The wifi is actually somewhat excusable, if they only ever connect to the internet at home or work and could have been years since those two networks were configured. Plenty of people never use internet on their laptop outside of two or three places.
However, it's pure lunacy on the part of the IT guy to expect people to know the specific proxy settings (including whether or not a proxy is needed), where to enter them, what sites exactly are being blocked, and how to diagnose where in the chain of powerpoint -> computer -> AP -> proxy -> internet your video is failing and how to fix it.
Going to cars, that's like expecting someone to be able to diagnose why an engine isn't starting when they turn the key in the ignition. Without any sonic or haptic clues.
Well yes - even an amateur has a chance of realizing from said clues whether their battery is dead, or they're out of gas.
But for network issues, the error message you're going to get 19 times out of 20 is some minor variant of "Server could not be reached." Which offers no additional information that you don't already know from it failing to work.
"Server can't be reached" gives critical, actionable information. Error messages can be searched for! If you can't search for an error message, you can't use a computer.
Or you can't search for it because you can't reach the internet.
Anyway, if you can definitively figure out which of the following is true from that message without the use of additional diagnostic utilities, well... (yes I have personally seen all of these (except exactly 12 which I've seen variants of but worded it the same way as the article))
1. Your cable modem can't find a signal, because of weather conditions
2. Your cable modem can't find a signal, but can once it's rebooted
3. Your access point stopped working, and needs a power cycle
4. The AP failed to give your computer any of: an IP address, DNS, a gateway, a working gateway
5. Your computer thinks it's connected to a wireless network, but the AP isn't receiving packets it sends
6. Your computer thinks it's connected to a wireless network, has the correct gateway, and can ping the AP, but nothing else (despite other computers on the same network working fine)
7. Your AP randomly resets long-lived TCP streams (due to a bug in its firmware)
8. Your ISP reliably corrupts traffic from eBay, fixed by getting a different IP address and gateway from the ISP (by changing MAC addresses)
9. Your ISP has the wrong DNS entries for the site you're attempting to visit
10. You need to visit a specific, unadvertised intranet page and sign in before your connection works
11. You need to manually enter intranet proxy settings before your connection works
12. Your intranet proxy is blocking Youtube and the player you're using doesn't bundle a general-purpose web browser
13. Youtube videos buffer at 3 kb/s from your laptop, but work fine from your tablet, on the same network
(okay 12 and 13 are cheating a little since they don't give any error message, but the point is that the error messages are basically never enough on their own to diagnose network issues)
Again, you can search with mobile, or someone else's mobile, someone else's laptop, etc.
I appreciate your point regarding the multitude of possibilities for a server error, but remember what we're talking about. The user did not even attempt to read the error message, did not know what it said, and kept retrying thinking things would change. He didn't take some next step to try to diagnose potential connection problems (e.g. check for ethernet cable), he just threw his hands in the air, said it doesn't work, and ran to IT. He can't use computers.
No, the problem is that complex systems fail in non-obvious ways. Even highly technical and computer savvy people still need to hit the reset button on a Windows PC or router, due to an un-diagnosable problem which then magically goes away. Computers are not intuitive without a large amount of experience to know how things 'should' work.
This is a recognised phenomenon in safety critical systems such as those protecting nuclear plants - simple devices fail in known, predictable ways, complex devices fail in non-deterministic ways. This is why humans generally don't 'get' computers, and aren't willing to invest even minimal time in understanding them - there's no payoff until you've invested a huge amount of time to cover the majority of the problem space.
The only solution is higher quality in the development of software and hardware, and that's back on us.
However, it's pure lunacy on the part of the IT guy to expect people to know the specific proxy settings (including whether or not a proxy is needed), where to enter them, what sites exactly are being blocked, and how to diagnose where in the chain of powerpoint -> computer -> AP -> proxy -> internet your video is failing and how to fix it.
Going to cars, that's like expecting someone to be able to diagnose why an engine isn't starting when they turn the key in the ignition. Without any sonic or haptic clues.