Your IT Provider Should Be Able to Answer These Questions. Can They?
There’s a simple test for whether your IT relationship is working.
It’s not whether your systems are up. It’s not whether tickets get resolved. Those are the baseline — the minimum you’re paying for. The real test is whether your provider can tell you, at any point in the year, where you stand. Not in vague reassurances, but in specifics.
Most can’t. And most business owners in Northern Indiana don’t realize it until something goes wrong and the conversation starts with “we’ll have to look into that.”
A managed IT relationship should include regular reviews — not just contract renewals, but actual conversations about how your technology is performing and where the gaps are. If yours doesn’t, here’s what those conversations should cover.
Security — the specific version, not the general one
“You’re protected” isn’t an answer. Ask what vulnerabilities exist today, which systems need patches, whether there’s been unusual login activity recently, and which users or devices are creating unnecessary exposure.
If your provider can answer those questions with actual detail, that’s a good sign. If the answer is a general reassurance, that’s useful information too — just not the kind you want.
Backups — tested, not assumed
A backup that hasn’t been tested is an assumption, not a safety net. Ask when a full recovery was last run, how long restoration would realistically take, and whether your cloud tools are covered alongside your on-site systems.
These are straightforward questions. The answers matter most during an outage, when there’s no time to find out you didn’t know them.
Where the team is losing time
Most productivity problems don’t show up as IT emergencies. They show up as small frictions — an application that loads slowly, a system somebody has quietly stopped using because it’s too unreliable, a workaround that’s become so normal nobody mentions it anymore.
Your provider should know where these are before you tell them. If they don’t, ask directly: what systems generate the most complaints internally, and what’s being done about them?
Compliance — current, not last year’s version
Requirements change. HIPAA, PCI-DSS, cybersecurity insurance — what applied last year may not fully apply today, and a business can drift out of alignment without anyone catching it.
Ask whether any requirements have changed recently, whether your documentation would hold up if someone asked for proof, and whether your current controls still match what your insurance policy assumes. Finding a gap in a quarterly conversation is significantly less painful than finding it during a claim.
What’s coming in the next 90 days
Aging hardware, expiring warranties, license renewals, planned upgrades — your provider should be tracking these and giving you a forward-looking picture of costs before they become surprises. Emergency purchases are almost always avoidable. They happen when nobody was paying attention.
What this looks like in practice
We work with businesses across the Michiana area — manufacturing shops in Warsaw, law offices in South Bend, small businesses throughout Marshall County — and this kind of regular review is part of what we do. Not because something is wrong, but because staying ahead of problems is easier than catching up to them.
If you’re not having these conversations with your current provider, a 10-minute discovery call is a good way to find out what you’re missing. Reach us at http://os.lecsit.com/l/discoverycall-july-2026-blog or call us at 574-857-4332.