How Adaptive Learning Changes Teaching Without Replacing It

If a student can get a perfectly tailored lesson from AI in seconds, what exactly is the teacher’s job, and what does school become? That question sits underneath every new adaptive platform, every AI policy debate, and every parent’s uneasy feeling that “personalized” might also mean “alone.”

We talk with Tom Woelper, Head of School at Cheshire Academy, about what’s genuinely promising in adaptive learning technology and where schools can go too far. We dig into why pairing teachers with AI can beat either one alone, how personalization can free up time for projects and real-world skill building, and why the best outcomes start with a simple habit: decide the learning goal first, then pick the tool (sometimes the best tool is still pencil and paper).

 Along the way, we unpack the real risk of cognitive offloading, when students stop thinking hard because the machine is always ready to think for them.

From academic integrity to smarter assessment, Tom shares a practical “traffic light” framework for AI use: red light (no AI), yellow light (limited AI), and green light (AI allowed with clarity and attribution). We also zoom out to the parts of learning AI can’t replicate, including teacher-student relationships, belonging, and the subtle cues teachers read in a room. And we make the case that libraries and librarians matter more than ever as guides for source quality, bias, and information literacy in an age of instant answers.

If you care about AI in education, student engagement, and the future of teaching, you’ll leave with concrete strategies and a clearer north star: keep human connection at the center. Subscribe, share this with a colleague, and leave a review with your take: where should schools draw the line on AI?

The Case for Private High School in a Tech-Driven World  

💡 This episode is CPD accredited! Educators can now earn Continuing Professional Development (CPD) minutes by listening. To claim your certificate:

1. Listen to the full episode
2. Visit https://thecpd.group/podcast
3. Enter code 800173 to check in and download your certificate

or direct link: https://thecpd.group/p/5VHDHTB

Thank you to our sponsors!

Dr. Gregg Hassler Jr., DMD
Trusted dental care for healthy smiles and stronger communities—building brighter futures daily.

Gail Krapil, Kathie Butler, Beth Donofrio, & Dianelys Labrador

Transcript

Copy Transcript Copied

AI, Teachers, And The New Balance

Dr. Lisa Hassler 0:19

If AI can create and deliver personalized instruction, how does that change the role of teachers? This question affects our children's classrooms all the way up to the colleges that prepare their future teachers. Today, we're exploring the balance between AI instruction and human connection and what that means for teachers. Welcome to the brighter side of education, research, innovation, and resources. I'm your host, Dr. Lisa Hassler, here to enlighten and brighten the classrooms in America through focused conversation on important topics in education. In each episode, I discuss problems we as teachers and parents are facing and what people are doing in their communities to fix it. What are the variables? And how can we duplicate it to maximize student outcomes? Adaptive learning technology can adjust practice and learning pathways in response to a student's performance. Some schools are building their schedules around these tools, combining focused academic instruction with more time for skill development. One example is Alpha School, a private school network with campuses across the United States. According to Alpha's description, students spend about two hours on core academics using adaptive learning technology, with the rest of the school day devoted to projects, workshops, and life skills. Teachers, called guides, support students' motivation and lead these experiences. And the intention is to personalize academic learning while creating more time for practical application and personal development. Alpha also offers a home learning program called Alpha Anywhere. These changes raise questions about how educators prepare for their evolving work. In June 2026, the online learning consortium explored that topic through two informal LinkedIn polls of its community. In the first poll, nearly four out of five of the 121 respondents selected either AI and digital fluency or adaptability and change management as the most important skill for online learning professionals over the next five years. In a separate poll of 91 respondents, student engagement strategies receive the largest share of responses at 41%, when participants considered where professionals should concentrate their efforts. These small self-selected polls offer a snapshot of the online learning community's priorities. They suggest that keeping pace with technology and supporting student engagement are both on the participants' minds. That focus on engagement brings us to the human relationships within learning. In a 2011 review of 99 studies, Deborah Rhoda and colleagues found that teacher-student relationships were associated with student engagement and achievement. And while those associations do not establish cause and effect, they do give us a reason to consider relationships carefully as students redesign learning. So as technology takes on more instructional tasks, how can schools help students develop independent thinking while maintaining strong connections with teachers? Here to discuss the evolving role of teachers in an AI world is Tom Wolper, head of school at Cheshire Academy in Connecticut. Tom brings more than 30 years of experience in independent education. He served as the founding head of New England Innovation Academy, and his career includes work in Gronton, Taft, and Hotchkiss. He holds a bachelor's degree from Princeton University and a master's degree in history from the University of Connecticut. He also earned a master's in educational leadership from Teachers College, Columbia University with a focus on private school education. In his November 2025 guest column for EdTech Digest, The Case for Private High School in a Tech-Driven World, Tom explores how teachers can help students develop the judgment and independence they need in a world shaped by AI. Tom, welcome to the show.

Tom Woelper 4:11

Thank you for having me.

Adaptive Learning Promise And Limits

Dr. Lisa Hassler 4:12

So, what do you find promising about school models that use adaptive technology for core academic instruction? And what should schools consider when adopting that approach?

Tom Woelper 4:23

Well, I think that the exciting promise of adaptive technology is to create these highly personalized learning experiences for our student. I think in a perfect world, every student would have their own IEP, their own personal tutor who could meet them exactly where they are to find that right amount of challenge with the right amount of kind of scaffolding. But our current school system uh doesn't work that way, right? A teacher will have at an independent school will have you know 12 to 16 students in a public school, maybe up over 20, 25 students. So they can't do that. So that's what I think that the exciting promise is is kind of the personalization of education for each student.

Dr. Lisa Hassler 5:06

Yeah, I definitely see that as promising as well. As a classroom teacher, I found that to be one of the most challenging things. While it sounds really easy, oh, just meet them where they are, find out what they're missing. It's so easy to say that. It's really hard to do. You have to have the right technology to be able to help you pinpoint those things sometimes because it may not be in your curriculum, but in a prior. And so that's really where you need something else. So I see that as a promising opportunity as well. What do schools consider when they're considering that kind of approach?

Tom Woelper 5:37

Yeah, I mean, there's maybe a danger of going too far, of maybe wanting to offload all of that to technology. But you don't want to lose sight of the fact that this is a tool that I think can be most effective when used well with a teacher. So give an analogy. I remember when Big Blue beat Gary Kasparov in chess, and that marked the beginning of technology being better than humans in doing chess, but they found that the most successful chess models is when a human partners with their AI, their technology that will outperform the technology by itself. So if you extend that back into the classroom, you want a teacher who might be using that AI to help create the personalized lesson plans. But teaching and learning in schools, I think, are still incredibly social and built on relationships. So you can never lose sight of that being at the heart and pursuing a test score at the expense of having students feel whole and empowered and supported in their learning.

Dr. Lisa Hassler 6:46

So,

Belonging, Body Language, Real Learning

Dr. Lisa Hassler 6:47

what is it that teachers bring that AI does not?

Tom Woelper 6:50

Well, first, just to make a quick comment about AI as opposed to other technologies. And we can look at the printing press, the internet as technologies that were really kind of paradigm shifts, but none of them really got to the heart of what does it mean to be human in quite the same way that AI does. And I think it really invites us to think deeply about that. And maybe in some ways, a teacher becomes even more analogous to a coach, like an athletic coach who is there to work with the students to really identify when they need to be pushed harder, know when they might need to be supported more, or a kind of metaphorical hug, understanding when they're getting tired and need to be redirected. I think part of good education isn't just about content and skills, is learning how to be in a community. It's often learning how to be a good citizen. It's developing those social and emotional skills that are so important and is such a part of the human experience. In some ways, that's always been part of teaching. And technology might allow some of that personalization we're talking about or rapid feedback. I think technology or AI can give to really focus on those other pieces that are so very important.

Dr. Lisa Hassler 8:11

I think it does do a great job when it comes to that personalization and being able to pinpoint those gaps. But when you talk about the relationships, I think that a teacher being able to pick up on body language, whereas AI is not going to, at least from what I've seen, I know that they are developing some eye movement um things to be able to track the eye movement to say, I think that they are not understanding something. These are confused eyes. I don't know how they exactly look at it. But I think about that body language and that the cueing. Here I am doing my lesson. I'm thinking, I am like knocking it out of the park. We've got the manipulatives out. Yes, let's go. And you look at them, and they're just like either confused or they're tired. And you and you just see, you know what? I've lost them. I've lost them here for a moment. Or you know what? They are tired. I maybe I spoke a little too long. I shouldn't have gone on. So then you go, you know what we're gonna do? We're gonna stand up. We're going to do a little brain exercises. So you're able to pick up on that cue to give them what they need in the moment that's not academic focused, to get them able to come back to focus on the academics.

Tom Woelper 9:17

100%. You know, to develop that sense of belonging is so key for deep and enduring learning. We've been doing some work with the Center for Transformative Teaching and Learning, Dennett St. Andrews School on Mind, Brain, and Education on the Science of Learning. And they come back to that deep sense of belonging and kind of connection to your teacher and to your classmates is like ground zero for deep and effective learning. And that's what AI can't do, even though I know as you were mentioning some of the new technologies, look at the eye movement to see whether you're still engaged. But that that's just a proxy for real belonging. And I think that can't be manufactured.

Dr. Lisa Hassler 9:58

Yeah, even though there is the whole students are having relationships with AI, like their girlfriends and stuff like that. I think that's uh that's different. So I mean, just yeah, I guess people are having relationships with AI, but they're more of the complacent um, you're the best. You never do anything wrong. And you know, and everyone wants a friend like that, I guess. So uh, but then there's the reality check of, you know what, maybe we could do better.

Tom Woelper 10:21

And I would bet that's gonna go down the line of say social media, where on the one hand, you you know, kids seem to be more connected than they have ever been. Yet they've never been more lonely. And I I I'm gonna bet that you know your AI girlfriend, boyfriend is gonna be like a kind of sugar high. It might feel good in the moment, but it's gonna leave you hungry and empty in the end.

Dr. Lisa Hassler 10:44

Ah, good point. Hadn't thought about that. A little a little dopamine and then uh then you crash, right? A little bit. Exactly.

Traffic Light Rules For AI

Dr. Lisa Hassler 10:51

So now Shasha Academy uses a traffic light policy guide that helps students with AI as well as teachers. Can you talk about how that works and maybe share a classroom example?

Tom Woelper 11:02

Sure. Like many schools, trying to keep up with and ahead of how to use AI in the classroom. And I know that we often are worried about students taking shortcuts and cheating and the cognitive offloading that can happen. But a lot needs to start with some good policies just to be clear about when students can use AI with their assignments. And so the simple notion of a green light, yellow light, red light is to define if it's red light, it means 100% you cannot use AI with this homework assignment with this assessment. And so you name that upfront yellow light, you define the kind of parameters for where it can and can't be used in that assignment. And green light, you can use it all the time. And what's really interesting to give an example, we have launched a new global citizenship diploma distinction at Cheshire Academy, and it has a really interesting seminar course. And we had some teachers experiment with 100% green light AI on everything. And it really challenged them to think about how to craft their assignments, how to have the students attribute what they use the AI for and what they learned in that process. And as much as that might sound frightening, I think, to many educators to just go, all right, use it all the time, but it can also lead to a different emphasis on what's important to demonstrate. Like, for example, with AI, asking really good questions and prompts is a prize skill. And to do that well, you actually have to really know what it is you want on the other side. And so it might be a different way to develop critical thinking skills, even further, I think, puts to the forefront a sense of judgment about what is appropriate to do and what's right. You can also ask questions that have students to go back and assess how accurate the AI is because it's not always accurate. So it's been really interesting just to add some kind of clarity, because I know we continue to have academic integrity concerns with AI, but by having a red light, yellow light, green light policy, you can really upfront kind of define how you want to use it and create space to maybe use it all the time and start to reimagine what that looks like for the students and the teachers.

Dr. Lisa Hassler 13:24

Yeah. And I and I love the way that you talked about how they have to know what it is that they want to be able to ask those questions. And it makes me think about how when teachers are developing units or lesson plans, they're always thinking with the end in mind. And with students, it's the same thing. This is what I want. How am I going to get there? What tool do I use to help me so that I get the best results? So that's really wonderful that you're able to give those students that space to use that well.

Tom Woelper 13:51

And it also gives you a chance to give them more sophisticated, complex tasks, perhaps earlier than you might think they would be ready for them because they have that tool to help them get to those things. And a lot of that can be more interesting and relevant to the student too, which is kind of cool. But again, this invites us to rethink how we teach, how we assess, and how we use our tools.

Dr. Lisa Hassler 14:14

So, how do you know what tools then to use? How are you able to keep on top of it yourself and help your teachers stay on top of it to be able to help guide your students with all those new technologies, new apps, new AIs coming out?

Tom Woelper 14:29

That's a great question. First, for me personally, I'm just a very curious person. So I think there's some place where you need to be curious and to try some things out. But it's back to what you were saying before. It still is just a tool. And you really have to know what it is you want as the outcome to know what's the best tool, which might still be pencil and paper, right? Might be the best tool for the outcome that you want. So, for example, I use otter AI when I do my uh leadership team meetings. So I record it. I'm able to work with the AI to create instant minutes and notes that are done minutes after the meeting. So no one has to separate their attention to take notes for the team and the action items. It does a pretty good job of that. It's not 100% kind of correct, but we can just focus on the meeting. Everyone, if they miss a meeting, knows they can go back to it. The thing that I was solving, I wanted people to be completely present. I wanted to have notes for people who weren't there, and I wanted to make sure that the action items were very clear. That tool did a better job than kind of humans did, even though it's not perfect.

Dr. Lisa Hassler 15:36

Yeah, I use Adder AI as well. I like it a lot, but you are right, it is not 100% accurate. You have to come back and go, that wasn't quite what they said, but we'll fix that, you know. I think students may have a false sense of authority where the AI said it, and so it must be. And then you kind of go, well, it can't make stays. I don't know if you've ever heard of the AI Connection Club. They're a great little community that lore and rate all the different AIs as they're coming out. And so they'll say, hey, this one came out, and someone from the community will test it and they'll go, This is what I found, and someone else will go, hey, I agree with that. And have you tried this? And it's good for this. And so a wonderful place to see the new things that are coming out and then how people are using them and what they recommend for different activities. I don't know if you've heard of AI for education, Amanda Bickerstaff, she's fabulous and gives weekly newsletters. You'll see them on like LinkedIn and stuff. But her website has wonderful things for up-to-date policies that Wools and teachers can use and teacher education, things for schools to give to parents. So wonderful toolkits there as well. So I don't know if you've ever explored anything like that, but those are two sources I find really helpful.

Tom Woelper 16:44

Yeah, I haven't worked with those sources. But one thing that I have found personally is that using some of the AI tools has made me more efficient in some of my other work that frees up time to do the things that are really important. So even for kind of educators, if managing all of your emails or having the AI help put together like priorities list for the day, like there, there are ways you can help with the other work that often makes it tough to get to your lesson planning or the other things that you want to do. Uh, it can be your kind of chief of staff, if you will. Not that teachers have a chief of staff, but but that's been a a place that I have found it actually in terms of my own workflow and the efficiency of certain things that allow me then to focus on the things that are really important.

Dr. Lisa Hassler 17:29

Yeah. No, I've used it as my personal secretary, but I feel like I'm checking my personal secretary too much sometimes. Let her do her.

Tom Woelper 17:37

There's a balance. There's a balance with all of this here, to be sure.

Libraries As Learning Hubs

Dr. Lisa Hassler 17:41

Your librarian has spoken with a newspaper and it talked about the importance of libraries. You're doing something special over there at Sheshire. Can you talk about the importance of libraries and librarians?

Tom Woelper 17:53

I think that regardless of the changes in technology, libraries and librarians will be so important to any educational community. And I think a lot of how that has evolved. And I'm old enough to remember when the library was about the librarian kind of shushing you to be quiet as you found your place in the stacks and the card catalogs that would take hours to try to find the books that you needed to get for your research. But our library has become a hub of learning and of community. So our students do go in there to do homework, to do academic research, but they also go in there to kind of connect with each other to work on projects. There's even spaces where, if they have a free moment, they want to do a puzzle, they can get together with classmates. So it really is a space to kind of connect students to the resources that they need to get done what they're trying to get done. That might be books, it might be an online resource, it might be talking with another student who's working on a project, it might be connecting with the teachers who have that kind of expertise. So I really see it as this hub and nexus of learning and community.

Dr. Lisa Hassler 19:02

Yeah, I loved going to the library after school. I would meet my friends there and we would buy cool pencils that they had for like a quarter on the machine. And so it brought me to the forefront of technology as well. It was like, I get to like use a copy machine. This is way back, of course. And so the library was always, of course, the source of knowledge, but it also integrated technology. I mean, when we started, I had the card catalog and moved to the computer. Then of course, um, we would have to write everything down to now we have copy machines. So they never shied away from technology. They embraced it, but still a core to the community to give you a sense of belonging, to collaborate.

Tom Woelper 19:39

I think part of the librarians too, helping students assess what the best sources are for the project that they are doing. There's lots of stuff out on the internet that that is not relevant, but to help them understand where the best information, the experts lie for the topic they are doing, how to understand bias, uh how to join the community of scholars to cite your sources. I mean, I think there's some things there that are gonna be timeless. And that's I think another important function that our librarians do and in concert with our teachers to help develop that skill set because you're gonna need that in life and beyond academia.

Dr. Lisa Hassler 20:16

Definitely. And as students are getting instant access to information, it's important to have a guide still there to say if you went here, that would be a little bit more relevant, or if you went over here, this is a little bit more trustworthy. So having that guide, I think, is really important. What

Avoiding Isolation In AI Schooling

Dr. Lisa Hassler 20:32

are you worried about students losing if technology becomes their primary relationship with their educational experience?

Tom Woelper 20:40

Yeah, I'll go back to something I kind of said at the at the beginning. I think that we humans are inherently social creatures. I think education is far more about mastering content and skills and passing the tests and taking the SATs. I think it's a lot about one's personal growth and development as a person. So the different social emotional stages, there are different points of time when from your childhood through your adolescence, you can take on increasingly complex tasks and can grow in your critical thinking and quantitative reasoning. But I think part of being well educated is learning how to be a good citizen. I don't want to lose sight of that. And we live in community and learning how to live and work with people who are different than you, might have different opinions, how to make assessments on your own, but also understanding the impact it'll have on others. I think that's part of what school is all about. And as much as I'm a fan for multiple different models to meet different types of learners, whether it's from homeschooling or if you want to go to an AI academy, if that makes sense for you, I still think at the heart of education is that social experience and learning how to live with others in the community. And that's what I fear could get lost if we go too far down the AI rabbit hole.

Dr. Lisa Hassler 22:02

Yeah, good point. There's a lot of isolation and loneliness that comes with technology. So while things can be custom and tailored to you, you is a lonely island to be on sometimes. As a school leader, are you doing any specific professional development? No, we talked about traffic light. Um, you have the the guides of faculty guidelines to follow with that as well. What kinds of things are you doing to help your faculty stay on top of it?

Tom Woelper 22:29

Sure. This is changing so rapidly. You feel like as soon as you provide any training or insights, it's outdated the next week. But but we started last year, one of our professional development strands was on AI. We worked with a group called Concilium that worked both with our teachers as well as with our administrators to just understand what the kind of potential and opportunity AI kind of presented to schools and teachers. The group brought some master teachers who seem to be ahead of the curve and how they've used it in the classroom. Some showed some possibilities to how AI could really empower students to be partners with faculty to solve uh challenges on campus, as simple as better methodology to place new students into math classes, all the way up to finding ways to pair tour guides with prospective families better, right? You can use the kind of AI and seeing examples of how other schools have been doing that. So I think some of this is both just understanding what the tools are and what they can do. And then the other is to see teachers who are really using this in a way that is getting the best out of what AI can do for their learning objectives. And so we did that work last year, and we are continuing that as one of our strands. We're looking to do some partnership with a program out of MIT just to stay current and to keep thinking about this rapidly changing technology. But it is one of these things, it's gonna be a combination of what the school can do and the people who are already exploring and pushing things to provide space for them to give support to colleagues.

Training Teachers For Rapid Change

Dr. Lisa Hassler 24:03

Yeah. I mean, just thinking about how different it is from when you or I had gone into the field of teaching and how those preparation programs developed us and prepared us for our first classroom. Things have changed a lot while we're trying to keep abreast as to how we can incorporate those tools into what we already know about teaching, into the existing program. Is there any advice that you have for teacher preparation programs? What should they help teachers understand and practice as AI changes their work?

Tom Woelper 24:33

I think I'd say even as the role is changing, the part of learning remains the same. And it in some ways simply you have to think hard. If we're talking about Vygasi's zone of proximal development, right? Anything is too easy, you don't learn. If it's impossibly hard, you don't learn. What is that space just beyond the reach of what you can do with the right support and scaffolding is where the deepest learning happens. And to never lose sight of that is that deep learning happens when you have to think hard and you have to be stretched. And all these tools can evolve and change. And if it leads to cognitive offloading, so you're not thinking hard, it's not working. If it's so overwhelming that you don't even know where to start, it's not working. So I would just kind of come back and realize that you know, we humans are wired a certain way and that being stretched and challenged to that place where we do things we don't think we can do unless with the support of a teacher is something we should always keep central in the teacher prep programs and in terms of what we do.

One Small Action This Week

Dr. Lisa Hassler 25:33

Absolutely. What is one thing a teacher or parent can do this week to strengthen that human connection while still making thoughtful use of technology?

Tom Woelper 25:42

Wow. I think that there is never anything better than face-to-face in-person conversation. And so let's start there. And maybe with the technology is having conversations with your child or your student. I think they view the world very differently. Sometimes they would want more constraints or restrictions on technology than maybe we adults think. As I said, I'm old enough not to be a digital native and uh, you know, grew up in a house that had a kind of rotary dial phone. So I've come on a long journey to be using this technology. And these students have grown up in a world where this is the air in which they breathe. And I just think the human kind of connection and just conversation and struggling, wrapping through this together is probably my best advice.

Dr. Lisa Hassler 26:30

Yeah, that I I agree. I think that sometimes they're sick of it too. You know? And so being able to say, hey, let's let's take a walk outside out, let's put it down for a moment while still creating that space and knowing that there is the tool that they need to use it for certain things, but then to also create the opportunity, right, for those human connections. So it can go a long way. All right. Well, thank you so much for sharing your perspective on the future of education and the changing roles of teachers as we are embracing this world with AI. So thank you for your time.

Tom Woelper 27:02

Thank you.

Dr. Lisa Hassler 27:03

If you have

Ways To Connect And Support

Dr. Lisa Hassler 27:04

a story about what's working in your schools that you'd like to share, you can email me at Lisa at dr lisaarhassler.com or visit my website at www.drlisaarhassler.com and send me a message. If you like this podcast, subscribe and tell a friend. The more people that know, the bigger impact it will have. And if you find value to the content in this podcast, consider becoming a supporter by clicking on the supporter link in the show notes. It is the mission of this podcast to shine light on the good in education so that it spreads, affecting positive change. So let's keep working together to find solutions that focus on our children's success.