Choosing an IT partner is one of the most important decisions an SMB makes. Yet it's often done based on a recommendation, a price quote, or a "that person seemed nice" feeling.
I've seen dozens of companies switch IT partners too late — after the damage was already done. And almost without exception, the problem wasn't technical competence. It was that nobody asked the right questions upfront.
Here are five questions that reveal more than any sales presentation.
1. "Do you sell products or solutions?"
This is the first and most important question. Many IT companies are resellers. Their revenue comes from what products they manage to sell — not from what's the best solution for you.
If your IT partner always recommends the same vendor regardless of the situation, they're not a partner — they're a salesperson. A good IT partner recommends what fits your situation. Sometimes that's Microsoft. Sometimes it's an open-source solution. Sometimes it's doing nothing at all.
Red flag: "We're a Microsoft Gold Partner" doesn't mean they're good. It means they sell a lot of Microsoft. Those are two different things.
2. "What happens when something breaks on Friday at 4 PM?"
In a sales meeting, everyone promises fast service. The truth reveals itself when something actually breaks.
Ask specifically: what's the response time? Who responds? Do they have on-call? Do you get the same person or does the technician change every time? Do you have to open a ticket and wait in line?
The best IT partners don't hide this in fine print. They openly tell you what service level is offered and what it costs.
Red flag: Vague promises without a written service level agreement (SLA). If it's not on paper, it's not a promise.
3. "Can we see a report of our current environment?"
A good IT partner knows your environment. They know what machines you have, what software is installed, which licenses are in use and which aren't, and what state your security is in.
Ask for a report. If the partner can't produce one — or one has never been made — that says a lot. It means they're handling tickets as they come in, but don't actually understand the big picture.
Red flag: "We have everything under control" without concrete data. Nothing is under control that hasn't been measured.
4. "What do you recommend we DON'T need?"
This question separates the salesperson from the expert. A salesperson never says you don't need something. An expert does.
I've told clients directly: "You don't need this license. It's unnecessary at your size." Or: "This problem is solved with a free tool, no need to buy anything."
An IT partner's job is to protect the client's interests — even when that means a smaller invoice.
Red flag: Every conversation ends with a quote. If your partner never says "not needed," they're optimizing their own cash flow, not your interests.
5. "If we switch partners, how does that work?"
This is the question nobody dares to ask. But the answer tells you everything.
A good IT partner isn't afraid of this question. They openly explain how documentation is handed over, how access rights are transferred, and what the transition process looks like. Because a good partner trusts that they won't need to be replaced.
A bad partner? They've built the environment so that switching is as difficult as possible. Admin accounts are in their name. There's no documentation. And if you try to leave, there's a surprise: "We won't release the passwords until the invoice is paid."
Red flag: An evasive answer or hints that switching would be "complicated." Lock-in isn't a service. It's a prison.
Summary
Five questions summarized
1. Do you sell products or solutions?
2. What happens when something breaks?
3. Can we see a report of our environment?
4. What don't we need?
5. How would switching partners work?
An IT partner isn't just a service provider. It's a relationship built on trust. And trust is built on transparency, not sales pitches.
If your current partner can't answer these five questions — or doesn't want to — that's an answer in itself.
Want an independent assessment of where your IT partnership actually stands? An IT health check will tell you directly.