Why Teachers Need to Begin Teaching Grammar Again and How to Think about It
Another round of insights from our work with an incredible class of 11th and 12th graders this past semester
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for sharing his amazing piece about literary frameworks for AI interactions. Check the amazing conversation between Mike and in the comments. In today's piece, Terry and I are sharing some insights about the novel approach to engaging with AI that's emerging from our deep analysis of our experimental "AI Theory and Composition" class this spring. If you enjoy explorations like this one, consider becoming a paid subscriber. And thank you to all of you who have already become paid subscribers“Why Teachers Need to Begin Teaching Grammar Again and How to Think about It”
Grammar is the hidden architecture that gives words their power to mean. It's not a collection of rules to memorize or structures to diagram, but the living system of relationships that allows language to breathe and evolve. When we understand grammar this way, we see why both traditional grammar teaching and Chomskyan abstractions miss the mark, and why we need a fundamentally different approach.
Words aren't static building blocks with fixed meanings. They're more like chess pieces whose power and function change dramatically depending on their position and relationship to other pieces. A pawn near promotion becomes almost as threatening as a queen; similarly, words transform radically based on their grammatical context.
Consider "run" – a simple word that transforms completely depending on its grammatical positioning. The athletes run daily. She has a run in her stocking. The newspaper will run the story. His luck has run out. The colors run when wet. None of these meanings are inherent to "run" itself. It's grammar, the relational system between words, that activates these different possibilities. Grammar isn't something applied to words after they have meaning; it's what creates the conditions for meaning to emerge.
Chomsky's famous nonsense sentence "Colorless green ideas sleep furiously" demonstrates this power. Despite containing contradictions and impossibilities, the sentence's grammatical structure forces our minds to search for meaning. We might imagine environmental concepts that haven't been implemented yet (colorless green ideas) remaining dormant (sleep) but with urgent potential (furiously). The grammatical relationships between words compel meaning-making even where none was intended.
This dynamic view explains why children acquire language so readily. They aren't learning rules; they're absorbing patterns of relationship. When a child says "I goed to the store," they're not breaking rules. They're extending a pattern they've observed, showing grammatical intuition that transcends memorized forms.
Traditional grammar teaching fails because it treats grammar as a set of prescriptive rules rather than as this generative force. Students memorize definitions of nouns and verbs without understanding how these categories are fluid, how words slip between them depending on context. "I need to water the plants" uses water as a verb. "I need some water" uses it as a noun. "It's a water plant" transforms it into an adjective. What allows "water" to shape-shift across these sentences isn't rule-following but the transformative power of grammatical positioning.
In the classroom, this perspective changes everything. Instead of teaching fixed categories, we explore how grammatical relationships create meaning. Take the sentence "Time flies like an arrow." This seemingly simple sentence has at least three interpretations depending on how we understand the grammatical relationships. Time passes quickly, with "flies" as a verb. Or perhaps we should measure the speed of flies, with "time" as a verb and "flies" as a noun. Or maybe certain flies, specifically "time flies," enjoy arrows, with "flies" as a noun and "like" as a verb. The words don't change, but the grammatical relationships between them create entirely different meanings. This isn't just wordplay. It's the fundamental power of grammar to transform.
This dynamic view explains why word order matters so profoundly in English. "The dog bit the man" and "The man bit the dog" contain identical words, but the grammatical relationships between them, created by position alone, completely reverse the meaning. It's not the words themselves but their grammatical dance that creates meaning.
Teaching grammatical perspective means helping students see and harness this transformative power. It means exploring how changing word order creates emphasis: "Never have I seen such behavior" versus "I have never seen such behavior." It means examining how grammatical patterns allow us to understand completely new expressions. When someone says "She Zoomed me yesterday," we instantly understand despite never having heard that usage before. It means analyzing how subtle grammatical choices change the reader's experience: "She opened the door and screamed" versus "She opened the door, screaming."
This perspective reveals grammar not as restriction but as the source of linguistic power and creativity. It shows students that meaning emerges not from words in isolation but from the grammatical relationships between them, relationships as subtle and complex as those in a chess game.
When students grasp this dynamic view, they understand that sentences aren't rigid constructions but organic systems where each element influences every other. They see that the same grammatical patterns that make "Send me the report" clear also allow us to immediately understand novel expressions like "Text me the address" or "Email me the details."
The Urgent Need for This Shift
The transformation in how we teach grammar grows increasingly urgent in our technological landscape. We stand at a critical junction where human language and machine language are colliding, and traditional grammar instruction leaves students woefully unprepared for this new reality.
When we interact with AI systems, we engage with a fundamentally different grammatical framework. These systems don't understand language the way humans do. They process statistical patterns of word co-occurrence without the intuitive grasp of transformative relationships that even young children possess. This creates a profound disconnect that traditional grammar education completely fails to address.
In human-to-human communication, we navigate ambiguity effortlessly through shared context and intuitive understanding. We know instantly that "flying planes can be dangerous" might mean either that piloting planes is risky or that planes passing overhead pose a threat. Our grammatical intuition disambiguates based on context. But AI systems lack this intuitive grammatical sense, leading to misinterpretations that can range from amusing to dangerous.
When we prompt an AI system, we're essentially speaking a distinct dialect, "machine grammar," that requires precision and explicitness far beyond what human conversation demands. Traditional grammar education, focused on "correcting errors" rather than understanding how grammatical relationships create meaning, provides no preparation for this new communicative context.
The stakes of this collision between human and machine grammar rise daily. As AI systems increasingly mediate our communication, draft our emails, summarize our documents, and translate our words, students who lack a deep understanding of how grammar creates meaning will find themselves at a significant disadvantage. They'll struggle to craft effective prompts, evaluate AI-generated content critically, or maintain control over their own expression in human-machine collaboration.
Moreover, as these AI systems become more integrated into educational settings themselves, students without this grammatical perspective will increasingly surrender their linguistic agency to machines that process language in fundamentally different ways. Without understanding the differences between human and machine grammar, they become passive consumers of AI-mediated language rather than active, critical participants.
The issue extends beyond practical skills to preserving human creativity and critical thinking in an increasingly automated linguistic landscape. When students understand grammar as a dynamic meaning-making system rather than a set of static rules, they maintain the ability to generate novel expressions, play with language creatively, and critically evaluate the output of systems that lack this human flexibility.
Traditional grammar education, with its focus on correctness and rule-following, inadvertently trains students to think about language in the same rigid, rule-based way that characterizes early AI approaches, precisely when they need to develop the fluid, context-sensitive understanding that distinguishes human language use from machine processing.
The collision between traditional grammar education and the realities of human-machine communication happens now. Students increasingly turn to AI systems for writing assistance without understanding the fundamental differences in how these systems process language. Teachers encounter AI-generated writing without the tools to help students see how machine grammar differs from human expression.
We must act now to shift our grammatical perspective. Every year we continue teaching grammar as a set of static rules rather than a dynamic meaning-making system, we send another cohort of students into a world where human and machine language increasingly intertwine, without the conceptual tools to navigate this complex linguistic landscape.
By teaching grammar as the living force that makes words work, that transforms them through relationship and context, we prepare students not just for traditional academic success but for thoughtful participation in a world where understanding the difference between human and machine grammar will become as essential as literacy itself.
Check out some of our favorite Substacks:
Mike Kentz’s AI EduPathways: Insights from one of our most insightful, creative, and eloquent AI educators in the business!!!
Terry Underwood’s Learning to Read, Reading to Learn: The most penetrating investigation of the intersections between compositional theory, literacy studies, and AI on the internet!!!
Suzi’s When Life Gives You AI: A cutting-edge exploration of the intersection among computer science, neuroscience, and philosophy
Alejandro Piad Morffis’s The Computerist Journal: Unmatched investigations into coding, machine learning, computational theory, and practical AI applications
Michael Woudenberg’s Polymathic Being: Polymathic wisdom brought to you every Sunday morning with your first cup of coffee
Rob Nelson’s AI Log: Incredibly deep and insightful essay about AI’s impact on higher ed, society, and culture.
Michael Spencer’s AI Supremacy: The most comprehensive and current analysis of AI news and trends, featuring numerous intriguing guest posts
Daniel Bashir’s The Gradient Podcast: The top interviews with leading AI experts, researchers, developers, and linguists.
Daniel Nest’s Why Try AI?: The most amazing updates on AI tools and techniques
Jason Gulya’s The AI Edventure: An important exploration of cutting-edge innovations in AI-responsive curriculum and pedagogy.
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Grammar isn’t hard to teach but like most subjects teachers can make it incredibly boring.
Reading this felt like stepping into a shared workshop of becoming where the act of teaching is less about transfer and more about presence, less about content and more about quiet, daily integrity.
In my own teaching and advisory work, I see how easily we slip into thinking of teaching as a deliverable rather than a living relationship. You capture that tension beautifully, teaching isn’t just an act, it’s a continuous invitation to learn again, to listen again, to embody the very frameworks we hope to pass on.
Your piece is a reminder that educators are not mere conveyors but stewards of possibility, shaping spaces where learning can take root beyond the syllabus or slide deck.
Thank you for holding this mirror up so thoughtfully. It’s the kind of reflection that lingers and keeps asking gentle, necessary questions long after reading.