1. Who owns a support request until it is resolved?
Ask how staff request help, how urgent issues are identified, and how updates reach the person waiting. A response is an acknowledgment or the start of work; resolution means the problem has been addressed. Make sure everyone means the same thing when discussing response times.
Ask them to walk through: An employee cannot access the application needed for today's work. Who picks it up, who keeps the employee informed, and what happens if another vendor must help?
2. What happens when our usual technician is unavailable?
Team size is useful context. So is the process that lets another person understand your business. Ask how responsibilities are covered during leave, overlapping incidents, or a complicated issue. The answer should explain access to documentation, escalation, and communication without relying entirely on one person's memory.
Ask them to explain: How would the next person find our important systems, current issues, and agreed support arrangements?
3. What gets maintained before someone reports a problem?
Monitoring, maintenance, and support are related but different. An alert can reveal a problem; someone still has to review it, decide what it means, and take appropriate action. Ask which systems are monitored, how updates are managed, and how recurring faults lead to a lasting correction.
Ask for an example: A computer repeatedly runs out of space. What would happen beyond clearing enough room to close the ticket?
4. Who is responsible for security alerts and account changes?
Ask about the work behind cybersecurity, including account protection, device management, alert review, and escalation. A list of installed tools does not explain who responds to a concern. Clarify which responsibilities belong to the provider and which decisions require your organization.
Ask them to walk through: An employee reports a suspicious sign-in. Who investigates, who can restrict access, and how is the business kept informed?
5. How do you handle an employee leaving?
Removing a license is only one possible task. Ask how the provider confirms an authorized departure request, reviews access to business systems, and preserves or transfers information the organization needs. The sequence matters, especially when files, shared resources, or a former employee's devices are involved.
Ask them to explain: What information does our manager need to provide, and how do we know the agreed offboarding work is complete?
6. What could we actually recover after a failure?
Discuss backup and recovery in terms of the systems you use. Ask what is protected, what is excluded, how failures are noticed, and what recovery checking is included. A successful backup notification is not the same as proof that every important system can be restored when needed.
Ask them to walk through: We lose access to a critical file or server. What would you check first, and what determines the recovery options and likely disruption?
7. Who controls Microsoft 365 and our business accounts?
Ask how administrative access, licensing, domain ownership, and account recovery are documented. You should understand how an authorized business owner can regain control if the relationship changes. Access needs appropriate protection; it should also have a documented owner and recovery process.
Ask them to explain: If we change providers, can our existing Microsoft 365 environment stay in place, and which administrative or licensing relationships would change?
8. How do you coordinate with our other vendors?
Phones, internet, accounting software, and network equipment can affect one another. Ask who coordinates troubleshooting when the cause is unclear. A provider cannot promise control over another company's response, but it can explain its role, escalation process, and how it documents the next step.
Ask them to walk through: Calls are breaking up, but the phone and internet companies both say their service is working. Who helps move the investigation forward?
9. What would the first part of a transition look like?
A useful answer starts with discovery, access, current commitments, and the systems the business depends on. It explains what can stay, what needs attention, and which changes require planning. Be careful with a fixed timetable or a guarantee that nothing can go wrong before anyone has assessed your setup.
Ask them to explain: What do you need from us and our current provider, what would move first, and when would you discuss work that could interrupt staff?
