01 · Security
When were our security controls last tested, and what did the test find?
Ask to review. A dated report with scope, findings, limits and a responsible person for follow-up.
Follow up. A product name alone does not show how the control is configured, monitored or tested.
02 · Security
Which of our accounts have administrator rights, and why does each one need them?
Ask to review. A current list with each account's purpose, permissions and responsible owner, including service and emergency accounts.
Follow up. A count alone, or “only the IT team.” Neither identifies the accounts or why their access is needed.
03 · Backup and recovery
When did you last restore our data from a backup, and how long did it take?
Ask to review. A date, duration, scope, test result and any unresolved recovery dependencies.
Follow up. “Backups run nightly.” That describes backup jobs, not a demonstrated recovery.
04 · Backup and recovery
If our main system failed this morning, how much work would we lose and when would we be running again?
Ask to review. Written recovery objectives, supporting test results and the assumptions or dependencies not yet verified.
Follow up. “We would have you back up quickly.” Quickly is not a number, and nobody can plan around it.
05 · Provider performance
What did we contract you to deliver, and can you show it was delivered last quarter?
Ask to review. The service list from the contract, set beside a report written against that same list.
Follow up. A ticket count alone. Relate activity and outcomes to the services and reporting period you agreed.
06 · Provider performance
Which items from your last report are closed, and which are still open?
Ask to review. The previous report’s actions, each with a status and a date.
Follow up. A fresh report that omits earlier actions. Ask whether they were completed, deferred, superseded or still need work.
07 · Technology spending
What are we paying for every month that we are not using?
Ask to review. Licence counts and usage, checked against business needs, with reasons to retain, change or cancel each item.
Follow up. “It is all bundled.” Bundling is a pricing choice, not an answer about what you use.
08 · Technology spending
Which of your recommendations earn you additional revenue?
Ask to review. A written explanation of resale margins, commissions or additional work associated with each recommendation.
Follow up. Discomfort, or “we are vendor neutral” with nothing behind it. You are asking about incentive, not integrity.
09 · Strategy
What stops being supported in the next twenty-four months, and what is the plan?
Ask to review. A list of systems with end-of-support dates, and the budget year each one lands in.
Follow up. “We will deal with it when it happens.” Ask for an owner and a plan before support ends.
10 · Independence
Who checks your work?
Ask to review. The name of an independent party, or an honest “nobody currently.” Both are real answers.
Follow up. “Our own internal process” without its scope or results. Internal review can be useful, but is not an external independent review.
That is the whole document. The five page version is the same ten questions laid out to print, with room beside each one to write the answer you were given.