A proposal can contain dozens of product names and still leave the important questions unanswered. Focus on ownership, user experience, recovery and what happens in the situations your business is most likely to face.
1–3: Support ownership
Ask who users contact, which hours the helpdesk operates, and what happens when a ticket involves another supplier. “We will log it with the vendor” is different from owning the issue through to the next useful action.
4–6: Microsoft 365 and device management
Ask who manages users, licences and access; which Windows devices are supported; and how security or configuration standards are applied to laptops used away from the office.
7–8: Joiners and leavers
Ask what information the MSP needs before a new starter, how much notice is required, and how accounts and equipment are handled when somebody leaves.
9–10: Backup and recovery
Ask what is backed up separately from the production service and how a restore is requested and tested. Avoid treating “backup enabled” as the same statement as “we know how the business gets back to work.”
11: Pricing and exclusions
Ask what is included in the recurring price, which work is billable, whether onsite support is included, and whether project or onboarding charges apply.
12: Improvement and accountability
Ask how the provider identifies recurring issues, ageing devices, Microsoft changes, security gaps and upcoming technology decisions. A managed service should have an improvement route as well as a ticket queue.
Frequently asked questions
Should I send these questions to potential MSPs before a meeting?
Yes. A provider should be able to answer the service-scope questions clearly. More technical environment-specific questions can then be discussed during discovery.
Can 39Degrees review our current support setup before we decide to change?
Yes. The managed IT review is intended to identify gaps and priorities before a proposal is prepared.