Transitioning from "first-gen" technology leadership requires more than just a handoff; it’s a strategic evolution. Retired directors Daisy Steele, Jeff Dayton, and Larry Kahn join the podcast to discuss the shift from building servers to managing complex ecosystems. They share essential insights on "brain dumps," outsourcing, and mastering "people chess" during retirement.

1. Veracross (School Information System)
2. Blackbaud (School Management Software)
3. Asana (Project Management & Documentation)
4. AARP Tax-Aide Counseling
5. Meals on Wheels America

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.

Well, hello. On this very chilly day, we are

just after snowpocalypse 2026, or whatever this was, but

everyone is cold, and everyone looks cold this morning. I'm

having a little bit of a weird experience right now, because

Hiram and Bill, you guys are looking at me and you both have

MKA gear on. This is a little weird. Hiram, you look like

you're sporting some MKA swag. Can you explain to our audience

what's happening here?

So for years, I have been asking Mr. William

Stites for some MKA swag, and I actually got him a very nice st

Christopher's golf shirt. And, you know, I've been waiting and

waiting and waiting. This is a great picture of us at a ball

game down in Texas. He's wearing the St Christopher shirt, and

I'm wearing my William and Mary shirt because I did not have an

MKA shirt. So after, I guess, I don't know what four years, I

finally get in the mail around Christmas time, a package from

MKA. And sure enough, Gulla, I finally have my MKA swag. And

it's very appropriate, considering the condition of my

dome.

Yeah, it's very cute. It's a little Ski hat

with a little puff on the top, and definitely in the colors

that I usually see Bill in. So good job. Bill, you got him

covered.

So I'm gonna say publicly, Bill, thank you.

You're welcome, Hiram. I wasn't sure whether it

makes you look like either, what was it, Yukon Cornelius, or the

bumble nice, given the cold weather and the beard and the

hat and what the audience can't see until we put probably a

snippet up on LinkedIn, they won't know what I'm referring

to, but you definitely look like you're prepared for the winter

weather.

Well, if I do this, I'm probably closer to

looking like William Stites.

No Stop it. You would never look so good, Hiram.

You guys are crazy. And I also want to get on

that four year long waiting list for some MKA gear,

as I've explained to Hiram, we closed our like in

person bookstore. So it's not like I can just walk in and,

like, grab something off the shelf and be like, hey ole send

this. You know, it's like, I gotta look online. I gotta go

through the order. It's not as easy as it once was.

So a tech director struggling with going online,

Oh, stop.

Just enough. Enough already. Let's go.

All right, I'm gonna break you guys up.

Always tried to start with something. I love it. Well, you

guys look, we're welcoming some really cool guests today, and

this one is pretty powerful grid of people sitting here on my

screen today as we walk into this conversation, we are joined

today by three powerhouses, because we want to have a

conversation around the transition from the first gen

tech leader, as I lovingly call you guys, the ones who have

grown up in technology leadership and independent

schools alongside the technology and now we're in this moment

that I think is pretty critical, and ATLIS has been paying a lot

of attention to, and that is that we're transitioning to this

next gen of technology leadership at your schools. And

it feels to me that where you guys had, in some cases, like a

zero entry pool now, the next generation of tech leaders are

just jumping into the deep end. I've been wanting to have a

detailed conversation around this for some time. So today,

not only do I have first Jen, my normal friends and brothers,

Hiram and bill, but we are also welcoming to the podcast. Larry

Kahn, Jeff Dayton and Daisy Steele, a powerhouse of

technology leaders. It is so great to see all of your faces.

Thank you guys for joining us today. I already apologize for

my co hosts and their friskiness, but I'm glad you

guys are here. I would love to give each of you a moment to

just introduce yourselves. You guys are very well known in the

Atlas community, but our podcast goes far and wide. Tell us a

little bit. Bit about your journey into technology

leadership in schools. Let's go to Daisy first. Hi.

This is Daisy Steele, and I was the tech

director at Catlin Gable school in Portland, Oregon, and I was

there 22 years, and spent about 10 years as a tech director. I

got started in public schools, actually, and then moved into

independent school and started as a technology support

specialist, and then moved my way on up to deployment and

helped with the network a little bit. So came through sort of the

IT route, even though I had a little bit of an educational

background teaching marketing in public schools. So then became

the tech director, and then about 18 months ago, retired

from that position, and am doing some consulting, and also all

the fun things as well in retirement.

Awesome. How about Jeff? Let's go to you.

Jeff Dayton, I'm the retired tech director from

the Madeira school in McLean, Virginia. I'd been at the school

for 25 years. I was hired on as the network manager, SIS admin,

do it all kind of guy, and after a couple years, I was made the

tech director. My path was pretty quick and straight

forward, and have been in it ever since I retired in June. I

am loving retired life. I'm actually not doing any

consulting, which is a bit of a surprise, not because it wasn't

available, but I quickly fell in love with doing other things

that had nothing to do with technology.

And Jeff is still an atlas board member, and

so you may say you're not doing consulting, but I think you're a

liar.

I wasn't sure if I was allowed to say that out

loud, so yeah, I am still on the Atlas board, which I love, and

it's been interesting doing that as a school person and as a

retired person. It's actually very nice to be able to focus

more time on the Atlas work that we're doing, because I still

feel very strongly about the importance of what Atlas does

for the whole community.

And Larry Kahn, Larry, you are the

significant other of our darling and beloved Susan Davis, who was

employee number two at ATLIS, and I am employee number four. I

have a history of working closely with Susan, so yes,

we're going to talk about you. But also, can you tell your wife

I love her and that I got her Christmas card and I hope she's

doing great.

I will, and I'll start off talking about her.

She's doing great in retirement, in her transition as well, and

writing lots of poetry and actually teaching a class right

now. So she's doing great. I'm Larry Kahn. I just wrote down,

you know, I retired in 2022 that gave me 40 years in technology,

about half in private industry started off as a tech writer,

became a computer programmer, ended up managing a data center

for a wholly owned subsidiary of a fortune 500 company. But my

beloved wife, Susan, was teaching English at a boarding

school outside of Baltimore, and I was driving down I 95 to DC

every day and back, and that was getting old really quick. And

ended up running technology at Garrison Forest School outside

of Baltimore, which cut my commute each way from 50 miles

down to five miles. And fell in love with working in education.

From there, went on to Kincade, where I had nine wonderful

years. So I've worked in boarding schools, day schools.

Last school was Trinity Valley School in Fort Worth Texas, for

six years, been retiring, and in retirement, I enjoy hiking twice

a week, doing music therapy. I'm on the board of choral group.

I'm enjoying singing, and I'm doing some consulting as well. I

love it well.

I'm so glad that you guys all joined us. And

let's start with this. Like I mentioned, I have this vision,

having been around for a little bit of you guys growing up with

the technology, that your role has slowly evolved over time

into what it is today. And I guess my question to start us

all, and Bill and Hiram, I'm love for you to jump in too.

What aspects of what you guys have done in your careers are

really hard to capture moving into this new generation. So I

kind of want to take the 30,000 foot view of this, because I

keep saying that it's going to be hard for somebody to kind of

jump into the deep end on the roles that you guys do. But is

that accurate? Do you guys also see it that way? Is it the

challenge that we're seeing and feeling at ATLIS? Is it

widespread? Do you think I'm kind of just trying to get the

sense of why is it just not that we could go out and hire a quote

new tech director to jump into your roles as you're retiring.

Why does this require management? So if I could ask

you to kind of zoom out for me and give me your thoughts on

that,

Christina, I think the difference between back then

and now is when we started. There wasn't a lot of technology

in schools. It was sort of an afterthought. It was there, and

it was not really integrated in the educational system at all.

And so that aspect of it, we grew up into this now, where

it's integrated into everything in the classroom. And, you know,

we don't have to go into the details on what that is, but

that's one focus, and then there the focus is the systems and the

software. Back in the late 90s, early 2000s we had to build our

own systems, and sometimes build our own software, databases,

write our own scripts, write our own programs, and now

everything's coming in off the shelf. It's highly complicated,

and some of our schools still have some of this old stuff

within their school system, and turning it over to someone who

didn't grow up with it is a daunting task for that new

person coming in. When I started, the biggest concern was

AOL instant messenger that was going to just ruin the world.

And we blocked it, we locked everything down. And now you

look at what what it's evolved into, it's just incredible. You

know, I went from running a network with a lot of servers

and maybe 50 workstations to now it's just 1000s and 1000s and

1000s of devices, and trying to keep up with all the new

technology all the time is just extremely difficult. And I wish

I had a really quick answer or really good advice for these new

people coming in, but just have your community, have your group,

have your networking back then it was the listserv. That's what

we just lived off of. That's how we got our help and assistance

with what we were doing. So yeah, it's a big challenge, and

then they throw AI at us, and that just sort of stirs the pot

one more time. It's tough

to follow up on that. It was a lot of building

things from the ground up, but now we have the ability and the

resources to get things like Veracross or Blackbaud and

several other myriad of systems to do whatever we want them to

do. And so the trick now is to be able to manage those systems

and the people using those systems so that things are

cohesive rather than siloed or broken apart, and trying to

bring all of the school together and strategically going in the

same direction, and having those systems all sort of integrate

smoothly and seamlessly is, I think, a challenge, and so I see

that being a big part of it. I also see managing communication

and managing people and managing personnel being very key to

ensure that the right people are in the right place, doing the

right work as needed for the technology department, as well

as throughout the school. And then, as Jeff said, AI being

thrown in there to make it just that much more fun.

Yeah, I couldn't agree with you guys more the

skills. That's really the big thing. The skills changing so

much. You know, the importance of people. Skills were always

there, but when they first had the leaders, remember working in

those little closets and having to fight for a bigger space or a

better space, having to fight for a seat at the table. And

then the school realizing the importance of that. Sadly, not

all schools have the whole school aspect of this, but the

skills that we had, you know, just thinking back about how

cyber security went from the fear of the little you know,

like the War Games movie, the kid doing something in computer

viruses, to eating up such a chunk of time and then having to

hire IT engineers with those skills and those certifications

as well, but the skills we had to develop instead of building

these systems, the contract negotiations and what's their

cyber security, and how are we protected, and how are we taken

care of? And then, you know, when we were starting out, we

weren't dealing at the board level, and now we're dealing at

the board level, and then also making sure that our strategic

plan, that we have a mission statement, that our strategic

plan is in line with the school strategic plan and the rest of

it. And, gosh, I'm glad I retired before the AI really

kicked in, you know. So the changes are happening faster and

faster. One of the great quotes I had was from a former head who

said, Larry, can you make that change slow down a little bit?

But yeah, I agree with everything you said. One of

the things I think is interesting, it piggybacks on

what all of you are saying is, I wonder, given where we were and

where each of you stepped out, the ability to replace what you

left with a singular person, maybe they're bringing in one

person to do like 80% of what you did. But where do those

other pieces land, depending on the school, the way in which

you've been able to grow the needs and those types of things,

I don't think you're going to see quite as many people, I'll

say, like all of us on the call, that had to do every aspect of

this job over the course of our tenure. In that coming in with

somebody with those skill sets, they're either coming in with a

degree in the ed tech side of things, or they're coming in

with a strong infrastructure background, or each one of these

things, you know, Christina has used the term unicorn a lot in

the past with what we've brought, and I think that horn

has grown for each of us over the years because we've been

asked to develop with that. And I don't think those people

necessarily exist in the way in which they had to as we were

coming up.

I would agree with you, Bill. I think the extra

piece to what everybody has been saying right now is when I think

back 30 years to what technology was. It was considered to be an

extra it really wasn't mission critical. It was, oh, let's

throw a computer lab together, and maybe we can get a couple

things going for boys or girls who are interested in this kind

of stuff. And now that you look at where technology programs are

today, they don't really technology programs.

Everything's mission critical now it is specific to your

school's mission to be a forward thinker, to prepare their

students for the world that they're going into after they

graduate. And I don't know of any other role other than

perhaps the head of school that impacts every constituent group,

the way that it directors do from as early as the inquiry,

when, if your admission software is not functioning properly,

that's the first interaction a constituent has with your

institution. Likewise, if once you're onboarding any software

that you have in place it that's not doing what it's supposed to

be doing, and if that data is indeed siloed, you end up with a

lot of frustration among your constituent groups, not to

mention the parents and what their interactions are. And then

let's add to the mix here, you know, the Internet of Things,

all these devices now that have to be connected to your network

that you really don't want on your network, but you have to

have them, because department X would like to have a bird feeder

camp so that the students can see the birds being fed or

hatching, or what have you. There all sorts of things. And

then when you add AI to it, once again, guess what you're talking

about, every constituent group, including those that are in

utero. They're not going to experience anything without AI

in their immediate future. And that is something that is

tantamount to what we are trying to do in terms of making our

schools as successful as possible. And I think the one

piece that all of you have excelled at, and my hat's off to

all of you, because I've worked with each of you, is the

relationship piece. We talk about this on the podcast, ad

nauseum. But there is no substitute for having somebody

that you can go to and talk to that recognizes the challenges

associated with the people. Those of you who've known me for

a while have probably heard me talk about this term called

people chess. We play people chess all the time with our

constituents at our schools, and sometimes you're not after a

win, you're after a stalemate, because all you want to do is

continue the conversation more than anything else, because

there's nothing worse than going into a meeting and having to say

no, and we've all been there.

Yeah, and actually, let's go to that for a

second, because Larry mentioned it too, that the people skills

have stayed the same. The technology has changed, the

scope and complexity of it has changed of the job, but the

people skills are still the same. Is that the only thing

that is the same, when you think about 2025, 3035, years ago

compared to now, is the people part of it, the only thing

that's sort of the same?

Well, we had to do a budget 2030, years ago, but the

nature of the budget has changed significantly. The complexity of

the budget has changed. And I think over time, at least at the

schools where I work, we came to a good understanding of what

should be included in the technology budget and what

should fall under it. That's a

tough question. Christina, I agree with Larry,

the budget process, you know, that's always been there, and

the relationships have grown in importance over the years. But

the thing that I think has increased and stayed the same as

the risk that you have to take as a tech director, sometimes

you have to make decisions on your own, by yourself in that

server room, in the dark at two o'clock in the morning, or make

choices or decisions on which way to go for your school that

you may get some input in, but it's still on you, and the

fingers will come back to you. So that risk taking element of

an employee, of a tech director, I still think, is very important

to the job.

That's terrific. And leadership the importance of

leadership as well.

Yeah. I would say that the thing that stayed the

same, including the people, is the idea that we need to be

responsive to whatever is happening. So if you know, a

server goes out, we have to go, jump and run and fix it. If the

network is down, if the wireless is down, or printer is not

working, everybody remember, printers seem to be the bane of

our existence sometimes, like I can't print, and so I think that

people expecting that just like electricity, it's just going to

be on, it's going to be working. I don't feel that that has

changed. And also just trying to help folks understand what we

do, providing insights into sort of the background of what tech

provides, and the complexity of that has just increased, but we

still have the role of trying to help explain that to the rest of

the school.

I love that part Daisy, because I think of the

recent outages with, say, CloudFlare, Verizon, everybody

starts to complain and saying, it's your SAS provider, or it's

Google that's down. I'm like, No, there's actually a major

outage taking clicks on the East Coast, and I can't fix it. And

they're so puzzled by the fact that outside of the bubble of

the school that we have control over that something that large

can impact the day to day activities. And it shows the

reliance of the technology and that the community really seeks

our guidance for that information.

Larry, let's go to what you were mentioning

about leadership. Piece of it that's also a piece that hasn't

changed over time. Your thoughts on that.

It's servant leadership, for sure, because

we're all serving the school to the points everyone has made

that the buck stops with you, and that it's a 24 by seven by

365, job that you're on call all the time. You're on vacation,

you're on call, you can have a backup there, but you're the

captain of the technology ship, and it's your responsibility,

and you want to have a great team. The importance of being a

leader, having the right people on your team, having the right

people, to use that analogy, you know, the right people on the

bus, and then the right people in the right seats on the bus,

and developing the team. And that's where an organization

like ATLIS, you know, gosh, for so many years in our careers,

you guys weren't around, so now that you're here, just to

leverage that as much as possible, we had relationships

with vendors over time, and that aspect hasn't changed. But one

thing that has changed that's a huge asset is having you guys

around to help us and keep us mindful as we're in the weeds,

doing things day to day, to stop back and take that time to think

strategically, which is so important for a servant leader.

Larry, you bring up something I think is really

interesting, and I think it's the fact that, you know, I've

said it before, the only time I feel like I'm ever actually,

truly on vacation is during winter break, because it's when

almost everyone else in the building is out and getting

those calls and the expectation around those calls. But I think

the one thing I would push back just a little on is that I think

when you sit at that leadership table, when you're a division

head, when you're the CFO, when you're the headmaster, I think a

lot of those people, you're never truly off, even when

you've got your vacation time around those periods where

there's issues going on. But the question that I actually have

for each of you, whether it was your last position or positions

you've had along the way, I think, as I said, that's an

expectation if you're sitting at that leadership table, and to

that point of leadership, how many of you were at that point,

at that leadership table, during those times, and what you saw as

the differences when you were

or weren't. I think you raised a great point about

the winter break, because that's the one time things shut down.

But sadly, when we have a major update to do, the window to do

those updates has really shut down, so that one time when

maybe you could have a break is when you got to grit your teeth

and do that critical update and hope it all goes well, because

those updates need to happen, or Those forklift upgrades need to

happen, and with the increased summer programs and the rest of

it and theater happening and sports happening, those times to

do that have become farther and fewer between than they were

years ago.

I kind of have to agree with you on that my breaks

were some of the busiest times of the year, and being at a

boarding school. We supported the campus residents as well,

and they were still living there with their families over break.

So if something went down, they were out. So, you know, we were

on call for that as well. But to your leadership question, Bill,

I was never on the leadership team the school, just sort of

they never had the tech director on the leadership team. Um, I

think the person before me was for maybe a year or two, but

since then, that was never a thing. However, I had access to

everyone on the leadership team at any time, so I never felt

like I was ostracized or anything like that. But that

goes to making sure you have really good relationships with

people. And you know, we've already talked about that a

little bit. So I never felt that it hindered me in my job, or it

hindered the school. And if there was something that needed

to be presented to the leadership team, all he had to

do is say, Hey, can I come to your meeting? And they were

like, oh, yeah, sure. Come on. Most of what they talked about,

you know, scheduling and all that other stuff, was like a

yawn or anyway, so I was happy not to be in those meetings to

begin with.

So I had a similar experience as Jeff, where I was

not on the leadership team, but I had made sure to develop

relationships with all of the leadership members so that I

could, as Jeff did, go and discuss whatever I wanted to

discuss about that. And I also wanted to say to Larry's point

that schools have expanded in activities so that it's much

more 365, not maybe 24/7, but even then, there are overnight

things. And you know, Robotics has their overnight activity,

and the PSAT is happening at 6am or so. We have more to do and

less time to do the behind the scenes work that we need to do

summer camp starts the day after school is out, and all the

robotics things happen during winter break. So there is a lot

more going on that the tech department has to support

leaving less time for getting that behind the scenes work done

to the leadership point, I had a different

experience in the sense that I was at a school where I wasn't

on the team, and I had great relationships with division

heads and regular meetings with the head of school. And still,

sometimes when they would be working on the strategic plan or

other things, other decisions that were taken, they take a

certain decision, and then they'd run it by me after the

fact, and I we might be able to tweak it some. But then at

Kincaid and Trinity Valley, where I did serve on the

leadership team, the experience was very different and very more

positive in that, you know, I did have a role on the strategic

plan. I did have roles with different board committees, you

know, because people who don't know technology don't know to

ask the questions that they don't know to ask. And I found

that at that leadership level, where you could be really

preliminary, be in the development of it, and to be

asking those questions, and to get people to think about those

things more proactively than reactively, it made a huge

difference to the school. In my opinion, I'm a big fan of a C

level technology leader sitting on the team and contributing in

that way.

I want to ask you guys, especially because

the three of you have recently retired, was your school ready.

How did you get them ready?

So when I left Catlin Gable school, but before

that, I had given six months notice, and then we went ahead

and did an audit to make sure that we understood all the

different roles that were in play and who was doing, what

role and what skill set each person had and who would be able

to step into at least some pieces of my role. There wasn't

a direct replacement of my role at that point. And so I did stay

on after I left as a mentor and as a consultant to help with the

transition and provide mentorship to the person who was

doing as much of the pieces that they could pick up. And then we

had consultants and some other sort of rearranging your roles

to help fill in the different pieces in the tech department.

And so I think making sure you do a full assessment of your

staffing. And then also if the tech director who's leaving can

stay on for a bit afterward, to be able to sort of guide the

school. In addition, I did a huge brain dump, and I used

Asana for that. I went through my entire calendar for a whole

year, and every single month I said, Okay, what did I do that

month? And I put that in Asana. Like on January one, I got to

get ready to make sure re enrollment is all set to go. And

on January 27 I've got to make sure that we're ready for the

PSAT or the robotics competition that's happening. And so I just

tried to dump as much as I could into that so that day by day,

month by month, someone after me could figure out, oh, this is

going to be happening, and be prepared,

Daisy based on that response. Or for all of

you, did any of your schools have to do a hiring of a plus

1.5 or plus two to replace the intellectual capital that was

being lost. I know Daisy in your case, they kept you on board for

a while, but did they actually have to add beyond you noting

that it was a substantial loss, they did not.

Not end up adding a 1.5 they kept me on. And then

they brought in someone who had been at the school prior, who

was a network administrator. They brought him back, and he

had some really good knowledge of the school. Had worked for

the school for about eight years, so he had sort of the

cultural knowledge and the intimate knowledge of the

networking system and all the background IT systems, and so

that was a huge help. But at the same time, they were hoping to

reduce the size of the technology department at the

time that I was leaving and try to eliminate some of the

different pieces. The Educational Technology

Specialist was originally in the IT department, and they moved

that person outside the IT department and under the

assistant head of school, and sort of in the through Dean's

area. And so that made our team look smaller. And I think part

of that was because of the index comparisons that they were

doing. It made it look like our team was much larger comparative

to other schools and say that they wanted to be more in

alignment with that, and say we're trying to sort of manage

budgetary concerns.

Yeah, Hiram, I, like Daisy, just did a huge

brain dump over the course of a year and put everything down

that I could get out of my head. And there was a couple of months

transition where I worked there and he worked there, and that

worked out just fine, but there were some hiccups afterwards,

but I consider them minor. There was one I think the school

considered major, but it was easily fixed. They forgot to

update the certificate on the RADIUS server, so Wi Fi went

down one day, but that's a quick enough fix. So I'm of the point

where having them make their own mistakes is how they learn and

how they remember to do things next year, when you have, you

know, 500 constituents mad at you because the Wi Fi is down,

you won't forget to do it over Thanksgiving break next year.

And I have not been back to the school, but a couple of times,

so if there's been anything else I don't know. So with that, and

in answer to your first question, I recommended that we

hire another half time or full time person, or we rely more on

outsourcing. I had already developed some really strong

relationships with some companies that I didn't

necessarily need because I could do the work, but I also needed

some help just because I was one person and I couldn't do it all

time wise. So by developing those relationships all along,

we had some good outsourcing companies in the box ready to

go. And that's the direction the school has taken. They've given

them more and more responsibility, especially with

the infrastructure, monitoring switches, monitoring servers,

doing all those updates that you have to do at two o'clock in the

morning. And that's been a I think that's going to be a real

positive for the school, because you get a huge knowledge base

with these companies. You don't have to be an expert at

everything, because they may have 50 experts all with their

specialties. And I think that was a good way to go for Madeira

and Larry. I'd like to touch base on how you

handled it at your last school because you had a rock star in

the making in Eileen Ford, and she ended up being the tech

director at your school. Yeah, to

back up, I was at Trinity Valley School for the

last six years of my full time career. After my first year, the

academic technology person left in August, at the start of the

second year. And as you know, when you're hiring an IT person,

you can pretty much do that year round and transition them to

working in a school through mentoring, but an educational

technology person, the good people were gone. You know, I

did a search. I heard from Eileen, and she said, we're

thinking of moving to your part of the world, but I've made a

commitment for this year. I'm not going to leave now, so I

decided, you know, we're doing a search, but if it doesn't work

out, we'd love to have you apply. And I did my best to fill

that academic role, in addition to wearing my hat for one year,

brought her in. And I'd known her from when I was at Kincaid.

And then, of course, I knew her technology director, Janet

thornson, when she was at duchy Academy of the Sacred Heart. And

I knew she was a rock star in the making. Got her into the E

cat D program the last year that it was named e cat, and she

shined there, and over the course of my career, got her

promoted from academic technologist to Assistant

Director of Technology, and then just gave her more and more

projects to lead. And then I gave my notice in the fall of my

final year, Eileen and I sat down and we mapped out a program

to gradually phase myself out, give her more leadership roles,

and then just met with her regularly to answer questions

and help her out. Having a great successor is one of the great

accomplishments of my career, so I can't argue about that at all

one of you. I alluded to outsourcing, taking

some of the stuff where the network management piece was

pulled off because they've got the level of expertise. What are

your thoughts on that trend for supporting the schools or

replacing or backfilling when people step out of those roles?

And what do you think the pros and cons are of that when

schools take that route,

I'll start with that. Since I brought it up, I

think it's a positive things for schools. And I'm really

impressed with some of the companies out there and what

they're able to do, and with AI really taking a role in this

space, being able to predict when something's going to go

down before it goes down, I think is huge. So I think over

time, it will be a real benefit, as far as keeping the systems up

those 24/7 365, on the flip side, when you're working with a

company, outsource company, you may not have the same guy coming

out to your school all the time, or dealing with the same guy

every single time. So you might get different levels of service,

but it's also very difficult for those people to really create

those relationships that we talk about that are so important in

schools. So by having somebody on site, you do have a community

member, it just integrates better into the school system. I

think cost wise, even though outsourcing may look on paper to

be a little more expensive, the cost to keep an individual up to

speed on all the new technology, and it's just impossible for one

person to keep up with it all. It's just too much to ask. And

what I always liked about outsourcing, another big

positive, was that they would have access to companies like

Microsoft, Cisco, Oracle, whereas if I pick up the phone

and tried to call them today, man, that isn't going to happen.

And you used to be able to back in the late 90s, early 2000s but

today it's just impossible. And having that expertise from those

companies, navigating the big companies themselves and the

licensing models, the licensing models just baffle me anymore,

especially Cisco is just trying to keep track of that. So that's

where I think outsourcing is really, really going to pay off

in the long run, and ultimately, probably be less expensive than

a single person.

I think another good place that outsourcing is

beneficial is in the cybersecurity realm. They're

trying to keep track of all the different variants and places

where you could be infiltrated or exfiltrated. Trying to do

that in house is near impossible, to try to keep up on

all the things that are occurring. So outsourcing that

and having a company who's watching that 24/7, and has the

AI behind it as well to detect in the anomalies, I think is

very important and worth the extra expense, versus trying to

have someone in house who can be that expert. Certainly you need

someone who can communicate knowledgeably with the company

about what your school needs are. But I think that's one

place where it's really beneficial.

I couldn't agree more on the cyber side and

trying to find an outside partner, whether you have a good

person in house, on the IT side or not, it's great to have a

partner who gets to know your school and you want to right

size them to the extent that you know there are the local

companies that sometimes do stuff for a doctor's office

that's a one or two person company that might be a little

bit too small, because you'll get the great relationships with

them, but will they be available? You got to have that

service level agreement. If you get a company that's too big to

the point need earlier, you get a different person every time

you're spending so much time getting that person up to speed.

But if you right size, it that you have the right people and

the right tools in place, you get that synergy. And then if

you do have someone in house who can be at least working with

those people to keep them honest and know what's right and not

trying to upsell you or anything like that, you want, definitely

want a company that's thinking long term and playing long ball

with you to develop that relationship. But you know, one

thing you got to watch out for as well, is if you outsource too

much, then there could be some issues with succession planning,

because you want to have someone in house to be able to step into

your role, or at least part of your role. So I think just being

really smart about it, and what fits your culture and what fits

your school and what fits your comfort level, and what's going

to be best for the school in the long term is really the way to

go with that.

So for schools that are going through this

potential transition with their first gen folks, what superpower

Do you encourage them to look for in the next IT director that

is going to step into the shoes of their current person.

They need someone that can communicate with all

constituents all the time. Be able to speak to a parent, be

able to speak to the board, be able to speak to the teacher. Be

able to talk to your HVAC guy on campus and be able to

communicate with the vendors and the people off campus. Because

when I was at school, everybody, oh, Jeff's so nice. He's always

so sweet. But then sometimes with vendors, you have to be the

bad guy. You have to raise your voice and make demands. So you

really have to step into a lot of different communication roles

and styles, and I think that's the biggest superpower that a

new person would need.

I couldn't agree more. I'm going to steal your

word Hiram people chess, meet people where they are, be an

excellent listener and be open, because you come in with your

opinion, and they might raise something that's a valid point

that you hadn't thought of to have those skills and to be that

servant leader, and to always put the long term interest of

the school and the kids first.

Yes, I also agree with the communication skills

being a superpower, and I would add to that, that you also need

the ability to be absolutely flexible and able to pivot to

expect the unexpected, and it changes the only constant. And

if you can manage that, then I think you definitely have a

superpower, because we all know from covid that we had to all

pivot and expect the unexpected in your storms that you're

having on the East Coast right now, there could be power

outages that occur, and then domino effects from that, and

being able to just manage those and pivot and problem solve

quickly and easily and say, Oh, well, if this doesn't work,

we'll just try this, and we'll just try that. Is also very

important.

We have one more question for the three of you,

and Mr. Stites, you're up.

One last thing I want to ask is, Is there

anything you had wished you had done before you left your last

job before you said, See you later. Is there one other thing

you would wish you had done or been able to do before you

stepped away?

Look at that, you got him. Bill, you got him.

That's a tough question. Bill, because I would

say I felt pretty good about the way I left the school. I had

this bucket list that, you know, I started 20 years ago, and I

literally finished my last thing on the bucket list the year

before I left, which was the SIS transition, which I've said I

will never go through this again. I will quit before I do

another sis transition. But I would say, if there's anything I

wish I could have gotten done before I left, I wanted another

FTE. I really, really felt the school needed one. They're kind

of running on two FTEs for a boarding school that's pretty

substantial size and pretty big infrastructure, and I felt they

needed one more. So that was the one thing I wasn't able to get

done before I left.

I was going to say the same thing. One of the

things I'd been working on during my tenure, and it made

great strides, was not just getting the right people on the

bus, but getting more people on the technology bus. Hiram was

part of a team that did an audit at my school, and that helped

out a lot with that as well. But having my fantastic successor,

the staffing has gone up, but I would have loved to have been

able to provide that for her before I left.

I feel fortunate that I was planning way ahead of

when I actually even announced that I was going to depart, and

was able to, similar to Jeff, get my to do list completed for

the most part, knowing that there are these bigger things

that I'm just not going to be involved with, like building a

brand new building was coming online as I was getting ready to

depart, and just letting folks know that I'm not going to be

involved in that, because I will be departing. One of my plans

when I was planning to leave was to make sure that I went out on

a high note. I wanted to have things all sort of running and

humming, and then step away and say, this is a really good pause

time for the next generation to come in. And so that was really

important to me.

It's great when you can step away and know things

that are working well and feel comfortable about that. Jeff, I

do find it hilarious. I can't tell you how many times I have

heard people say that it's the SIS transition that is, like,

the breaking point for them, where they're like, enough is

enough. Yeah, I've done this twice. I'm not doing this the

third time. Peace out. I'm done. Let this be somebody else's

project to take on and own.

And doing it right after coming out of covid was

just awful.

We did it during covid. You can imagine what that

was like.

Oh my gosh, yeah. And I wanted to just touch base

on what Daisy said. I really like that term pause time, I

felt like I was in a really good place as well. With pause time,

there were no major systems that were going to need upgraded for

the next two to three years. All the copier contract was new, the

Wi Fi contract was new, and it just felt good to be able to

slide out and let somebody else slide in, get their feet wet,

learn the job. Before the next phase of change was coming down

the road in the next two to three years.

As you guys are now in your retirement, tell

us what to look forward to. What are you loving about your

retirements?

Oh, it's the best job ever. I really have enjoyed

being able to wake up and figure out what I want to do with my

day, the flexibility to do some consulting if I want, but then

also go paddle boarding, camping, fishing, be in the

outdoors a lot more than I was able to. Also just doing all

that wellness stuff you're supposed to be doing, yoga,

exercising, eating, better, meditating, and just all of the

things. Just feeling like life is a lot more balanced than it

was and taking time and resting and just really enjoying life

and just grabbing every piece of it, it's been wonderful.

Yeah, I have to echo what Daisy said. Self Care

is a big thing. Being able to have time for exercise and

working out and being outdoors and playing tennis. I have eight

grandchildren, getting to spend time with them without having to

look over my shoulder at what's going on at the school is just

wonderful. You get up and the day is yours. You can choose

what you want to do with it, and some days you just don't want to

do anything. That's okay too, because no one's going to really

miss you. But yeah, it is the best job ever. I love it, but

I've been thinking about it for a long time, planning for it for

a long time. I'm doing some volunteering, which has been

great to give back. I drive for Meals on Wheels. I serve on the

lake Montclair Community Foundation Board. I just became

certified as an AARP tax counselor. I will start helping

people do their taxes next week. I'm a tax geek, as Christina

would probably guess so, yeah, it's just been great.

I can't agree more with everything you said, from

following your passions to giving back to sleeping in to

spoiling grandkids. I think the only other thing I'd add is

being able to travel, not during peak times. It's a wonderful

thing.

I love it. Thank you guys so much for

giving us this insight and for joining us for this

conversation.

Thank you all for being here today. Bill and I are

hunkered down doing school stuff, whether at school or at

home, in the midst of the snowpocalypse and ice pocalypse

we thank you all for your

time. Thank you for having us.

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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