Carol runs a small accounting firm. In February, her server failed. The I.T. provider arrived within two hours and asked where the backup was.
The backup software had been running every night for three years. Every morning it sent a notification saying the backup had completed successfully. What it did not say was that four months earlier a software license had expired. The agent kept running. It kept sending success notifications. It backed up zero bytes of data and called it a success every single time.
The last working backup was from four months before the drive failed. Those four months contained the active work for sixty-three client engagements. Three clients left afterward. Two threatened legal action. The reconstruction took four weeks.
The most unsettling part, Carol said later: "We got an email every morning saying the backup worked. We assumed the email meant what it said."
This book contains the fifteen questions that would have caught the problem at any point during those four months. Most require no technical knowledge to ask. Question 6 alone would have been enough: it asks when someone last actually restored files from the backup and verified they were readable. The answer would have been never. That would have been enough.
The fifteen questions cover the ground where backup failures most commonly hide. Whether the backup scope actually includes all critical data or has quietly drifted as the business grew. Whether three genuinely independent copies exist or whether two of them share the same failure mode. Whether at least one copy is offline or immutable and therefore unreachable by ransomware. Whether the backup frequency matches the actual data creation rate. Whether the retention period extends far enough back to provide a clean restore point after a ransomware dwell period. Whether a test restoration has actually been performed recently, not just the logs checked. Whether the restoration time is known before it matters. Whether Microsoft 365 data is independently backed up or assumed to be safe because it is in the cloud. Whether databases are backed up with application-aware methods or just file-copied. And whether anyone would notice within hours if the backup silently stopped working tonight.
Each chapter explains why the question matters, what a solid answer looks like, what a weak one reveals, and what to do next. Chapter Sixteen has follow-up questions for each of the fifteen. Chapter Seventeen is a one-page action checklist you can print and bring to the meeting.
IT Support 101 Inc. is an independent advisory firm working exclusively with business owners and executive teams on the technology decisions they cannot afford to get wrong. No commissions. No vendor relationships. Just clear, honest advisory work on your side of the table. Learn more about the firm, the advisory services, and the full book catalog at itsupport101.com
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