1You're paying for things nobody uses.
Licenses for people who left, a second file-sharing tool nobody remembers buying, a security add-on that duplicates one you already have. Subscriptions are easy to start and nobody's job to stop. It's one of the most reliable places to find money: seats and services that no one would miss.
2Their incentives aren't always yours.
Many providers earn a margin on the hardware, licenses and add-ons they recommend. That doesn't make the advice wrong, but it means the person deciding what you buy is also the person selling it to you. Someone on your side of the table should be checking.
3A backup you've never restored is a hope, not a plan.
"Backups are running" is not the same as "we restored the accounting system last quarter and it worked." Ask when the last real restore test was, what was restored and how long it took. If nobody knows, you don't really have a backup yet.
4Your contract lists what they won't do.
Read the exclusions. Projects, vendor management, software selection, security questionnaires and long-term planning are often out of scope or billed extra. Those are the decisions that matter most, and they quietly fall to whoever at your company has the least time for them.
5Nobody's reviewing their work.
They send a monthly report. Who reads it? Without someone who knows what good looks like, the report becomes a receipt. The best provider relationships I've seen all had someone on the client side asking hard, friendly questions every month.
If the answers are fuzzy, that's normal, and fixable. The free IT self-check takes two minutes and shows where to start.