Students Need AI Today to Succeed Tomorrow
The AI and technology that students (and others) are using now is the worst the technology will ever be.
The more we cling to traditional instruction, the more obsolete we make our students.
If AI can convincingly complete an assignment, then the assignment (not the student using AI) is a problem.
Career readiness includes how you position yourself, tell your story, and show you can create value.
Source: Seth Ebenezer Tetteh/Unsplash, used with permission
This is Part 5 of a series on AI in education. See Part 1.
In November, 2022—just 1 day before OpenAI launched ChatGPT publicly—teacher Winston Roberts's daughter was born. Roberts said to his wife something like, "This tool is going to change everything!" and his wife said, "That's great! Now hold the baby."
The connection between the two was not lost on Roberts: (a) a groundbreaking AI tool and (b) youth who will need to navigate AI to thrive.
Roberts has been on a mission ever since to help teachers leverage AI in ways that will prepare students for a world we haven't yet seen. Roberts is an educator, AI strategist, and founder of Teacher in a Suit; his answers follow each question below.
Jenny Grant Rankin: What role does AI play in students’ readiness for the world’s rapidly changing career landscape?
Winston Roberts: As teachers, we all say our job is to prepare kids for the real world. But too often, we mean the world of our parents or grandparents—the world we’re comfortable with. The truth is, our students are stepping into a future where AI is everywhere, and this is the worst the technology will ever be.
At its core, AI is built on pattern recognition and replication. That should force us to ask two questions:
How much of the world runs on patterns that can be automated?
And how much of school is training kids to master predictable patterns—worksheets, formulas, five-paragraph essays—that AI can now do in seconds?
The more we cling to that model, the more obsolete we make our students.
The opportunity is to flip the script. Instead of training kids to reproduce what’s already been done, we should be challenging them to imagine new solutions to real problems—and then decide where, or if, AI belongs in the process. That’s not just job readiness; that’s rethinking the very purpose of school.
JGR: What do you say to those who believe AI use in schools equates to cheating?
WR: That depends on how we define cheating. Cheating is only breaking the rules we set, and our rules were built for an education system designed to produce factory workers. For over a century, schools trained kids to read large amounts of information, memorize it, and reproduce it in predictable formats. Now we have a tool that can do all of that faster and better. In that sense, yes—it “breaks” the old system.
But the real question isn’t whether students are cheating. The question is: Do we have the courage to design a better system? If a task can be completed convincingly by AI, maybe the problem isn’t the student—it’s the assignment.
Instead of banning the technology, we should be challenging students to use it creatively, to solve problems in their communities, to think bigger than a five-paragraph essay. AI isn’t a shortcut—it’s a mirror, showing us where education has become obsolete. And that’s our invitation to reimagine learning.
JGR: Your background working for Google exposed you to the kinds of skills companies are looking for. What did you learn about what students need to be career-ready?
WR: At Google, I saw how unforgiving hiring could be. Brilliant candidates were dismissed—wrong school, not enough impact, not presented the right way. Once I helped classmates rewrite their resumes to highlight initiative and value, doors opened. Suddenly, they were landing jobs at Deloitte, NASA, Boeing, and Johnson & Johnson.
The lesson hasn’t changed: career readiness isn’t just about what you know; it’s about how you position yourself, how you tell your story, how you show you can create value. That’s one reason I became a teacher—to help students see that their brilliance only counts if they can communicate it.
What excites me about AI is that it can now do what I once did for my peers—help translate accomplishments into a language the world recognizes. You don’t need insider knowledge; you just need the imagination to ask the right questions. The real divide won’t be between those who know AI exists and those who don’t. It will be between students empowered to use it—and those punished for trying.
JGR: How can teachers leverage AI to help students develop crucial real-world abilities (like financial literacy)?
WR: It starts with mindset. This is the worst AI will ever be, and it’s already powerful. Picking one tool isn’t what prepares kids for the future—it’s designing experiences that mirror the real world.
In my financial literacy class, I recreate my time as a Google intern in New York City. Students get the same salary I did and must budget for housing, food, transportation, taxes, and utilities using real costs and links. AI is allowed, but it isn’t the point. The project demands creativity and critical thinking. If AI helps with research or presentations, great—but students still have to defend their choices in person.
The other layer is possibility. The gap between idea and product has never been smaller. With AI, a student can define a problem, analyze solutions, brainstorm new ones, storyboard, vibe-code a functioning app, generate a website, design a pitch deck, and even create a Hollywood-style ad—all in an afternoon.
So the question becomes: How big is their imagination? There’s no reason every graduate shouldn’t leave with a published book, a startup idea, or a UN-level proposal for solving global problems. That’s the kind of world AI makes possible—if we design schools that let them use it.
JGR: How can educators best make use of AI without robbing students of the chance to develop key skills?
WR: The skills students need aren’t siloed. Critical thinking, collaboration, problem-solving, storytelling, leadership, media literacy, and now AI literacy—they all overlap. Yes, we want kids to be strong readers and writers. But if our system is only optimized for test-takers, then as Ted Dintersmith puts it, we’re just producing “slow, imperfect versions of AI.”
Multiple-choice tests and five-paragraph essays may be efficient, but efficiency isn’t the same as effectiveness. Do they measure the abilities we’ve said kids need for decades? Not really.
When you zoom out, the question shifts. It’s no longer “Will AI replace learning?” but “How can AI support the kind of learning that actually matters?” That’s the challenge—and the opportunity—for every educator.
AI won’t replace teachers or students—but it will expose whether we’re preparing kids for the past or empowering them to imagine the future.