I had someone take an email they received about a technical problem someone else was having. They then printed it out, highlighted the important part, then scanned it back in as a picture all offset and grainy, then used that picture in a web chat to request help for that third person without direct contact

They were an IT Manager

The worst sentence is the last sentence, when you really think about what it implies.

When you don't understand the tools, every possible solution that reaches your end goal seems equally valid, no matter how convoluted. Unfortunately, the design philosophy that attempts to make every tool as compatible as possible with every other tool enables this sort of Rube Goldberg-esque nonsense (and creates development hell and permanent legacy dependencies).

It's... difficult for someone who does understand the tools to even imagine being in the mental space of someone who doesn't, which is why IT people frequently come off as arrogant, judgy, even rude - they expect other people to understand things the way they do, when they've been taking computers apart since high school. What seems reasonable to you is perfectly opaque to them. Also... sometimes people who are technically literate are the hardest to pull out of their batshit processes (doctors are the worst patients).

When you are trying to help someone, always keep the XY Problem in mind. They've arrived at a solution which seems insane to you, not because they're unreasonable, but because they ran into an obstacle and bounced off of it in a path-of-least-resistance direction and they have shit they need to get done. Try to solve the real problem, not the problem that is presented.

Get out more. This is entirely realistic in my experience.

The worst one I ran into was early in my career. This was back during the XP days.

The lady who who did the job before had a certificate e-mailed to her from a lab. She printed the certificate off then slipped two certificates front and back into a plastic sheath and put them into a 4" 3 ring binder.

She then deleted the labs e-mail and electronic copy to save space in her mailbox.

There were around 4,000 of these certificates every year for 5 years when I started. So around 20,000 pages. We had ONE physical copy of a legally required certificate.

Around 15 shipments per year required her to find around 300-400 specific certificates She then had to pull them out of the plastic sheaths, make 3 physical copies and scan one PDF to load to the government agencies webpage.

She would then delete the PDF, and laboriously refile the certificates back into the the plastic sheets.

Oh the binders were also ordered in a way that nobody but her could find anything. It was about as close to random as you could get.

The 15 shipments took around 50% of her time every year.

I hired two temps and gave them a few very boring days. When we were done the certificates were all organized in a logical numerical order and in long-term secure storage. I had a folder on the server with 20,000 PDF files all with a unique name. It took me around 15 minutes to locate, print, and upload the required files for each shipment.

Corporate IT is fun!