Buyer's guide
Questions Every Business Should Ask Their MSP
Twelve questions to ask your current or prospective managed IT provider — and what good and bad answers sound like.
Whether you’re evaluating a new provider or auditing the one you have, these twelve questions surface the truth quickly. Good answers are specific, documented, and boring. Bad answers are reassuring and vague.
Security
1. When were my servers and workstations last patched, and can I see the report? Good: a report within minutes. Bad: “We handle all that.”
2. If an employee clicked a phishing link right now, what happens next? Good: a specific sequence — isolation, password reset, log review, notification. Bad: “Our antivirus would catch it.”
3. Who at your company can access my systems, and how is that access controlled? Good: named roles, MFA, logged sessions. Bad: surprise that you asked.
4. What happened during your last security incident — yours, not a client’s? Good: an honest story with lessons. Bad: “We’ve never had one.” (Every mature provider has handled something.)
Recovery
5. When did you last test-restore my backups, and what came back? Good: a dated test with results. Bad: “Backups are running fine.”
6. If my main server died at 9 a.m. today, when would my team be working again? Good: a number, from a documented plan. Bad: “As fast as possible.”
Relationship
7. What does my monthly fee include, and what costs extra? Good: a one-page answer. Bad: “It depends.”
8. What are my numbers — response time, ticket volume, recurring issues — for the last quarter? Good: a report they already track. Bad: they’ve never measured.
9. When did we last talk about the future instead of the current fire? Good: a standing quarterly review. Bad: you can’t remember one.
10. If I leave, how do I get my passwords, documentation, and data? Good: a written offboarding process in the contract. Bad: hostility at the question — the biggest red flag on this list.
Fit
11. How many clients my size and in my industry do you support? Good: several, with references. Bad: you’d be the biggest, smallest, or first.
12. What should I be budgeting for in the next two years? Good: a roadmap with numbers. Bad: silence until something breaks.
If your current provider’s answers make you uncomfortable, that discomfort is data. A no-cost, no-pressure MSP comparison report will show you what the answers should look like for a business your size.
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