Aug. 9, 2025

Episode 333: Kyler Cheatham

Episode 333: Kyler Cheatham

AI in Schools: Strategy Over Shiny Tools with Kyler Cheatham When it comes to AI in school districts, rushing in without a clear why can cost millions, crush teacher buy-in, and derail your entire tech strategy.

 AI in Schools: Strategy Over Shiny Tools with Kyler Cheatham

When it comes to AI in school districts, rushing in without a clear why can cost millions, crush teacher buy-in, and derail your entire tech strategy.

In this episode of My EdTech Life, I sit down with Kyler Cheatham, a system architecture expert in AI and predictive analytics, to break down what districts are getting wrong and how to get it right.

Kyler shares hard truths about AI adoption in K-12 and higher ed:

  • Why CTOs must own their “I don’t knows”
  • How to avoid the “move fast and break things” trap
  • The real cost of chasing buzzwords without solving actual problems
  • Why 50% of your implementation team should be end users
  • How to keep vendors honest and ensure they meet your district’s needs

Whether you’re a district leader, tech director, or educator navigating AI, this conversation will give you the questions, strategies, and fail-safes you need before signing that next contract.

 00:00 – Welcome and introduction
 02:17 – Kyler’s background in AI and education technology
04:26 – The toughest challenges districts face with AI adoption
07:00 – Teachers as “speedboats, tugboats, and anchors”
09:14 – Advice for CTOs feeling overwhelmed
12:32 – The dangers of rushing into AI for the sake of hype
15:43 – Why vendor partnerships can make or break implementation
20:00 – Building a core team with 50% end users
22:58 – “Phase Zero” and defining your why before selecting tools
32:21 – The AI sticker joke—and why labels aren’t strategy
35:15 – Two wins and two losses Kyler sees in AI adoption
40:42 – Final advice for districts, CTOs, and vendors
46:25 – Closing thoughts and how to connect with Kyler 

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00:30 - Welcome and Guest Introduction

02:19 - Challenges in EdTech Implementation

06:06 - Advice for School CTOs

11:43 - Managing EdTech Investments Wisely

19:05 - Building Effective Vendor Relationships

28:04 - Getting to the Root Problem

39:37 - Wins and Losses in K-12 AI

45:14 - Final Questions and Contact Info

Dr. Fonz Mendoza: 

Hello everybody and welcome to another great episode of my EdTech Life. Thank you so much for joining us on this wonderful day and, wherever it is that you're joining us from around the world, thank you, as always, for all of your support. We appreciate all the likes, the shares, the follows. Thank you so much for just sharing our content, for all the positive feedback and, as always, we love to bring you some amazing conversations and amazing guests and, as always, my friends. Today is just as great as every other episode, but I'm really excited that I have been able to connect with today's guests, following them on TikTok, what they share about technology, technology, innovation, talking about AI. So I figured that today, what she has to offer is something that is wonderful as well for the K-12 and higher ed space. So I would love to welcome to the show Kyler Cheatham. Kyler, how are you doing today?

Kyler Cheatham: 

Oh, I'm great. Thank you so much for having me. I so appreciate being here today.

Dr. Fonz Mendoza: 

Excellent. Well, I am excited that you're here. Just like I mentioned in the introduction, I stumbled upon your TikTok account and everything that you said just really resonates with me. Being a fellow ed tech lover myself and just seeing the changes in educational technology and just technology as a whole from you know, when I first got immersed in it in 2018 till now, and, of course, seeing the big boom with AI and what you share, I was just like this really resonates and this needs to also be heard, you know, within our K-12 higher ed space. So, before we get into the conversation for today, can you please give us a little brief introduction and what your context is within the technology space?

Kyler Cheatham: 

Yeah, absolutely so. I am a system architecture expert that specializes in AI and predictive analytics, and that's just a really fancy way of saying. I help people figure out what technology is best for their business or their public sector environment A lot of times at school districts or higher education and just decide what the best way is to implement this emerging technology within their overall culture so their team doesn't freak out and they can have, you know, this synergy of really maximizing technology outcomes. So my consultancy works across the globe and we're very, very privileged to have great contacts like you and a lot of different verticals throughout industries.

Dr. Fonz Mendoza: 

Oh, that is wonderful and that's great that you share that with us because, as you know and I always go back and, just FYI I just defended my dissertation yesterday and it was really on talking about the implications of artificial intelligence within the school setting and it's really like 70 episodes that I did from November 22 to December 2024.

Dr. Fonz Mendoza: 

So it's a nice snapshot there. So we'll talk a little bit about what I've observed and then just kind of run parallel to what you have observed. But I love that you mentioned that you do have that experience in speaking with schools and working with teams, because I know that not everybody has it quite figured out and it's still very much so like the wild, wild west. So, yes, exactly, so we'll go ahead and get into that. So I just want to ask you, first and foremost, you know, as far as your background in the technology space and, like you mentioned, consultancy in AI what are some of the big things that you're seeing right now within your consultancy within the education space? What are some of those fears or barriers that you're currently trying to help school districts kind of overcome so that that way they can get these systems to work for them and for their educators and students?

Kyler Cheatham: 

Absolutely Well. I mean, as you well know, a school district or an educational environment is one of the most difficult and complex to implement new technology in, just because of not only the cultural dynamics, but they don't have a lot of backfilling on, you know, their core team or on their staff. They are already pretty strapped when it comes to implementing that, and we did one of the largest school districts in the United States and it was the largest implementation I think I've ever seen. I'm pretty confident in saying that just because there had to be movement in staff so much so that they had to bring in temporary staff to be able to oversee how the technical implementation was being tested and we're kind of over here like that's great, that's cool that you saw a solve for that. But you need to be able to own your technology strategy and really understand what that means, especially when it comes to AI integration.

Kyler Cheatham: 

Because no offense to teachers, love teachers but a lot of times our academic colleagues can be very, very resistant to change right Just because they've been doing their job the way that they've done it for so long. And adding a level of technology in already, you know, a very hectic classroom environment can be incredibly stressful. So totally valid, right. But when it comes to what we're seeing in AI at the school district level and I'd be curious if you agree there is so much data and so much foundational needs and processes and assessment of cultures. Each school is a different culture, each district is a different culture and each one really needs its own implementation strategy in order to maximize the output of their technology. So really there's still so much in the forefront of building out what that foundation looks like. Ai hasn't been something that they can really utilize quite yet, just because of all of that front end work that needs to be done to, you know, really implement it in that kind of complex structure. And again, I'd be curious your thoughts on that too.

Dr. Fonz Mendoza: 

Yes, no, absolutely, and that's something that we see. And one thing that you did mention is really the lack of resources, and not necessarily that I'm talking about, you know, chromebooks or devices and things, but the human resource Exactly, not enough people within a district. And now you're adding this additional component for people that may not be equipped or aware of what's happening. And many times, like you mentioned, yes, in the classroom and the teachers you do have. And I always love to quote my friend, renee Dawson, who says you've got your speedboats, your tugboats and your anchors, you've got those that will go to a conference or see a video on TikTok and that's it. They're just going to go ahead and run in and implement without any just regard to privacy or regard to accounts or anything, and they're just going to go for it because they think like, okay, this is going to go ahead and save me time.

Dr. Fonz Mendoza: 

Then you've got the kind of in the middle, like the tugboat, where I'm like, okay, I'm kind of waiting and seeing, but then, like you said, there is that, uh, resistance faction, and that's one thing that is very interested, interesting and does coincide with the findings in my dissertation, where it we see in the second quarter of you know my research we did see this kind of branch of now you have the resistors and you have the hey, let's move fast and break things kind of crowd. And then I always say it's like I always like to be in the middle and bring these conversations to the table to see where we can kind of meet. But you're absolutely right. And in the sense that right now a lot of school districts are kind of getting that guidance, but there's still a little loss because there's still that disconnect between the classroom, where teachers kind of have that autonomy in the sense of you know, I have control of my classroom and they may just bring in apps just to use and use them, because it's either hey, somebody's using it on Twitter, I'm doing it for social media, or I'm actually trying to help that work without the CTOs knowing what may be happening.

Dr. Fonz Mendoza: 

And then, of course, there's that risk of data. So what are some of just your, some of the best advice? Maybe two to three tips just that you can share with CTOs during this time, because I'm sure they have their hands full. And again, like you mentioned, we need to make sure that we're all conveying the same message and moving in the same direction. What can you tell them to kind of put them at ease? Maybe two to three things to get them started.

Kyler Cheatham: 

Absolutely, and a CTO for a school district or an educational entity is no joke, right, that is this, you know, definitely a very challenging position. I always say the CTO or the CIO in the organization is really the loneliest position. Right, you're supposed to be this know-all center for all things technology, but ideally, especially right now, we see typically that those CTOs don't know a ton about technology because that wasn't, you know, the generation they were educated in, so they're still learning just as much as their team, and so my advice would be to own those I don't knows. Right, there's never going to be a full baked answer that anyone expects you to have. Lean on your team, lean on your consultants if that's what you're doing. Lean on your vendor and make sure that you understand that I don't know is a fine answer. I don't know what to do about this issue that we're having at this said school district. I understand that it's causing a lot of chaos. I hear you that you're frustrated, but I don't know how to solve it. But what I can promise you is I'm going to put my full energy into listening to you, hearing to you and finding a solution for you. So that would be one tip.

Kyler Cheatham: 

The other thing I always tell CTOs, especially educators, because they're used to, you know, being so involved and engaged in their culture, that a lot of times when those senior administrators get to that level, they still think they have that same pulse on what's going on with each school and they don't Like, at the end of the day, even if you are the best award-winning CTO in the entire universe, there is still an executive bubble that you don't hear what's going on on the front lines. So you need to look at your implementation and those organizational assessment data as absolute goldmine nuggets of data. You need to understand that your teachers, your staff, your other administrators are really telling you what you need to hear, and a lot of times, luckily, our teachers can be very engaging in that type of thing because they're teachers. You know they're used to those types of, you know surveys and qualitative, quantitative feedback mechanisms. So know that the organizational assessment data is going to be so foundational to setting your technology strategy. Don't try and set something when you haven't heard the problem yet.

Dr. Fonz Mendoza: 

Oh, I love that.

Dr. Fonz Mendoza: 

And those are great tips and that's for that side, like I mentioned, those that are still trying to figure it out and owning those I don't knows. I think that's something that's very important. Because now I want to ask you on the other side, what if we have those CTOs that are just running and gunning and just saying, hey, we're just going to open this up and just because maybe we want to have that notoriety or we want to just open this up because we want to be the cool kids and things of that sort, what might be some of the risks that they may run into, that they need to consider that, instead of doing the move fast and break things, that's kind of be more intentional of what we're doing. So what might be, you know, two tips that you would share with that type of CTO?

Kyler Cheatham: 

Absolutely. And you know those CTOs are sometimes scarier than you know the CTOs that have kind of this tenure, they might be more not digital literate in that way. That CTO right, we still need to listen to our communities, we still need to have that foundational piece. But, knowing you can't argue with data, I always say when I go in to talk to a CTO, understanding the risk of failure from a quantitative level, If we spend $30 million on this new AI pilot project and it fails, not only are we losing $30 million because we rushed it and we didn't listen to our staff or our communities, but also now we have to go in to calculate the time loss and the fatigue with that implementation, Because you mentioned the lack of resources. It's like running uphill in sand at that point because you've lost buy-in at every level. And we always say the most important or most expensive piece of an implementation are those re's, redesign, redo, re-engage, because that is so much harder than starting off on a strong, solid, intentional foundation plan that's been engaged at every level of your organization.

Dr. Fonz Mendoza: 

Excellent and that is wonderful. Like you mentioned there, just really kind of just slowing things down and really talking to stakeholders, really taking everything into account. Now, in my experience not only just speaking for my district but for friends that work at other districts is currently within our education space. We're starting to see, you know, kind of a couple of applications, maybe like the top five, that are really kind of making their way and separating themselves from the rest, and obviously people get excited about that. They're like, hey, we need a subscription to this, we need a subscription to that.

Dr. Fonz Mendoza: 

And my biggest fear has always been, you know, if you do buy in and get that subscription, you're spending that much money. But what if something happens? Because for the most part, all of these applications are wrappers, you know they plug into OpenAI's API and or any other large language model, and so what happens with that company is no longer there, maybe within a year? Because what if Google you know, with all the releases, that it's done? Is it going to go ahead and kill off some of those apps, the things that OpenAI now is offering? Is it going to go ahead and kill some of those apps?

Dr. Fonz Mendoza: 

So, how might you suggest that? Navigating the space to find that point where, okay, we can feel safe about this investment, or maybe you know what? Maybe this is not the time, so what can you share there to make better decisions in that case?

Kyler Cheatham: 

Yeah, that's such a good question, you know, definitely starting with that mindset of thinking that way, and so when we're talking about budget, the first thing we need to look at that first part of your question is what is the total cost of ownership? So a lot of this sneaky software subscription model I always compare it to no other business or industry blatantly lies to their customers outside of, like organized crime or like the cartel, right. So you know there isn't a ton of trust in that industry. So you really need to sit down and go. Okay, I'm signing this contract. I know from the day I sign, that's when I start paying. They don't care how long it takes me to implement that If I use it.

Kyler Cheatham: 

You know what is that support structure looks like? Are they going? And that's one of those things where you really really need to be disciplined in who I'm working with For my clients. We never work with a vendor that can't prove it. You might be on even my quantum clients. Okay, so you, quantum is new. We have a lot of new people, new innovation to the industry. That's awesome, but we're not going to be the first. All right, we're going to go in and spend with vendors who we look at this like a selection what do we get, how much is it? What's our support and how do we make sure that you're not going to ghost us after we leave? Who have you implemented before in a school district? And I'm going to call them. So you need to prove it. Never don't check those references. Even if it's a small, tiny $25 subscription a month, you still are responsible to your community, especially in the public sector, for understanding what that cost means and what you get after that.

Kyler Cheatham: 

There's been so many clients that I've had that have come to me being like, hey, I just kind of robot, this AI, you know system, because it claimed to integrate with my ERP, my CRM, my LMS, you know, really quickly and I thought that that was going to be, you know, a great option, because I wanted to fix this breakage and now they won't talk to me and I can't figure out what's going wrong. I can't even figure out a phone number to call them. There's no email, there's no anything, and that is where clients get stuck is in that ghosting phase, as I always call it. So being sure that you're meeting this vendor and holding them accountable as a partner to you, that's what they need to show up, not a set it and forget it.

Kyler Cheatham: 

You bought my system. I'm done with you, especially in a school environment where we don't have you know, you have maybe what one, two IT people per school, you know, with six grades, and that's something that we need to make sure that we understand how the vendor is going to show up and support us, or the SI is going to show up to support us in that way.

Dr. Fonz Mendoza: 

Yeah, and you know, that's something that you mentioned. That is so important because I have heard, I have seen where you know there's vendors that come in and say, okay, you know, for adoptions, book adoptions, things of that sort. And it's like, hey, this is what we offer, they share it. And all of a sudden it's like, oh, this is the greatest thing, this works great, this is going to plug into this LMS, this is going to do this, and so on. But, like you mentioned, the surprise is okay, we got it, but wait a minute, why isn't it plugging in? Well, you know, it's not quite there yet, you know, and things of that sort. And then all of a sudden it's you know, you bought into that, but now the teachers or the end users are now like you know what? Like this, I'm not using this. This is not going to work for me, you know at all, and that's because there is a committee of teachers that goes and vets all of these.

Dr. Fonz Mendoza: 

But I want to ask you for, in that case, because you mentioned something that's very important, because we need to do our due diligence and always make sure that all our stakeholders are at least well informed. So, in that situation that you are making that tough decision, what might you recommend as far as a CTO? Who should those conversations be had with, at least to make sure that you kind of have that fail safe in case, like they're all in. But then you know you have somebody that kind of balance things out and says, hey, well, maybe have we thought about this yet or come up with this component, because sometimes I feel that a lot of decisions can just be done abruptly and then it's kind of like all right, we did it, now we got to be all in, but now we can't get that buy in. So what might be just some fail safe advice for any leader, whether it's superintendent, cto or curriculum?

Kyler Cheatham: 

Absolutely, and I mean that's such a good question. And when we do any sort of technology implementation, even if it's super small, it needs to have a core team and that core team needs to be made up of whomever is sponsoring the project from an executive level, whoever is managing the project, whoever is responsible for developing the project from an executive level, whoever is managing the project, whoever is responsible for developing the project, and then the end users should make up at least 50% of that core team, because if you don't have them in the room, you're building blind. You have absolutely no idea what their requirements are, especially in an environment like education, because they don't have time, you know, to run around and sit or sit, and that's why a lot of times when we come into a school district, there can be a lot of friction between the vendor and the district. This is not a normal business, right, and they're treating you like a normal business and you're so frustrated because you don't have time to sit down and have 37 meetings a day about requirements. You need to do it differently and meet each other where it's at.

Kyler Cheatham: 

I think in that situation, really engaging those end users from day one. We always call it phase zero, right Before we've selected anything, we have an idea we want to be on the forefront of AI because we think our students deserve that, and we're going to start to move towards that. We're not sure what that means, we're not sure what problem we're solving. So there we come, to the end users what is your experience and what is something that you feel like could really benefit your processes in the classroom, and so that's where we really understand where that core team comes from. But the minute I walk into a steering committee meeting and there's no end users in there, I'm like this meeting is pointless. It really is Like, respectfully, this is pointless because the people that actually matter in this conversation are not in the room.

Dr. Fonz Mendoza: 

That is wonderful. Advice Definitely resonates and, like I said, it's just things that even through research and you know experiences and hearing things out, oftentimes that's one of the things that happens is that not everybody that needs to be in the room is there, and at the end the final decision maker just says, hey, this is what we're going to go with, and now we just got to make it work. And so it's almost like you're working a lot harder and it's very similar to what you mentioned. It's like you're running uphill in sand because you're trying to make it work and you're going to tire out. You're not going to be able to make it all the way to the top and try to take everybody up with you. I mean, you need to really have those end users in mind.

Dr. Fonz Mendoza: 

So I'm going to switch things up a little bit and now I want to ask you because we've been talking about, just directly, school district to vendors. So now I want to talk to you about vendors, some of these platforms, in the way that they are approaching or maybe in the way that they are selling to a district what are some things that they might do better? I know for myself. I'm always looking for, I'm always looking at the privacy settings, I'm always looking at the terms of service, I'm looking where the data is stored, what kind of data is stored, and it's definitely one of the things that I'm always looking for is full transparency of their systems. So what are some things that, if you are working with vendors and I'm sure you have that experience what are some things that they can do better to put their final you know, either that school district they're working with and those end users at peace and ease.

Kyler Cheatham: 

Absolutely. And I mean, I think we can't always rely on vendor salespeople to do better. Right, I do think there's a level at which they, you know, do take responsibility for what they sell, but these are salespeople, they have quotas to meet and they don't always give the best recommendations when it comes to systems, because their main job is to sell it. So if I were speaking to a vendor, I would say have a school district practice, right? You guys, come in here, you fail all the time. When it comes to school districts, you know there ends up being this huge fight and this chaos, which nobody wants on either end. Nobody wants a failed implementation. It's embarrassing for the district, it's embarrassing for the vendor and it just doesn't go well. So you need someone that is a specialist in this environment, just like you have specialists in manufacturing and you have specialists in distribution and you have specialists in food and beverage. School district is not a normal business. So go in and look at those requirements that actually matter to them. And, by the way, why don't you use your data set that you already have in front of you and ask your current users what would you like to see differently? I think that's one thing that I'm always so perplexed why they never seem to do and how they act, like they've never been in a school district in their lives and they're like, well, you know, we're not getting the engagement. And it's like, because they're teachers, like they're not sitting around all day just waiting for your call. Right, they are very busy educating the youth of America, so you have to go to the table and meet them where they are. When you're talking about things like requirements, you're not talking to technical people, so you need to bring people in the room that are able to speak the same language. And I call myself and my team professional translators, because a lot of times what they're saying and then the client looks at us like what? And we're like, okay, you know, this is what that means, this. Then the client looks at us like what? And we're like, okay, you know what this is what that means, this is the functionality. And then they kind of shut down because they're so overwhelmed by this entire process.

Kyler Cheatham: 

So I would say you know to the selection committee again should feature over 50 percent in you end users that they need to know going in there that this is a war. Right, they need to come in with their requirements ready, that they built, not the vendor right, that they built, not the vendor right. And then also, they need to understand that they have every right to say you know what? That was very cool, all of your slide deck there, great, awesome. But what about my needs and my functionalities that I want to see? Can you show me that? And if that vendor's like well, you know we don't really do that they're telling you what kind of partner they're going to be in that conversation and you want to take that as a huge consideration when you're making that choice. Right, it's not what was best for, you know, new York City school district. It's about what's best for your school district and who's going to show up as an implementation partner, not just a vendor, and same with the SIs.

Kyler Cheatham: 

In my experience I don't know if you have the same experience school districts have a lot of challenges with system integrators. They are technical integrators. That is their job. It is like oil and water mixing them with the school district because they don't have the counterparts that they would have in a normal industry business right, and that can be a huge struggle for both people involved and that's a lot of times why we have to, you know, bring in temp workers or, a lot of times, an additional third party to backfill those, because there's just so much work to do that this district doesn't have that resource to make that happen.

Kyler Cheatham: 

But remember, it's your demo, it's your software, it's your environment and you're allowed to ask whatever questions that you want. And that's a lot of times what we're doing in the room, my team right, and saying all of that is very cool, we're super excited. You have all this on your roadmap, but this is what this client is looking for. Can you go ahead and show us that? We go over the scripts with the vendor beforehand to make sure that they're clear about, like, we don't want to hear any crazy mumbo jumbo. That's not happening in this environment. You know, innovations can be 2% part of the conversation, but these people, their time is limited and you need to make sure that you're, you know, really addressing what they're looking for.

Dr. Fonz Mendoza: 

Amazing. There's definitely so much to unpack there and I really wish that you know a lot of the platforms that we work with. You know K-12 and going to conferences and everything it's.

Dr. Fonz Mendoza: 

I understand that there's a show aspect of it of like, wow, you know, look at what we can do and look at all the bells and whistles and so on, but at the end of the day, I love what you said and being able to sit down and just say, okay, this is what we are needing, can you provide that? And well, but we've got this button, but we've got that button. It's like no, no, no, no. And sometimes I think, like you mentioned the importance of having somebody like you or your team there, especially when there might be, like you know, somebody that's like hey, like let's go, let's just go for it, let's just move fast, and we're just going to get it, and so on, thinking like, hey, we get it, like everybody's going to use it, because this is what everybody's using, or this was the next big thing that I saw at the conference. So we, you know, really have to get it.

Dr. Fonz Mendoza: 

But at the end of the day, I think one a lot of the content that I see that you put out, especially like recently with a couple of videos, is many times I think that when we are trying to say like, oh well, we want to be innovative, so we're going to get this app, we never really get to the root of the problem, you know, as far as is it really the technology that's going to help enhance the learning and the pedagogy, or might it might even work backwards, where sometimes I feel that maybe some of the tech may enhance bad pedagogy because you know, we're not meeting at the same place or trying to solve the same problem. It's just layering something else on top of that and hoping like, hey, this will be gone. So what advice might you suggest to school districts that may not really see, or trying to get to the root of the problem before they purchase something?

Kyler Cheatham: 

Yeah, and I see this happen all the time in school districts, again, just because they don't really understand the process, Like on average. You know, we see a lot of districts that haven't purchased new like core operational software in 30 years, right? So it's not like they have like tenured teams that have been through this and that's pretty typical, right, when you're looking at a bigger ERP system or something like that, that there's not a lot of people that have been through that. So, define what you need, right, Whether you're working, you know, with a consultant like our team, or you know, your internal. Define, because the vendor is going to define that for you very quickly If you don't have the knowledge to say like, thank you very much for your input, but this is actually what we need, and a lot of times, school districts don't have the time, they don't have the industry insight to know that's what happens.

Kyler Cheatham: 

And they also, you know, they want to be able to get something done on a quick timeline so they can, you know, service their community, so they can service their teachers. Even the, you know, most well-intentioned project sponsors want to get this done so that they can, you know, prove to their communities that they got it done, but what we have to do is sit down and be disciplined around the why. You know it's like you know that executive. I walk in and they're like you know, 2025, our initiative is AI, like full stop, and I wait for them to finish and we're like okay, cool, Like, why, though? Like, what problem are you wanting to solve? Are you just wanting like?

Kyler Cheatham: 

We could call your ERP system AI if you wanted to, because technically it is. You know, there's predictive analytics in there, there's predictive maintenance in there, All AI. You already have AI right In some level shape or form. We could give you a sticker that says AI, or already have AI right in some level, shape or form. We could give you a sticker that says AI, or maybe a hat right, but in that capacity, we have to understand why are we doing this, how much does it cost and what is it going to take to implement. And remember I just remind school districts, because sometimes they forget that the why is going to be different for each end user, and that's where you need to source it from, Not, you know, the board room, but the classroom.

Dr. Fonz Mendoza: 

Oh, that was powerful. I really love that. And oftentimes it's the other way around. Oftentimes you know where it's like straight from the top and this is what we're going to do instead of going from you know, like you said, the classroom up, because eventually those are those teachers that you want that buy-in. And who's better to give you more data than the teacher that's there using it, working with the students? Is it really going to enhance it or is it really just? Does it turn just into compliance? When it's like, hey, just do it 30 minutes per day or 30 minutes a week, you know, for per subject, then it just becomes compliance. And so is it really enhancing the teaching or is it just like, ok, just make sure you do it. Just on my reports, it shows that you did your 15 questions for the week and you're good to go, and you know that that's the sad reality of it. So I really love that.

Dr. Fonz Mendoza: 

That last statement was so powerful that you said it's really taking into account your teacher, how it's working with the students, or how it might or might not work, and then take that feedback to the top and say, OK, let's see what we can do here and are we making the right and proper decision, because, at the end of the day, it's something that's going to cost money and so you're going to lose out on other resources that might be more helpful, because you're all in on something that you think is going to solve the problem. And one of the things that you mentioned that I love too is right now, because everything is AI. It's really just seems more of that marketing term like, hey, this is AI, this has AI. But I love what you said and say, hey, you know what like that one platform or you know what that one thing like, maybe, like you said, just put that sticker there that says AI. Maybe you might feel more like calm about it and say, hey, I'm already using AI, yeah, but you didn't know it.

Dr. Fonz Mendoza: 

But because it's not the AI that is being shown at the conferences and the next shiny tool and the one that's going to solve the world's problems with a chatbot that's going to teach your student you know the content, and so on. So sometimes it's like it's okay to slow down and really see things through and make those clear decisions and points. So I really really like that a lot. So, kyler, as we kind of start wrapping up. I want to ask you you know in your experiences and maybe you don't have to get into too much detail, but maybe we can share like two wins and maybe two losses that you're currently seeing as you're working in the K-12 space and maybe even higher ed what are some of the positives that you're seeing with AI and some of the not so positives that you're seeing with AI?

Kyler Cheatham: 

Yeah. So I love that question of my higher ed colleagues bring more industry into the classroom and be able to help their students bridge that gap between what does it mean to, you know, be on my computer coding AI, building those triggers and all of those different things in the classroom, but then actually going out and doing it in the industry, because it is so much different as any AI engineer would understand, and a lot of times students don't come out of a higher ed classroom, even a high school classroom, with a project that they've built, and I'm seeing that really transition to teachers reaching out to their academic or their industry colleagues to build these types of programs that are moving forward. I'd also say you know that we're seeing the new frontier of students in the classroom that are, you know, bringing the. We had digital natives as a generation, but now we have AI natives, which is crazy. I can't imagine you know, teaching that generation. But we have teachers that have dedicated their lives to educating our students wherever they are. Whether we have, you know, children that don't have computers at home or we do. We work with a a lot of STEM nonprofits and I just see these teachers show up and chameleon for these students wherever they are.

Kyler Cheatham: 

I, you know I I am so biased there. My mother is a previous retired principal, my sister is a first grade teacher. My dad was a teacher, so I worship teachers, like even my kids teacher. They want the shirt off my back. I'll give it to them. I think that they are, you know, just absolute angels on earth when it comes to this. But to see them rise up and embrace students that want to talk about things like chat, gpt yeah, let's talk about it. Let's talk about the risks and the benefits. It's not blacklisted, right, because it's not going to be blacklisted in the workforce, it's not going to be blacklisted on their home computer. So let's get curious about what this means. What are the risks and what is this tool? How do we understand it? Just like we understand anything else. And I'm really proud of our education system.

Kyler Cheatham: 

You know the ones I've seen for starting to make that shift of our education system. You know the ones I've seen for starting to make that shift, and I would say the two negatives. And I know I can be long-winded so I'll keep it short. But education is not a business, right, we have something that is financially responsible and we understand that, but when we have leaders that are leading it like a business and not a community organization in which it is, then that's where I see them get in trouble. Educators and administrators, leaders that have never been in the classroom please go spend three weeks in the classroom shadowing different grades and you will have a totally different outlook on what that means.

Kyler Cheatham: 

Negative is bringing in those fancy CTOs, bringing in those fancy CIOs thinking, oh, they're going to revolutionize our architecture like it's, you know, ford Motor Company. That's not the same thing. So I would invite leaders to remember that those administrators serve their teachers, not the other way around. And then the second negative thing I would say is not teaching students the understanding of basic AI in higher education, so the understanding of data and risks and things like that. They often come out of the workforce. Come to us. They've never, you know, really experienced messy data. Go out in your communities, find a local business I promise you their data is a mess and give your students an opportunity to do service in their communities by helping those small businesses figure out how to automate their data. So those types of things where they think you know, this is just a simulation, absolutely doesn't have to be. That way, we can arm our students with this type of experience.

Dr. Fonz Mendoza: 

I love it. Thank you so much for sharing that, and there was definitely so many just gems that you just dropped there that I know all our listeners are definitely going to take that and sprinkle it onto what they're already doing great. So thank you so much for sharing that, kyler. And before we wrap up with our last three questions, kyler, I want to ask you, or actually give you a little bit of time If there is a school district currently, right now, a leader, an influencer that's listening to this podcast right now, how might they be able to get a hold of you, reach you and make that contact?

Kyler Cheatham: 

Sure, absolutely. Well, I'm. You know my DMs are always open. That's how we met right on TikTok. You can also DM me on LinkedIn. I have a personal goal and mission to answer every single one of my DMs personally, so I'm happy for for to have an informal conversation. I'm always up to talk tech. Obviously, I'm super passionate about it and, as I said in the beginning of this episode, which was why I'm so excited to join you this is one of the most complex environments, so give yourself grace and feel free to just reach out for a random chat. We can have a call and talk about what you're going through. If nothing else, it's always a good vent session.

Dr. Fonz Mendoza: 

Excellent, and that's true. Kyler was so kind. Like I said, I was going scrolling through TikTok and here I get this video and immediately I was like heart follow and I was like hey, would you like to be a guest on the podcast? And I got an answer and we made it happen and we're here today. So definitely reach out, guys. It doesn't hurt to just again, just get some knowledge, get a little bit of direction, and Kyler, like she, just offered herself up as far as her DMs and her account. So take advantage of that.

Dr. Fonz Mendoza: 

Ctos, if you're listening, if you have some questions, and maybe you can build a great collaborative relationship with Kyler and her team, make sure that you do reach out. So thank you so much, kyler. But before we wrap up, we always love to end the show with these last three questions. So, kyler, I hope that you are ready, all right. So question number one as we know, every superhero has a pain point or a weakness, and for Superman, that kryptonite was what weakened him. So I want to ask you, in the current state and we'll say, of AI, all right, what would you say would be your current AI kryptonite?

Kyler Cheatham: 

Just the speed of change. You know I am super dedicated to helping our young engineers, but at this point I even had a call today where I was like I got to be so real with you guys. I have no idea what you're talking about at this point, because you know they're so far above me. You know they're building things on Catapult and doing all these amazing innovations. I want to be there to support them, but sometimes I have to just get out of their way and let them do their thing. So the speed of change of this technology is never something I've experienced in my career. So, you know, it's about this balance of guiding them but also not, you know, ruining the call with all of my like, very basic questions about what they're doing, because they're doing great stuff out there. So I would say that is probably my kryptonite on the AI side.

Dr. Fonz Mendoza: 

Oh, there you go. But that's pretty cool, though. I mean sometimes, like you mentioned earlier, you've got to embrace that, I don't know. But hey you know what, we can figure it out, so don't worry. So that's great, kyler, all right. Question number two Kyler and why?

Kyler Cheatham: 

I would have a billboard that said tell the truth. And I would put it right outside of like SAP's headquarters, you know, in Pennsylvania and Germany and all of my other vendor partners which we we get. We are frenemies, right, we get along with our vendor colleagues as long as they show up for our client, but they need to tell the truth. Like it is time, you guys, like it just looks bad for everyone involved. No one wants to fail the implementation. Just tell the truth in your sales processes. That's all. That's all I'm asking you to do. So that's what would my billboard? Probably with my face, like pointing at them or something like that is perfect.

Dr. Fonz Mendoza: 

Actually, that billboard could definitely go a long way in the k-12 higher ed space too, for all the platforms and all the apps that are out there. So I love it all right. Last question, kyler, is if you can trade places with one person for a day, who would that be and why?

Kyler Cheatham: 

yeah, um, I think that that's such a great question I spent so much time thinking about that one because it's such such a good one. And I would probably say Sarah Blakely, you know, I really admire her entrepreneurial journey and you know, just, I've admired her as a female leader in a space that didn't have a lot of innovation and though you don't think of, like Spanx, and you think of innovation, right, that actually was something that didn't exist before she created it. I think the way that she's built the culture of her business is something I'd really love to be a fly on the wall of. Like how did you build it and maintain that culture? Through growing it through a billion dollars? You know, that is so incredible to me. I really admire it. I've read all of her books and I would probably you know just be so honored to be in her presence or trade places with her for a day.

Dr. Fonz Mendoza: 

Excellent. Well, thank you so much for sharing and, kyler, thank you again. I really do appreciate you hopping on the podcast. Thank you again, I really do appreciate you hopping on the podcast. Thank you so much for accepting my invite and, again, I'm a huge fan of your content. I definitely learn a lot from it.

Dr. Fonz Mendoza: 

I know I comment on there a lot, saying like, hey, say it louder for the K-12 space to you, and things of that sort, because I think that what you're doing is great and the messaging is wonderful and a lot of people need to be, you know, in tune with what you're saying and I think that's very helpful. So I definitely recommend all my listeners everybody listening to this show. Please make sure you follow Kyler, follow her TikTok she has some great content there and, again, follow her on LinkedIn and make sure that you do connect. But thank you as always and for all of you all, make sure you visit our website, myedtechlife, where you can check out this amazing episode and the other 330 episodes that we've done over this five-year span. It has been a wonderful experience and thank you so much for your continued support.

Dr. Fonz Mendoza: 

I want to give a big shout-out to our sponsors. Thank you so much to Book Creator, eduaid and Yellowdig for sponsoring our show, believing in our mission and again just bringing some amazing guests like Kyler and amazing conversations into our K-12 higher ed space so that we may continue to learn and move forward. As we know, technology is going to be changing from day to day, but it's always great to be readily equipped in season and out of season. So make sure you check out all those episodes and, my friends, until next time, don't forget, stay techie.

Kyler Cheatham Profile Photo

Kyler Cheatham

CPO & Founder, The Confluencial

Kyler Cheatham is the global Chief Performance Officer of The Confluencial, a high-impact enterprise technology firm known for driving meaningful business outcomes through the strategic alignment of people, process, and technology. With a background rooted in business performance and human-centric strategy, Kyler specializes in building nimble, interdisciplinary teams and cultivating leadership capacity in complex implementation environments.

A 2025 #empowHERaccess Global Prestige Awards Finalist and 40 Under 40 Award Winner, Kyler has become a respected voice in Women in AI, recognized by publications like Solutions Review for her work shaping the future of tech leadership. She is also the founder of ByteSized, a thought leadership platform and podcast that breaks down big technology ideas into digestible strategies for business professionals, educators, and innovators.

Kyler’s mission is to empower companies and communities alike. As a lecturer at Colorado Mesa University’s School of Business, she mentors young women in the software space and advises organizations on how to future-proof their workforce. Her work at The Confluencial reflects a unique blend of strategic vision and tactical excellence, especially in the manufacturing sector, where she leads initiatives focused on productivity gains, supply chain optimization, predictive analytics, and risk mitigation.

At the heart of Kyler’s approach is the belief that authenticity, accountability, and adaptability are the keys to building resilient systems and resilient people. She’s not just opt… Read More