Clunky to Clever: AI's Journey from Clippy to Classroom Chatbots
by Jason Kosmiski, M.Ed.
This article was written with contributions from Jill Skala, Teacher of English, Greater Latrobe Senior High School.
The Clippy Calamity: When AI Was the Annoying Office Guest
The first chatbot that I ever encountered was named Clippy. Remember typing in Microsoft Word and being annoyed by an animated paper clip asking, "It looks like you're writing a letter. Would you like help?" Clippy first came packaged with Microsoft Office 97. It was one of the first AI assistants to utilize natural language processing and context to support users. Users hated Clippy. He popped up and got in your way while you were typing. Users called the chatbot annoying, intrusive, irrelevant, and obvious. Despite Microsoft spending millions of dollars on user interface research, Clippy still became an example of bad human-computer interaction. In 2010, TIME Magazine even named Clippy one of the 50 Worst Inventions. User complaints grew so intense that in 2001, Microsoft shipped Office XP with Clippy disabled by default. He made a final appearance in Office 2003. Then, in 2007, Office 2007 was released with no Office Assistant at all. Clippy was relegated to being a punchline – a nostalgic pop culture joke.
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Cassidy, Benjamin. (2022, August 23). The Twisted Life of Clippy. Seattle Met. https://www.seattlemet.com/news-and-city-life/2022/08/origin-story-of-clippy-the-microsoft-office-assistant |
ChatGPT Unleashed: The AI That Flipped the Script (and Scared the Teachers)
Two decades later, however, the AI assistant would re-emerge — this time, not as a cartoonish helper, but as a powerful generative tool capable of reshaping entire industries, not just word processing. In 2022, education would involuntarily evolve thanks to a chatbot, not unlike Clippy. To much fanfare, artificial intelligence start-up, OpenAI, publicly launched its AI platform on November 30, 2022. ChatGPT was an AI-powered chatbot using GPT-3.5, a Large Language Model (LLM), to mimic human-like conversations via natural language processing. As more educators became aware of this new technology, a sense of fear gripped them, especially English & language arts teachers. This thing could write essays – accurately – with quotations from the source material – and MLA documentation. ELA was dead – and ChatGPT killed it! It was true; during one of my first sessions using AI, I prompted the chatbot to generate an essay on the symbolism found in J.D. Salinger’s “Catcher in the Rye,” which it did in about 30 seconds. It generated the essay I tasked it to – complete with evidence and documentation. Was this the first step in the obsolescence of teachers? This would completely destroy critical thinking skills! Districts immediately responded by discouraging AI use by their students and rushing to ban student access to all artificial intelligence platforms.
I was apprehensive about AI, too – at first. It took me three years actively using ChatGPT and Google’s Bard (later Gemini) in my classroom to understand the power of artificial Intelligence as an assistant for educators – a smarter, better, and more well-rounded Clippy. During this time, I have used AI to generate writing prompts, brainstorm lesson ideas, draft sensitive parent letters, and build rubrics. I discovered that these tools weren’t replacing me – they were actually supporting me in ways that made my teaching sharper and more efficient.
"O Romeo, Bot!": 9th Graders Get Chatty with the Bard
We read Shakespeare’s Romeo & Juliet in my 9th-grade class. Every year, it is a struggle to make a connection between Gen Z and text that was written over 400 years ago in iambic pentameter. I want my students to understand Shakespeare as a human being – the man behind the legend. I dug out my A&E Biography DVD from my cabinet and showed it to my classes. It did little to dispel the mythic stature of William Shakespeare – in many ways, the video built him up even more. I developed a way to meld cutting-edge AI technology with a man who wrote over 400 years ago as a way to humanize him for my students. I introduced a custom AI chatbot that role-played as William Shakespeare himself.
I already had some experience building chatbots in Magic School AI. Located on the Magic Student side of the platform, this feature lets students “chat” with any “historical figure, author, or fictional character” in a controlled, teacher-monitored environment.
Magic School allows educators to build student rooms and deploy these AI tools in a very controlled environment. A dashboard lets teachers monitor usage, the AI will flag inappropriate interactions, and generate activity summaries that highlight tool use, student behavior, strengths, interests, and areas for growth. The platform also includes the ability to activate and deactivate access to these rooms to ensure security. Magic School is also FERPA and COPPA compliant and emphasizes student privacy by avoiding the collection of personal data.
Leveraging the controlled environment and customizable tools offered by Magic School, I was able to implement a specific learning experience centered around a customized AI chatbot housed within a virtual student room. Students were encouraged to “interview” William Shakespeare “himself” in chatbot form. They were tasked with creating five questions about his life, his writing process, the motivations of his characters, and the meaning behind famous lines. Once the students wrote their questions, they “chatted” with the “Bard bot,” recording its responses. Suddenly, Shakespeare wasn’t just a mythic Elizabethan icon – he was a living voice, responding in real time to their curiosity with wit, insight, and Elizabethan flair. Lastly, students wrote reflections about their experience with the chatbot.
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Kosmiski, Jason M. (2025, March 19). A Chat with William Shakespeare Lesson Plan. Google Classroom. |
These written reflections revealed just how deeply the chatbot experience shaped their understanding of Shakespeare – not just as a playwright, but as a real person. One student admitted, “I didn’t know much about Shakespeare in the first place, but this definitely helped me learn more about him.” They were surprised to discover how actual historical events, human nature, and even Queen Elizabeth I influenced his work. Another student was intrigued by how Shakespeare’s plays had to appeal to diverse audiences, writing, “I didn’t realize that so much had to be taken into account… so that they could be enjoyed by all.” Both students found the chatbot experience more “entertaining and specific” than traditional methods of learning – like passively watching the A&E video. The most telling comment came from the first student, who concluded, “After this, I don’t think I have any more questions for or about Shakespeare – I definitely have a better understanding about him now.” Allowing students to directly engage with William Shakespeare through AI made the experience of learning about his background more memorable and exciting than traditional approaches had ever achieved – at least for some of my students.
The Mid-Winter Slump: From Bard to Bored
While the Shakespeare chatbot initially sparked student engagement and a richer understanding of his life, this success gradually gave way to a noticeable decline in enthusiasm during the long stretch from New Year’s Day to Easter. I had been pushing the limits of my creativity, trying to develop new and exciting learning experiences in my classroom, while my students sighed and rolled their eyes at everything I did. In frustration, I posted all the cool things I had been doing for my Facebook friends, many of whom are teachers, to appreciate instead.
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Kosmiski,
Jason M. (2025, March 21). Facebook post. Facebook |
Across the Teacher-Verse: Sharing AI Strategies with a Colleague
Not long after my post appeared on Facebook, I received a Facebook message from a friend, former Saint Vincent College classmate, and colleague, Jill Skala, who teaches 9th-grade English at Greater Latrobe Senior High School. She was looking for a way to inject some AI into one of her lessons, one that would be observed for her yearly evaluation. I shared my experiences with the chatbot with Jill. She was teaching To Kill a Mockingbird by Harper Lee. Jill developed a lesson where students “talked” to the main characters: Scout, Jem, and Atticus, asking them ten open-ended questions about the novel (events that have happened, other characters to ask about, thoughts about the setting, etc.), plus supplementary follow-up questions. Her students also wrote a reflection paragraph at the end of the experience.
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| Skala, Jill. (March 2025). To Kill a Mockingbird Character Chatbot Form. Click to view full size image. |
Jill’s students responded to the character chatbot activity with enthusiasm and insight about the experience. Many reflected that it helped them connect on a personal level with Scout, Jem, and Atticus. Students described the experience as “fun,” “cool,” and “honestly really fun.” One student noted, “It made the characters so much more personable, and really added to my understanding of the story,” while another shared, “I feel more connected to Atticus, almost as if he taught me in a nearly fatherly way.” Several students discovered how the AI responses revealed subtle traits in the characters that they hadn’t noticed before, like Scout’s attention to detail or Jem’s quiet empathy. A few even wrote that the chatbot felt surprisingly human: “I was surprised… it was really like talking to a real person.” The experience even changed how students viewed the book itself – one student even wrote that the activity helped them see the novel in “a new way, rather than a dark, gloomy book.” As in my experience, Jill’s students also found that the AI (often portrayed in the media as a cold, calculating, murderbot) brought human warmth, personality, and connection to characters that have only existed on pages in a book.
From Pesky Pop-Up to Powerful Pedagogy: The Evolution of the Chatbot
From the days of awkward Clippy ungraciously interrupting our workflow with unsolicited advice, chatbots have evolved by leaps and bounds. Today’s sophisticated AI can do far more than offer clumsy letter-writing tips as we type. This constant evolution mirrors the timeless wisdom of Jedi Master Yoda. In Star Wars: The Empire Strikes Back, Yoda wisely tells Luke, “Always in motion is the future.” The same can be said for teaching English language arts. Unlike Clippy – who was often swatted away with a click – today’s AI tools empower teachers to stay relevant and engage students in fresh, dynamic ways.
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