You know the feeling. You’re in a meeting room, or on a call, and there’s a slide deck. The vendor is friendly and clearly knows the product cold. Somewhere around slide six the acronyms start. LMS. SSO. SIS integration. Adaptive something. A word like “ecosystem” gets used the way most people use “the.” And you nod, because everyone else is nodding, and you’re the one who has to carry this back to a board and defend it, and quietly, underneath the nodding, a small voice is asking: do I actually understand the thing I just agreed sounded good?
I spend a lot of my working life teaching people who don’t think of themselves as technical how to work with technology, and I’ve watched a lot of capable people sit in that exact chair. Principals, deans, communications leads, the operations person who somehow ended up owning the software decision because nobody else would. Smart people. Responsible people. People who run a building full of staff and students without breaking a sweat. And then a forty-minute pitch turns them into someone who feels behind, like there was a class on this they missed and everybody else took.
Here’s what I want you to know before we go any further: the mystery is mostly manufactured.
Not always on purpose. A lot of it is just how technical people talk when they’ve forgotten how they sound. But the effect is the same either way. The jargon makes you feel like you can’t judge the thing, so you defer to whoever sounds most confident in the room, and that is exactly backwards, because the confident-sounding pitch and the good decision are two completely different animals.
The good news is you already know how to do this. You do it every time you take your car to a shop you’re not sure you trust yet.
Think about how that goes. A good mechanic tells you what’s wrong in words you understand, shows you the worn-out part, and tells you plainly what happens if you leave it: “You can drive on this another month, but past that you’re risking the transmission.” Someone who’s padding the bill does the opposite. He buries you in part numbers and urgency and a tone that says you couldn’t possibly follow the details. Anyone can tell those two people apart. You only have to notice which one is willing to explain.
A technology vendor is the same. So here are the questions I’d want you asking, and not one of them needs you to know a single acronym.
Make them say it plainly
Ask them to explain it in words your board would understand. Not the demo. The thing itself. “Explain to me what this does the way you’d explain it to a room of parents.” Then watch what happens. Someone who genuinely understands the product can always go simpler. They can meet you where you are, because they know the real shape of the thing. Someone who’s hiding behind the words can’t go simpler, because the words are the hiding place. When the plain-language version finally arrives and it’s still fuzzy, that isn’t you being slow. That’s information.
I’ll admit something here, because I’d rather you learned it off my tab than your own. For years I was the guy filling the room with acronyms. I thought it made me sound like I knew what I was doing. Mostly it meant I hadn’t yet done the harder work of learning to say the thing simply. The people I trust most now are the ones who can explain a genuinely complicated system to my mother in about two sentences. That’s the actual skill. The jargon is just what you reach for before you have it.
Separate the teaching problem from the software problem
The vendor is selling you software. You are responsible for learning. Those are not the same problem, and a good pitch will quietly blur them together, because “our platform improves outcomes” sounds a great deal better than “our platform is a tidy place to put things.”
So pull them apart on purpose. Ask: what does a teacher actually do differently on Tuesday morning because we bought this? What does a student learn, or learn faster, that they weren’t learning before? If the honest answer comes back as “well, it’s all in one place now,” that can genuinely be worth it. A school drowning in several scattered tools might want exactly that. Just name it for what it is. You’d be paying for tidiness, and tidiness and better teaching carry wildly different price tags. Both are fine things to buy. It helps enormously to know which one is actually on the invoice.
Ask what happens the morning it breaks
Every tool breaks. Yours will too, and it will almost certainly pick the worst possible morning to do it: mid-exam, the first day of term, the evening report cards are meant to go out. Everything is reliable in the demo, so the demo tells you nothing. What you want to know is this. When it goes down at 8am on a Tuesday, who picks up the phone, how fast, and do they talk to you like a customer or like a ticket number?
Ask who fixes it. Ask what that costs. Ask whether “support” means a real person in your timezone or a form you fill out and hear back from in three business days. Then get the answer in writing, in the contract, not just in the room. A promise made across a conference table is worth exactly what it says on paper, and the vendor knows that even when you’re too polite to say so. This is the part vendors are least eager to sit in, and it’s the part that will define your actual daily life with the thing for the next five years. A tool you love on the good days and can’t reach anyone about on the bad ones is a tool you’ll come to resent.
The one question underneath all of it
There’s a single question hiding under everything else, and the acronyms are very good at keeping it out of sight. It is never really “is this good technology.” Good technology that doesn’t help a teacher teach or a student learn is an expensive screensaver. The only question that earns your signature is whether a real person in your building is better off on Wednesday than they were on Monday. Everything else is detail, and you are allowed to keep asking, gently and repeatedly, until the detail connects back to that person.
And you are not behind. I want to say that as plainly as I can, because the whole setup is designed to make you feel that you are. Doing this well asks something quieter and far more valuable of you: stay the responsible adult in the room, asking the plain question while everybody else nods along. That person, it turns out, is the most useful one at the table.
So the next time there’s a deck and the acronyms start, try two questions. First, “Explain that to me the way you’d explain it to a room of parents.” Second, “Walk me through the morning this breaks.” Ask those two, notice how willingly the answers come, and you’ll learn more than the other thirty-nine slides were built to tell you. That instinct you’ve been second-guessing in those rooms? Trust it. It was reading the situation correctly the whole time. If it helps to see what this looks like when the software is already chosen and the job is making a team fluent in it fast, I wrote about training a newsroom on WordPress in two days, and the same rule ran the room: name the human outcome first, let the tool follow.
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