I worked for a company where the head of IT was impressively incompetent. Our division relied on working technology to keep all our, er "appliances," flying and recording in the sky, so to speak. There were backups of backups, redundancies, encryption, and high level secured stuff. Because we required "advanced" technological comprehension, we had our own shadow IT just to keep the lights on. But for things like the office network, getting your laptop, and the office network, this guy "Biff" was in charge. He was a real piece of work. I was told by other managers that he kept his job because they couldn't find anyone else that would "just do" with such a low salary requirement, which while I have no idea if that was true, it seemed plausible. When I started there, he had already been with the company for 10 years.

First, he was a Microsoft fanboy, and I am not saying "Windowz suxx" or anything like that, but he was a fanboy of Microsoft like "the Star wars kid" was a fanboy of George Lucas. Anything not MS "sucked." He refused to support it or learn anything about any other technology in a useful way; for example, our Cisco infrastructure or the VMware server fleet with all the Windows servers for the internal part of the company. His list of "not MS things that sucked" were sometimes surprising, Like SSL certificates.

Second, he was intimidated by anyone who knew more than him, so he had two "assistants" who were lukewarm bodies who had basic literacy and comprehension problems. Biff never did any job that he couldn't send one of these guys to do for him, because out of the four floors of our office, he stayed pretty much in his bunker, a darkened room with a cubicle and old CRT monitors. Biff loved speaking about them in the third person in their presence, using "joking and joshing" comments about how dumb they were. How they stood this, I have no idea. They weren't allowed to do ANY work while he was gone, and he was gone "on Microsoft training" several weeks a year, company paid, in addition to his vacation and sick leave.

While I was there, he had some extra special events happen, not the least of which, the office had 3 ransomware events in 2 years. Because my division was segmented and largely Linux-based, we weren't affected just by using the minimum of safety protocols. We had firewalled ourselves from the office and it saved our skin more than once.

We had to have our own file server because twice he'd been known to wipe out file shares without warning. He also "didn't believe in backups" because "they are unreliable and outdated, anyway." Okay...

Was paranoid about being filmed to the point he was able to skirt the fact video on conference calls was company mandatory. "A man in my security profession can't afford to be photographed." Sure thing, buddy.

I discovered too late to be useful, but all the Cisco equipment was default passwords of cisco/sanfran. I discovered this when a legacy employee told me how to check for whether an interface was up to diagnose my network patch panel issue (it was administratively turned off, I turned it back on and fixed it myself). We had to have our own wireless network because the office wireless was so oversaturated, it was next to useless.

Thankfully, because we managed our own segment, we rarely had to work with the guy. But the few times a year we had to work with him, he was shockingly overconfident and patronizing for the skills he actually had.