Are your employees background-checked? Is your company insured?

Start with why this matters more here than with almost any other vendor: an MSP's technicians end up with administrator credentials to your computers, your server, your email, and often your line-of-business and financial systems. That access is the whole point of the service, and it is also a decision about who you trust. Background checks on every hire should be standard practice at a professional MSP, and the answer you want is a plain yes, said without hesitation: not 'our people are trustworthy' but 'yes, every employee, at hire.'

Insurance comes in three forms worth asking about by name. General liability covers the ordinary physical mishaps, like a ceiling tile cracked during a cabling job. Errors and omissions (also called professional liability) covers mistakes in the work itself, the kind that cause data loss or downtime. Cyber liability matters because IT providers are themselves targets: if an attacker ever compromised a provider's tools, that coverage is part of how a serious firm has planned for its worst day. Ask for a certificate of insurance. Insurers issue them routinely, and providers with real coverage produce them without drama.

The reaction is as informative as the answer. Professional providers field these questions from every serious prospect and respond immediately: who runs the checks, what the coverage amounts are, here is the certificate. Vagueness, defensiveness, or 'nobody has ever asked that' tells you the provider has not been operating at the level your business deserves. Add these two questions to the list in our guide to what to ask before hiring an MSP.