
Loading summary
Jason Hill
And if we don't teach students how to utilize AI, it's the same as not teaching students how to do math or how to read.
Chris Daigle
You've kind of been ringing the bell about, hey, let's do something about AI. How has it been received by your peers?
Jason Hill
Everybody could think of all the horrible reasons why not to adopt AI. And I was trying to figure out how do I get past that. I went to my C suite, right, and said, I want to push AI. Will you give me permission to do that? And we flipped it on. Not for students, but for all staff with no training, no policies, no execution. We just turned it on and I told everybody I use AI and it's okay, let's figure out how to do this together.
Chris Daigle
What questions should they be asking of the administration of their educational environments that their kids are plugged into to make sure that they're not missing out and have comfort that they can sleep at night, that their administrators of their educational environment are doing this the right way
Jason Hill
if they're going to turn on AI? One, what level of access will my child have? And two do you have filtering protections in place? Great questions that catch if my daughter were to start talking or discussing self harm within that chat.
Chris Daigle
Jason Hill is a leading voice in AI adoption for K through 12 education and deputy Superintendent at Redlands Unified School District. He helps school leaders move beyond fear, build responsible AI systems and prepare students for the future of work. Welcome to Using AI at Work. I'm your host Chris Staigle. Each week we'll be learning how today's business owners, entrepreneurs and ambitious professionals are getting more done with smart use of tomorrow's tech. Let's get started. Right now, every business leader is asking the same question. What are we going to do about AI? If this is you, chiefaiofficer.com has the answer. We give you a simple path forward where we provide executive and team training so your people know exactly how to safely use generative AI in their day to day. We also manage the deployment and implementation to make sure tools actually get adopted and deliver results. And we'll also guide company wide transformation so AI becomes part of your operating system, not just another shiny object. The companies that act now will increase productivity, cut costs and grow faster than their competitors. Those that wait will get left behind. So if you want to make AI work in your business, visit chiefaiofficer.com and see how we're helping companies of all sizes finally get results from AI. Alright everybody, welcome to Using AI at Work. My name is Chris Daigle. I'm the host and today, Today our guest is Jason Hill. And Jason's the deputy superintendent for Redlands Unified School District in Southern California. And his main purpose there is to oversee the business services side of the district. Now, I don't know if any of you have much context on the annual operating budget of a school district. It ain't cheap. Right now, Redlands has got over a 330 million dollar annual budget which is going to give Jason an incredibly large scale operational lens on AI adoption, not just the business side of it, but what I'm particularly excited about today is asking and digging into some of the questions on the educational side. This is something that we haven't had the opportunity to really cover in 100 plus episodes that we've done of this podcast. And I wanted to be careful. Sure I could get people's opinions and those sorts of things, but Jason is an executive in actually doing the thing in the trenches and in the educational environment. So this is a unique opportunity for us to hear what's actually happening, you know, because I hear all the time people are saying, what about my kids? What should my kids be studying? And those sorts of things. So we've got somebody who could actually tell us how it's impacting not just the operational side of the school, but also what his experience has been, even anecdotally with seeing how the teachers and the students are reacting to really some major changes that Jason has hallmark or kind of led in the Redlands Unified School District. Now, how we met, he was already on the AI journey, but shoot, last year sometime he enrolled to go through our Chief AI Officer certification program. And the feedback that he was giving to the rest of the community indicated to me that this is somebody, he gets it. He's really like, not only does he understand its application, but he's fully committed to upskilling his own capabilities when it came to this stuff. So we're in, you're in for a real treat with our guest today, Jason Hill. So, Jason, before we get started, anything you want to share with everybody about what you're up to and your positions on AI?
Jason Hill
Well, thank you for having me. Like you mentioned, I, I'm the deputy superintendent of a K 12 school district, about 20,000 kids. We have 26 schools that we, we have here and AI is upon us. So, you know, I would say a couple of years ago when I started to kind of get talked about, I was trying to figure out, how is that going to impact a school district? How does that impact kids? And that's where I came across the Chief AI Officer certification. And I haven't looked back since. So we'll go kind of get into some details throughout the call.
Chris Daigle
You're crushing that. So just for everybody listening, I definitely want to cover, like, what does this mean for, you know, your children and those sorts of things from somebody who's working with your kids. But I also, one of the things that I'm interested in particularly is some of the lessons that you're learning on the educational side and like the administration of education and that, like what, what are those lessons that can also be applied to really any business? So we'll maybe start there. I know that in our conversation before we recorded this, we did a pre interview, as I always do. One of the things that stuck up was that or that stuck, stuck out was the, the, the policy conversation wasn't necessarily as fast as maybe the execution or the application of the tools. And I think that that's probably something that a lot of the listener companies might also be experiencing. There's been ongoing dialogue about what are we going to do about AI, but it hasn't quite gotten the traction yet. So can you kind of share what your experience has been since you've kind of been ringing the bell about, hey, let's do something about AI? What is that? Like, how has it been received by your peers? What have been the challenges from both the administration side, the teacher side, but maybe also the parents and things like that?
Jason Hill
Yeah. All right. Well, if we go back a couple years when AI was starting to kind of get out there, right. So it was being talked about, it started to show up in the news. Students started to kind of pull it up on their phone. Parents were kind of skirting the idea of what is this thing that's coming? And that's about the same time that I, I stopped in. So I checked in and chat GPT was kind of there. They came out with scheduled tasks and what I had running every morning was ChatGPT scouring the news across the country about what our districts, what are counties and what are states doing about AI. And what I was getting, it was almost like cut and paste from no matter what district you were in, what state you were in, what county you were in. It was a cut and paste script is we're all stuck on policy. Everybody was afraid that students were going to cheat. Yeah, everybody was afraid that students would just not get the rigorous mindset that they need. They would, they would be dumbed down through AI. And so there was. They were stuck on this policy concept. And I was kind of, at the same time going through some leadership type focuses. And I was focusing on a book by Chris Voss, and he does a negotiation book. And he talks about this concept of getting people to say no versus getting to people say yes, guess, and the comfort levels that our brain goes through with those two answers. And at the same time I was doing that, I was starting to realize that everybody could think of all the horrible reasons why not to adopt AI, Right? And we don't need to go. You list them, right?
Chris Daigle
Yeah.
Jason Hill
You see them on the news every day. And everybody was trying to prepare or write policies on how to present, how to prevent these bad things from happening. And nobody was getting past that. And I was trying to figure out, how do I get past that? And so that's when I hopped in chiefaiofficer.com and what I was noticing in the business world is you were teaching us go to the C suite, right? Go to the top, go to the president, go to the CFO and get them to understand the importance of AI. And so I stopped for a moment and I thought, well, how does that equate to education? And that's where it did. So I went to my C suite, right? My executive cabinet, and said, I want to push AI. I want to turn the switch on. Will you give me permission to do that? And I'm a business guy right now. I have an educational past. I was a. You know, I've been on the educational side of the house for 30 years. It's only in the last five that I've been on business. So I said, I know how to do this. Let's just flip the switch. So what we did is we immediately jumped into this concept of which AI, right? In California, and I am specifically in California, there's a lot of laws on student privacy, student protection, family rights, things like that. Ferpa, coppa. So the big names in the house are Google and Microsoft. But Google and Microsoft at the time was taking this really, let's wait and see approach, right? You had these private companies like Anthropic and OpenAI that's pushing fast. And you had Google and Gemini just kind of. Or Google and Microsoft kind of holding back. But we went with Google because we're education. We have, you know, the Google educational suite. Yeah. And. And we flipped it on, not for students, but we flipped it on for all staff with no training, right. No policies, no execution. We just turned it on. I, I stood at the top and I told everybody, I use AI. And it's okay. Yeah, let's figure out how to do this together. And that's what started it. I created a forum, a community, it's using circle, like you are, called the Redlands Launchpad. And we opened it up to managers and teachers and custodians and office staff. And we said, like, we're all in it together. We all enter artificial intelligence together. You know, the custodian or the office manager, the teacher or I are all in the same learning circle. And if you've been involved in artificial intelligence for a while, you fall in and out of that learning circle because there's new products and new things that pop up. And I may think I'm an expert in AI, Then you start talking about mcp and I'm like, what are you talking about?
Chris Daigle
Yeah.
Jason Hill
Right. So now I'm a beginner again.
Chris Daigle
Yeah.
Jason Hill
And it's almost giving permission for everybody to accept that we're all beginners and we're all in this together. And that's where we spent year one. We were starting to pilot with kids. And I'll be honest with you, parents were not on board. Right. Parents were also afraid of the cheating and their kid not being pushed towards that rigorous level. So we pulled back on the students and we continued to push hard on teachers and staff. Parents started to comment, well, your teacher, your teachers are using AI and we don't like that because they're using AI to grade and they're using AI to lesson plan, and they shouldn't. And my conversation with them is, why do we expect an accountant to use a calculator? Like, that's okay. Yeah. Do we expect our leaders to use tools that make them better or make them more efficient? And that was the conversation. Right. With parents saying, look at our teachers should be using AI because they can customize content, they can customize quizzes, they can cater to specific students needs quicker and faster than they ever could before. I had to acknowledge that teachers shouldn't be using AI to grade and not use their feedback. Right. It's okay to kind of assist, but we also want the human in the teacher, right? Yes. Not the robot in the teacher. So we stepped back and then we started creating policy. And so I would say the last three or four months, it's been policy creating that cheating policy, creating the proper use policy. So now when a teacher says, here's the assignment, you can use AI level three. Right. Because we have levels of AI use one through five, and they can actually call out that AI is acceptable using a level two which is using it to generate ideas, Whereas a level 5 is completely immersed in AI. AI is giving that product back.
Chris Daigle
Yes.
Jason Hill
And then we had to give teachers tools to grade and judge students work based on AI. And we also had to give parents tools to question if a teacher is accusing their child of cheating.
Chris Daigle
Interesting.
Jason Hill
Okay, so these policies that we had to create were policies for students, for parents, and for teachers. Where we are at in the process is I'll be rolling those policies out to our board of education in July so that they can. Right. Because our board was kind of, you know, a little on the teeter about this. Right.
Chris Daigle
Okay.
Jason Hill
We're going to roll that out in July. And if all goes well, because we took student feedback, parent feedback, staff feedback, if all goes well, we will continue the push with our staff. We'll roll out the policies that we now can refer to, and we're going to pilot with our students. And that's kind of the evolution we had to stop and pull back. But I honestly believe if I hadn't flipped the switch.
Chris Daigle
Yeah, we'll still be talking.
Jason Hill
Yeah. We actually put an article into the local newspaper that said that Redlands Unified School District is partnering with Google to turn on Gemini for everybody. Like we put it right out there. We said, this is what we're going to do.
Chris Daigle
Yes.
Jason Hill
I didn't expect the kickback I got, but I wasn't surprised. It just required me to pause and say, okay, I have to meet the needs of the community as well. How do I do that?
Chris Daigle
I got a couple questions. This is fascinating. One of them is a thought. As parents get, they start getting exposed. Something that I've heard in my past, and I believe it wholly. A confused mind always says, no, if I don't understand something, there's no risk with me saying, nah, I'm not going to do it. Right. And I know that initially and listeners like this, all this stuff, the same thing applies to your business. If your stakeholders or your clients or your internal team is confused about it, expect some resistance, expect some no's. Yeah. Do you think that as. As the parents, because you're talking about like this, this. You've been doing this for over a year now or about a year or how long? A little over about a year.
Jason Hill
We're moving into July 1st will be our second year with our Gemini contract.
Chris Daigle
Okay. As parents who a year ago were like, wait a minute, this is, you know, they're at work. At work, they're probably getting exposed to a chat GPT license or they're using Gemini, do you expect that because of what's happening at the. At the parents job that they're not going to be as skeptical, or do you think they're still going to say, I don't see how what I'm doing at work and my understanding of that translates to the impact it'll have on my children?
Jason Hill
The latter. Right. I still think parents are afraid that their kids won't learn how to read or write or do math. The spin I've taken lately is we teach mathematics because we know that adults need to know how to perform math to function in life. Right. You have to know how to balance a checkbook, so you're going to have to do math. We teach reading because reading is required. If you're an adult, AI is the same way.
Chris Daigle
Yes.
Jason Hill
AI is being used in businesses, and it's growing in the use of businesses. And if we don't teach students how to utilize AI, it's the same as not teaching students how to do math or teach students how to read. We have to prepare them for the life that's ahead of them. And if I don't, then what I'm doing is I'm providing a disservice to our students who are entering into fields with AI and don't know how to use it because we didn't allow it. And that's kind of the evolution of all of this thought. I think in the beginning I was excited about AI, so I was 100% in, and I was expecting everybody to dance with me about it. Yeah. When I. When I got hit with the resistance, it made me stop and think, okay, the resistance is real. Let's think about that and let's talk about that, and hopefully we can meet in the middle. And those conversations have happened a lot this year, and it's caused me to pause and says, okay, I'm an educator in my profession. And then what I went to college for was to learn how to educate humans and children. And what do I need to educate them to make them marketable. Right. And I think we had a conversation the other day in the forum about the evolution of AI and how a year ago it was prompting, and now it's workflow management. Right. With cowork and codex and claws. It's thinking about how to utilize these tools to increase efficiency and in a business, increase that bottom line. And our job as caios is no longer to go in there and say, okay, I can teach you how to prompt. It's to go in and teach you how to think different, to Think in this automation role and to think, okay, you sit in front of your desk and you have tasks all day. If I told you I can automate some of those, what would you do? And I find myself on a daily basis sitting here trying to figure out, okay, what now can I automate?
Chris Daigle
Yes.
Jason Hill
That inquisitiveness, that curious mindset is what we have to teach our kids. AI is just the tool. Right. That they're going to use. I don't need to teach AI. What I need to teach is how do you utilize this product to think different, to automate, to be valuable to the person, you know?
Chris Daigle
Yeah.
Jason Hill
Someone told me the other day that if you're worried about losing your job, it means you're not valuable enough to the guy making the decision.
Chris Daigle
Right.
Jason Hill
And if you were to go into a company, the safest person in the company is the one that allows the boss to sleep that night. Because there's going to be things that keep the CEO awake. And if I can keep that CEO sleeping at night by automating or doing that, that's what I need to teach our kids. And AI is a tool to do that. But really it's a mindset.
Chris Daigle
So this is an interesting shift for me. Like, I've been looking at AI as the thing. And the educational side, it's a thing. It's. There's reading, there's writing, there's AI, there's physical education or physical fitness. Like, there's. Yeah, it's. It's not the thing.
Jason Hill
Yes.
Chris Daigle
And now in businesses, I've been going in and looking at it, looking at it as like, it's now going to be the thing that everything gets built around. But I'm thinking that the listener, if you're in your business, if you're getting pushback, introduce it the way that Jason did, where it's just another thing that they learned. It's not the thing. It's not taking over everything. But if you, if in the educational sense, if I'm not teaching kids how to read and write, there's a disservice. If I'm not teaching kids how to use AI or think about using AI as an accelerant, as a tool, I'm doing a disservice on the business side. The same kind of thing as a change management approach, maybe it's not, hey, we're transforming the business with AI. Maybe it's like, hey, we're going to introduce something that's going to support your role. Right. So it becomes less intimidating of, oh, my gosh there's this huge sea change it's about to occur. Even though it is maybe the narrative that you bring in as a business person to the rest of your team isn't that. But it's like, oh, we've got this thing that we're going to start to bring into. You're still doing your job, we still need you, but now you're going to have a tool that helps you do it better. Now, one of the things that came up for me as you were talking about this, because you've dealt with the parents, you've dealt with the students, you've dealt with the educators, you've dealt with the administration, you've dealt with the media. What questions, like listeners here, some or most of them will have children at some age that are going to be exposed to AI. Maybe it's already starting to happen, whether it's elementary, all the way up to advanced education. What questions should they be asking of the administration of their educational environments that their kids are plugged into to make sure that they're not missing out and have comfort that they could sleep at night, that their administrators of their educational environment are doing this the right way?
Jason Hill
You know, I'm going to look at it as me, as a parent. Right. I have, I have daughters. Yeah, right. That utilize versions of AI. And my conversations with them and my conversations with their teachers has been about what level of AI use do they have.
Chris Daigle
I like that concept. Yeah. This level thing.
Jason Hill
We've decided in our upcoming policies that the K5, which is our elementary levels, will not have direct access to AI, but we will educate them on what AI is, how it's not human, that it makes mistakes, how it thinks, why it's so complimentary and appeasing to you as the user. Right. Those conversations are what we're teaching our elementary kids when you move into the middle school. What we've decided is that teachers can utilize AI in the classroom and teachers can give AI tools to the students. For example, like a Google notebook. The teacher will design the notebook and the student can interact with the notebook. A teacher will design that GPT and the student can interact with the GPT, but the student themselves will not have direct access to the chatting agent. Right. It's not till the high school where we're going to give access to the chat agents. Right. So now they're using that as a co worker or a partner in their educational journey. And so my question to my teacher or my question to my administrator, what level of access are you giving my child?
Chris Daigle
I Like it? Yeah.
Jason Hill
Because I have concerns over their own maturity levels. Right. My own daughter probably got too close to it, is a friend, it is a partner. Right. And she named it and I have no problem with naming something. But the thing is when you name it, you humanize it and you just do. It's natural. So when I would find her asking advice and I'm thinking, okay, well the problem is it's always affirming device. Right. And I had to have conversations with her about, okay, you realize that how these language models work and had to have those conversations with her and at one point she stopped using it. But I'm also a guy that's proficient in this and so I can have those conversations. But I'm going to expect me as an educator and my teachers to have these conversations with their kids. Interesting. Yeah. So we're building lessons that will allow them to have these conversations and it's going to be hard. We have, you know, 1300 teachers and will they all do this with fidelity? Because they're all at their own comfort level. So we have to give them little, little nuggets of information that they can repeat. But we're open to have these conversations and we're open to say, you know, AI is, is, is not all great. Right. There is some negatives to it and but we also have to be mindful of what safety features do we have in place. So for example, we had to switch our filtering products because our old filtering product did not scan through chats. Right. It scanned through like their Google Docs or their Google emails. Right. And it would alert us if there's self harm or things like that.
Chris Daigle
Yeah.
Jason Hill
Google would, in their educational version of their Gemini that they will, they will recognize self harm type talk and then stop them and give them phone numbers to call. But they weren't alerting us of any of that. So we had to switch our filtering platforms that will allow us to search through those chats and give us alerts when certain chats and tell us who to go reach out to. Yeah. So that is a protection that we had to take on and that's the same protection that your listeners should be also asking their school district. Right. So if they're going to turn on AI, 1, what, what level of access will my child have? And two, do you have filtering protections in place? Great. Questions that catch if my daughter were to start talking or discussing self harm within that chat.
Chris Daigle
Yeah, yeah.
Jason Hill
And there are products out there that will do that. Right. Because they have to, you know, and we don't need to go to the techno thing, but they pull apart the packets that are going back and forth and can filter those contents. Some do, some don't. You know, Google by default doesn't have those in their own systems yet. They're working in that direction, but they're not there yet. So we had to purchase that separately.
Chris Daigle
So, and, and again, listeners as yes, we're talking about this experience in the educational environment, but I'm seeing a lot of parallels about how they're dealing with this and how you as a team lead or as a, an owner of a company or a decision maker can also be using this because just change the name of student to employee or teammate. Right. As a parent, how would you suggest that the listener get involved if this is now something that their school districts are exploring? Because the listeners of this, obviously they have a little bit more understanding of about AI and then the average. Right. Somebody who's listening to Joe Rogan, nothing against Joe, but you know, like that's a different topic. So the people that are listening to this, they have a little more savvy, I would suspect, than some parents who are just like, oh hell no. Like we don't want our kids being dumbed down. So how would you suggest that I, as a parent or other listeners, as a parent get involved? What can we do to make sure that our understanding of it is introduced into helping the administration make a decision based on real world or based on not necessarily like fear based, but like the, the upsides of AI?
Jason Hill
You know, this is a. An age old question about what's the parent role in edu. In education.
Chris Daigle
Sure.
Jason Hill
And you know, as an educator, I'm always employing parents to become more involved. What parents do often is they reach out to the board of education or they show up to a board meeting that is their right and that is a public version of tackling this issue. But you're not speaking to the people directly who are employing it. You're not speaking to the people who are implementing the systems and working with their kids. Those people are the teachers. Right. The teacher themselves. And so my, I would be having conversations with my teachers. I would start with maybe site administration just to find out how AI is used and what protections are in place with it. Principal site administrators should know, should also be on the district website if they're a good district. Right. Because they're listing their AI use and their AI policies. And this is common. But involving the teacher and showing up to those parent conferences and reaching out to the teachers is always encouraged because There's a piece to this, right? Teachers have to think differently with the age of AI Back when we were young, we didn't have typewriters, so we hand wrote our reports. I remember back in the day when we had to have handwritten outlines by certain dates before you'd have an outline and then a draft and then the second draft and then the final report. I have seen that didn't go away. But it's far less common today than it used to be. With the advent of computers, they just want the report. Well, that's what AI can just give you is the report. And so the teachers have to think differently. I was at my Father's Day last weekend. I was up with my father and my brothers and sisters, and my niece was up there and she's a freshman in college. And AI came up as a topic. And she goes, I don't like AI. I go, why? She goes, my classmates just cheat. They don't know how to write a paper. They just don't know how to write a paper. And they just use AI and the teacher just grades it, and they get good grades. And it frustrates me because I know they don't know how to write. And I'm watching them use AI and my response was, okay, I love AI. So what's my response going to be? And I thought, well, you're a freshman in college. Shouldn't the student know how to write a paper? So if they don't know how to write a paper, well, that's the problem, because AI has only been around a couple years. If they're now a freshman in college and can't write a paper, then the school system failed them long before AI came.
Chris Daigle
AI yeah.
Jason Hill
And I said, how did your teacher take that? And she goes, well, it was just. It's a paper they turned in. Well, whatever happened to oral presentations? Whatever happened with drafts? Whatever happened with show us how you got there? Whatever happened to the conversations that happened long before you actually turned in the final draft? So I asked her, I said, do you think the teacher's doing a good job at grading that AI paper? And she goes, well, no. And I said, well, there's your problem. This is a teacher student problem. It's not an AI problem. AI was the tool she used. But back in the day, it was an encyclopedia, right?
Chris Daigle
Yeah, yeah, yeah.
Jason Hill
Then it was Google, then it was Wikipedia. Yeah, it doesn't matter what it is. Teachers have to accept work in different modalities, right? Maybe produce a video, maybe produce a PowerPoint, maybe get up in front and talk in groups. Maybe put your students into small groups and have conversations about their reports and then mismatch those. Those are all tools teachers should be doing. And if I'm a parent, I'm going to have those conversations. I'm going to say, hey, thank you for this report coming back. Can I ask you why you gave the a. Is this the only way that you would turn this in? If I know they're using AI, yeah, I'm going to ask those questions. And, yeah, you don't have to know what I know. You can go in as a parent and just ask the question, do you guys use AI? Yes. No. Well, how do you use AI? I'd like to know a little bit more about that. Well, if. If students are just turning in a paper, how are you. How do you know if they're cheating or not? Like, be inquisitive. Right. Ask questions. Sometimes you're just wanting to know.
Chris Daigle
You're not challenging them.
Jason Hill
Yeah, yeah, you just want to know and. Right. And it's the same thing for businesses. Right?
Chris Daigle
Yeah.
Jason Hill
If an employee point turns in this report, where did you get the report from? We had a report turned in the other day, and they said, I used AI on it. So I kind of read through that report, and honestly, I threw it in AI and said, can you check against the data? And it found inconsistencies. And so I had replied back, well, hey, there's some inconsistencies in here. And they go, oh, well, after I threw it in the AI, I swapped some slides out. Well, when they swapped the slides out, the slides that they swapped out didn't match. Right. And so it's a business. I wanted to make sure the data was presented right. I use the same thing, you know.
Chris Daigle
Yep. A perfect.
Jason Hill
I mean, here's a perfect example of how I use AI in business. So my. I'm the deputy superintendent, so I have directors that do the reports. So in the old days, in my report, so it's called a sax report, it's 200 pages long and it's all numbers. Right. There's just no way that I can go through there. So I have trained myself to look at certain lines on certain pages for certain trends. But I can throw that whole thing in there now and say, analyze this for me and pay attention to these lines and these trends. And it turns that there's a narrative and a PowerPoint that's also generated where I used to go through and I used to proof those narratives and PowerPoints. I'd spend Hours just checking grammar. I'd spend hours just totaling the charts so that they would total 100. Well, now I can throw the PowerPoint, the narrative and the SAX documents in a folder. I can say Cowork. I want you to go through and analyze all of them. I want you to verify that the Data in the PowerPoint matches the data in the. The Sacks documents. I want the. I want you to then look separately that the narrative matches the SACS documents. And then I want you to compare the PowerPoint to the narrative. And I'm telling it to do these comparisons. And this is the first time I was using Cowork to do that. Right. Because Chat used to max out my context window, but I don't have that problem anymore. So then it was done. It told me what it found difference, and it says, would you like me to make those changes for you?
Chris Daigle
Yeah.
Jason Hill
And I said, well, sure, but I want you to save them as a separate document called Corrected. And then I want you to highlight those changes so I can give them back to my director so that they can see the errors they made so they don't make them again.
Chris Daigle
Yes.
Jason Hill
And that whole process took me 10 minutes where it used to take me hours. And I never got past the grammar.
Chris Daigle
Yeah.
Jason Hill
Yep.
Chris Daigle
Yeah.
Jason Hill
I never got to the point where I was comparing the numbers across the three documents because it would just take me days.
Chris Daigle
Yeah.
Jason Hill
To do.
Chris Daigle
You know, you keep referencing this levels of use, and I like that a lot, especially for the kids. I think that, that starting with the elementary to where they get educated on it, like the K through 5, then the next level up is using tools that were built with AI and so that they're interacting with natural language, like understanding, like, oh, I chat with it, but they're not necessarily able to go chase rabbits with it. And then at the high school level, introducing. Now you have a little more discretion in how you're going to use it to create something. Right. Not just. Not just enter information. And I think at the business owner level, that might be something to consider. There was an AI consultant out there that had. I think the concept came from Matt Church in New Zealand with his Thought leaders kind of school. But they created these belt systems just like with martial arts. And the benefit from a business side would be that if you had people who had kind of gone through level one training, level two training, level three, and you knew that if I was a level three trained employee and I was talking to a level one trained employee, I would have context on, oh, this is what they understand. This is, this is how they're thinking about AI. And I would be able to communicate in a way that they could, that they could understand based on what I understood to be their, their level of knowledge. Right. So as a business owner, maybe think about what that would look like identifying, even if it's self identification initially where somebody is on the learning journey now. One of the things that this, this idea first hit me when we were presenting and speaking at the EOS National Conference and I guess that was April of 2025. These people would come up to our booth and they would say, you know, how much can I learn in a day? Because we've always done like a one day immersion kind of thing. And I would explain to them like I could have you close to being an expert level user. You're not going to be an expert at AI, right? There's a lot to learn there. But you can think in a way that you're using AI way past what somebody who is brand new at this stuff would be doing. And they asked me how that was and like on the spot I had to think about traditional education for you to get where you are now. You invested a lot of time in your career and like you had mentors that you've mentioned in the past. There was a lot of that that was going on and it took like there was a sequence of activities that had to occur that built on the previous activities you did. Okay, I've achieved this level, now I'm ready to ascend to the next level of understanding. And then I thought about, you know, Adam, one of our chief AI officers working with that, a Saudi company that is a, they build islands for the Saudi government. Adam's never built an island before, but if he could ask somebody, okay, well what do you want to know? And they could ask him a question. He didn't need to have all of that foundational understanding. He was able to access all of that information. So this paradigm of learning went from I need to invest years, advanced degrees, you know, all that type of thing to be able to be the person that on demand, when my subject matter is needed, I'm able to recall it. The old paradigm, new paradigm is, hey, what's your, hey, expert, what's your question about your, your expertise? Hold on, let me see. Hey ChatGPT, hey Claude, what would I do here? And I'm almost like I'm able to access expert level information, but the missing piece is if I don't understand the industry or the application of that, I don't know the Question to answer. So it's changed a lot from being somebody who is got the information, waiting for somebody to force me to recall it into, you know, I don't know the question to answer, to ask even though I've got access to, you know, expert level information. So this idea of, I think for now for sure, especially with kids, the ascension path that you've got with your levels of access and understanding is fantastic. I'm wondering what the, you know, 10 years from now, fast forward and the kids that are in second grade now have had 10 years of, of it before they graduate. Like they've been exposed to AI, they've been using it at home. The games that they play are now AI enabled. Their parents are using AI to manage the household or to plan the vacation or whatever. And it becomes this completely different thing to where what you were, you were talking about earlier where you and I had to go through this thing of writing things out and learning that process now to where it's, we've got the shortcut. So what do you think this paradigm of learning is going to look like? I mean, next year, next school year, much less 10 years from now?
Jason Hill
I think it'll be behind us. And what I mean by that is, you know, we've all heard the comparisons to AI to the automobile. Right. The tire, the printing press. Right. The calculator and all of those things disrupted the system. Yeah. Internet disrupted the system. Right. In 91, 92. This is disrupting the system. We are thinking about AI actively today. Once it becomes normal, I think it's going to be just another tool. I mean, I can remember when the Internet came out, interesting. Kids were just getting cheat. Right? And then when Wikipedia came out, there was all kinds of policies and rules on how to use Wikipedia. You can't use it or you could use it, you know, in, in, in behind the scenes. You have adopted textbooks, right? So all districts go through these textbook adoptions and your children have come home with big fat textbooks. That's money, right? That's a financial engine that I think drives that.
Chris Daigle
Yes.
Jason Hill
Then you had this thing called teachers pay teachers that came out and it was teachers creating content that they use in their classroom, hosting it online and other teachers paying for that content. It's like a teacher version of Etsy.
Chris Daigle
Okay.
Jason Hill
It freaked everybody out in education. Well, you can't do teachers pay teachers. It's not real content, it's not the text textbook, it's not this. But you know what teachers were doing were filling their gaps that these textbooks weren't giving them. And I'm not here to make a. Be a proponent to say teachers for teachers is this great thing. I understand that you can host things that are probably not the best for kids, but the concept of that teachers had to adapt and figured out how to fill a hole. I think AI is similar to that right now. It's big. It's a thing. We talked earlier. It's a thing still.
Chris Daigle
Yes.
Jason Hill
While it's a thing, it's going to be a thing and we're going to have policies and rules and it's going to take everybody's jobs and it's sucking up all the water and all these things until it's not a thing anymore. And Siri and Alexa, when it came out, was a thing.
Chris Daigle
Yeah.
Jason Hill
And then it just. No one cared about it anymore. And it was AI, Right.
Chris Daigle
Yeah. Yeah.
Jason Hill
You know maps, right. Oh, we're using maps. And so many people didn't like using their maps on their phones because they wanted to pull out their Thomas Guide. You don't even think about maps anymore. It's just what you do. I watch Landman a lot. Right. And I laugh because he says all the time, just drop me a pen, Drop me a pen. Drop me a pen. It's such a part of the show that that's all they do.
Chris Daigle
Yeah.
Jason Hill
Dropping a pen five years ago was like foreign.
Chris Daigle
Yeah. Interesting.
Jason Hill
And it's natural. And I think AI is going to be the same way. I think eventually it's going to become just a part of what we do. It's always something that teachers, students and parents are going to have to worry about. Right. Because it is a method of cheating. But so is going on Google. So is going on Wikipedia. So is us back in the day going and just pulling the encyclopedia out rather than going and pulling out the other books.
Chris Daigle
Yes.
Jason Hill
It's this. It's just another thing. And that's the way I think about it.
Chris Daigle
Yeah.
Jason Hill
How do we make it today to get through the thing? And that's what we're here for, right?
Chris Daigle
Yeah.
Jason Hill
The conversations. That's what we're doing. And it's marketable. Right. There's businesses surrounding themselves about this. But you know what? 10 years now, I don't know that there's going to be a market for pushing AI into companies, because it's going to be there already. Because we're going to educate kids and we're going to now get these kids coming out of our school. If we're teaching, AI don't need us. They're going to be us in the company.
Chris Daigle
Yeah, right. Just by default, like, everybody will be an us,
Jason Hill
but we're in this period of time where it's a thing.
Chris Daigle
Because you mentioned Wikipedia and I was like, that's so benign. Like, Right. But at some point it was considered, like, cheating to be able to. And just like, people are looking at that now with, with AI, whether it's a work product that you're creating or an educational product that you're creating as a, as a user. Interesting.
Jason Hill
You said something earlier about the levels, and I'm going to throw it into the businesses this way.
Chris Daigle
Okay.
Jason Hill
I think another way for a business to accept AI use is to create levels of acceptable use, meaning we call it 1, 2, 3, 4, but call it whatever, to say, okay, it is acceptable for you guys to use AI to proof your work. That's one way of doing it. It's acceptable for you guys to generate ideas with AI and it's acceptable for you guys to use AI to give us a finished product, like the presentation that you're going to present. And as a business leader, I'm going to tell my employees what's acceptable upfront. Right. Because I'm going to give them permission, say, okay, yes, you can use AI. I'm not going to chase you down, I'm not going to look over your shoulder. But my expectation is the product that you're going to give me is an AI product. It's your product, but it's okay if you used AI to get it. It's being upfront with your employees to say, okay, AI is out there and I'm hiring new guys that know about it and it's okay that they use it, but I want the product however you want it. Right. You might be okay with an AI driven solution. And it's hard because with spreadsheets now, I don't even know that the spreadsheet's not AI driven. I mean, I can just have Cowork build me the spreadsheet.
Chris Daigle
Yeah. So how we are addressing that, I think that's great how. And I didn't realize that we were kind of doing this, but how we address that in AI use policies when we work with companies is we kind of call it like a green light, yellow light, red light environment, where, hey, green light, if you're doing these activities listed totally fine to use AI, yellow light, you can use AI, but get approval first. Red light, hey, this company, we don't use AI to do these certain things. And I think that this idea is another concept. And you're familiar with it from being in a chief AI officer community. But when we're working with clients, we explain to them this concept of 1080, 10. And that's something that I learned from my buddy Mark Moss. If anybody knows who Mark is, the first 10% of working with the models is you being clear on what you want and you being able to clearly describe that to ChatGPT or Gemini or whatever you're using. Not just, hey, write me an email to a subcontractor. But, hey, here's a situation. Subcontractors behind, we've already paid them. But the more context you give it in that first 10%, the better the result. The 80 is what the models do. You hit Enter after you've put in your prompt. But what we always tell people, and a lot of people don't, don't think about this. The last 10% is you as the human going back through the output. You've got context on the solution, on what, what is good quality answer to this. You've got an understanding from your industry or your business experience of what a good answer would look like. So it's up to you as the user to still go back in on that final 10 and say, is this how I would have worded that? Like you said, with the, with the analysis of the, the narrative and the, the, the slides and everything, you understand what good looks like. If you didn't go back through what AI gave you, you would be opening it up to hallucination or maybe AI didn't quite understand it. So as a human list, as the listener and the human that's using the tools, you're responsible for the first 10% and that last 10%, exactly what Jason said he was doing right now. Yeah, AI did 80%. It takes a minute what used to take days. But it's. Once he hits Enter and gets that output, he's not done. He's still going to use the experience that he's got of doing it the old way, the manual way, to be able to look at AI's output and say, is this quality? Is this what I would have done? Is this how I would have said it? So as a user, you know, see how you can apply that to your own usage as well. So go ahead.
Jason Hill
I would just never once in the entire time that I've been involved in AI and pushing the district did I ever think about reducing staff. Right, Interesting. It's always been about optimizing our time and growing the capacity amongst my team. A little tip that I did it was an online. I couldn't tell you the guy's name. It was on YouTube. But, you know, the custom instructions sections of all these models and we put in there don't use EM dashes. Unprofessional. We put in what we want the output to kind of look like. He had a little tip to put in there to rate its output. And if it doesn't between 0 and 10, and if it doesn't rate above an 8, run it again.
Chris Daigle
Interesting.
Jason Hill
And run it again until it hits above an 8. And then give me a better structured prompt.
Chris Daigle
Interesting.
Jason Hill
And so at the bottom of every one. So that's in my custom instructions underneath using AIM dashes. So at the bottom of every answer that I get, there's a score. It's the language model score. But then it gives me another prompt that's better than what your original prompt was. What my original prompt was?
Chris Daigle
Yes.
Jason Hill
And often I'll just take that prompt and I'll throw it in a news chat to see if I get a better response. And so I'm allowing the model to train me. Every single time that I ask it a question, it trains me how to write a better question next time.
Chris Daigle
Great tip, for sure. Hey, so, Jason, we're at the top of the hour, but I want to make sure that everybody who's listening to this, I hope. I hope that you have a better understanding of what's going on behind the administrator's door at your children's school, whether that's a university or that's a kindergarten. Right. I hope that you walked away with an understanding that you're responsible for communicating with the people in the classroom with your children about how they're using AI. And hopefully, if you're, you know, you're listening to this stuff and you're using it, you may be able to present some suggestions to the teachers that are working with your kids on how, hey, here's how I use it. Maybe that can apply to you, to the educator. So be active. Don't just assume. Because I would be surprised if most school districts had a Jason working with them or that was part of their, like, invested in not just AI, but invested in AI across the school district. I would be very sorry. Are you finding that at all? No, no.
Jason Hill
Most of them are the tech guys.
Chris Daigle
It's not the same.
Jason Hill
Not the same.
Chris Daigle
That's not who you want, Right. So this is. This is a very unique. So if your kids are in Redlands, congratulations, you got somebody like Jason at the helm of this stuff, which is what you need. If not, please pay attention to the narrative that's coming out of the school district, the administration of that school district where your kids are, and pay attention and listen. Do they get it or do they have the cto, you know, who's a great database administrator or whatever, trying to figure out the AI policy. It's not the same. And then this, this levels of, of identification and access for usage. Figure out how you do something, you translate something like that into your own business. I think all of those are huge takeaways. And then I, I guess any, any last comments, Jason, for the listener, on both the business considerations as well as the educational considerations?
Jason Hill
No, it. Out of all of this, what I think I wish people had was a natural curiosity. Right. It's to ask the questions, it's to be open with hearing what you want to hear. AI is out there and we can fight it. But if people were curious about how it's used and how it works, people would be more open to it, right? Yes. Kids are going to use it and if we're not teaching it and not giving them access to it, they're going to have it on their phone shadow usage. Yeah. So why don't we talk about this and let's have this conversation together on how we can better educate their child. And parents are ultimately the control of their child. If they don't want their kid to have access to it, we can shut it off.
Chris Daigle
Sure.
Jason Hill
But I hope they don't do that because it's putting a disadvantage because when their child enters the same job force that all the other kids are, that's just one tool that they're not going to have in that competitive market. So be curious and be open.
Chris Daigle
Awesome. Jason, I've enjoyed this conversation. As I mentioned, we haven't had, I don't think we've had any educators or people involved in education that have sat with me and shared the perspective. But you're not just thinking about it, you're leading it across a large school district. So this is a very unique opportunity for the listeners to get that perspective of what's. And not just from somebody who's like, oh, I was curious, but you were already like, you're a professional. You're an AI professional who happens to be in the school or the other way around. You're a educational professional who happens to be an AI expert. So it's been very enlightening for me. So I really want to say thank you for taking the time out of the busy summer of doing this, man. So. And Jason, if anybody wants to kind of follow your perspectives, I know that you're producing content, you're sharing, you're speaking regularly. How, what's the best way for them to kind of see your opinions on things?
Jason Hill
LinkedIn is a good one. You know, I'm available on LinkedIn under Jason Hill and we'll add that to
Chris Daigle
the show notes as well.
Jason Hill
Yeah, so you can find me. It's, you know, I'm, I'm just looking at what it was, but I can give it to you later. But yeah, it's, I'm out there on LinkedIn. I don't do a lot of other social media. I have a YouTube site I'm just created to kind of start doing some of this stuff. But, you know, if you're in the California market, you know, I'm a part of AXA and a part of Casbo, and you know, I talk at various conferences and can always reach out via email. Man, I, I, I love to share and we're all in this together.
Chris Daigle
Then we'll include Jason's email as well in the show notes. So, and for the listeners, like, thank you for, for taking this little journey with us today. It was a bit of a deviation from, you know, the traditional just business talk about AI, but I think it's a very important topic and it's one that's under addressed just in general with AI related content. So feel free to pass this along to anybody else who's concerned about, like, what does this mean for my kids and that sort of thing. But thank you so much for listening. We're gonna have another fantastic episode next week and if again, if you got value out of this, please feel free to forward that along to somebody who you think would benefit from it. And Jason, again, thank you so much for taking the time very much out of the busy summer to help us with this. So thanks everybody. We'll see you on the next episode.
Jason Hill
See us.
Chris Daigle
Thanks for tuning in to Using AI at Work. Don't forget to subscribe for more conversations about how to use AI at work. And a special thank you to our sponsor, Chief AI Officer for empowering businesses with AI education and training. Visit their website for a free AI Readiness Assessment and AI Strategy Guide to help you get started using AI at work. That's www.chiefai officer. Follow us on Twitter at the handle usingaiatwork and visit www.usingaiatwork.com for free resources to help you harness AI in your role.
Episode 110: AI in Education: Building Trust While Preparing Students for the Future
Host: Chris Daigle
Guest: Jason Hill, Deputy Superintendent, Redlands Unified School District
Release Date: June 29, 2026
This episode explores how AI is being introduced and responsibly adopted in the K–12 education system, specifically through the lens of Redlands Unified School District in Southern California. Jason Hill, Deputy Superintendent and an early champion of AI in education, joins Chris Daigle to discuss overcoming resistance, building policy and trust, equipping both students and teachers for an AI-powered future, and transferable lessons for business leaders navigating AI change management.
AI as Essential Literacy:
Parent Resistance:
Reframing AI as a Tool, Not ‘the Thing’:
Leading By Example – “Flipping the Switch”:
Stuck on Policy, Not Progress:
Applying to Business Change Management:
“Levels” Approach for Safe, Gradual Adoption:
Policy Creation Is Iterative:
What Should Parents Ask Administrators?
Guardrails and Safety:
Advice for Parental Involvement:
Teachers Must Adapt, Not Just Ban Tools:
Learner Pathways, Not Just Access:
Ownership of Tasks Remains with Humans:
The “Normalization” of AI:
The Disservice of Avoidance:
"AI is not the thing. It's just another thing you need to learn—like reading or math."
“A confused mind always says, no.”
“Permission for everybody to accept that we're all beginners and we're all in this together.”
On policy creation and feedback:
On the future of AI in the workplace and schools:
AI for Efficiency, not Job Cuts:
On Human-Centric AI Use:
| Topic | Time | |---------------------------------------------------------|------------| | Opening theme: Why AI literacy is essential | 00:00-00:52| | Jason's background and Redlands USD context | 04:32-06:32| | Overcoming "policy paralysis" and staff-first adoption | 06:32-11:30| | Permission to be a beginner; inviting all staff in | 11:26-13:54| | Parent fears and teacher AI use debates | 13:54-14:39| | Policy development: Levels of AI use | 14:39-15:10| | How to approach parent education & resistance | 16:33-17:42| | What parents should ask their schools about AI | 23:27-27:04| | Filtering and safety provisions | 27:04-28:25| | Parallels for business AI transformation | 28:25-34:28| | Human vs AI contributions (The 10-80-10 Rule) | 48:31-50:58| | The evolution of learning and AI normalization | 42:12-46:07| | Final thoughts: curiosity and open communication | 54:28-55:42| | How to connect with Jason Hill | 56:36-57:16|
For more from Jason Hill, connect with him on LinkedIn (also in show notes).
For AI readiness resources for your organization, visit chiefaiofficer.com.
This summary provides actionable, real-world insights from the episode, with direct quotes, key segment timestamps, and clear guidance whether you’re shaping AI policy in schools or leading business transformation.