Hot Takes and Cold Server Rooms

Welcome to the place where IT meets opinions. I cover AI, cybersecurity, infrastructure, industry trends, and the occasional life update from someone who manages servers by day and goats by night. I have spent 15+ years in the trenches of healthcare, education, and tech, which means I have seen things. Breached things. Fixed things. Automated things that absolutely should have been automated three years earlier. And formed opinions about all of it. Grab a coffee. The good stuff is just below.

Sherry Jones Sherry Jones

The Org Chart Is a Lie. Here's How IT Actually Works.

The most effective IT professionals are not always the most technically brilliant ones but the ones who know which business stakeholder actually controls the budget despite what the reporting structure suggests. These are not political skills in the pejorative sense. They are organizational literacy skills, and they are as learnable as any technical certification.

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Sherry Jones Sherry Jones

Your Documentation Is Lying to You (And So Is Everyone Else's)

Documentation debt works like financial debt: you cannot pay it all off in one dramatic gesture, and the interest keeps accumulating while you are working on the principal. Good documentation is an act of professional generosity toward every person who will ever have to work in the environment you are building.

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Sherry Jones Sherry Jones

Nobody Talks About the 2 AM Call Until You've Had One

Infrastructure resilience is built in the daylight and tested in the dark. The runbook either tells you exactly what to do at 2 AM or it tells you it was last updated in 2021 and references a tool that was decommissioned. That difference was determined weeks before the incident, in the quality of documentation produced during calm periods.

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Sherry Jones Sherry Jones

Goodbye, Sierra. We Barely Understood You.

Every technology we implement will eventually be decommissioned. The question isn't whether the systems we steward will be replaced. It's whether we designed them in ways that make the transition survivable.

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Sherry Jones Sherry Jones

Nobody Told Me IT Leadership Was 40% Therapist

The system nobody uses isn't a technology failure. It's an adoption failure, which is a people problem wearing a technology costume. The security policy nobody follows isn't a policy failure. It's a communication failure. Every single one of those outcomes is addressable with the same skills your therapist uses, minus the couch and the hourly rate.

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Sherry Jones Sherry Jones

Day One Is a Test. Most IT Departments Are Failing It.

What happens in the first two hours of day one does not just set the tone for the employee's relationship with IT. It sets the tone for their relationship with the entire organization, because for a new hire, IT infrastructure and organizational competence are indistinguishable from each other.

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Sherry Jones Sherry Jones

The SaaS-pocalypse Is Here. Or Is It?

The vendors who treat this moment as a fire drill rather than an extinction event will likely find a path forward. For IT leaders managing SaaS portfolios worth millions in annual spend, now is exactly the right time to be asking which subscriptions are genuinely earning their seat at the table.

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Sherry Jones Sherry Jones

The Ticket That Taught Me Everything About IT Leadership

The technical certification gets you in the room. The ability to handle the 4:45 Friday ticket with grace is what gets you promoted. Look at your most recently closed tickets and ask yourself whether your team is solving problems or closing tickets. Those are not the same thing.

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Sherry Jones Sherry Jones

The Password Policy Nobody Follows (And Why That's Your Fault)

Every policy that treats the human as the problem to be constrained rather than the behavior to be supported has generated a creative workaround that is usually worse than the original risk. The sticky note on the monitor is not the enemy. It is a design failure wearing a Post-it costume.

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