Sysadmin

Hello everyone, I hope I came to the right place to ask my stupid question. I'm currently working in a company that stuck way way back in time. I'm talking some people are still working in DOS level back in time. There is some revamping of this in progres, but it's going to be a long run.

The "IT department" (called computing department, lol) consist basically of 2 people, boss and me. Boss loves the old days, he's "happily" using Win XP on his computer and hates everything newer than Win7, although half of everything he tries to do doesn't work there anymore (and don't even start with security of the OS). Anyway... that's about the company background and what to expect.

During currently ongoing upgrades to get this company at least to 21st cwntury, there will be some sw licencing happening. I'm expecting like buying dozens of Office 2021 keys and some other standalone soft too. But there's problem with managing those keys, as there is no precedence, no rules and everything's going to be from the scratch almost. People are coming and going, PCs are dying (remember, there are still some DOS machines), hard drives replacing, etc. etc. Windows domain? Not in this company. Ever.

So, how do you keep track of what is installed and where? Thank you very much.