WEBVTT

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You know that feeling when your phone updates,

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like overnight? You wake up, you go to turn off

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the alarm, and the button isn't where your thumb

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thinks it is? Oh, yeah. It's moved like three

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millimeters. And for the next week, every time

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you try to turn on the flashlight, you're, I

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don't know, opening the calculator? The phantom

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tap. Yeah. It's a very real, very frustrating

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thing. It's maddening. And look, that's just

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a phone. That's just me before I've had coffee.

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Now, imagine that same feeling, but you apply

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it to an entire organization. a whole school

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district, a whole hospital. Right. Suddenly the

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upgrade that was supposed to make everything

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more efficient is actually costing thousands

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of hours because no one can find anything. Exactly.

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The digital furniture has been rearranged. And

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that's what we are getting into today. We've

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got this really fascinating kind of contrarian

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piece from Gary Ackerman at Hack Science Education.

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It's a blog post titled Contingencies and Technology

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Planning. Yeah. Published just this month, February

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2nd, 2026. And, you know, don't let that title

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scare you off. Right. Contingencies. It sounds

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so dry. Like something you talk about with your

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insurance agent. It does. But he isn't talking

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about Plan B here. He's using it in the... the

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engineering sense, the idea that everything that

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exists now depends on this messy, complicated

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web of things that happened before. It's like

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the butterfly effect, but for an IT department.

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That's a perfect way to put it. You can't just

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change one thing without shaking the whole web.

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And if you're a manager, a CEO, or even just

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someone wondering why your office software is

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so clunky, This is for you. OK, let's start with

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a word he uses that I think is just perfect.

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I hadn't heard it in this context before. The

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Cluj. Ah, yes. The Cluj, K -L -U -G -E. That

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sounds like a German pastry or something. Yeah,

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or maybe a heavy boot. But no, it's in the computer

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science world, a Cluj is a solution that's clumsy.

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It's inelegant, inefficient. But, and this is

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the most important part, it works. It's the duct

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tape and chewing gum solution. Exactly. It's

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the workaround that became permanent. But here's

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where Ackerman really drops the bomb. He argues

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that in most schools, the entire IT infrastructure

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is basically one giant kluge. That sounds harsh.

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I mean, surely these things were designed by

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professionals, right? We spend millions on this

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stuff. They were, yes. But they weren't designed

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all at once. That's the key. Ackerman says school

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IT systems aren't built from a single blueprint.

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they evolve, more like a coral reef. Okay, I

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like that image. Well, think about it. You had

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a server put in, say, 2018. Then in 2021, you

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bought a bunch of iPads. Then in 2024, the state

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mandates some new security protocol. So you're

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constantly just bolting new shiny parts onto

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old rusty ones. Exactly. And to make them talk

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to each other, to make the new 2025 software

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work with the old 2018 server, you have to write

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custom scripts. You create these weird configurations.

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You create a Cluj. Which explains why the IT

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department always looks terrified when you ask

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to change something. I just thought they were

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being difficult. No, it's because if you pull

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the wrong thread, the whole sweater could unravel.

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It's a house of cards. And that gets us to the

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first big idea of this article. just dismantles.

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The myth of the clean slate. Oh this is a huge

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one. We've all had this fantasy right? You look

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at your slow computer or the Wi -Fi that cuts

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out and you just think let's burn it all down

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throw it out and buy the new version. The whole

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seal replacement dream. Let's just start over.

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So why is that a myth? Is it just about the money?

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Because hardware is getting cheaper isn't it?

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The hardware is sure but the system is more expensive.

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Ackerman talks about the iceberg of costs. He

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says the sticker price of a new computer is like

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a tiny fraction of the real cost. So what's the

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rest of the iceberg? It's engineering the network.

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Okay, break that down for me. If I replace a

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server, what's the big engineering cost? Don't

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I just plug it in? I wish. Remember the contingencies.

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That old server you want to get rid of. It might

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be running some custom script that lets the library

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database work, or it might be the only machine

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that knows how to talk to the ancient printers

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in the science wing. So it's not just a box.

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It's a box with a decade of handshakes and secret

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agreements with all the other boxes. That's it,

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exactly. And to replace the hardware, you have

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to re -engineer every single one of those handshakes.

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You might have to hire outside consultants because

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the internal team doesn't even know how the old

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Kludge was built. Because Dave, the guy who built

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it 10 years ago, retired and didn't leave a manual.

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Dave is a legend. But Dave kept it all in his

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head. So you end up paying for forensic engineering

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just to get back to where you started. That's

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the legacy trap. You're a prisoner of past decisions.

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And that brings us to the real core of the article,

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I think. Because Ackerman says, even if you had

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unlimited money for the hardware and you paid

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all the engineers, you still haven't paid the

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biggest bill. The greatest hidden cost. Right.

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He pivots from the wires to the people. He says,

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and I'm... Quoting here, perhaps the greatest

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hidden cost of upgrading is the habits of users.

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It's such a profound point. We tend to treat

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users, employees, teachers like they're just

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software, like they can just download new instructions

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to their brains. Just read the memo, you'll be

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fine. Exactly. But people don't work that way.

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And he uses this perfect example. The learning

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management system, the LMS. So that's your digital

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classroom. The Blackboard, Canvas, Google Classroom,

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things like that. It's where the homework lives.

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It's the teacher's office. Now imagine an instructor.

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They have spent years building their online classroom

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in the current system. It's a ton of work. I

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have friends who teach. They spend summers on

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this. They're not just uploading PDFs. They're

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designing a whole workflow. That's it. It becomes

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muscle memory, cognitive automation. They're

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not thinking about the software anymore. They're

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thinking about teaching. The tool becomes invisible.

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Precisely. Now the administration comes along

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and says, great news, we're switching to LMS

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2 .0. It's got a fresh new logo. And you just

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hear this collective groan from the entire factory.

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They panic. And for good reason. Ackerman calls

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out the export import lie. The IT team always

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promises you can just export your old class and

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import it into the new one. It's seamless. It's

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the cloud. And it is never seamless. He points

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out that the formatting always breaks, the links

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are broken, the images don't load right, the

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quiz answers get scrambled. So the teacher is

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basically digging their course out of the rubble

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of a digital earthquake. Perfect analogy. And

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while they're spending hours fixing links and

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reuploading photos, what are they not doing?

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They're not teaching. Not giving feedback. Not

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improving their lessons. That is the hidden cost.

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productivity just plummets and you have these

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highly skilled professionals spending their days

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trying to figure out where the submit button

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went instead of doing their actual jobs. You

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know, we usually see resistance to change as

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some kind of character flaw, like, oh, they're

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just being stubborn. But he's saying it's not

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laziness. It's a rational economic calculation.

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Yes. They've optimized their life for the clues

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they have. When you break the clues, you break

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their workflow. The frustration isn't about being

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anti -tech. It's about being anti -inefficiency.

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OK, so if the costs are this high financially

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and in terms of morale, Why do we keep doing

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it? Why are organizations constantly churning

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through these massive system overhauls? And this

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is where you get into the psychology of it all.

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Ackerman identifies what he calls or what we

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can call the new sheriff in town syndrome. OK,

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set the scene. A school district hires a new

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technology director or a company hires a new

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CIO. This person comes from a different organization,

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one that ran on, say, Microsoft, and now they're

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in a Google based place. And as we've established.

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Every Cluj is unique. Exactly. So the new leader

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walks in. They look at this messy, complicated

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system. The one that actually works, by the way.

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And they feel uncomfortable. They feel lost?

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Right. They don't know the shortcuts. They don't

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know why the main server is named Gandalf and

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why it can never be turned off. They feel like

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they're driving a car with a steering wheel on

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the wrong side. So they have choice. Option A,

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learn the messy history of the new place. Or

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option B, make the new place look just like their

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old place. And human nature almost always prefers

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option B. Ackerman says they will quote, prefer

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the systems they have recent experience using.

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But here's the line that really hit me. He writes,

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the familiarity that comes from recent experience

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cannot be confused with better performance. That's

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the whole argument in a nutshell. Just because

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the new leader is personally faster with system

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X doesn't mean system X is objectively better.

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for the thousand other people who have to use

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it. It's a massive conflict of interest, isn't

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it? The leader is basically prioritizing their

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own comfort over the productivity of the entire

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organization. It might be unintentional, but

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yes, they frame it as modernization. They use

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buzzwords. But really, it's often just them seeking

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their own comfort zone. They're shifting the

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burden of learning from themselves, one person

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to the entire staff. Wow, when you put it like

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that. I don't want to learn your system. So all

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thousand of you have to learn mine. It's a huge

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source of friction and cynicism because the teachers,

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the staff, they know the new system isn't really

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better. It's just different. It's just the new

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box's favorite toy. And that cynicism just destroys

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trust. Exactly. You burn all your political capital

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on a software swap. So let's talk about the solution

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because Ackerman doesn't just complain. He has

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a very specific warning for the people at the

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top. the CEOs, the superintendents. He does,

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a very stern one. He says you need to be very

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cautious of any new hire who comes in with a

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demolition plan on day one. The I'm going to

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fix everything immediately candidate. Right.

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If someone says in an interview, I see you're

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using system A, that's garbage. We're migrating

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to system B in the first quarter. That should

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be a massive red flag. Isn't that what we hire

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leaders for? Vision. Decisiveness. Not with IT

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planning. Not when there's a clues involved.

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Yeah. Because that candidate doesn't know the

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contingencies. They don't know why the system

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is the way it is. It's that idea of Chesterton's

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fence. Oh, that's a perfect fit. Remind us what

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that is. It's a principle. If you find a fence

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in the middle of a road and you don't see why

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it's there, you can't just tear it down. You're

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not allowed to tear it down until you first understand

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why it was put up in the first place. Right.

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Maybe it's keeping a bull out of the road. Maybe

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it marks a property line you can't see. And Ackerman

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is applying that to IT. That clunky old server

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might be the fence keeping the payroll system

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from crashing. So the advice for the CEO is don't

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let them swing the hammer until they've read

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the blueprints of the old house. Ackerman literally

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says a new leader should not be authorized to

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make big changes until they fully get the existing

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systems. That requires so much patience, though.

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We tend to reward action, right? We reward the

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person who shakes things up. We do, but in this

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case, shaking things up is just breaking things.

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True leadership, he's implying, is the humility

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to learn the system before you try to change

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it. It's asking why before you ask what's next.

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It's about respecting the history of the place,

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respecting the clues, and respecting the people

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who have built their entire professional lives

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around it. Exactly. And understanding that the

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total cost isn't just a number on a spreadsheet.

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It's the stress level of your staff. It's the

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hours of lost productivity. It's the phantom

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tap times 1 ,000. This is really compelling.

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It makes me look at every update now button with

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deep suspicion. As you should. So let's zoom

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out. We've been talking about schools, but this

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supplies everywhere, doesn't it? Oh, absolutely.

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Think about a new manager taking over a sales

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team. The team tracks leads on this weird color

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-coded spreadsheet instead of a fancy CRM. Then

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the new manager hates it. They want dashboards.

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Right. But maybe that spreadsheet captures some

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nuance the CRM can't. Maybe the team's speed

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relies on that clues. If the manager forces the

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switch without understanding the why, sales could

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just tank. It's the same exact pattern. Familiarity

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versus actual performance. Yep. It happens everywhere.

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We try to impose this clean, logical order on

00:12:04.220 --> 00:12:06.600
a messy reality, and we just end up making a

00:12:06.600 --> 00:12:08.639
different kind of mess. A new mess that we then

00:12:08.639 --> 00:12:10.799
have to maintain. And the cycle starts all over

00:12:10.799 --> 00:12:12.860
again. So what's the big takeaway for someone

00:12:12.860 --> 00:12:14.679
listening, whether you're the employee suffering

00:12:14.679 --> 00:12:16.960
through an upgrade or the leader planning one?

00:12:17.080 --> 00:12:20.799
If you're the leader, my advice would be slow

00:12:20.799 --> 00:12:25.009
down. Hunt for the contingencies. Before you

00:12:25.009 --> 00:12:27.309
announce the big change, ask your team, if I

00:12:27.309 --> 00:12:29.570
change this, what breaks? And actually listen

00:12:29.570 --> 00:12:33.789
to the answer. And if you're the employee, the

00:12:33.789 --> 00:12:36.570
one staring at all the broken links. Validate

00:12:36.570 --> 00:12:38.610
your frustration. It's not just you being bad

00:12:38.610 --> 00:12:42.210
at tech. You are feeling the real cost of a system

00:12:42.210 --> 00:12:44.590
that wasn't designed around your habits. And

00:12:44.590 --> 00:12:47.590
if you can, try to articulate that hidden cost

00:12:47.590 --> 00:12:50.190
to your boss. How do you do that without just

00:12:50.190 --> 00:12:51.929
sounding like you're complaining? You speak their

00:12:51.929 --> 00:12:54.850
language. Don't say, I don't like it. Say, this

00:12:54.850 --> 00:12:57.029
change will cost me 10 hours of project time,

00:12:57.169 --> 00:12:59.710
or rebuilding this workflow will delay our client

00:12:59.710 --> 00:13:02.690
report by two weeks. You put a price tag on your

00:13:02.690 --> 00:13:05.230
habits, you make the hidden cost visible. Make

00:13:05.230 --> 00:13:07.289
the hidden cost visible. That's really powerful.

00:13:07.330 --> 00:13:09.370
It is. You know, I want to leave our listeners

00:13:09.370 --> 00:13:11.629
with one final thought. We live in a culture

00:13:11.629 --> 00:13:14.879
that worships disruption. We love the story of

00:13:14.879 --> 00:13:17.159
the innovator who comes in and just smashes the

00:13:17.159 --> 00:13:19.539
status quo. The modern genius archetype, right?

00:13:19.679 --> 00:13:22.259
Right. But based on what Gary Ackerman's laid

00:13:22.259 --> 00:13:25.580
out here, is that disruption always innovation?

00:13:26.559 --> 00:13:29.299
Or is it sometimes just ego? That's the really

00:13:29.299 --> 00:13:32.350
uncomfortable question. If a new leader proposes

00:13:32.350 --> 00:13:35.529
a massive overhaul on day one, are they truly

00:13:35.529 --> 00:13:37.909
serving the organization or are they just trying

00:13:37.909 --> 00:13:39.789
to make their new world look a little more like

00:13:39.789 --> 00:13:41.549
the one they just left? Are they building a better

00:13:41.549 --> 00:13:44.029
future or just a more comfortable mirror for

00:13:44.029 --> 00:13:46.350
themselves? A mirror that everyone else is forced

00:13:46.350 --> 00:13:50.350
to polish. That lands hard. On that note, good

00:13:50.350 --> 00:13:52.570
luck with your next system update. May your links

00:13:52.570 --> 00:13:55.210
stay unbroken. Thanks for exploring the Cluj

00:13:55.210 --> 00:13:57.629
with us. My pleasure. See you on the next deep

00:13:57.629 --> 00:13:57.850
dive.
