📂 Introducing “The Chatbot Files”
Last week, I told you about something I want to try in my classroom … a big question I want to think through this school year: “Can AI chatbots actually help students?”
Or, more specifically … “Can I use AI/tech to give students more help without losing the thinking?”
(By the way … our DTT online community shared LOTS of thoughts about the role AI chatbots should play in the classroom. Take a look — and share your thoughts, too.)
It’s complicated when the same tool students use to avoid thinking and shortcut learning is the SAME(ish) tool I want to use in class to support them … provide feedback to them … get them thinking.
And, big picture, I think this is one of the big questions lots of us have about the place of AI in the classroom.
So … to keep things neat and organized … and so you know when I’m referring to this big question and line of thinking, I created a new recurring theme: The Chatbot Files.

Introducing: The Chatbot Files
I’m planning on doing experiments throughout the school year — and lots of thinking and writing about the subject. This way, you’ll know right away what it’s about.
(By the way … That doesn’t mean that the whole newsletter is going to be about chatbots now. I’ll just come back to it on and off throughout the year.)
Today is our first dive into The Chatbot Files: Using chatbots to help students get past the blinking cursor on the blank page. Check it out in today’s 💡 Big Idea.
Inside:
💻 Free AI Literacy Course: Personalized to Your Classroom
👀 DTT Digest: 4 resources worth checking out
👥 Community: “What’s one thing you learned this week?
🎯 Quick Teaching Strategy: 60 second strategy: Professional courtesy
💡 The Big Idea: The Chatbot Files: Getting ready to work
😄 Smile of the day: Your disorganized desktop (desk AND computer)
👋 How we can help
💻 Free AI Literacy Course: Personalized to Your Classroom

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It's completely free, platform-agnostic, and over 8,500 educators have already taken it. When you finish, you earn a certificate automatically (no hoops, no fees). Just proof that you showed up for your own growth. 😎
👀 DTT Digest
4 teaching resources worth checking out today
🤖 Claude for Teachers: How to get started (plus 8 ways to use it in class) — Learn more about how Claude natively integrates with state academic standards, evidence-based curricula, and everyday classroom tools to help teachers easily differentiate lessons.
🎲 Paper, dice, and counters: Turn any worksheet into an analog board game— Learn how you can take almost any standard worksheet and instantly transform it into a high-engagement, analog board game using three simple items you probably already have in your classroom
♻️ Station rotation to engage AND save time — Station rotation gets students moving AND thinking. Use these ideas and templates to get started.
ICYMI 🍁Try this no-prep Fall Explore Board — This interactive “Explore the Magic of Fall” board is a simple, no-prep way to bring the wonder of autumn into your classroom and support a variety of learning styles. Get more activities like this in the free activity library at virtualescaperooms.org.
📢 FROM THE COMMUNITY: TOP DISCUSSION 📢
Nobody Has "It" Figured Out, and That's the Point

The community talked about what they learned this week.
Last Friday we started to ask the community: what's one thing you learned this week?
We’re going to ask this question every week on Friday.
This first time around, it was great to see that people were giving honest answers even if what they were telling us was difficult or confusing. Some highlights:
A science teacher watched a student who can't focus in a class of 23 become the most helpful kid in a small room, and ended up questioning how school is set up.
A computer science teacher found a hole in his own data privacy setup, said so publicly, and went to fix it.
And a Founding Member of the DTT community, one of the voices who helped populate this place, admitted she's still working things out.
We are so proud of this group for choosing honesty and the admission of what sometimes can be wild messiness. This is what we are here to witness for each other, and this is why community is SO important!
Here are a few specific thoughts that stayed with us:
"He went over and demonstrated (with good explanations) how to use the equipment, turned in his own lab, then went back to his study hall." — Carrie Baker
"Then it hit me. What if you have a personal account that is linked to your school account - is that still protected? In short, no."
— Judson Birkel
"I handed my neighbor kid a VHS tape to see the cover and told him he could watch the show. He took it out of the box and asked, ‘How do I watch, there's no screen?’" — Caren Matteucci
"I am learning, I need to figure things out. I still do not have "it." What ever "it" is." — Joyce Brister
What do you think? Open this discussion and add your thoughts here …
We will also have a new thread on Friday to reflect on this past week.
Not a member yet? Join the free DTT Community to read ideas like this, connect with other educators, discuss, and share ideas of your own.
🎯 QUICK TEACHING STRATEGY 🎯
💻 60 second strategy: Professional courtesy

If you teach in a 1:1 device environment (which many of us do), you know the struggle: you start talking, but half the class is still staring at their screens, typing, or scrolling.
Instead of raising your voice or counting down, try Professional Courtesy.
How it works:
Set the Expectation: Treat device usage like a professional workplace meeting. Explain that when someone is speaking to the group, listening is a basic professional courtesy.
The Cue: Give a simple, non-disruptive cue—like asking students to "45" their laptops (tilt screens halfway down) or place phones face down.
The Pause: Pause briefly until all screens are tilted down before you speak.
It shifts the dynamic from a power struggle ("Close your laptops right now!") to a real-world digital citizenship skill. It respects their work while keeping your instruction front and center.
💡 THE BIG IDEA 💡
📂 The Chatbot Files: Getting ready to work

Can a chatbot help students get mentally prepared for important work?
The big question I’m really curious to answer — “Can I use AI/tech to give students more help without losing the thinking?” — is actually a complicated, multi-faceted question.
That’s because there are different answers depending on when and how you use it.
So let’s dive into one area that I think is particularly promising …
Prework.
Pre-writing. Brainstorming. Organizing. “Getting your ducks in a row.” 🦆🦆
Why students struggle with prework
Students have a big writing assignment. Or a multi-step project. Something where they need to follow a set of steps to get to the finish line.
Often it starts with a topic …
Students might think: “Oh, I know exactly what my focus is!” … and it’s just not a great fit to the project.
Or they might think: “I have no idea what to write about … and I don’t even know where to start.” That’s where procrastination sets in.
After they have a topic, the process goes from finding a broad concept (the topic) to making it narrower and more focused.
They might need an outline. Or a set of subtopics. Questions to answer.
Part of the whole thing are the executive functioning tasks of knowing how to organize it, what steps to do in what order, how to pull it all off.
All of this is hard. But most times, it isn’t even the thing that we want to assess! We want to know how well the student understands the topic … what observations they made, what conclusions they drew, what new ideas they’ve learned.
To get to the good stuff, they might need some support … and in some instances, and AI chatbot might help them get there.
What we do/don’t want an AI chatbot to do with prework
Really, we want the student to be responsible for the good, important thinking and work. But if the chatbot can help bring out their own good human thinking and work, we’re probably good with that, right?
Honestly, that’s the kind of support we usually provide students as teachers … assuming that we can get that one-on-one face time with them (and that they ask for it).
So, imagine if we create an AI chatbot that …
Asks students questions about their interests in the work
Broadly suggests topic ranges without specifying specific ones
Helps them vet whether a topic would be good
Provides specific feedback (and what to do with that feedback)
Guides them in next steps in their project
Doesn’t give them an outline or set of subtopics
An example: Pre-write brainstorming chatbots
A common misconception for getting AI support on student writing: creating a broad “writing coach” chatbot.
Don’t get me wrong … the “writing coach” chatbot is great sometimes. I use them on little short writing assignments in my Spanish class and they’re GOLD.
But on a bigger project like this, it’s better to create very specific AI chatbots with very specific tasks. In this case: A pre-write brainstorming chatbot.
In this example, I used Spaces (their student-facing AI chatbot feature) in SchoolAI.
For the instructions, I just told it that it was going to support students in finding a topic for an essay … some details about the assignment … the role I wanted it to play (ask questions, identify interests, help them judge whether it would be a suitable topic, etc.).
Try out a pre-write brainstorming chatbot!
In these examples, I created a standard, normal “what you would expect” pre-write chatbot …
But then I had some fun with it. I created three others, using the same base instructions but telling them to give the same pre-write feedback BUT with a BIG personality.
Here are the ones I created (click a link to try one out):
Stanley, a crusty, curmudgeonly newspaper copy editor who doesn’t mince words and shoots you straight
Captain Inkbeard, an over-the-top swash-buckling pirate personality
Zorplax-9, a futuristic cosmic robot from the Interstellar Bureau of Human Communication
PRO TIP: Use AI to write instructions for these chatbots
You might be looking at this going: “I have no idea how to write instructions for these chatbots. I can’t code. How will I do this?”
First of all, you can write these chatbot instructions in your natural language, just as if you were telling a human teaching assistant how you want (and don’t want) them to interact with students.
Secondly, you don’t have to write them at all. You can use an AI tool like Google Gemini, ChatGPT, Claude or something else. Just tell it that you want to create instructions for a student AI chatbot (tell it which tool you’re going to use) and what you want to accomplish. Keep going back and forth with it until you get what you want.
Third, you might not even need to go to a different app in the first place. SchoolAI, the tool I used to make these pre-writing chatbots, offers TWO places to help you write instructions (see image below): the blue “Create my Space” button (where AI takes your instructions and improves them for you) OR the “Brainstorm with Space Designer”, an AI chatbot that helps you write instructions for AI chatbots.
(And yes, I realize how ridiculous it sounds to have AI write instructions for AI. But it works!)

AI can help you write instructions in SchoolAI Spaces.
When to use — and not use — a prework AI chatbot
There are a few things I really like about this.
For one, this prework chatbot scales nicely. I teach a class of 31 high school juniors and seniors. As much as I’d like to provide them adequate face-to-face interaction, I’m very limited as one single human teacher.
But if I can create instructions that preserve what I would tell students anyway, it’s a way to expand that out to everyone — and not just the students who raise their hands and ask for it.
Also, by picking the tiny part of the project / assignment that can use some AI support, we’re not handing the whole thing over to AI. We’re picking ONE part where we hand AI a VERY SPECIFIC role … then we’re doing the rest of it with our human capacities.
Finally, it uses one of my biggest rules for students AI interactions: human thinking before AI. The AI tool is actually prompting students to THINK, not doing the thinking for them.
If you’re designing the learning task and you realize that you want students to do this thinking themselves — or talk it out with a partner, then don’t use AI for this part.
But if you have problems that traditional approaches like that can’t solve — like a mass of students who are stuck looking at a blinking cursor on a blank screen with no idea where to go next, then this could be really helpful.
We’re just getting started with The Chatbot Files
This is just one part of this series on finding places where AI can actually support student thinking — instead of doing the thinking for them.
And remember, I’m not encouraging you to use more AI for the sake of using it.
But when it can help us achieve our goals and get students thinking in ways that we couldn’t otherwise, we have to at least give it a shot.
What should I look at next? If you have suggestions — or something you really want to figure out, just hit reply and let me know!
😄 Smile of the day
There are only so many things one can keep organized.

Source: cheezburger.com
👋 How we can help
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Read one of my six books about meaningful teaching with tech.
Take one of our online courses about practical and popular topics in education.
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