Boss Who Knows Nothing About IT Demands Impossible Security, Then Has A Meltdown

In the world of IT, sometimes you get asked to do the impossible, like ensuring no one, including yourself, can access files. One Redditor, a CTO at a disastrously managed software company, was tasked with ensuring a pastor’s office files were completely locked down.

But when the inevitable computer crash occurred, and the chairman ordered a restore, the CTO had one simple question: “What backup?”

The moment the chairman realized that access restrictions had prevented any backups from being made was pure gold. The silence that followed his furious outburst was the kind of poetic justice only a long-suffering IT professional could truly appreciate. Scroll down to see how this absurd situation played out.

CTO was ordered to block access to files, but a problem arose

We’ve all faced situations where authority figures make decisions that, on the surface, sound sensible, but upon closer inspection, are riddled with contradictions.

In this story, the CTO is caught in a classic conundrum: ordered to comply with an illogical decision that not only undermines their expertise but also sets the stage for failure.

What makes this story so satisfying, though, is how the CTO handles it. Instead of outright defying the chairman’s orders, they let the absurdity of the situation play out, knowing that the inevitable fallout would expose the flaw in the plan.

This strategy is a perfect example of malicious compliance, following the letter of the request while subtly making the consequences of that decision undeniable. By asking, “What backup?” the CTO highlights the core contradiction: how can you protect data you aren’t allowed to access?

In doing so, they not only pointed out the flaw but also did so in a way that required no further explanation; sometimes, silence and a well-timed question speak louder than any rebuttal.

Psychologist Adam Grant, in Think Again, explores how people often get trapped in their own assumptions, particularly when they occupy positions of power.

He suggests that authority figures often make decisions from a place of expertise in one domain, only to apply that expertise inappropriately to unfamiliar fields.

In this case, the chairman’s decision was rooted in his own authority and experience in flight engineering, not in an understanding of the nuances and technical realities of managing IT systems. His request to restrict access to the files, though well-intentioned, was based on a flawed understanding of how data management works.

The CTO’s response also reflects a deep understanding of organizational dynamics. Sometimes, rather than confronting poor decisions head-on, the best approach is to let them unravel on their own, exposing the underlying flaws.

It’s an effective reminder that sometimes the most powerful move is to allow those in charge to see the consequences of their actions, rather than constantly fighting against them.

How often do we find ourselves in situations where following the rules to the letter exposes a flaw in the logic? Would we ever think to use silence and a single, pointed question as a way of highlighting an issue, or do we feel compelled to speak up immediately?

Here’s what the community had to contribute:

This group shared humorous stories about people resorting to drastic and comically ineffective solutions to computer problems

These users added more context or speculation to the original story, offering a mix of funny, irreverent

These commenters expressed their personal frustration with people who default to reformatting as a solution

This user shared a classic example of old-school tech mishandling

Have you ever had a customer who thought they could bully their way to a freebie? How did you handle it? Share your thoughts below! We’re all ears for your own tales of customer service revenge.