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The Teacher in a Suit Taking AI to the Streets: A Conversation with Winston Roberts
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Winston Roberts is raising a toddler and watching ChatGPT grow up—literally at the same time. As “Teacher in a Suit,” he’s bringing AI into classrooms not as a gimmick, but as a real tool for student agency, equity, and future-readiness.
In this episode, Brett and Rebecca dig into Winston’s origin story, his viral PD sessions that leave teachers shook in the best way, and his unflinching take on what happens if schools play it safe while the rest of the world races ahead.
He’s not here for performative tech use or AI panic. He’s here for project-based learning, powerful prompts, and students who can actually speak in public.
What You’ll Learn:
📘 Why banning AI is a waste of time: (and how Winston builds AI into the lesson—without losing control)
📘 The assignment that changed skeptical teachers’ minds: It starts with heartbreak and ends in songwriting
📘 Which tools Winston swears by—and why: (Hint: ChatGPT isn’t even his favorite for research)
📘 How AI is helping students conquer public speaking fears: Spoiler—it's more effective than flashcards
📘 What happens when you don’t see the tech trends coming: A story from 1970s Flint, MI that hits hard today
📘 The one thing AI still can’t do well: And why spreadsheets might be the final boss
🎧 Tune in and hear why Winston believes learner-centered AI could be education’s most exciting frontier.
12 episodes
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