Too many teachers are struggling with getting good results from AI. Sometimes it just goes “off the rails,” or they might get good results one day and not the next. The same thing happens with students as they use AI. Problems caused by not understanding how AI works leads to lost time, confusion, and sometimes even student misuse. Much of this problem is related to the context window of AI. How do we understand AI and the context window? How do we teach about this?
Today’s guest is Rob the AI Guy. He started his work leading a major social media agency but now runs a thriving community focused on AI agents and automation. He is my favorite AI YouTuber, and I joined his Skool this year, which I’ve found to be my most helpful resource for keeping up with everything AI. Rob clearly explains how AI works, but perhaps the most useful concept he shares is how the context window works. If you’re struggling to use AI well, trying to understand it, or grappling with how to explain it to your students, this is the show for you.
Key Takeaways for Teachers
- AI tools behave inconsistently because they rely on a limited context window that fills up and resets.
- Starting a new chat can dramatically improve AI responses when results drift or become unreliable.
- Different AI models have different strengths, and using more than one can lead to better outcomes.
- Students need explicit instruction on how AI works so they don’t overtrust or misuse it.
- Critical thinking is more important than memorization in a world where AI can retrieve information instantly.
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Robert Benjamin – Author Bio as Submitted
Robert Benjamin breaks down the latest in AI automation as a serial entrepreneur and YouTuber known for making complex technology accessible. Having consulted with over 350,000 clients through his social media agency, he now runs a thriving community focused on AI agents and automation, bridging the gap between cutting-edge technology and real-world business applications.
Blog: https://www.skool.com/ai-automation-school
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2 comments
This was really insightful; especially the explanation of the context window. I think a lot of the frustration students (and honestly teachers too) feel with AI comes from expecting it to “remember” everything or be consistent without understanding its limits. The idea that simply starting a new chat can reset and improve results is something I hadn’t really thought about, but it makes a lot of sense.
I also appreciated the point about teaching students *how* AI works instead of just letting them use it. Without that understanding, it’s easy for them to over trust the output or misuse it. It seems like AI literacy is becoming just as important as digital literacy.
One thing I’m curious about: how do you think teachers can practically introduce concepts like the context window to students in a way that’s simple but still accurate?
I have my REAL format that I share and I have presented on (I shared some of it here Blog post.) But I actually just build and start simple. First we learn about basic prompting. Then, we move from there. The best method of discussing this if the students are old enough is the recent tragedies like the case of Adam Raine b/c he kept one big huge chat and it led to terrible consequences. When AI goes off the rails, it is almost always, from what I’ve observed, a huge context window and it gets very confused. So, talking about examples and what could have happened — as long as it is age appropriate and approved by admin — is one way we discuss context window. It is a big deal as you move to agentic AI like Claude Cowork for sure. I’m guessing I need to write more on this. Thank you for your thoughtful comment, Briana. I’m not sure I can give you enough here but I guess the question is are you able to teach about AI and you can build in the curiculum you already have.