It’s a tale as old as time: A superstar IT pro has been running an entire company’s digital systems for years. She built the asset management, remote monitoring, and ticketing systems herself, and whenever anyone has a question, she’s the one to ask.

But what happens when she puts in her two weeks’ notice or announces her retirement? What if leadership requires that IT offload some of its day-to-day work to AI? How can all the human expertise be passed on to others, or partially automated?

As boomers retire en masse over the next few years and AI continues to integrate into IT workflows, situations like these will become a reality for many IT pros—for some, they already are. The solution is consistent documentation and, importantly, documenting workflows as a continuous, accessible, and centralized process.

Why IT pros aren’t documenting, here.—TC

Things Rob Gregory hates: broccoli, unkempt grass, uncomfortable chairs, and passwords…the latter so much so that he is actively working to eliminate them from his organization.

Gregory, who is CISO at cybersecurity advisory firm Optiv, told IT Brew that the password-elimination project is the second passwordless initiative in his career, and that the shift to passwordless will be a solid solution to several cybersecurity risks, including phishing attacks and data breaches.

“Passwordless is really the building block that everyone should be building their identity and access platform around today,” he said.

Gregory isn’t the only CISO sailing in the anti-password boat: More than nine in 10 CISOs either have implemented or are planning to implement passwordless authentication within their organization, according to a Portnox survey querying 200 CISOs.

No password required for this.—BM

It’s safe to say that Prasad Tharippala, Asia–Pacific field CISO at Versa Networks, is no stranger to security incidents, having made it through a breach and the aftermath with his career intact.

From 2017 to 2020, Tharippala ran his own cybersecurity company, helping clients navigate cyberattacks. He recalled one early case in which one of the largest textile firms in India had been attacked.

“I went there, and then I took charge of the situation where the company is being completely ransomed,” Tharippala said, adding that he helped operations resume within one and a half days.

Gather around, it’s storytime. We caught up with Tharippala to talk about when, as a CISO, he helped a global company thwart a third-party breach. (One in three breaches in 2025 involved a third party, according to a recent Verizon report.)

The only way out is through…this link.—BM

What’s the five-letter word for a site consulted by hypochondriacs? If you think you know, try your hand at Volume 2 of the Morning Brew’s Book of Crosswords (this clue’s on page 42). Now with free shipping for IT Brew readers.