When did you last test a restore?. A backup nobody has restored is a folder of hope.
Where is my staging environment?. Updates that go straight to production are not updates. They are gambles.
Who patches, and how often?. If the answer is nobody, security is a project waiting to happen.
How will I know before my customers do?. Monitoring should reach a person, not a dashboard nobody opens.
What is the escalation path?. A ticket queue is not a support plan.
Can I leave with my data?. Ask before you need to, not after.
Who has admin access?. The answer is usually longer than expected.