You know that scene in every heist movie where the mastermind explains the plan to their crew, everyone nods knowingly, and then everything goes exactly according to script?
Well… implementing EdTech often is the opposite of that.
It's more like if Danny Ocean (from Ocean’s Eleven) planned the perfect casino heist, explained it to his accountant, who told his assistant, who left a Post-it note for someone who's never been inside a casino and thinks "poker" is an annoying Facebook user.
Won Ko, our Senior Customer Success Manager at Subject, realized education runs on this backwards heist logic after jumping from normal B2B sales into the beautiful chaos of school districts.
For two years, he watched expensive software get passed down through more layers than a wedding cake, arriving at classrooms like a game of telephone played by people who speak entirely different languages.
The good news is he’s found a way to stop treating tech rollouts like Mission Impossible stunts, and he’s sharing with us exactly how to do just that.
Here’s what’s on the dashboard this week:
Today’s Deep Dive: How to stop playing telephone with your tech budget
Reading Rainbow: City kids discover wildlife + schools graduate to AI policies
From Our Desk: The school that refuses to give up on “throwaway kids”
Watch of the Week: A rare example of a successful group project
Won is pulling the curtains back on education's dirty little secret:
The person with the credit card never touches the keyboard. Meanwhile, teachers are staring at mystery software like it's some weird alien tech, wondering if they accidentally signed up for a timeshare presentation.
After watching districts burn through tech budgets, he built a four-step survival guide for actually making EdTech work. Think of it as couples therapy for schools and their software—except with better results and fewer tears.
Four Steps to Making Tech Work For Real Teachers
Step 1: Play Detective with the Org Chart
Won maps out who really runs the show versus who just has the fancy business cards. He befriends the people getting groomed for bigger jobs, because when admin plays musical chairs every two years, you need friends who'll still have desks when the music stops.
Step 2: Become a Classroom Spy (The Good Kind)
Instead of celebrating login numbers while teachers quietly plot revenge, Won combines spreadsheet data with actual human intelligence. He roams hallways like a friendly detective, discovering gems like "kids love this, but the tutorials make them want to throw laptops out windows" or "parents tried helping with homework, and now everyone's crying..."
Step 3: Build Custom Solutions Instead of One-Size-Fits-Nobody Disasters
Rather than shoving every school into the same box, he creates programs that actually match what districts need. At Subject, our setup works like educational Legos—he can build specific configurations for different student groups without everything falling apart when someone sneezes.
Step 4: Turn Wins into More Wins
When programs actually work, Won uses those victories to expand into other schools. Success stories become his golden tickets. Instead of cold-calling superintendents with the enthusiasm of a telemarketer selling extended warranties, he can say: "Remember how we fixed your graduation crisis? Want to see what we can do for your middle schoolers?"
If you’re looking for proof, you’ll find it in places like Napa Valley.
We now run every high school plus middle schools and after-school programs. Teachers report they’re actually connecting with students instead of wrestling with tech that seems designed by people who've never met a kid.
Find Won’s extended survival guide in our latest playbook.
NYC Kids Find Actual Wildlife Instead of Going Feral Over TikTok: Twenty students gathered around a baby bird during lunch instead of forming their usual phone-zombie clusters. The city's cellphone ban is creating unexpected miracles, though some teens still think life without constant scrolling is "kind of bad, honestly" (shocking absolutely no one who remembers going on MySpace).
New Teachers Learn Boundaries Before They Become Educational Martyrs: A veteran educator shares her origin story of writing encyclopedia-length feedback on student journals at 9 p.m. on Friday nights while slowly losing her will to live. It turns out work-life balance doesn't magically appear like fairy godmothers. Sadly, you have to actually work on creating it.
Schools Write AI Policies That Don't Sound Like Panic Attacks: Districts are graduating from "AI will steal your soul" policies to actually helpful guidelines that treat artificial intelligence like a tool instead of the Terminator. Some schools even explain what "generative AI" means because apparently that's not as obvious as everyone pretended.
Former Grade Perfectionist Exposes Why Letter Grades Are Educational Snake Oil: A reformed straight-A student shares how chasing perfect marks taught her to game the system instead of actually learning anything useful. Her new school uses "learning credits" where five-year-olds can explain what they're still working on instead of just hunting for gold stars like cute and tiny academic mercenaries.
The School That Refuses to Give Up on “Throwaway Kids”
White Mountain Institute, part of Show Low Unified School District, is redefining what school can look like for students who don’t fit the traditional mold. Best of all, Subject is a part of it! Watch here.
Our pick of the week: Ocean’s Eleven
Why We’re Obsessed: Danny Ocean’s team pulls off the impossible, because everyone knows their job and nobody tries to be the star of someone else's scene. It's basically the only group project in history where everyone actually did their part. Plus, the ridiculously good-looking George Clooney makes leadership look as smooth as his Nespresso commercials.
Recommended lesson integration:
Group project bootcamp (Grades 7-8): Students create their own "mission impossible" to solve a classroom challenge, complete with role assignments and backup plans.
Character study through trash talk (Grades 7-8): Analyze how each crew member's personality shows up in their dialogue and questionable life choices.
Math meets mayhem (Grades 8-12): Calculate casino heist success rates while learning that math is everywhere, even in criminal enterprises.
Vegas history without the hangover (Grades 7-12): Explore how Las Vegas transformed from desert wasteland to neon wonderland.
Film comparison chaos (Grades 9-12): Watch the 1960 original and Clooney's version back-to-back, then debate which one aged better.
Leadership lessons from professional criminals (Grades 11-12): Study different management styles and what makes teams actually function instead of falling apart.
Creative crime writing (Grades 10-12): Students plan their own "heist" where they steal something beneficial, like bringing books to book deserts or sneaking vegetables into school lunches.
Thank you for joining us for another edition of On The Subject. We’ll see you again in a week, with more stories from the hallways.
The Subject Team
Want to learn more about our curriculum offerings? Contact us today.
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