About the Episode
About the Episode: Mallory is joined by Winston Robert. Known as “Teacher in a Suit,” this innovative middle school teacher shares his journey from aspiring lawyer to influential educator. He discusses the integration of artificial intelligence in his classroom at KIPP New Jersey, and his exciting transition into UPenn’s Master’s in Education Entrepreneurship program. This episode is a must-listen for anyone interested in how forward-thinking teachers are embracing — not fearing — artificial intelligence and preparing their young students.Key Takeaways:
- Practical AI Applications: Winston Roberts utilizes AI to make his financial literacy classes more relevant and practical, preparing students for a future dominated by technology.
- Impact of AI on Jobs: Discussion on the transformative role AI will play in creating new job opportunities and the necessity to adapt educational curricula accordingly.
- Educational Innovation: Insight into Winston’s upcoming participation in UPenn’s innovative program, blending business acumen with educational reform.
- Advocacy for Modern Teaching Methods: Winston advocates for a shift in educational approaches to embrace technology and prepare students more effectively for future challenges.
- Career Transition: From a legal assistant to a pioneering educator, Winston’s career journey highlights the importance of impactful work over traditional paths.
From Law to the Classroom: Winston’s Journey
Winston Roberts didn’t start his career in education. After studying political science at Morehouse College and working at a law firm, he realized he could make a bigger impact as an educator. Teaching at KIPP New Jersey has given him the opportunity to inspire young minds and tackle real-world problems head-on.
Initially teaching math, Winston struggled to make abstract concepts like box-and-whisker plots feel relevant to his students. That frustration inspired him to launch his own financial literacy course, which has grown from 10 students on Zoom to 600 students across two schools. The course focuses on practical skills like budgeting, understanding loans, and evaluating the return on investment (ROI) of college—a skill set more important than ever in an AI-driven future.
AI in K-12: Preparing Students for the Future
Winston’s passion for practical education extends to his embrace of AI in the classroom. While many K-12 schools are hesitant to adopt AI, Winston sees it as an essential tool for preparing students to succeed.
Rather than punishing students for using generative AI tools like ChatGPT, Winston encourages them to share how they’re using the technology. He believes every assignment is now an open-book test, and his students still need to present their findings and articulate their learning, even when using AI as a co-pilot.
At the ASU+GSV Airshow, Winston highlighted a critical question: Who will benefit from the equity created by AI innovation? His mission is to ensure that students from all backgrounds are prepared to share in the opportunities AI creates, rather than being left behind.
What Higher Ed Can Learn from K-12 Innovation
Winston’s approach to AI offers a lesson for higher ed institutions, which he describes as moving “glacially.” Reflecting on his own time as a student, Winston notes the parallels between the resistance to Wikipedia in the early 2000s and today’s skepticism toward AI tools like ChatGPT.
The difference now is that AI skills are becoming essential in the workforce. Winston cites an example from Wharton professor Ethan Mollick, who asked his MBA students to create an AI bot capable of replacing their target job roles. Winston plans to bring similar assignments to his middle school classroom, reinforcing the idea that students must learn to work with AI, not avoid it.
Mallory adds her perspective as an employer, emphasizing that AI experience is now a qualification she actively looks for in job candidates. Higher ed, she argues, must catch up to this reality if it hopes to prepare graduates for a competitive job market.
UPenn’s Master’s in Education Entrepreneurship
Winston’s next step is a one-year master’s program at the University of Pennsylvania, blending business, innovation, and education. The program’s capstone project challenges students to pitch and develop their own scalable solutions for the education sector, with guidance from faculty across Wharton, Penn GSE, and other top schools.
Winston plans to apply his learning immediately, both in the classroom and through his broader work as an AI consultant. His goal is to build tools and programs that empower educators to adopt AI and equip students for the future.
Parting Thoughts
As Winston succinctly puts it: “The time for wait and see is over. We cannot prepare students for industrial-era factory work. We must prepare them to be competitive for the jobs of the future.”
Winston’s story is a call to action for educators at all levels. Whether you’re teaching fifth graders or undergrads, it’s time to embrace AI, rethink traditional education models, and prioritize real-world skills.
Connect With Our Host:
Mallory Willsea
https://www.linkedin.com/in/mallorywillsea/
https://twitter.com/mallorywillsea
About The Enrollify Podcast Network: The Higher Ed Pulse is a part of the Enrollify Podcast Network. If you like this podcast, chances are you’ll like other Enrollify shows too!
Some of our favorites include Generation AI and Confessions of a Higher Education Social Media Manager.
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