AI in Schools: Strategy Over Shiny Tools with Kyler Cheatham
When it comes to AI in school districts, rushing in without a clear why can cost millions, crush teacher buy-in, and derail your entire tech strategy.
In this episode of My EdTech Life, I sit down with Kyler Cheatham, a system architecture expert in AI and predictive analytics, to break down what districts are getting wrong and how to get it right.
Kyler shares hard truths about AI adoption in K-12 and higher ed:
- Why CTOs must own their “I don’t knows”
- How to avoid the “move fast and break things” trap
- The real cost of chasing buzzwords without solving actual problems
- Why 50% of your implementation team should be end users
- How to keep vendors honest and ensure they meet your district’s needs
Whether you’re a district leader, tech director, or educator navigating AI, this conversation will give you the questions, strategies, and fail-safes you need before signing that next contract.
00:00 – Welcome and introduction
02:17 – Kyler’s background in AI and education technology
04:26 – The toughest challenges districts face with AI adoption
07:00 – Teachers as “speedboats, tugboats, and anchors”
09:14 – Advice for CTOs feeling overwhelmed
12:32 – The dangers of rushing into AI for the sake of hype
15:43 – Why vendor partnerships can make or break implementation
20:00 – Building a core team with 50% end users
22:58 – “Phase Zero” and defining your why before selecting tools
32:21 – The AI sticker joke—and why labels aren’t strategy
35:15 – Two wins and two losses Kyler sees in AI adoption
40:42 – Final advice for districts, CTOs, and vendors
46:25 – Closing thoughts and how to connect with Kyler
Big thanks to our sponsors for supporting these important conversations:
📚 Book Creator
🧠 Eduaide.ai
🗣️ Yellowdig
Listen in, take notes, and as always…Stay Techie!
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