How to Evaluate a Managed IT Provider: 12 Questions Before You Sign

Choosing an MSP is a three-year bet on reliability, security, and how much leadership time you'll spend on IT drama. Proposals look similar on paper. Quality diverges in what's excluded, undocumented, and unstaffed.

Use this scorecard when comparing providers, including us.

1. Who answers the phone?

Ask for after-hours process, not marketing language. Will you reach someone who knows your environment, or a national NOC reading a script?

2. Is EDR included and triaged?

"Antivirus included" is not EDR. Who reviews alerts? What's the escalation path for confirmed threats?

3. Are backup restores tested?

Request last restore test report, date, system, success/failure. "We monitor backups" without restore testing is incomplete.

4. What's the onboarding documentation deliverable?

You should receive network diagram, asset inventory, admin account list, and license summary within 60–90 days of start, not "we'll get to it."

5. Do they run quarterly business reviews?

QBRs should cover ticket trends, security posture, roadmap, and spend, not only upsells.

6. How do they handle projects vs. support?

Clarify what's in the monthly fee vs. project SOW. Ambiguity becomes invoice surprise.

7. Multi-cloud and M365 depth

If you run Azure, AWS, GCP, or IBM/Oracle alongside M365, can the same team administer them, or will you need another vendor?

8. Security compliance experience

For PHI-adjacent or regulated data: ask for examples of controls they've implemented (MFA enforcement, DMARC, training cadence), not "we're HIPAA compliant" stickers.

9. Client retention and references

Ask retention rate and for two references in your size range, not only enterprise logos.

10. Escalation and account ownership

Named technician or account owner? Or rotating pool? Continuity matters for environments with history.

11. Contract exit and documentation

What do you receive if you leave? Runbooks, passwords, diagrams, some MSPs hold environment knowledge hostage.

12. Honest fit assessment

The best MSPs tell you when they're not the right fit. Ask what they won't support.

Scoring tip

Weight security and documentation higher than per-user price. A $30/user gap disappears after one preventable incident or one botched migration.

Request a comparison audit, we'll review your current MSP relationship or help you score proposals side by side.