I am kind of glad that he is trying to learn something. Don't take me wrong I would be happy to help with Ubuntu or Debian setup given that it is going to take some little extra time and in exchange we all learn something. I myself use Mint and Mac OS. I see the benefit. But I can't with clear consience tell the customer that we use the time meaningfully if we are spending 30 minutes trying to set up his vpn client.

We are here to work not to spend hours trying to learn core linux features on our paid time.

What would you guys do? I told him that I would be much happier if he used some more user firendly distro. Doesn't have to be debian based. Just something kind of works.

You use what the rest of the team use if you need support

Give him a laptop to do his job on with an operating system that everyone else uses?

Use a good base Os like Ubuntu and then use Virtual machines to mess with Arch etc.

Windows + wsl is the answer.

As it’s work, get him to use the same as the vast majority of the team use. Aside from less issues getting things working, he can tap a pool of greater knowledge from colleagues without irritating people or disproportionately burning billable time.

Getting an old bit of kit like a laptop or old workstation out for a learning/studying machine however is 100% a solid idea. If there is any flexibility in the schedule for study time, then it can be planned and structured. 4 hours a week, 2 on Tues and 2 on Friday. Or if you do read-only-Friday, great opportunity to mentor and develop a junior. I would argue however there might be more relevant aspects to learn that are directly applicable to their role, like setup dev versions of whatever systems are in use, or deploy automation from scratch to mirror what is used in prod etc.

No matter what you choose, it’s great that you encourage their development, not all employers/managers encourage or allow this.

Even more true for the users - we had a Comms/Marketing query last week - "Can new hire X please have a Mac for graphic design tasks?". Our answer was "yes, but only if they don't need support from the support team" because we don't have that expertise and don't have time to learn it to support 2 users.

They were understanding, thankfully.

Part of growing up

My initial venture to the computer world is the insatiable pre-teen urge to haxx everyone in the world using Kali Linux, while wearing a black hoodie (I live in a tropical country)

I fucked around with Linux Desktop from 2018-2023 across various distros

Almost a decade later, I use Windows on my desktop systems and Linux on my servers

In my experience they often are understanding initially but then want support anyway.

With AI these days kids learn on their own. Ask him to install opencode with his chatgpt subscription and try to configure things on his own.

I used to use Arch Linux during my early days trying out different distros mainly because of the "I use Arch btw" Meme
I saw it as a challenge to manually Install the OS etc.
After having to Troubleshoote why my X Server wasnt working every other week after Pacman -Syu I quickly learned to enjoy stable Channel distributions rather than rolling releases

As some Others have Said give him a OS you Guys actually run and let him have Arch in a VM to Play around

What would you guys do?

Step 1: Stop dealing with personal devices.
There's no step 2.