Most IT support providers look nearly identical in a sales meeting. The differences only become visible six months into a contract, by which point you're locked in. I've sat in enough post-mortem conversations with business owners who signed the wrong contract to know which questions actually separate good providers from the rest.
Ask how many clients each engineer handles
This is the most direct indicator of whether you'll get genuine attention. A provider running 120 client companies per engineer is a volume business. Tickets get resolved, but nobody is watching your environment proactively.
There's no universal threshold, but I get concerned above 80 clients per engineer for a contract that includes proactive management. Below 40-50 is where you start to see providers who actually know their clients' environments.
Find out who actually handles your day-to-day issues
Many providers close the sale using their senior engineers, then route day-to-day tickets to junior staff or an outsourced helpdesk. That's not inherently wrong, but you should know what you're buying. Ask directly: when a staff member calls with a problem at 2pm on a Wednesday, who picks up? What's their experience level? When does it escalate, and to whom?
The answer tells you whether you're buying a senior-led service or a tiered support model. Both can work. Know which one you're getting.
Ask for actual SLA performance data, not just promises
Response time and resolution time are different metrics. Response time means someone acknowledged your ticket. Resolution time means the problem is actually fixed. Both matter.
Ask for the SLA document in writing, across severity levels. Then ask for their actual performance against those SLAs in the last quarter. A provider confident in their numbers will produce this without hesitation. Hedging or vague answers is a meaningful signal.
Speak to three current clients, not testimonials on a website
Ask for three references at similar company size and sector, and actually call them. When you do, ask: have there been any significant IT incidents in the past year? How were they handled? Is there anything you'd change about the service?
What you're listening for is honest answers, not rehearsed positives. A client who says "the response times could be faster but they always get to us eventually" is telling you something useful.
Ask specifically what onboarding involves
A provider who installs a remote monitoring agent on day one and calls that onboarding will not understand your environment when something goes wrong. Good onboarding involves documenting your infrastructure, identifying your critical systems, meeting key staff, and learning what normal looks like for your business.
Ask how long onboarding takes. A week is not enough for most businesses. A month with structured handover stages is more realistic for anything above 15-20 users.
Understand what happens at 7pm on a Friday
Some providers offer genuine 24/7 cover. Others offer business hours support with emergency-only out-of-hours. Others don't cover outside normal hours at all. Make sure what's in the contract matches your actual risk. A business that can tolerate overnight downtime is in a different position to one with customer-facing systems that run around the clock.
Get the data ownership question in writing
Ask who owns your system documentation, passwords, network diagrams, and configuration records if you leave. The answer should be unambiguously you. Some providers make this documentation proprietary, which creates switching costs that are genuinely intentional. If they won't confirm it in the contract, treat that as a warning sign.