Chicago greeted us the way only Chicago can, wind off the river, deep dish in hand, and conversations that felt bigger than the conference itself.
We came to COSN 2026 to do what we always do: listen.
Not just to the keynote stages or the big booths, but to the people in the in-between moments, the CTOs navigating impossible budgets, the district leaders trying to make sense of AI, and the partners trying to prove they belong in education for the long haul.
What we found wasn’t just insight.
It was a pattern.
The Shift from Vendors to Partners
One of the most honest moments came in a conversation with a district CTO who framed it simply:
Technology will break. The question is, who’s still there when it does?
That distinction, vendor vs. partner, came up again and again.
Districts aren’t looking for tools anymore.
They’re looking for relationships.
They want:
People who understand their students and communities
Companies that stay when things go sideways
Partners who care about outcomes, not just contracts
And that aligns deeply with what we believe at Thinkering:
Learning is relational.
Implementation should be too.
This mirrors what we’ve seen across our own fellowship, mentorship, trust, and human connection are what actually drive outcomes, not just the tools themselves .
AI Isn’t the Question Anymore, Implementation Is
At COSN, AI wasn’t hypothetical.
It was everywhere.
District leaders weren’t asking if they should use AI.
They were asking:
How do we govern it?
How do we implement it responsibly?
How do we actually save time and money with it?
One conversation stood out:
Districts are actively exploring how AI can reduce operational costs, not just enhance instruction.
That’s a major shift.
But alongside that excitement was tension:
“Everybody and their dog has an AI product now.”
Budgets are tight
Cybersecurity risks are growing
This is where things get real.
Because AI without intentional design doesn’t create transformation, it creates noise.
Cybersecurity = Human Behavior (Layer 8)
One of the most memorable metaphors we heard:
“Layer 8 is the human layer.”
In a world obsessed with tools, this was a grounding reminder:
The biggest vulnerability in any system isn’t the software, it’s the people.
Cybersecurity conversations at COSN weren’t just technical.
They were behavioral.
Training
Awareness
Culture
This matters deeply for education.
Because if we don’t design systems that support human decision-making, we’re not solving the problem, we’re just adding layers on top of it.
Big Tech Energy, But District Reality
The floor had a different vibe this year.
More enterprise presence
More big logos
More polished solutions
But underneath that?
District leaders are still asking:
“Can we afford this?”
“Will this actually work in our classrooms?”
“Who helps us implement this?”
There’s a growing gap between:
What’s being built
And what schools can realistically sustain
That gap is where innovation either succeeds, or dies.
The Real Opportunity: Human-Centered Implementation
If there was one thread connecting everything we heard, it was this:
Technology isn’t the bottleneck. Implementation is.
And implementation is human.
At Thinkering, we’ve seen this firsthand:
Educators want to innovate
But lack time, support, and collaborative structures
81% of fellows are actively seeking better ways to design meaningful, student-centered learning experiences
The opportunity isn’t another tool.
It’s designing ecosystems that support:
Reflection
Mentorship
Iteration
Storytelling
That’s the missing layer.
What Comes Next
Walking away from COSN, a few things are clear:
AI will continue to accelerate
Cybersecurity will remain a constant pressure
Budgets will stay tight
But the districts that succeed won’t be the ones with the most tools.
They’ll be the ones with:
The strongest relationships
The clearest implementation strategies
The most human-centered systems
Final Thought: The Future Isn’t Built in Booths
It’s built in conversations.
On riverwalks
Between sessions
In honest moments where people admit:
“We’re still figuring this out.”
That’s where real learning happens.
And that’s where we’ll keep showing up.
We’ll be sharing more voices, more conversations, and more stories from COSN 2026 soon.
Until then, keep thinkering, and keep building what matters.
— Thinkering Collective
