WEBVTT

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I want you to picture a scene. It's a Tuesday

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morning, maybe 10 a .m. We're in a conference

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room at a big school district's central office.

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Oh, I know that room. You know that room. It

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smells like stale coffee and floor wax. And around

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this huge table, you've got the power players,

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the superintendent, assistant superintendent

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for instruction, maybe HR. Well, comfortable.

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Mm -hmm. They're leaning back. They know each

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other. Exactly. They're laughing at some inside

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joke about state testing. And the vibe is just...

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it's coherent. They speak a shared language,

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finish each other's sentences about, you know...

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pedagogy and stakeholder engagement. It's club.

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It's a club. But then I want you to shift your

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focus to the far end of that table. There's one

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person sitting there. Yeah. And they're not laughing.

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They're looking at a laptop, maybe typing furiously,

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maybe just staring. Physically in the room, but

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mentally somewhere else entirely. He might as

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well be on Mars. That is the perfect image to

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start with. Because today we're talking about

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that person. the tech leader, and why, according

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to the research, they are the loneliest person

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in that room. Welcome back to the Deep Dive.

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We're doing something a little different today.

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Usually when we talk ed tech, we're talking about

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the gadgets, right? The VR headsets, the AI tutors,

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the Wi -Fi. The shiny objects. The shiny objects.

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But today, we are ignoring the hardware. We're

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looking at the human architecture that decides

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how all that hardware gets used. And that is

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such a critical pivot. We so often blame the

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technology when things go wrong in a school.

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Oh, totally. The app is glitchy. The network

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is slow. But the source we're looking at today

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argues the glitch isn't in the software. The

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glitch is in the org chart. We are digging into

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a really fascinating piece called School Leaders

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in Technology. It was written by Gary Ackerman

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for Hack Science Education, and it just came

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out February 2026. So this is, you know, fresh

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thinking. And Ackerman really puts his finger

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on a structural tension. He argues there's this

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fundamental disconnect between the people who

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hold the power in schools, the traditional leadership,

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and the people who hold the digital keys. And

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it all starts with what he calls the pathway

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to power. I love that phrase. It sounds like

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a documentary about medieval kings, the pathway

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to power. It does, doesn't it? But in this case,

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it's really just about the resume. How does someone

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get to sit in the superintendent's chair? Ackerman

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breaks down the typical career arc. Walk us through

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that. It's remarkably consistent. If you look

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at the resume of almost any high level school

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administrator, where does it start? The classroom.

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Exactly. They start as teachers. They spend years

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with students, grading papers, dealing with the

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day -to -day of instruction. Then they decide

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they want to lead. So what's the next step? They

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go back to school. Get that admin credential.

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Right. They go to grad school. And let's look

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at what they study there. They study school law.

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They study finance and budgeting, personnel management.

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All the nuts and bolts of running a physical

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school. Precisely. Then they become an assistant

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principal. They spend a few years breaking up

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fights in the cafeteria, dealing with bus schedules.

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Then they become a principal and eventually they

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move to the central office. So by the time they're

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making these big decisions, they have 20, maybe

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30 years of experience, they are absolute experts

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in the rhythm of the school system. They are.

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But, and this is the massive but that Ackerman

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highlights, at no point in that whole 20 -year

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journey was technology stratagem. core requirement.

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Wasn't a gatekeeper. Not at all. You can become

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the CEO of a multi -million dollar school district

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without ever really understanding how a server

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works or what an API is or how data privacy architecture

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is built. That is wild when you really think

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about it. In 2026, a school district is basically

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a massive data corporation that also happens

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to teach kids. How can you run the place if you

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don't understand the infrastructure? And Ackerman

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makes a really subtle distinction here. He notes

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that these leaders do use technology. They're

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on email. They use the student information system.

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They're glued to their phones. Of course. They're

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consumers. Exactly. But there is a massive difference

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between consuming technology and managing it.

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It's a difference between driving a car and being

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a Or, to take it a step further, it's the difference

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between driving a car and being the city planner

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who designs the whole traffic grid. Ackerman

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points out that while these leaders are prepared

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for almost everything else, legal, financial,

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pedagogical, they just have not built a career

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around studying or deploying technology. And

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what I found so interesting in the article is

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that this isn't some secret. They're not trying

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to hide this. No, not at all. Ackerman notes

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that most school leaders will freely admit it.

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How many times have you heard a principal or

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a superintendent say something like, oh, don't

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ask me, I'm not a tech person? A million times.

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It's usually said with a little chuckle, like,

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oh, I can barely program the microwave. Exactly.

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It's the socially acceptable admission of ignorance.

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But let's just swap the nouns for a second. Imagine

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if a superintendent stood up at a budget hearing

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and said, with a laugh, Oh, don't ask me about

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the numbers. I'm just not a finance person. I

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don't really get how money works. They would

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be escorted out of the building. Immediately.

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Or imagine them saying, you know, I'm not really

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a child safety person. You cannot say that. It's

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disqualifying. Of course not. But in education

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leadership, saying I'm not a tech person is seen

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as a perfectly valid standard limitation. It's

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almost a badge of honor, like it proves you're

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focused on the human side of things. But the

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irony is that the human side. now runs on digital

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rails. You can't protect student safety if you

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don't understand cybersecurity. You can't manage

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the budget if you don't understand software licensing

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costs. That is the crux of the issue. We've put

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people in charge who self -identify as novices

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in a critical infrastructure layer. But Ackerman

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goes deeper. He says the problem isn't just the

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individual leader, it's who they hang out with.

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The group. The advisory circle. The cabinet.

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Whatever you want to call it. Okay, so, let's

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play devil's advocate for a second. If I'm a

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CEO and I know I'm weak in tech, shouldn't I

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just surround myself with people who are good

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at it? I mean, that's management 101. You would

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think so, but Ackerman highlights a phenomenon

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called homophily. It's a fancy term that basically

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just means birds of a feather flock together.

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Okay, so how does that play out in the superintendent's

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cabinet? Well, look at who gets hired for those

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top roles. Yeah. The assistant superintendent

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for instruction. Former teacher, former principal.

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The director of student services. Former teacher,

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former principal. The director of HR. Often a

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former principal, you see the pattern. It's the

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same resume, just with different names at the

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top. Essentially. Ackerman points out, this group

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is made up of professionals on a path just like

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the one the CEO took. They have, and I'm quoting

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here, similar preparation and similar experiences.

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They share a professional DNA. They do. And Ackerman

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is fair about this. He notes, that has huge gilfits.

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Right, the shorthand. They can move quickly.

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Exactly. They don't have to explain to each other

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what a formative assessment is or why bus duty

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is a nightmare. They share a mental model of

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how a school should work. They get the same jokes.

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But the downside is pretty big. They all share

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the same blind spot. Correct. It leads to what

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he calls groupthink. Because they have such similar

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experiences, they tend to validate each other's

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perspectives. If the superintendent says, I'm

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not a tech person, so let's just buy what the

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district next door bought, Everyone else nods.

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That makes sense. We aren't tech people either.

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It becomes this echo chamber of technical avoidance.

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It creates a consensus reality where technology

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is just a commodity like buying paper towels

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rather than a strategic lever. And because they

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all agree, they feel confident in the decision,

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even if that decision is, you know, technically

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a disaster waiting to happen. Which brings us

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right back to our lonely figure at the end of

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the table, the one person who is not a former

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principal. The tech director. The single voice.

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Ackerman really emphasizes this. In most of those

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leadership cabinets, you're likely to have only

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one technology professional. Just one. Against

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a whole phalanx of former principals. Think about

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that contrast. The curriculum director has a

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team. They have instructional coaches, principals,

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department heads. They all speak curriculum.

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They have peers to bounce ideas off of. And the

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tech leader is a singular entity at that level.

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A singular entity. And Ackerman says they work

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in isolation. Yes. And he doesn't just mean they

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sit in a different office, right? No, he means

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intellectual isolation. This is the part of the

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article that really hit me. Ackerman writes that

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the tech leader has limited access to others

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on the leadership team to brainstorm or otherwise

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problem solve. Let's unpack that word brainstorm

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because I think people hear it and they think

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of like sticky notes on a whiteboard. It's much

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deeper than that. It's about the cognitive process

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of solving a complex problem. To brainstorm effectively,

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you need a partner who actually understands the

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nuances of what you're talking about. Give me

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an example. Okay, so imagine you're a principal

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and you have a crisis with a parent group. You

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walk into another principal's office and say,

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the PTA is revolting. The other person immediately

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gets the context, the politics, the stakes. They

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get it. You can riff. You can bounce ideas back

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and forth. What if we tried this? No, that would

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backfire because of X. You're building a solution

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together. Because you speak the same language.

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Precisely. Now... Imagine you're the tech director.

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You realize that the new AI platform the board

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wants to buy is going to require opening up firewall

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ports that create a massive security vulnerability.

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OK, that sounds bad. It is bad. So you go to

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the assistant superintendent to brainstorm. You

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explain the port issue. You explain the firewall

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architecture. And they just look at you like

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you're speaking Klingon. They literally cannot

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process the information. They can't offer a suggestion

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like, well, what if we routed it through a proxy?

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because they don't know what a proxy is. The

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conversation just dies. They just ask, well,

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can we use the app or not? So the tech director

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isn't having a strategic dialogue. They're just

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reporting a status. It's a yes or no. That is

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the brainstorming deficit. When the tech leader

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works in isolation, they're forced to simplify

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these incredibly complex problems into binary

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choices. They can't walk the team through the

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why or the how. They can only deliver the what.

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And that feels like a really dangerous place

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for an organization to be. It's incredibly dangerous.

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It means the organization is making major decisions

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without ever understanding the trade -offs. It

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silences all the nuance. It also seems like it

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would force the tech director into a corner.

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If you can't explain the nuance and you know

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there's a risk, you basically just have to say

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no all the time. And you become the department

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of no. This is such a common complaint in schools.

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Oh, IT blocks everything. It won't let us have

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any fun. We've all heard that. But Ackerman's

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analysis suggests this isn't because IT people

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are grumpy. It's because they are the only ones

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carrying the full weight of the risk. That is

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a great point. If a reading program fails, Who

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takes the blame? The whole team. They all reviewed

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it. They all agreed on the pedagogy. It's a collective

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failure. But if the network gets hacked... It's

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the tech director's fault. One hundred percent.

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Exclusively. So you've got a situation where

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the tech director has the highest personal risk

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and the lowest amount of collaborative support.

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Of course they're going to be conservative. Of

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course they're going to block things. They're

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defending the castle all by themselves. Meanwhile,

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the group is getting frustrated because they

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don't understand why they can't just buy the

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cool new thing they saw at a conference. And

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because of that group think dynamic we talked

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about, the group usually wins. Ackerman suggests

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the collective desire of the administration just

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overpowers the solitary concern of the tech professional.

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So the group says we're doing it anyway, and

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the tech person is left to frantically try and

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patch it all together in the background. Exactly.

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The tech professional becomes a contractor in

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their own house. They aren't helping to shape

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the strategy. They're just being told to execute

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a strategy that was decided by people who don't

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understand the tools. This explains so much.

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I mean, if you're a listener and you've ever

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wondered... why school technology feels so clunky

00:11:59.100 --> 00:12:01.980
or disjointed or like it was bought by someone

00:12:01.980 --> 00:12:04.159
who has never used a computer. It's because it

00:12:04.159 --> 00:12:06.659
probably was. Or at least the decision was driven

00:12:06.659 --> 00:12:09.840
by a group who prioritized educational theory

00:12:09.840 --> 00:12:12.879
over technical reality. And the one person who

00:12:12.879 --> 00:12:15.080
could have bridged that gap was structurally

00:12:15.080 --> 00:12:18.129
sidelined. And it's important to say again, Ackerman

00:12:18.129 --> 00:12:21.529
isn't saying these are bad people. The superintendent

00:12:21.529 --> 00:12:23.990
isn't trying to cause problems. No, absolutely

00:12:23.990 --> 00:12:26.730
not. These are dedicated, intelligent professionals.

00:12:27.409 --> 00:12:30.690
Ackerman is critiquing the system, not the individuals.

00:12:31.529 --> 00:12:34.690
It's a structural flaw in how we set up our educational

00:12:34.690 --> 00:12:37.889
hierarchies. We have a preparation gap where

00:12:37.889 --> 00:12:40.669
we don't train leaders in tech colliding with

00:12:40.669 --> 00:12:43.429
an isolation factor, where we don't give tech

00:12:43.429 --> 00:12:46.559
leaders any peers. It's like building a hospital

00:12:46.559 --> 00:12:48.840
where all the administrators are brilliant surgeons,

00:12:49.120 --> 00:12:51.480
which makes sense. But the person running the

00:12:51.480 --> 00:12:53.899
electricity and the life support systems is kept

00:12:53.899 --> 00:12:56.019
in the basement and only allowed to speak for

00:12:56.019 --> 00:12:57.840
two minutes at the end of the meeting. That is

00:12:57.840 --> 00:13:00.259
a perfect analogy. And when the power goes out

00:13:00.259 --> 00:13:03.240
during surgery, everyone yells at the electrician,

00:13:03.279 --> 00:13:05.799
even though the surgeons all voted to cut the

00:13:05.799 --> 00:13:08.000
generator budget because they wanted nicer scalpels.

00:13:08.059 --> 00:13:09.740
And the electrician is just standing there saying,

00:13:10.100 --> 00:13:12.980
I tried to tell you. I sent you a memo. But because

00:13:12.980 --> 00:13:15.879
the memo was technical, nobody read it. So, okay,

00:13:15.879 --> 00:13:18.419
we've diagnosed the patient. The school system

00:13:18.419 --> 00:13:21.000
is suffering from this disconnect between authority

00:13:21.000 --> 00:13:24.580
and technical competency. What's the takeaway

00:13:24.580 --> 00:13:26.559
here? If I'm listening, why does this matter

00:13:26.559 --> 00:13:28.960
to me beyond just, you know, schools are messy?

00:13:29.200 --> 00:13:31.080
I think the big takeaway from Ackerman's work

00:13:31.080 --> 00:13:33.740
is that we need to stop looking at technology

00:13:33.740 --> 00:13:36.879
as a product that schools buy and start looking

00:13:36.879 --> 00:13:39.460
at it as a competency that schools need to embody.

00:13:39.679 --> 00:13:42.039
What does that mean in practice? It means we

00:13:42.039 --> 00:13:44.259
probably need to rethink that path to power.

00:13:44.409 --> 00:13:47.370
Maybe we need to start requiring technology strategy

00:13:47.370 --> 00:13:50.269
as part of the admin credential. Maybe a principal

00:13:50.269 --> 00:13:52.009
shouldn't be able to get certified unless they

00:13:52.009 --> 00:13:54.230
can demonstrate they understand data privacy.

00:13:54.649 --> 00:13:57.370
So close the preparation gap. Right. And stop

00:13:57.370 --> 00:13:59.710
accepting I'm not a tech person as a valid excuse.

00:14:00.230 --> 00:14:02.029
In 2026, if you're not a tech person, you're

00:14:02.029 --> 00:14:05.090
not a leader. You're a liability. Ooh, that is

00:14:05.090 --> 00:14:08.009
harsh. You're a liability. It is harsh, but look

00:14:08.009 --> 00:14:11.179
at the world. Look at AI. Look at the data breaches

00:14:11.179 --> 00:14:13.860
happening every week. If the person at the top

00:14:13.860 --> 00:14:16.500
doesn't get it, the entire organization is vulnerable.

00:14:16.679 --> 00:14:19.039
And what about the loneliness of the tech leader?

00:14:19.360 --> 00:14:21.700
How do we fix that part? We have to break the

00:14:21.700 --> 00:14:24.639
silo. Ackerman implies that the isolation is

00:14:24.639 --> 00:14:26.620
the root cause of that brainstorming deficit.

00:14:27.059 --> 00:14:29.320
So maybe the cabinet needs more than one tech

00:14:29.320 --> 00:14:32.179
voice. Safety in numbers. Or at least diversity

00:14:32.179 --> 00:14:35.080
of thought. Maybe you need a chief technology

00:14:35.080 --> 00:14:39.110
officer and a chief data officer. Or maybe the

00:14:39.110 --> 00:14:41.190
assistant superintendents need to be cross -trained

00:14:41.190 --> 00:14:43.210
enough that they can actually be thought partners

00:14:43.210 --> 00:14:46.149
on this stuff. They need to learn to speak just

00:14:46.149 --> 00:14:48.049
a little bit of Klingon. Just enough to have

00:14:48.049 --> 00:14:50.990
a conversation. Just enough to say, OK, I understand

00:14:50.990 --> 00:14:53.850
why that firewall port is a problem. Let's brainstorm

00:14:53.850 --> 00:14:56.009
a different way to get this data. That feels

00:14:56.009 --> 00:14:58.360
like the dream, right? a roundtable where everyone

00:14:58.360 --> 00:15:00.179
actually speaks the same language or at least

00:15:00.179 --> 00:15:03.120
enough of it to function as a real team. That's

00:15:03.120 --> 00:15:05.259
the goal. But until we address these structural

00:15:05.259 --> 00:15:08.240
issues, the resume gap and the silo effect, we're

00:15:08.240 --> 00:15:10.399
just going to keep seeing this friction. It really

00:15:10.399 --> 00:15:12.440
changes how you look at a school board meeting,

00:15:12.600 --> 00:15:15.080
doesn't it? You see that row of people up there

00:15:15.080 --> 00:15:18.059
and you realize there's this invisible wall between

00:15:18.059 --> 00:15:21.399
the one person with a laptop and everyone else.

00:15:21.639 --> 00:15:24.220
It's a reminder that organizations are just people.

00:15:24.600 --> 00:15:26.840
And if those people are sorted into buckets where

00:15:26.840 --> 00:15:28.860
they can't effectively talk to each other, the

00:15:28.860 --> 00:15:31.720
whole organization is going to stutter. So let's

00:15:31.720 --> 00:15:34.440
wrap this up. We've unpacked Gary Ackerman's

00:15:34.440 --> 00:15:37.159
piece, School Leaders in Technology. We've seen

00:15:37.159 --> 00:15:39.960
the preparation gap. We've seen the isolation

00:15:39.960 --> 00:15:43.960
factor and the danger of groupthink. And we've

00:15:43.960 --> 00:15:47.240
seen why the tech person always says no. Justice

00:15:47.240 --> 00:15:49.440
for the tech person. But seriously, I want to

00:15:49.440 --> 00:15:51.080
leave our listener with a final thought to chew

00:15:51.080 --> 00:15:53.070
on. We've been talking about the present, but

00:15:53.070 --> 00:15:55.570
let's look, say, five years down the road. Okay.

00:15:55.789 --> 00:15:58.250
Technology is not getting any simpler. It's getting

00:15:58.250 --> 00:16:00.429
exponentially more complex. We're talking about

00:16:00.429 --> 00:16:04.570
immersive VR, biometric data tracking, AI that

00:16:04.570 --> 00:16:06.909
runs the curriculum. The stakes are getting higher

00:16:06.909 --> 00:16:10.809
every single day. So if we don't fix this structural

00:16:10.809 --> 00:16:14.230
disconnect now, if we continue to have decision

00:16:14.230 --> 00:16:17.230
makers who openly admit they don't understand

00:16:17.230 --> 00:16:20.370
the tools they're buying, here's the question.

00:16:21.579 --> 00:16:25.240
Are our schools structurally designed to lose

00:16:25.240 --> 00:16:27.980
control of their own future? That is the haunting

00:16:27.980 --> 00:16:30.240
question because if the leadership can't understand

00:16:30.240 --> 00:16:32.379
the machine, eventually the machine just runs

00:16:32.379 --> 00:16:35.340
itself. And on that slightly terrifying note.

00:16:35.659 --> 00:16:37.759
Sorry to bring the doom. No, it's good. It's

00:16:37.759 --> 00:16:40.179
what we do here. We dive deep. We certainly do.

00:16:40.379 --> 00:16:42.259
Thank you for helping us unpack the human architecture

00:16:42.259 --> 00:16:44.200
of our school. Always a pleasure. And thank you

00:16:44.200 --> 00:16:46.019
for listening. We'll see you on the next Deep

00:16:46.019 --> 00:16:46.240
Dive.
