Buying technology
How to tell when you’re being sold something you don’t need
Let me start out by saying most technology vendors aren’t trying to rip you off. The people selling hardware, software, and monthly contracts are mostly decent, and plenty of them are good at what they do. But they get paid when you buy something. That isn’t a character flaw, it’s just how the business works, and it quietly shapes every recommendation that comes out of it.
So your job isn’t to work out whether someone is honest. It’s to work out which conversation you’re in: someone solving your problem, or someone selling their product. From the outside those look identical if you don’t know what to listen for.
I don’t sell products. No hardware, no licenses, no reseller agreements, no commissions, and no affiliate deals with any AI company. My goal is to help you work through what you’re being recommended and make sure it was built for you, not just sold to you.
Here’s what I listen for.
1The recommendation showed up before the questions did
This is the big one, and it’s the easiest to catch.
If someone tells you what you need before they’ve asked how your business runs, they didn’t diagnose anything. They matched you to a product. Maybe it’s the right product. But nobody checked.
A real diagnosis is boring and time consuming. It sounds like someone asking who does what, where things get stuck, what happens when the person who knows everything is on vacation. It takes a while, it isn’t fun, and that’s exactly why it gets skipped. Doing it properly costs the vendor time they would rather spend closing.
What to ask: “Before we talk about what to buy, what did you learn about how we do business?”
2Nobody can say what the product fixes in one plain sentence
Ask what problem this solves. If the answer needs a diagram, a comparison chart, or three acronyms, that isn’t a complicated product. That’s an unclear one.
Anyone who genuinely understands what they’re selling can say what it does in a sentence a twelve year old would follow. When they can’t, it usually means one of two things. Either they don’t understand it either, or the honest sentence is “it doesn’t solve a problem you have.”
What to ask: “What problem does this fix?”
3The urgency belongs to them, not to you
Pricing expires Friday. The promotion ends this quarter. There are only so many onboarding slots left.
None of those are facts about your business. They’re facts about their sales calendar. A real problem in your business has its own timeline, and it’s almost never the last day of a quarter.
Genuine urgency does exist. Your server is failing. You’re out of compliance. Somebody is about to leave and take everything they know with them. That kind of urgency has a reason attached, and the reason is about you.
And don’t be afraid to ask them to stand behind their price. If you buy today and the same thing gets discounted at the end of the quarter, will they match it and give you the difference back? It costs you nothing to ask, and how they answer tells you plenty about how they’ll treat you after the sale.
What to ask: “What happens if I wait until next quarter? And if the price drops after I buy, will you match it?”
4Nobody will tell you what happens if you do nothing
This is my favorite question and almost nobody asks it.
Doing nothing is always an option, and it’s often the right one. A good advisor can tell you what doing nothing costs you: this many hours a week, this much risk, this thing breaks eventually. Then you get to decide whether that’s worth the money.
Somebody who can’t answer it, or who treats the question as unserious, is telling you they never worked out whether you needed this in the first place.
What to ask: “What happens if we just keep doing it the way we do it now?”
5You can’t find the exit
Read the part about leaving, not just the part about joining.
How long is the contract. What happens if you cancel in six months. Who owns your data, and can you get a copy of it in a form that works somewhere else. What does it cost to switch.
None of those questions are rude and none of them are unusual. If asking them makes the room uncomfortable, you’ve learned something important.
What to ask: “If this doesn’t work out, what does leaving look like and what does it cost?”
6The answer to “what do you make on this” isn’t a straight answer
You’re allowed to ask this. Out loud. In the meeting.
“Do you earn a commission or a margin on this recommendation?”
A yes is fine. Plenty of good people work that way and do honest work inside it. What matters is whether you get a straight answer. Someone who says “yes, we resell this and we make about fifteen percent” has just told you exactly how to weigh their advice, and you should respect them for it.
What you’re listening for isn’t the commission. It’s whether they’ll tell you about it.
7Everything is bundled and you can’t see the pieces
One monthly number that covers support, licenses, monitoring, backup, and something called managed services.
Bundles aren’t automatically bad. They’re simpler and sometimes genuinely cheaper. But you should be able to see what’s inside one. If nobody can break the number into parts, you can’t tell what you’re paying for, you can’t tell what you’d save by dropping something, and you can’t compare it against anyone else’s quote. That’s often the reason it’s bundled in the first place.
The other thing a bundle hides is promotional pricing. Something in there is frequently discounted heavily for the first year, and the number you’re shown isn’t the number you’ll be paying in month thirteen.
What to ask: “Can you show me what each piece costs on its own? And if any of it is promotional, when does that change and what does it change to?”
8They say partner, but every meeting starts from zero
Everyone calls themselves a partner now. The word has nearly stopped meaning anything.
I’m not asking anyone to keep your setup memorized. I’m asking whether they keep records and look at them before they show up. That isn’t a high bar, and it’s the whole difference.
I spent eleven years on the other side of this. The bad conversations were never the ones where somebody forgot a detail. They were the ones where nobody had opened the file, and I ended up explaining our own environment to the company we were paying.
A partner does the homework. A vendor asks you to catch them up.
What to ask: “What did you look at about us before this meeting?”
The short version
If you only remember one thing, make it the questions. You don’t need to know anything about technology to ask them, and they work on any vendor selling anything.
- Before we talk about what to buy, what did you learn about how we do business?
- What problem does this fix?
- What happens if I wait until next quarter, and if the price drops after I buy, will you match it?
- What happens if we just keep doing it the way we do it now?
- If this doesn’t work out, what does leaving look like and what does it cost?
- Do you earn a commission or a margin on this recommendation?
- Can you show me what each piece costs on its own, and what changes when any promotional pricing ends?
- What did you look at about us before this meeting?
Eight questions. Read them off your phone if you want. Anyone worth buying from will be happy you asked.
Sometimes the answer is yes, buy it
I want to be clear about something, because an article that never once says buy the thing is just a different kind of sales pitch.
Sometimes the vendor is right. Sometimes you genuinely need the new system, the monthly contract really is the best way to get it, and the person selling it to you is the right person to buy it from. Being careful isn’t the same as being suspicious, and the goal isn’t to talk yourself out of everything.
The goal is being able to tell the difference. If you ask those eight questions and get eight straight answers, you’re probably in good hands. That’s the whole test.
I’m Scott Olsen. Twenty one years of leadership, fourteen of them in technology, finishing as a Chief Information Officer in local government before I started pivot here in Palm City.
I don’t sell any of the things above. If you’re looking at something and you want to talk it through with somebody who has no stake in it, give me a call. Ten minutes on the phone is usually enough to tell whether something smells right, and that call is free.