Keeping Schools, Students and Teachers Connected
21 Jun 2022 · 27 min
In this GovTech weekly podcast, host Dustin Haisler (joined by Joe Morris and Jed Presgrove) interviews Joe Cicero, a former high‑school social‑studies teacher who now serves as a senior program manager on Microsoft’s Security Compliance Management team and evangelizes Intune for Education. The conversation traces Cicero’s journey from classroom teacher to Microsoft, then dives deep into how the COVID‑19 pandemic forced K‑12 districts to shift from shared‑cart, lab‑style computing to 1‑to‑1 device deployments. They discuss the rapid adoption of cloud‑based management tools—Microsoft Endpoint Manager, Intune for Education, and Windows Autopilot—and how these enable zero‑touch provisioning, remote updates, and streamlined enrollment. The dialogue explores the new lifecycle management challenges that arise with massive device fleets: break‑fix workflows, hot‑swap replacements, asset and inventory tracking, provisioning packages, and the unique serviceability of the Surface SE laptop. Funding sustainability and compliance are examined, highlighting how federal grant spikes can create procurement spikes, the need for sustainable budgeting, breakage‑rate planning, and rigorous asset accountability. The episode concludes with practical cybersecurity guidance for K‑12 districts, emphasizing multi‑factor authentication, strong password policies, Windows Hello, regular patching, Defender, “impossible login” monitoring, and incremental steps toward a security operations mindset. Finally, Cicero shares where educators can follow his work (Microsoft Education site, Twitter, LinkedIn). The podcast blends personal anecdotes, industry insight, and actionable recommendations for school IT leaders.
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All right, TGIF, it is that time again. Welcome to In Case You Missed It, GovTech's weekly government technology news roundup, where we take a look at some of the biggest GovTech news from the past week and give you our thoughts on what it means for government citizens in the market. I'm Dustin Haisler, joined again by Joe Morris and Jed Presgrove. Today's episode is brought to you by Microsoft. Microsoft's products help teachers, students, and staff stay online and on task, and during the pandemic, they were instrumental. Now, the new Microsoft Surface SE. This is a laptop designed specifically for hybrid learning. It gives teachers, students, and staff the most collaborative, powerful, and secure learning tools ever, and all at an affordable price. To learn more, visit microsoft.com/surface or check out our story notes for more resources. Now, our special guest today is Joe Cicero. Joe is a senior program manager for Microsoft Security Compliance Management team, but he started off as a high school social studies teacher. He now evangelizes for Microsoft's Intune for Education device and app management program. In other words, he's the guy you want to call if your school district wants to distribute, onboard, and manage devices for teachers, students, and staff. Let's bring Joe into the fold. Joe, thanks so much for joining us.
Thank you. But now I feel awfully intimidated by the person to call for all of your deployment needs. Hopefully my cell phone isn't going to flash across the screen because I know The needs are great and I am limited.
We can always arrange for the cell phone number to be shown, but let's start first with, you know, digging into actually your background. From being a high school teacher to working at Microsoft, you made a career of really working in education. Tell us a little bit about yourself and that career path.
Yeah, education's all I know. I grew up on an old dairy farm. I live in New York in the middle of nowhere, upstate New York. And the coolest thing, the most exciting career that I could have growing up was to be a teacher. They were the folks in my neighborhood who had the nicest houses. They had summers off. So that was my career path, and that's, that's what I've stuck to. I taught in the Rochester City School District, and it was there I really learned about technology and how it could bring hope to a lot of the students I was working with. Obviously, you know, students as everywhere had certain challenges to overcome. I, as a teacher, a new teacher, had a lot of challenges to And gosh, it was during the time period where we were seeing more technology in the classroom, really going from overhead projectors to digital projectors to the idea of mobile tech carts where kids could get a laptop and 20 minutes after logging into the computer, we could go do a web quest. And that, that set me off on a journey into technology. And now I get to sit at Microsoft as an engineer working with our global partners really work with them as we develop new products so that they can bring it to schools around the globe and be able to make it easier, more easily manage devices, really make the experience a lot better, faster login times, not having to worry about updates, all of the struggles teachers have when they start using technology in the classroom and really trying to solve those before they even get into the classroom.
You know, when I look at the K-12 space, it's Phenomenal, right? With 15 years that I've been following it or invested in it, technology was kind of an also-ran. Then it's been now kind of really integrated. But the last 2 years have been something that at least I'd never seen before, particularly on the device front, right? So how has the events of the last 24 months started to reshape the thinking around devices, distance learning, and around learning in general?
Yeah, really the role of— when I was a teacher, when I worked in schools, I'd offer this professional development, this training, and we'd have to beg teachers to come to learn about how they could use tech in the classroom. It wasn't very exciting. They still had a lot of curricula that they were using. I had to come up with raffle items to get people to attend. And teachers during this time have become very thirsty for what is the technology that I can bring to better motivate, to better connect with my students. And obviously over the last 24 months or so, whatever the exact month count is when the pandemic started, schools went remote. And that meant that schools didn't go to physical school. However, I heard all of these stories of students still going to school. Their parents were still driving them to school. What was happening is schools were having to issue laptops, right? If you weren't a 1-to-1 school, you needed a laptop because there's only so many worksheet packets you could hand out. Maybe the first couple weeks they had it, they went to school and they got books of worksheets to do, but eventually there was that move to, oh, now we need to hand out laptops. And some handed out existing inventory laptops, and a lot of those students had to come back to the parking lots in order to get the updates, in order to get the, the latest version of an app installed. So even though the school buildings were closed, they were almost being reconfigured as distribution centers for technology, for remote learning, for updates that could have been remote but weren't remote for that school yet. And then even the community centers turning into these mobile distribution spots of get your laptops, get your Wi-Fi cards or your mobile hotspots, and all of the All of the excitement that created, both positive and negative, of bandwidth limits and how do we make sure that kids at home can use the technology to log in, to connect to Mr. and Mrs. Smith's class and get back to social studies.
Joe, thank you for all of that. So have you ever seen anything like this before, like everything that's going on with the K-12 market right now?
Well, no, and probably for good reason, right? We've never had this amount of technology that was purpose-built for education. That's one thing. And we've never had such a screaming need for it, right? If school is closed tomorrow, right? I live where it snows. We don't have snow days anymore. That makes people a little upset because there's something nostalgic about the snow day. But if a student can't go to school, Now we have the technology possible that they can log in, they can get their assignments, they can still collaborate. If they're out ill, maybe they're traveling for sports and can't physically attend, there's all of these options, right? So there is this remote learning piece, but there's also this added benefit of things that you can do with technology that you never could have done in the classroom, right? Virtual field trips, citizen science, right? Being able to actually dig in and do a lot of stuff that otherwise I personally couldn't have done in my classroom.
So through the combination of federal funds and standard budgets, school districts have been procuring low-cost laptops in numbers that we've never seen before. But I'm curious, how are you seeing these districts manage all these devices right now? Are there any challenges here involved?
Yes, yes, there are challenges. So pre-pandemic, there was a lot of customers who were legacy managing their devices. They had on-prem device management. We'll say some dirty words here: GPOs, SCCM, right? A lot of this bulk, hard Microsoft infrastructure that schools struggled to manage even when it was on-prem just because of the size of the solution based on the needs of the school and the staffing capabilities of what the school had to put in place. But they were making it work. They were reimaging Windows devices every year. They were going through a gold image process of figuring out what every device was going to look like from an operating system perspective, what applications were going to be on there, and then they were cloning the devices every single year. Now, what we've seen during this challenge is post-COVID, pandemic or during the pandemic, really that push to, oh, well, all of these things that we're doing require a lot of physically present, physical touching of the device. It really required IT to be on-site for the staff, the student user to be on-site. With the pandemic, there became this now awareness of these cloud-based management solutions, right? I don't need to be in my office. The student does not need to be on site in order to get the policies, in order to get the applications, in order to get the updates. And we've seen a lot of growth in our Intune for Education product because whereas pre-pandemic we were running around the planet, it felt daily, evangelizing, telling them the good news about cloud-based device management, faster login times, not getting updates during the middle of class, being able to push apps, the need became very relevant during the pandemic, and we saw an increase of adoption. So now we see schools that are using Intune for Education to manage devices alongside Autopilot. So Autopilot means that the device comes pre-enrolled to the school, to the student, to the user so that the user can get the device and just start learning. So at the school level, we've even seen laptops directly shipped to students at their homes so that no one had to touch the device. Except that student or directly to that staff member. And they get that experience of opening up that brand-new, in this case, a Surface SE, getting that nice smell of newness as they open it up, as they log in, as they personalize the device, and not having to wait on IT to gold image it, asset tag it, enroll it, make sure it has all the updates. Does it have Office on it? Does it have all of the apps we need it to have, right? Getting rid of all of those steps and saying, let's just, let's get the student, let's get the staff member the laptop, let Autopilot enroll it, and let Intune for Education manage it.
That's kind of where I wanted to go with this because, you know, what you're describing was the way that it was. Then we had this moment of crisis that began now to not only, like, change the experience but reshape lifecycle management, device management. But you're also talking about a fundamental shift in the experience. What you just outlined there, the unboxing, the connection maybe even to the district being different. So what are some of the changes that you maybe forecast seeing in terms of the experience and expectation and the road ahead in terms of lifecycle management of these devices?
Yeah.
Before the pandemic, it was all about shared carts. Shared carts were very popular. You know, even in, even in my former schools I worked in, we'd buy, you know, thousands and thousands of devices and we'd put them in carts and we could roll the cart around. And sometimes we would do some type of fake one-to-one initiative where the student had a number in every classroom. They'd go in, they'd pull the device out of the cart, they pull the laptop out of the cart and get to work. And from a Microsoft standpoint, we invested a lot in shared PC mode, which made it so that kids could log into multiple devices and it wouldn't slow them down. Because if you've ever worked in a traditional computer lab, they start the year fast and they get slow over time because they have multiple users using them. So that was a lot of our engineering work pre-pandemic. With the pandemic, now seeing the burst to 1-to-1, right? Every school went 1-to-1 that possibly could go 1-to-1. They did it in creative ways and tried to piecemeal it together wherever possible. But that changes how you do business, right? You have all these carts that are no longer being used. And now you have every student with a laptop. What does that look like for your help desk? How are you going to service these? And if you adopted cloud management during this point, whether you're using Microsoft Endpoint Manager or Intune for Education, they write to the same backend, but people have preferences on which they use. I prefer Intune for Education. But with one-to-one, we now have also break-fix, right? So if a computer would break in a computer lab or on a shared cart, the teacher would probably open that ticket, Let the help desk person know, the school's IT person know, hey, this device has a cracked screen, fix it. Now it's pushed onto that student of, oh, that student has a broken device, what do we do? Now, some schools will sell insurance policies. I know from my daughter's school, we buy an insurance policy that if her laptop breaks, it's like covered for it to be fixed, right? There's been that shifting of responsibilities there. But then on top of that help desk work that now has to occur for what the student has to do to make sure that their device is ready, there's also some technical requirements of, oh, well, the laptop's broken and I need to replace the motherboard, right? And with the Surface SE laptop, it's the first Surface that a school's going to be able to take apart and replace parts in it. And as things get replaced, and hoping it's not the motherboard, it's probably most commonly the screen from my experience of kids trying to, close the screen with markers and textbooks in the middle. Just personal bad experiences with what students can do with technology. But if they do have to change a motherboard or any hardware of the device, then they might have to rejoin it to Autopilot, or they might have to use a provisioning package to rejoin that device. So as you service it, it might lose some of those unique identifiers that let Microsoft know that the school owned it and and what that device was. So we also have a program out there called Set Up School PCs, which is an application that allows an IT administrator to quickly create a USB provisioning package, small file that lives on a USB stick, and put it into the side of new devices or newly reset devices that re-enrolls them or gets them enrolled in Intune for Education. So all of those policies and apps can come down because... If you're a 1-to-1 school now, right, when you're 1-to-1 and the device breaks, your teachers have already changed their practice for how they deliver curricula. So it can't be, oh well, Johnny's gonna go use the textbook now while we're all in, you know, cyberspace creating virtual worlds and, you know, recreating ancient worlds in Minecraft. Johnny's gonna read the textbook chapter, right? That's no longer okay. Right, especially when we talk about equity, we can't have one student that's like, oh, well, my screen broke, so I have a horrible learning experience and I'm not going to get the full thing. So see a lot more work with hot swap devices. I'm not going to wait at help desk. I'm going to send the student to the help desk to provide their device that's broken and needs fixing. But I also expect the IT to give that child a loaner device or to just replace that device. Right, in a cloud-managed device, we don't need to— Rebuild Johnny's computer. Johnny's computer can be fixed and then reassigned later to somebody else. We can just give him a new one, have him sign in with his Azure Active Directory account— that sounds kind of technical— his Office email. He might not have email turned on, and get all of the things so that Minecraft will be automatically installed from the cloud so that by the time he's back in history class, he's not missing out on learning, right? Those are the same things we saw at home, But now we have to also see what that looks like in school, that, you know, a piece of technology is as essential as a piece of pencil, which is also a piece of technology.
Yeah, that's great. Now, I know we've talked at length previously about there's unprecedented funding that's available for these districts that are out there to do all kinds of different technology improvements. And one of the elephants in the room is always around compliance. And I'd love to get your take on if there's any impact with Compliance related to this unprecedented federal funding available to school districts?
Yeah, account for your technology. If it went home, hopefully it's coming back, right? Because people are gonna ask where it went. Many horror stories out there. And understand what it means if you bought it for student use. Is it being used by a student? If you bought it for staff use, is it being used by staff? If you're having to refresh it, are you keeping track of all the serial numbers? Do you have good asset and inventory management so that when one device has to be swapped out or mailed in, you've got a replacement coming in that you know exactly what that is? I also want to touch on the funding piece because I think it's created a little bit of a curve in how we purchase technology. So oftentimes we'll try to purchase laptops in small batches over a period of years so that there's a sustainability to it all. Right? I buy a laptop for my students. I expect that laptop to last 3 to 5 years. And then at the end of that time period, at the end of that 5 years, I'm going to buy another set of laptops, right? And schools try, you know, 2019 and before, they try to space this out. So it's not, we're going to buy a million laptops this year, and then we're not going to buy laptops for 5 years because we're going to— and then we're going to have this problem of having to buy a million more laptops. Right? So there's a lot for schools to think about here, especially if they've used grant funding to purchase laptops or they're using it to purchase laptops today. Are they doing it in a way that's sustainable? Because the government grants that exist to go 1-to-1 today might not exist 5 years from now when there's a refresh. Also calculating in breakage rates, right? Devices will break because students are students, teachers are teachers. Teachers will spill coffee on a laptop, students will drop it, do creative things to destroy their device. And a lot of schools calculate breakage rates differently. It could be, you know, 10% to 15% a year could break. And when we're talking 1-to-1, that can be a very significant number. So how are you planning for that? Some folks will do overbuys where they'll purchase 10% or 15% more than they actually need so that as devices break, they have those hot-swap replacements. Others will not and will try to, do some repair on their own. But I think schools looking towards the next couple years are going to have to see if they can do some early refreshes if possible, even if they don't plan on deploying right away, so that they don't get to year 5 and realize that they have, you know, 50,000 laptops to replace and there's no government program that's going to make that possible. Otherwise, you're gonna end up with students with an 8-year-old laptop and— I'm hoping that the technology 8 years from now is, you know, a million times better today because that's great and that's progress. And also, you know, electronics over time are just gonna lose some performance. So really trying to plan ahead knowing that your laptops might be really shiny right now, but you should start thinking about that every year and budgeting that in so it's not going to be a painful surprise.
Yeah, I think that's sound advice for district leaders. Now, the other elephant in the room is around cybersecurity, and we know this is a, you know, a hot topic across the board in school districts around the country. Tell me a little bit about how K-12 organizations should be approaching cyber and cyber resilience right now.
Yeah, it's a balancing act with education. So I work with folks in the industry, energy industry. I work with folks in the financial energy financial industry. When I work with those CTOs, those CISOs, their security departments, they have security operations centers, they have blue teams that are going around finding insider threats, they have teams looking at external threats. It's a huge part of their business to protect their data, and their data has financial value attached to it. Schools, Also have very important data. Yeah, sure, they have financial data, but the most important data that they have is their users, is their students, right? As a parent, as a former teacher, right, we care a ton about that student data, that student privacy, and really trying to protect that, knowing that there are some limits on what a school can do to create security that makes sense, right? We're not going to have kids running around with FIDO keys. and having biometric scans in order to access information, that at some point there's going to be some barriers to what we can ask staff and students to do in an education environment. That doesn't say that the work is any less noble or important. The first thing to recognize is security is more than a strong password. Obviously, you need that to at least start somewhere. But some simple things are possible for schools to do, right? And we can take small steps. that eventually lead to creating some type of security operations center for the school, even if it's going to be more ad hoc, a couple IT admins who are going to see the security. But some small steps are MFA, multifactor authentication for admins. If you're not doing that today, like, that's, you know, pause, pause, stop, walk away, or wait till the end of this show. Go do that. Second thing is to look at what Look at MFA for your teachers, your staff. What does that look like? Can you have them authenticate with a phone app? Can you use the Microsoft Authenticator app? Is that possible or not? Depending on the state, depending on the school, that's possible, that's not possible. It's a great step if it is. Complex passwords, right? Make sure that the passwords are not easily findable, especially for our students. Have them create unique passwords. frequently update the passwords, have them change the passwords. I know that's all of a pain. Depending on the school, they might be very comfortable with turning on Windows Hello, which allows your face to unlock your device. That gets you to more of a passwordless experience. But all of those are small steps from a user security standpoint. Then there's also the device security, right? At Microsoft for Windows, we're publishing updates monthly for security. Make sure your devices are patched. Make sure you're using Windows Defender to get all of those updates. In Intune for Education, you can set it so Windows Defender is running nightly. It's updating, it's checking so that anything we, Microsoft, find with all of our signal is being brought to bear on those individual devices. Because now we have all of these endpoints that are accessing the network in interesting ways. It's not just the schools and the devices in the library in the school, so therefore it accesses the resource, The laptop could be with a kid on a cruise ship in the Bahamas. Good for the kid. But now this creates a whole interesting realm of how is the kid accessing data? Do we want to track login locations? Do we want to turn on something called impossible login so that if the same student is logging in from multiple places, this is going to red flag the account, right? What are some simple things that we can do that are not hiring a 30-person security center? to do, knowing that at some point we're gonna eventually get to more of a security operations center model, probably not 30 people, depending on the size of your school, still probably not 30 people. You'd probably be a really big school to have that, but starting to become more aware of that. And then I, just like how large companies have these blue teams that are going out looking for these threats, maybe this is an internal hackathon that you as an IT team can put together where you— you know, take an hour, take a couple hours, just like teachers have PD. Maybe you're gonna do a hackathon where you're gonna look through your network, you're gonna look through your posture and figure out where your issues are. Maybe it's SharePoint, maybe you need to tighten up some sharing, maybe it's passwords, maybe you have some utility accounts that you've created that have admin rights. So maybe you at some point created a printer utility admin account, and now that account accesses many things that it shouldn't. Or at some point you had a contractor come in and do some work, You gave them an admin account, but you never removed it, right? There's a lot of cleanup. So staying up to date, cleaning up your accounts, MFA for your admins, making sure you have passwords, and then looking at what those next steps are— Windows Hello, maybe multifactor, and then just other security settings that you can begin to enable, knowing that you can't do it overnight. And a lot of things that we see happening in enterprise just don't make sense in education, right? And that's the balance that we all are trying to figure out. And that you listening as an IT person in your school have to have those conversations. And I think transparently with the school leadership, with the superintendents, with the board of, hey, we can do XYZ. This is the impact on students. Where is the middle or what's the line that we want to draw? And I think in a collaborative effort, you can come up with a pretty good security posture that will make a lot of sense. The worst thing that you can do is do nothing because you think that the task is too hard. And I think there's a lot of schools that have seen security as too intimidating to tread into. But I think it's something that we have to look at, and we have to take a learner's perspective into figuring out what we can do to actually secure our environments.
Well, Joe, that's a lot to think about, but it's some sound advice in there as well. The easiest question that you're going to get today is, where does our audience go to keep up to speed with you?
I think the Microsoft Education site is a great site because that's going to link you out everywhere. I am on Twitter, so you can find me on Twitter. I'm not cool, so it's just my name, Joe Cicero Jr. Same is true for LinkedIn. I post a lot to LinkedIn. I find that's a really easy way to feed our community of tech directors. They're a very active group there. Connect with me there. There's chat as well. I know we didn't flash my cell phone number, but if you want to bother me on the LinkedIn chat, Utility, I will respond.
All right, well, great. That's all the time that we have for today. Thanks again to Joe for joining us and sharing your insights, and to Microsoft for helping make this episode possible. For those of you watching, join us again next week, Friday at 12 o'clock Pacific. Thanks and take care.
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