Jason Curtis, Director of Technology at the Windsor School, shares insights on navigating career transitions within independent schools. The discussion covers the importance of "listening tours" when starting new roles, the nuances of the interview process, and balancing transparency with current supervisors when seeking new opportunities.

• The Winsor School: https://www.winsor.edu/ 
• The Hockaday School: https://www.hockaday.org/ 
• Laurel School: https://www.laurelschool.org/ 
• World War Z (Audiobook): https://www.audible.com/pd/World-War-Z-Audiobook/B00BIKAVHS 
• FirstClass (OpenText): https://www.opentext.com/products/firstclass 
• Weird NJ: https://weirdnj.com/

Dan, 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. Christina Lewellen,

Hello everyone, and welcome back to

talking technology with ATLIS. I'm Christina Lewellen, the

President and CEO of the Association of technology

leaders in independent schools.

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.

Hello, gentlemen, how's everything we

are recording right after Thanksgiving? How you doing

coming in a little with a little cold. So if people

are wondering what's going on with Bill today and I sound like

Barry White at any point you'll understand why.

How are you, Hiram?

I'm doing well. I had a fabulous Thanksgiving with all

of my kids being in town. So it's the benefits of having

everybody living in Richmond and a daughter coming back from

Virginia Tech. So everybody's good, everybody's been well fed

and happy and looking forward to the Advent season.

I love it. So you guys know that I texted

you in our pod group chat over the holiday because I listened

to World War Z yay. At long last, I finally listened to it.

Now I will say, Do we have a convert? Okay, here's the deal.

I talked to Barry kelmeier Earlier this week, and I shared

this with him, and he understands my position, so I

come in with reinforcements. I really enjoyed the story. It was

so well done, almost a little too well done, because I had

such anxiety listening to it, like, by time I got to the back

third of it, I was just like, you know, because they

introduced these characters, and then you don't hear from the

characters again. And I'm like, Well, what happened to that army

girl, and did she find her dog? And, you know, like, I just got

anxious, and the farther down the path. And obviously, there's

probably a reason you are meant to feel anxious, and you are

meant to read between the lines on this apocalyptic story, but

it's a little too close to home or a little too real or

something. But I was so anxious, and when it finally ended, I was

kind of relieved, though I did value the artistry in the story.

So Can that be like my book review, I guess for the day,

I call that a win, Bill, what do you think? Oh,

100% Yeah. Now let me ask you this Christina, which accent Did

you enjoy the most? Because the storytellers are from different

parts of the world,

so good. I mean, there were a few, but the

ones that had that kind of like Russian vibe were very

authentic. And again, the fact that there were the different

accents, some Asian accents and perspectives in there, it just

made it feel very global from right away, like early, early in

because I did listen to the audio book, and actually that's

a really amplified way to experience the story, right?

Because it definitely gave you the perception that all of the

world was affected by the zombies, the undead, whatever

they were calling them. So it was crazy. I think it's

particularly funny when you talk about, like,

reading the story by Max Brooks and feeling anxious about it,

and you know, like everything that you're describing with it

when his father is Mel

Brooks. I know, right?

And you know, like, how different can the two of

them be in terms of what they're writing about and the feelings

you get after experiencing that is quite different?

Yeah, there's a pendulum, for sure, in

that situation, that would have been an interesting Thanksgiving

table to be at, I think. But it was good. I appreciate the

recommendation, and I did it, and there you go. I read a

zombie book, or I listened to a zombie book.

We've got a podcast for you next. Oh Lord,

I don't know that we're gonna go that far.

All right, enough zombie talk. Exactly.

I'm so glad to have you guys here. I'm very

thankful for you and our podcast experience. As always, we are

welcoming a good friend of ours to the pod today, Jason Curtis

is coming in and joining us. He is the Director of Technology at

the Windsor school in Boston. Jason, hello. How are you? How's

everything? And have you read World War Z Hello.

Jason Curtis, TLIS: It's very nice to be here with you, and I

appreciate you inviting me on. And no, I haven't read World War

Z, wasn't it Brad Pitt or something, two

very different things. It touches on the idea

of bouncing around the world like you get that perspective,

but it's a singular voice, whereas the book is. Multiple

stories and multiple voices. This, of course, is following

Brad Pitt around the world because it's Brad Pitt, and

that's what you do.

And there's no Alan Alda cameo like there is in

the book.

Yeah, this is the next stop on my zombie

journey. Is the Brad Pitt version, but Jason, welcome.

Glad to have you here. You have been a world traveler yourself,

or at least running around the country for new jobs and all

sorts of fun stuff. So we're glad to have you here. We're

going to talk about what's going on in your world. But why don't

we start by just giving you a second to introduce yourself to

those who may not know you.

Jason Curtis, TLIS: My name is Jason Curtis, and I have been

kicking around independent schools for the last couple of

decades, I have worked at several different schools around

the country, and have just started a job here in Boston at

the Windsor School, which is a girls school for ages fifth

grade through 12th grade.

I feel like I identify with this so much

because I had an all girls in their teenage years kind of

experience. This is not the first all girls school that

you've worked at, right?

Jason Curtis, TLIS: That's right. I've worked at two

others. I worked at the Hockaday school in Dallas for a while,

and then prior to that, I was at the Laurel School, which is in

shake our Heights, Ohio. When I originally started there. I said

Cleveland, Ohio, and I was quickly corrected that it was

not Cleveland. It was Shaker Heights.

Let's stop there for just a second. This

was your third all girls school. What is it about the single

gender obviously, Hiram does that too. So what makes that

different than mixed gender school?

Jason Curtis, TLIS: It's really interesting. I've worked at co

Ed schools. I've worked in public schools, and I've worked

at independent girls schools, and I'm really passionate about

girls education. I'm a father of two girls and a son, and I

really believe that in this day and age, girls need support.

They need strong role models. They need trusted adults who can

stand up for them and teach them how to stand up for themselves.

And that's a big deal for me.

That's really awesome. You know, we

have quite a few single gender representatives in the ATLIS

board leadership. Molly is at Harpeth Hall. And now we have

your former school, Laurel School, we got Dan McGee and

Hiram. Am I missing anybody with a single gender? I think I got

everybody. It's interesting because everyone who tends to

work at the single gender has an affection for it. They really

feel strongly that it's a really unique way to deliver education,

especially in those middle and high school years. Tell us a

little bit more about the Windsor school, like, what makes

that something that was interesting to you? And why did

you decide to make the move up there?

Jason Curtis, TLIS: I've known about the Windsor school for a

long time, like I said, I've kicked around independent

schools for a long time, and had heard about Windsor and

understood them to be an excellent academic institution,

and they were doing really good things for girls, you know,

helping girls to be strong, resilient, independent. And to

me, that was the big draw. And so I like Boston, I like the

East Coast. And really, summers in the south are too hot, so I

figured I'd trade out summer for winter, and the first snow storm

comes today.

Are you questioning your life choices

now that you're surrounded in the white fluff? Not yet. Okay,

we'll check in with you at the end of this winter. As someone

who grew up in the snow, it's not cute after a while. That is

one of the things that we wanted to invite you onto the pod to

talk a little bit about. We'll come back to how you kind of

made your way into independent schools, but moving around has

been kind of a hallmark of your career. You've been in Ohio,

you've been in Dallas, you were in Arkansas, and now you're up

in Boston. Tell us a little bit about like, is that part of how

you're wired, or is it really been more about your career and

just sort of how it's unfolded. Did you think that you would be

the type of person to move for jobs as your trajectory kind of

unfolded?

Jason Curtis, TLIS: I didn't, you know, actually, career wise,

I started as a teacher in elementary schools and public

education, and loved it, and honest to goodness, thought I

was going to teach elementary school, fourth grade, just

outside of Houston for the rest of my life. I mean, that was

really my, my life plan. And I kind of end up feeling a deep

call for something else. I think there's a ton of value in people

who started a place and finish at a place over a span of 30 or

40 years, or whatever, that's amazing to me. And I'm not one

of those people. I get restless. I get the itch, I don't know. I

feel like I do some good work in a place, and then I'm Mary

Poppins right out of there to another place. And that's how I

guess it is, how I'm wired. And I never imagined that would be

me.

I love. You were early childhood Ed. You know

fourth grade. You're speaking my language, because as a former

third grade teacher, it's exactly what I thought I was

going to be doing. I thought I was going to be in a third grade

classroom for my entire career, and here I am, 30 years later

and 27 years out of the elementary classroom. It was a

quick shot in one of the questions I actually have is as

you've moved around, when you've looked at those positions, you

of course, are looking at the school as a whole. But when

you've looked at the positions, have you looked for alignment

with what your current skill set is, and looking to have as close

of a match as possible with that? Or are you looking for

things where there's some alignment and then you know,

there's going to be the new challenges that really keep you

kind of invigorated and going? What has that process been like,

particularly in this most recent case, when you've looked at the

job description and who you are and what that skill set is? It's

a

Jason Curtis, TLIS: good question, and it's funny,

because I think about going through the interview process

and all of that work that goes into it from my perspective, but

there's also work that goes into it from the school's

perspective, and often what I found is schools post job

descriptions that are very aspirational, that don't always

entail the actual day to day work, and so I do look at the

school as an institution, because I'm an old guy and I've

been around for a long time. I have a pretty good network, and

so I can typically call someone at the school that I'm thinking

about going to, or who knows someone at the school, and get a

little bit more context for the position, which is super

helpful. I like to find places that I know I can make a

difference in. And sometimes that means saying, Hey, these

are my strengths, and I think they can serve you in this way.

And sometimes that means going in and saying we're going to

learn together, because this is uncharted territory for me. I

have experience that will support us as we do this, but I

don't know how to do the things that you want me to do, and I

think that's okay I say that, and I do want to qualify it by

saying I have gotten positions by saying that, because you can

go into any interview and say, No, I don't know how to do that,

and then you don't get the job. But I think a lot of

institutions are open to that kind of growth mindset. And

really, I value a place that says we value the learning and

the growth and the transparency together

in those cases, and I mean, we're not talking about

a ton, it's not like you're moving every other year. But

have you seen like when you come in and you bring that skill set

that might be different than what they've posted, you know,

those plus one things that you bring in? Have you seen in those

conversations like, oh, we might be willing to evolve or modify

this job. Because, if you're mentioning that, you know, I can

do X, Y and Z, but I can also do one, two and three and bringing

those pieces up. Have you seen shifts, or have they really

focused on wanting you in that specific wrapper that they put

you or put the job in?

Jason Curtis, TLIS: No, I think that most places are pretty open

to being flexible. The places I've worked at least, and I did

actually move into a position where they restructured the

department based on what I perceived as a need and on my

recommendations. And in that particular instance, we kind of

unified the technology and department in the library, and

it worked out beautifully.

So Jason, as a follow up, knowing that you've

been at several schools, which means you likely have done

several interviews across the board, some positions, you may

have felt that you may have dodged a bullet by not going to,

you know, school X or school y talk about those experiences,

because I think a lot of tech directors forget that the school

is interviewing you, but you're also interviewing the school.

Jason Curtis, TLIS: That's right, absolutely, you know,

I've had a lot of time in my career to kind of formulate a

philosophy in my belief system about what this job is and what

this work is. And I have had more than one occasion where I

was kind of proceeding through the interview process, even into

the hiring process, and I finally just said, Listen, I

just think there's a mismatch here. Philosophically, we're not

aligned, and in one case, structurally, it just was not a

good fit for what I wanted to do. And you know, to be clear,

I'm not trying to be cryptic about it. You know, I really

believe that technology leadership is something that.

Needs to be a leadership position in the schools. Other

people may think differently, and that's their title to that.

But in my career, I think that moving into the year 2026 with

AI having such an impact on the world school leaders, heads of

school, they need someone who's really skilled in technology and

understands this stuff to whatever degree we can, to

advise them, to help them, to help move things in a direction

that's productive. And if a school says, you know, we don't

see this as a leadership position, then we just have a

mismatch in philosophy. It doesn't mean that their position

is invalid. It just means that we're different.

It's really interesting. The idea of kind of

career mapping like that right like it just means that it's not

the right fit. And I think that all too often these jobs,

especially because tech directors don't always move

often, it puts, I think, a lot of pressure on when they do

decide to look at a different job, there's a lot of pressure

on the situation, right? They may feel like they're fighting

or scrambling to get it, but what you're saying is that

there's a balance. There's a dating period where both the

school and the tech director have to have like the right

alignment and fit, and that takes a certain amount of

discipline, right? Especially if you're not particularly happy in

your current environment, or if you're getting a little stale

and bored, it's not that you're unhappy, but you're just looking

for new challenges. And maybe that's not where your current

school is. It's easy to get riled up about these things, but

not take the disciplined approach like what you're

talking about, which is to say, hey, love you, but I'm not sure

that this is the right fit. It's a big part of why we wanted to

have you on because I think that there's plenty of at least. My

observation is that there's some shifting that's happening. Some

schools are waking up and saying, Hey, maybe we need the

skill set, and other schools are content to stay where they are.

And so I think we're going to see a lot of moving and shaking

in the next couple of years in our space?

Jason Curtis, TLIS: Yeah, absolutely. And I think that as

we think about that, if I say philosophically, I should be a

part of the leadership of the school, helping guide a school

into the future, not just about technology, but helping write

policy, helping advise people, then I, as a tech director, have

a responsibility to the school to make sure I'm sharp, to make

sure I'm ready and able to be that leader. Yeah, 100%

so you evaluated, in this most recent

case, that you were going to move to be at the Windsor

school, head up to Boston. So it's a big, long distance move.

How do you begin to get to know your new community? How do you

know what to tackle first or what to prioritize? Because

you're doing the normal start of school chaos layered on top of

the fact that you're new and you're not even sure where your

spaghetti strainer is because you haven't fully unpacked yet.

So help us understand how you sort of mentally juggle

Jason Curtis, TLIS: all that I learned at one of my schools

that jumping in and tackling problems making changes was not

necessarily a recipe for success, because I don't know

anything about this place. I know the people I interviewed

with, I know the contacts and colleagues that I've kind of

gotten to know over the last few months. But realistically, you

can't know a school's culture in that short of time, nor can you

understand the complexity of the systems and why they do what

they do. And yes, I mean, if the internet goes down every day,

sure I get that we don't have that problem. But there are some

big things that are easy to fix and identify. Otherwise, I just

kind of hang back and learn and try to spend time with people.

So that means meeting with different folks, just having

conversations, asking a lot of questions. Why are we doing it

this way? Why do we do this? And it's never asked with judgment.

It's just asked with curiosity, because there are often very,

very good reasons to do things that I never thought about doing

right? Because who am I? I'm just the new guy learning. And

so I think the most important thing about starting in a new

space is taking the time to understand the school, and you

only do that by spending time with the people. Then I can

understand their goals, then I can understand their wants and

their needs with technology, but also with their classroom or

what they want for the kids, and all that stuff that helps me to

better support the school in the long run. So in a nutshell, I'm

not making big changes until I have at least a little bit of a

handle on that stuff. And if I can tell a story at a school I

went to that I took a job with the school. If you remember,

there was a email system called first class. Yes, back in the

day, I don't think it's an email system anymore. I think they

just do document management.

Oh, you're going back in time. Back in Time.

Deep cut by Jason Curtis, that's right.

Jason Curtis, TLIS: And I had been convinced that the entire

school hated it and wanted to move off of it, so in my first

six months, I transitioned the school to Office, 365 outlook,

it took me about two years to gain the trust back from the

faculty and staff, who were furious with me for making that

change. They couldn't believe the audacity some strange guy

comes in and takes away their software that they love dearly.

So from then on, and the two moves I made since I just kind

of let things ride until I learn,

and Jason, you're actually talking about

developing relationships, which we talk about here on the pod

frequently, and getting to know the community, I have found that

the most effective heads of school and Division Heads that

come into new positions, they do the exact same thing, and the

tech director is in that position of senior leadership

that impacts every constituent within the school community. And

I guess it's safe to say you're not changing sis systems or LMS

systems this year. Are you

Jason Curtis, TLIS: not this semester?

Well, maybe next semester, maybe we'll see

No, I haven't moved. But the idea of you go in

and you're kind of like in listen mode, versus the idea

that, and you kind of touched on it, if you're going in to a job,

people, to some degree, may expect change, like this new guy

is going to be coming in. This new person is going to be coming

in, particularly based on where the school is at the time, and

whether or not you come in with a mandate. You know, I'm working

with my oldest, who is now in the throes of applying for jobs

and trying to talk to them about what's involved with that. And

one of the questions that I've loved is the idea of, in a year

from now, what is going to be the criteria for success that

you're going to hold me to in this first year? Like, what is

that going to look like? Because that can help guide you in some

way in terms of the work that you're doing. So I'm curious,

coming into this job, or coming into any of the other jobs that

you've taken, was anything like that ever impressed upon you

that was like, Hey, Jason, we really need you to tackle x. And

what was that process for you of managing that change. You know,

you gave the example of the first class server. How do you

tackle those types of things as you begin a new role?

Jason Curtis, TLIS: So when I started at Laurel School, I was

hired by the amazing Anne Klotz, who is a legend and a wonderful

human being. And probably less than a month into the job, we

had a meeting, and she said to me, Hey, we need a new phone

system, and I want it done by December. And I said, Okay,

we'll get it done. And then I left her office and started

Googling, how do you buy and install a new phone system?

Excellent, good research. I knew nothing, but I got it done, and

it was fine. It required a little TLC and kind of rolling

out, but I think overall, people were pretty satisfied with it.

But it was, as you said, kind of one of those expected changes

bill because, you know, the system they had wasn't working

and whatever. So ultimately, it was a win. But you talk about

scary, it was a scary proposition to just have moved

across country and be told you're going to implement

something you have no idea how to implement, and it better go

well,

yeah, there's a lot of pressure,

especially if there's like, a backlog of projects that they're

like, Okay, now the new guy's coming. Let's get him to do it

right. Couldn't get it done before, or whatever. So do you

have a method to the madness in terms of when you get there and

you're doing your listening tour? How do you evaluate it,

like, how do you know when the phones? Obviously, if your head

of school comes to you and says, we're getting new phones, then

we're getting new phones, but I'm sure that there's a backlog

or some pent up demand that comes at you when you go into a

new environment, because people are going to be like, Well, I

didn't get the attention of the last person. And so now I want

you to take on my pet project. How do you prioritize that? And

what's the best way to learn how to rank those requests.

Jason Curtis, TLIS: It boils down to time, and it just takes

time. Unfortunately, there are people, I'm sure it's happening

here that there are people who are ready for me to jump on

things and move forward with things that they're interested

in, which are all good because we're all. Looking at the kids

and wanting to support them in the best way we can, right? And

I have to just keep having those conversations around the school

to put all the pieces in the puzzle, because I can't

arbitrarily say, Oh, this resonates with me, because it's

important to me too, so let's do it when it may be a lot less

important to the institution, and the only way to know that is

to do the listening tour and to take the time. So I know that

that can feel frustrating to me, to people around me, but I have

made no qualms about this to anyone here. I've said, Look,

I'm not going to make any changes. I'm not doing anything

big. I'm just trying to get to know you. I'm just trying to get

to know the school and a lot of the work that we do in

technology. I'd say more than technology work is people work,

and a big part of that needs to be setting appropriate

expectations. If people know what they can expect for me,

then usually they're fine. But if they have a high expectation

or expectation of immediacy or something like that, and I'm not

doing it, but I'm not telling them why, then they're going to

get really frustrated. And again, the only way to do it is

taking the time

absolutely and one of the things that I

want before we kind of move off of this topic of onboarding and

taking a new role. If there's someone listening who is looking

at a new role in the next year or so and has not been through

an interview process in some time, can you share, just from

your perspective, what to expect? Like Bill and Hiram have

been at their places for a long time, right? Like, if you got

somebody who's finally gonna go back out there into the world

and interview for the first time in a long time, I'm sure that

things have changed quite a bit. What are schools asking of tech

leaders? In your experience,

Jason Curtis, TLIS: I find it's really a varied mix. I really

have found actually the interview process. It gives you

a lot of insight about the institution. So I just want to

back up and say I probably interviewed for close to two

years before I took the job at Windsor and talked to many,

many, many schools. Some said Thanks, but no thanks. Some took

me up to the end of the process, but none of them were a good

fit. And I've heard the gamut of things from Okay, well, how are

you going to make sure our email doesn't go down, which tells me

what the role of their technology leader is at that

school to questions about how I'm going to advise the head

when it comes to communicating about AI with parents, and that

gives me a different picture of that institution. And so

surprisingly, I learned, and I didn't do this, but I have

learned that a lot of what happens in interviews now is the

interviewee goes in with a PowerPoint or a Slides

presentation ready to go to talk about their merits and all that

stuff, which is great and it's not what I did. I don't think

it's necessary. I think it's probably useful in some cases. I

think it all speaks to finding the right match. Because if I go

in full bore with a presentation like that, and it's a place that

really isn't interested in hearing all that, they just want

to talk to me, then it's a mismatch, and vice versa. If

someone expects to see my grades from my school and a term paper

that I wrote about how great their school is, then they're

going to be disappointed in that match as well. So it was an

interesting journey. I'll say that

one of the things that I want to get your

perspective on, because, as I said, I've been here at MKA for

30 years, but it's not like, I haven't, like, tested the

waters, and I've reached a point where I was actually offered a

job and had to turn it down for a variety of reasons that I

won't get into. But one of the things that I've always found

interesting, and particularly with that piece in general, is

how public Are you during that process with the people at your

school? Because, you know, some of the best advice I was given

was to let the head of school know that you're looking and you

don't need to go wide with it. You know, one of the things I

didn't want to do is I didn't do is I didn't want to rock the

boat in that wise Bill looking what is going on here, because

then the school has to go into a process. They have to understand

where you are, they have to understand your timeline. They

have to understand that they may lose you. So they have to start

doing a little work on their end if that eventuality comes

through, because I've heard from people who have let their heads

know, and the head has told them, not in a tech position,

but the heads told them and said, if you're looking, you

might as well plan on leaving that you want to avoid at all

costs, because you don't know whether you want to leave. It

could be that you look and you realize what you. Have is pretty

awesome, and you want to stay where you are. There's also, you

know, you start looking, and once your resume gets out there,

I can remember for the job that I got but didn't take, I had

let, like, three people at the school know. And one day, my

athletic director walked into my office and said, Hey, what's

going on with you and school X. And I was like, how do you even

know? And it's because he went to college with somebody that

was on the search committee at that school, and they reached

out. So it's a tight circle.

Oh, independent schools are so incestuous. Oh,

it is.

So what is the tech bin that you've taken during

that process of looking like you mentioned you were interviewing

for two years. What has that process been like for you? And

what have you found has worked best as you try to

Jason Curtis, TLIS: manage all of that? I think it really

depends a lot on your relationship with your head and

your supervisor, if it's not the head. In my situations, I've

always had conversations with my supervisor, whoever that was,

and if it wasn't the head, I also had conversations with the

head. And just said, Hey, listen, I'm looking. Here are

the reasons I haven't accepted anything. And I just want you to

know that I'm looking and in all those cases, it's been fine. I

haven't had any situations that were uncomfortable. I've had

good leaders who supported me. Because let's be realistic, do

you want an employee who doesn't want to be there if someone is

unhappy, then you wanted to go be happy and successful

somewhere else, and that's the kind of leadership I've been

under. I haven't shared with my staff until I get to a point

where I'm traveling for interviews, because, for the

same reason that Bill said I don't want to worry people,

because, like I said, it was a long span of time that I was

talking to schools, talked to a lot of schools, and none of them

worked out. And so if I had said to my staff every time I was

having a phone call or whatever, they would have constantly been

worried about what was next, what's going to happen. So when

things start to kind of solidify, and you feel like

there's a good match, and you feel like there's a good

probability. That's when I pull my folks together and talk to

them a little bit about the possibility. And then we do some

planning as far as what we would need to do if I were to leave,

which I think actually is a great thing to do, even if you

don't get a job, because to have the stuff documented that you

need to document, to have processes in place who's going

to bear these responsibilities. Just going through that exercise

is a benefit to the school. So to me, it's all good provided

you have a good relationship with your supervisors and your

staff

and to follow up on that this period of self

reflection is such a fantastic growth opportunity for the tech

director like Bill I've been on a number of different

interviews, and it's an opportunity to also hone in on

what is really important to you. And sometimes, when you're in

the weeds, you don't take that time for that self reflection

and some of that growth to occur. And it's not until you

have to put things on paper, until you actually have to

interview with someone that you can articulate what is truly

meaningful to you. And sometimes you realize that the place that

you're at is actually the best match to date, and that is, I

think, in my case, and in Bill's case, you know, we've been at

our schools for over 30 years. It's a testament. It's actually,

I think, a very healthy exercise to go through, because it does

force you to dust off the resume and all of a sudden realize,

wow, I've done a lot of really cool stuff, and sometimes your

schools know about it, sometimes they don't, but it's an

opportunity for you to sit back and go, Okay, I do understand

this craft. I do understand how to play people chess and bring

schools to the next level.

Yeah, I think it's particularly interesting because

when you know you've got that security of the fact that I can

look and not have to worry about being replaced. Your

conversations with those schools are vastly different.

Absolutely. You can be calmer. You can be much more yourself,

not that you're hiding anything. But you know, you mentioned

coming in with the PowerPoint. I'm not doing that because, as

you said, I'm coming in with what you've got, that all a

bill. That's a lot of bill. It is a lot of bill, but, you know,

coming in with all a bill, but I'm just going to sit there and

I'm going to have a genuine conversation with you, because

if I like the job, if I see what's going on at the school,

particularly when you go on site for. Visits, you get a real feel

at that point for the people, for what's going on. And you can

be your genuine self when you realize that I'm going to come

back and this is going to work or it's not going to work, but

regardless, I'm going to be landing on my feet either way.

And I think that's great when you have that, and when you've

got a head of school that recognizes that looking doesn't

mean you're leaving. Looking doesn't mean that you're

unhappy, per se, looking means that you're open to challenges.

You're open to different things that may align. And for me,

every time I've looked, I'm looking for specific

opportunities. I'm not like looking and saying, Oh, my God,

I want to apply here and here, because I need another job. I

need to get the hell out. It's like, this looks interesting.

Yes, you know, I haven't done this before. This is where I

asked about the challenges for a lot of what I think about after

30 years is like, was it luck, or can I really do this again?

You know, it's the imposter syndrome. Am I that good at what

I do, or is it just been the people that have been around me

and I've benefited from that, so it's a great process and a great

place to be when you've got that support.

It's all those trips to South Jersey and

Atlantic City bill, it's all luck for you. I wish,

no, I appreciate that you guys are

willing to talk so openly about this, and it's really one of the

things I was hoping to get to with this conversation, because

it tends to live in the shadows. I'm grateful to the three of you

for sharing your experiences, because wherever people are

listening in their car, on the treadmill, they might be

considering a change and really wrestling with some of these

issues. If I can come back to one piece of it, Jason, when you

finally do decide that you found a good fit, you're ready to pull

the trigger, and then you have to let your staff and your head

know, or your supervisor, does it soften the blow a little bit

that you've given them? That heads up like, then it's not

like this big shock, right? And so you can really start focusing

on the transition piece of things. Have you ever gotten

resistance to doing it this way?

Jason Curtis, TLIS: I wouldn't say resistance. I think that it

makes it a lot easier for people when they know it's a

possibility. And if you've done some planning for that

transition, whether it comes or not, people feel a lot more

secure. Because, I mean, here's the thing, if a program is

wholly dependent on my presence, then I haven't done a very good

job building a program. And it's not so much fixing it so that

it's like that before I leave. It's helping the people

understand that I'm not the linchpin. I'm just a part of the

system, and they're a part of the system, and we put processes

in place to make the system work, and it's going to work

without me, and that's what I want them to know. And that

tends to make people feel a little bit better,

if someone's listening and considering that

they're going to go out into the market and give it a go.

Obviously, there's all the immediate steps of updating

resumes and cover letters, but do any of the three of you have

any advice for people who are tippy toeing out into the job

market?

I'm a bit of a purist when interviewing, even

if it's on a Zoom meeting, I'm always wearing a jacket and Tye,

I believe in the formal look for an interview. I think

Independent Schools pride themselves on some of that, and

I think it's an important piece.

Hiram is a tie guy. I've seen the BIG

thumbs down from Bill Stites is not having it. Have you

seen the size of my head and my neck? Seriously, I

put a tie on. It looks like a child's tie. It comes down to,

like, midway on my chest. It's the Fred Flintstone tie, because

I gotta wrap that thing around it's like, 20 inches around the

neck. It's like, I gotta go to, like, the big and the tall, tall

guy. And I'm not that tall, just the neck.

All right, no tie for Bill. No.

I wear the tie. My piece of advice, though, is read

the job description, and don't just have your resume be the

same resume you send out to everyone. Look at your resume.

Look at the job description. Think of the ways in which you

can tweak your resume to highlight the things that

they're looking for in the job description. Because I think

that is something that can only help, because it shows that

you're really invested in the process. I mentioned my son and

what he's going through right now. And, you know, you got to

be a grinder at this. You got to do your research, you got to do

your work. You got to look on the website. You've got to, you

know, figure all of these things out and not just see the

description and let it go.

So Bill, what's interesting with that? You say

that about, you know, looking at what the job description is, so

many schools today are also using AI to scan resumes and the

letters of interest that if you don't make. Make that resume and

or letter topical to the school, you'll be bypassed almost

immediately.

Jason Curtis, TLIS: Well, unlike Hiram, I usually wear cut offs

on a tank top to interviews, it really gets their attention.

It's the Arkansas boy

you do not such a liar, all right? Well,

before we get into this place where you guys are giving

fashion advice, that is not the point of all of this, I am

interested, Jason, you decided a couple years ago to get involved

with Atlas leadership at a more extensive level. You are on the

Atlas board. Does that ever come up in your job search process,

or I guess, if not a part of the application and interview

process. Does it help overall with your leadership that you

provide at your school? Being on the Atlas board,

Jason Curtis, TLIS: yes, yes and yes and yes and yes. I'm new to

Windsor, and the head of school that was here when I was hired

was on her way out, she was retiring, and so I'm new, and my

head of school is new, which is always a little unnerving. And I

feel like I've won the lottery because our Head of School spent

some time doing ed tech work. And so I feel like she very much

understands the work that I do, and values it, and that's really

a nice thing. And because she understands what I do, I think

that she values my Atlas board membership more than someone who

didn't have that experience. She immediately knew ATLIS. She

asked me questions about it the first time we met, I think that

the T list certification was really a plus because she and

the school understood that I had experience and I had been

through enough to be able to support them effectively. So

yeah, I think that just being a part of the board was

instrumental in me getting this position, and I think that my

time on the board has helped develop me as a leader, so I

think I'm going to be better at the work because of it.

Yeah, I appreciate that. That's a huge

part of what we've tapped into in the last couple of years in

our governance evolution at Atlas is that a lot of the

times, the folks who run for the board are looking for a

professional development opportunity, as much as they are

looking to give back. What an awesome situation for me, for

the staff for Atlas, that we have these leaders who want to

give back, and they're really open to learning. They don't

come in with a preconceived notion of what governance looks

like. They're super open and receptive to the training and

learning what good governance looks like for an association,

and that naturally will bleed over into the Independent School

world that they come from. So it's been a really very

interesting thing, from my perspective, to see the

development of the folks on the board and how far we've come

together. It's really incredible. So before we wrap

up, Jason, you have a really interesting hobby, and I've

learned about this during our time together on the ATLIS

board. You are a crazy person, and I don't know if you're out

looking for zombies or what, but you explore abandoned buildings.

Nice. Can you please explain yourself? Are you looking for

trouble? Like, what is this all about? I'm just

Jason Curtis, TLIS: a curious kind of guy. He

brings the Lobo with him.

I mean, I am a little curious, if you take a

weapon like I would be literally peeing my pants going into some

of the I've seen the pictures people, we'll put them in the

show notes.

Jason Curtis, TLIS: I haven't taken a weapon, but when I see a

place, there's a part of me that I think never grew up because

kids love to explore. And if I see a place that's kind of

falling apart and abandoned, I want to see what's inside. And

so I've done it a bit. I wouldn't say it's every weekend

kind of thing, but I'm very unlikely to pass up an

opportunity. The first time I did it, my son was probably

about five years old, and we were in Dallas, and we were at a

park and saw a big drainage tunnel. It was huge, like 10

feet tall, whatever. And I said, I wonder what's in there? And he

said, I don't know. I said, you want to find out? And he said,

Yeah. So we started hiking through the drainage tunnel. It

was not a sewer, it was a drainage tunnel, and the water

was at our ankles, and then the water was at our knees by the

time it was to his chest, I was thinking, but it started to go

down a little bit. So then we were sloshing through about Shin

height water, and then we got to kind of a wall at the end of the

tunnel, and on it was the scariest looking skull that had

been spray painted green. Phoebe painted on there. And I was

like, we're gonna die. We're gonna die. But I couldn't say

it. I mean, we had probably walked for almost half an hour

underground in this thing.

Oh, my God. That gives me anxiety just

thinking about

Jason Curtis, TLIS: it well. And I couldn't let on, because I

didn't want to scare him. I was like, let's head back, buddy.

It's time to go back.

Bill, I'm in,

you may both. You know, it's interesting because I

find myself when I'm like, Doom scrolling Instagram, those are

the videos I stop and watch those people that find those

places, like, particularly the ones that are like, from World

War Two, and we're like, abandoned, you know, like

outposts, or their old military things that are down. Like,

around here there's actually an abandoned psychiatric ward that

people go into all the time. They're not supposed to, but

they go into all the time.

Jason check out the king's Park Psychiatric

Center that's my hometown, and it's listed as one of the

scariest places around in terms of abandoned buildings.

There's a, I don't know whether it's a website now

or Matt used to be magazine was called Weird New Jersey, and

it's got a lot of these things in there as well. Picture of

Bill's house exactly.

Jason Curtis, TLIS: I love getting out there and just

exploring. I think kind of the unwritten code is you don't

touch or take anything. You only look take pictures and don't

disturb and you know, I've been in kind of industrial places,

but you can go into, I think I sent you some pictures of an

abandoned factory, which was fascinating, because it really

felt like everyone just left one day and everything was still

there, so creepy. And as I walked through, you know, I'm

thinking, how much asbestos am I breathing, how much whatever.

But there was kind of an office, and it was as if the person just

walked out. There were open books on the table, like

ledgers. And for me, my other hobby is like projects. I'm

fixing up old radios and stuff, and there were huge just this

cache of vacuum tubes. And I was like, I wish I could take those,

because, you know, they're hard to come by, and they're

expensive, but it really is fascinating to me to see these

kind of moments frozen in time in these places. And the police

came, and I was a little nervous at that point, because obviously

you're not supposed to be in there, but evidently someone had

called the police and said there was a guy roaming around,

and so you talked yourself out of that one.

I actually didn't

Jason Curtis, TLIS: have to even talk it was one of those

situations where if you act like you're supposed to be somewhere,

people will leave you alone.

Yeah, the yellow security jacket on.

Jason Curtis, TLIS: Well, no, I was probably wearing, like board

clothes, because it was not like I planned it. I just saw it and

wanted to see so I just kind of waved at the police officer and

walked out and it was fine. He had a tie on. Bill will say that

I fully recognize my privilege in that. And you know, it's

unfortunate that not everybody could do that, but I just skated

by,

Jason, I will tell you, I'm going to go home and

I'm going to take two pictures and send them to you, because my

house was built in 1939 and in my basement, in one of the

closets, you actually open up. And it is an old vacuum tube am

radio that was built into the closet door that has the

controls on it. It's got the speaker, and I've always wanted

to see about getting it going. And then I have an old kind of,

like, stand up that I got from my great aunt, a stand up am

radio that you would have sat around like listening to. I'm

gonna send you pictures of both of them, because I need to get

both of them up and running. And you're now the guy I'm turning

to.

I love it. Come on the podcast and leave

with a homework assignment. Sorry about that.

Jason Curtis, TLIS: Yeah, thanks for joining us on old guy chat.

Yeah,

no kidding. Well, you know what? Whatever

keeps you guys interested and engaged. Well, Jason, I really

appreciate you joining us, and I know that you're very early in

your tenure with the Windsor school, and so I hope that

you'll come back and we'll get deeper into your experience

there and the things that you're working on. But I in particular

wanted to just talk about your transition, and I am so grateful

you were so open to sharing pieces about how you made this

decision to make a big move. So want to extend my

congratulations to you on your new position, and hopefully you

end up having a really great back half of your first school

year.

Jason Curtis, TLIS: Thank you very much. It's been so nice

seeing you and visiting with all of you. Miss you guys, and look

forward to talking to you soon.

This has been talking technology with ATLIS,

produced by the Association of technology leaders in

independent schools. For more information about Atlas and

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