What should a 10-person Windsor business expect from an MSP?

A structured onboarding—not just remote-access software

Onboarding should identify users, computers, mobile devices, Microsoft 365, internet connections, network equipment, printers, backups, servers, vendors, domains, and critical applications. Administrative access should be documented securely, and unsupported or unknown systems should be called out.

The result is a prioritized baseline: immediate risks, stability work, lifecycle concerns, and longer-term improvements. A small team should be able to understand that list without needing a technical translator.

A predictable support experience

Employees should know how to request help, what information to provide, and when a request becomes urgent. The MSP should communicate who owns the ticket, what is happening next, and whether another vendor is involved. Repeated issues should produce a permanent fix or an explicit business decision—not an endless sequence of workarounds.

Security and backup with named responsibilities

At minimum, discuss multi-factor authentication, account administration, endpoint updates, malware protection, email security, device encryption, backups, and employee access changes. Backup scope must identify which data is protected, how long it is retained, and how restores are tested.

The MSP should also explain what is not included. Microsoft 365 availability, recycle bins, retention, and third-party backup are related but not interchangeable.

Planning, documentation, and an exit path

A useful MSP relationship includes lifecycle planning, licensing review, vendor coordination, and a short roadmap tied to business priorities. Documentation and customer-owned accounts reduce dependence on individual technicians.

The contract should describe renewal, cancellation, data return, credential transfer, and offboarding. Good support earns retention through value, not through technical lock-in.