Questions to Ask Your Managed IT Provider Every Year

Hiring a managed IT provider is only the beginning. The best relationships include regular check-ins where you ask direct questions about what is being done and what comes next. These are the questions we recommend Boca Raton companies ask their provider, whoever it is, at least once a year.

Security

• Is multi-factor authentication turned on for every account? Including admins, shared mailboxes and remote access.
• What security incidents did you handle this year? And what was changed afterward?
• Are all devices protected and fully patched? Ask to see a report.
• When was our Microsoft 365 security last reviewed? Settings drift over time.

Backups and Recovery

• When did you last test a restore, and how long did it take? Ask for the result.
• Are backups protected from ransomware? Look for immutable or offline copies with separate credentials.
• How long would recovery take if our main server or Microsoft 365 data were lost? Compare that with how long you can afford to be down.

Support Quality

• What are our most common tickets? And what is being done to prevent them?
• Are you meeting response targets? Ask for numbers.
• Is anything waiting on us? Sometimes fixes are stuck awaiting approval.

Planning and Budget

• Which devices or systems will reach end of support soon? And what will replacement cost?
• What should we prioritize next year? A good provider has a roadmap.
• Are we paying for licenses we do not use? Regular license reviews save money.
• How do our controls compare with what our insurer and clients expect?

Documentation and Ownership

• Is our documentation current, and can we access it?
• Are domains, accounts and licenses registered to our company?

What Good Answers Look Like

A strong provider answers with reports and specifics, admits gaps and has a plan to close them. If answers are vague or reports do not exist, it may be time for an independent review. See how Simplitfy reports to Boca Raton clients or book a free consultation.