great. There is always one tech director at every

school, right? There's not four options at every school. And so

your options may be limited, and especially if you don't have the

luxury of just up and moving to a different side of the country,

which is a luxury. And so knowing when to look knowing

when to leave, I think, are really important. But you know

when it doesn't feel right, and that's when you need to look

that's

a really good distinction. The idea of

career mapping and looking for advancement versus moving on

because you're discontent, those are clearly two different

things, and hopefully it's more about the next opportunity than

it is about not being satisfied. Your current place, but things

happen, and not every organization is the perfect fit

for every leader. Yeah,

and I'm thinking like a lot about what Matt said

and both my own career journey, and then I feel fortunate in

that a lot of people in the Atlas community have reached

out, as they were like, considering new jobs and going

to new places and wanting to talk through the possibility of

change, and in some cases, if a friend trusts you to be

vulnerable and share that they're looking for a new job

and put themselves out there, especially in a community small

as ours, being a person to ask really thoughtful questions

about why they're looking to make a change and have them see

for themselves whether they're ready to make that change or

not. Is really important. There have been times where I maybe

had doubts whether someone was ready for a change, but it's not

my place to make that decision for them, but I knew as like a

friend and someone who cared for them, not as like a direct

colleague, but as somebody in my PLN that I was going to ask

questions so that hopefully, maybe they could reflect on

their own leadership journey prior to considering making a

change. I think that's really important, sort of connecting to

what Matt was saying. And then when it comes to applying to a

school, I think the first thing that you really need to see, and

that goes back more to what Bill was saying is that does the

school's identity, do their mission and values align with a

place that you want to be at? Because technology is part of

how a school functions, and if you don't see the way in which

your role as a technology leader connects to the mission and the

values and the vision of a school it's going to be not the

greatest place for you to work. The other thing that I learned

as I made my transition to my current role is that I want to

know everything I can about the person that I'm reporting to, so

whether the technology leader reports to a CFO or head of

school, you want to really get a sense of, Am I going to enjoy

working with this person? Do I get the sense that they'll care

about me as a professional and the ways in which I want to

grow? Are they going to be someone who has my back? Because

inevitably, in technology, things go wrong, and if you get

the sense during an interview that this person might throw you

under the bus when something bad happens, that could make a very

divisive working environment. So really, interviewing your

potential boss is just as important as the school

interviewing you, and then I think some people conflate being

a really good manager with being a leader, and that's sort of

what I was getting to at the beginning, when I just started

talking about being ready to assume a technology leadership

position or not. Management involves the way that you assign

people tasks and get projects from the start to the finish

line, but a really good leader has a strategic vision for where

things are going to be in the future. They're not only

managing the day to day, but they're saying 510, years from

now, I want to see our school operating in this space. And I

would say, honestly for me, that did not happen until I was in

the role that I was in currently, and I happened to be

reporting to a head of school who was super dynamic, Doreen

Kelly, who's retired this past year because she wasn't in the

weeds managing my role as a technologist. She was like, what

kind of leader do you want to be? And it forced me to ask

questions and do things in my department that I never thought

I would it's important

because I think that as leaders in this

space, we're acknowledging and part of why we're having this

conversation is that it's certainly not getting easier.

It's getting more complex. And I guess you could argue that all

things get complex over time, but in particular, the role of

the technology leader at schools, there's just a lot of

things for which you're responsible. So how do you guys

juggle that, whether you're new to your job or whether you've

been there for a long time? What are some of the ways that you

look for and find balance in terms of just all the

conflicting priorities and people pulling you in a million

directions?

Yeah, I was smiling because as a leadership team, we

recently read an article from Harvard Business for you, it's a

very old article about whose monkey is it when you're talking

about time management, and how sometimes people will come to

you they've got a monkey on your back. And our new head of

school, Derrick Willard, really did a great job of getting us to

think way more critically about different kinds of time, things

that are imposed by the system that you're in, things that are

imposed by your boss, and things that you have some autonomy over

as well. And so when I think about all the things that maybe

fall into other duties as a sign. And that appear on a job

description. For a technologist, the less autonomy you have on

your time, the harder it is to make those sort of strategic

moves. I mean, you think about something like AI and what it

means to integrate that into the technology program at your

school, both on the operational side and on the teaching and

learning side, you need to be able to sit down as a tech

leader, understand the landscape of tools the way people are

using them, how it impacts cyber security. And it's impossible to

do that if you're sitting in your office and people are

constantly wanting your help to run this report or fix this

issue. Back to the whole idea of time management and monkeys

really delegating things well to the members of your team, giving

them a sense of ownership of the work that they do, so that they

can support you, and your ability to function

strategically, I think, is very key, and it's hard to do that

when you're wired to want to fix things and get them off your

list quickly, but I think ultimately it's what helps you

to be a really great leader. Yeah,

to Lewis's point earlier, like I think there's a

fair number of tech folks who are happy being good managers,

good tech managers, and not necessarily good tech leaders.

And I know of colleagues who are in similar positions and their

schools are not really pushing forward, and we don't really

have the luxury of not pushing forward right. Whether it's a

cyber security threat or AI is coming on, whatever there might

be, you have to be operating in that strategic space. I

definitely see how being somebody with, like, boots on

the ground, understanding what's going on in the day to day will

help you figure out just how to manage tasks well. But I think

that also lets you identify, like, where there can be

efficiencies, how life can be a little bit better, where are

there possible risks, and how can you mitigate those? And then

keeping all of that in mind while you're also thinking

about, as Louis said, like, where do you want to be in five

years? Like, you can't just get there. What do you need to do

today in order to get to where you are 510, years from now? And

certainly for me, like a huge piece is just keeping up with

everything. It is so easy to just put that off and just not

do it, because there are so many things happening in the day to

day, to day, whether or not it's running a report or fixing a

switch or doing something, but if you don't keep up with all

the stuff that's going on, you're never going to be able to

devote enough time to figuring out where you need to be. And

for us, that's like the most important thing is evolving with

everything that's happening, and making sure that our schools are

prepared to do that. That is the whole point of Atlas, right?

Making sure that our schools are prepared to do all this stuff.

And if we're not doing our part, whether or not that's going to

conferences or just keeping updated with our PL ends, we're

not able to do that, and then we're doing a disservice to our

schools 100%

it's the team, and it's a leadership style. You've

got to successfully develop your team. You've got to prioritize

the work that they're doing. Lewis, you mentioned earlier,

you know you're not micromanaging, you're not

sitting there on top of them. You delegate, and then you lead,

and it depends on the leadership style that you choose, and can

see that in yourself, and know who you are as best as possible,

and then know who you have under you that is working with you. I

shouldn't even say under you working with you, because it is

that team approach. And then moving forward, because Matt,

you said it, there's so much that goes on in the day to day.

There's so many pieces that we're sitting there struggling

with that could just consume us in the day to day that we would

never get to that visioning piece, if not. I also think the

visioning piece, and Matt, you mentioned this, being seen as

that thought partner, getting into those conversations, making

sure that you're involved, I think, is really helpful. And I

think if you're starting a new position, figuring out how to be

invited to those or maybe even crash those conversations in a

respectful sense, I think, is important. And part of all what

we need to be thinking about when we make those types of

changes, or when we're in our current place for 31 years, and

we need to keep those conversations going absolutely

so before we run out of time with you guys

today, the last thing I would really love to spend a brief

moment on is the role of the T list so the technology leader in

independent school certification, all three of you

were instrumental in helping this program get up and running.

If there are folks in our space who aspire to be a CIO or a

technology director at a larger school, really kind of looking

to map out their career and take those next steps. Can you help

us understand how the T list can help in these types of career

transitions? I was having a conversation

with the head of school who was hiring for a tech

physician. He had an English. Background, and said, if this

was an English position, I would know what to look for, but it's

a tech position, I just don't know what to look for. Then I

started to explain what the T list was, but I'm hiring right

now for a position on our team, a network and Systems

Specialist. And you know, there are certain things that I want

to see in the resume. There are certain like keywords that I

would love to see. And some of them have them. Some of them

don't have them. And when I think about the T list in terms

of going for tech positions, like if I saw T lists, I would

know that they have an understanding of certain things.

So I don't necessarily need to see every single keyword in that

resume. Just by them having that certification, I know that they

have exposure, depth of knowledge, and just a logical

understanding of all these different domains that are

covered in the T list. So I don't have to worry as much

whether or not they have five extra years of job experience

that has all these bullet points. I know that they contain

that knowledge and are ready for a leadership position.

Yeah, one of the things that I think is the most

powerful differentiators of the T list is the fact that it gives

you real insight into the way a technology leader thinks. And I

know that as we were in the process of developing the

certification, I was in the middle of like a master's

program at the same time, and when I think about some of the

questions that we developed in the way that we approach this

test, the level of intentionality around assessing

somebody's thought process when they're confronted with a

particular scenario in using their IT knowledge and that

leading to what is the correct answer on the exam stood out to

me. So clearly, I just thought to myself so many times, this is

something that is at the level of master's level work, or

something beyond it, because you can teach somebody how to create

a network or manage systems or do AV work, or, you know, all

the technical things that go into our job, but applying that

knowledge in a way that's going to drive things forward is

something entirely different. So when you think that the whole

certification is aimed at endorsing people for leadership,

yes, like Matt said, it's assumed that you know how to do

X, Y and Z things, but those four letters say, not only do

you know those things, but you can apply that knowledge in an

independent school environment. And I think that's

crucial, and that's really where we started

the T list journey was that you weren't going to be able to

memorize answers out of a book and take this exam. It was very

scenario based and very leadership based. So that's why

I wanted to hit on that briefly, because I think that if a person

is an aspiring CIO or technology director, studying for that exam

might be a little bit harder, because you really do need the

experience to be able to apply your expertise in certain

scenarios, but it also can prepare You to possibly step

into these really complicated leadership roles. So yeah, I

appreciate your reflection on that, and what I hear a lot from

our first generation tech leaders is, man, if that had

been around 20 years ago, that would have been really useful.

But really, technology does change a lot. So we can't just

teach technology. We have to teach the leadership skills

around how to make decisions about technology from that

strategic lens, which is really hard, but also really important.

Okay, so before we let you guys off the hook, this has been so

incredibly helpful, I want to thank you both for sharing your

perspective. I know that changing jobs is always a pretty

complicated decision, and starting a new job is quite a

lift. So I appreciate you guys bringing some of your

experiences to the podcast and sharing them with our audience.

I'm sure that you help many, many more people than you

realize, who might be kicking some of these thoughts around.

So thank you very much for that. Before we let you go, I would

love to just ask you briefly, what is the thing you're

thinking about today at school, as you're wrapping up this

school year, what are some of the big picture things that you

guys are wrestling at your schools? For me,

it's definitely AI. Is just something that we talked

about at our professional growth day. And I think the question

that we left on is with the use of AI, what could we get to that

we're not currently getting to? And I think that's a really

great thing for us to think about, especially when we're

talking about it in terms of teaching and learning. And are

you offloading skills that need to be taught versus not using

AI, but where could AI get us that we just can't get to right

now, I think there's a great conversation to have, and

certainly as a tech leader in an independent school, it's not

only very timely, but I think we have to have that conversation.

I

definitely would echo what Matt is saying about

a. AI, but probably on an even larger scope, I think this year,

having gotten to teach an entrepreneurship class for the

first time, and seeing all the ways that the value proposition

of independent schools is changing in terms of the

modality in which schooling is offered, I'm starting to think

what ways can technology, including AI, help us to flip

the system on its head and maybe offer school in a different way

that shows that independent schools can offer something to

students for teaching and learning that's dynamic and

thriving and that will continue to be relevant in the next 10

years. And I know that might sound obtuse, but I think it's

because it's the confluence of all these things like blended

learning, meets AI meets experiential Ed that's more

career focused, as opposed to just getting kids ready for

college. And so beginning to wrap my head around that is what

I'm thinking about. I love

that you guys are the big brains. Thank

you so much for spending this time with us. It's been such a

pleasure. You really were the perfect folks to have this

conversation. So thank you so much for joining us, and I look

forward to seeing you soon in person.

This has been Talking Technology with ATLIS,

produced by the Association of Technology Leaders in

Independent Schools. For more information about Atlas and

Atlas membership, please visit the atlas.org if you enjoyed

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