110: AI in Education: Building Trust While Preparing Students for the Future  with Jason Hill artwork

110: AI in Education: Building Trust While Preparing Students for the Future with Jason Hill

Using AI at Work: AI in the Workplace & Generative AI for Business Leaders

June 29, 2026

Send us Fan Mail AI in education is no longer a future debate, it is a leadership decision happening now.
Speakers: Jason Hill, Chris Daigle
**Jason Hill** (0:00)
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** (0:06)
You've kind of been ringing the bell about, hey, let's do something about AI. How has it been received by your peer?

**Jason Hill** (0:11)
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** (0:38)
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** (0:52)
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, firewalls that catch if my daughter were to start talking or discussing self-harm within that chat?

**Chris Daigle** (1:07)
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 Daigle. Each week we'll be learning about 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.
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All right, everybody. Welcome to Using AI at Work. My name is Chris Daigle. I'm the host. And today our guest is Jason Hill. And Jason is 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 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 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 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 Eye 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?

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