Sysadmin

Q: How do you eat an elephant?

A: One bite at a time.

Whilst you are faced with a multitude of issues, don't get lost in the weeds by details when you are trying to untangle the past to move it forward.

A simple spreadsheet to track hardware, licenses and other details like location, specs and primary contact is a perfectly reasonable starting point.

I say that because you don't know what you don't know yet. You might for example discover that some shops are doing their own thing, regardless of company policy.

Creating a ticketing system is useful to track stuff for everyone. I settled on trax with web access to people who need it, but the computer literacy levels might prevent some from using this.

Burnout is a very distinct possibility in an environment like this, so make sure that you set aside time for you to think. Call it a meeting, call it an on-site visit, whatever you do, take time to think.

Also, remember to backup your work. It's not unheard of for it to vanish unexpectedly if you are perceived as a threat.

Source, I've been working in this profession for 40 years.

If you're buying dozens of Office keys, then a site license for Windows and Office makes a lot more sense.

And those licenses are managed between you and MS. Then it's a simple count of Office installations and you know how many licenses you should be using. You typically do an annual license "true up" with MS.

I always wonder how these relics make any money using systems that old. To do business with some of our clients, they audit us for ISO 27001 compliance once per year. Anything out of support would be flagged and we could lose a lot of business.

Mobile Device Management software to keep track of what’s installed on devices (probably won’t work with DOS)

I personally use a password manager to keep track of software keys, but realistically you should probably look for a way to get licenses that doesn’t involve typing a key everywhere.

If you can get the organization to switch to Debian, you could do it all with free software and manage the whole thing with Ansible.

I mention this because if the org is running Windows software that old, then current generation FOSS software is going to be a breathe of fresh air, by comparison.

It might not work if someone with a C title has a specific magical Windows package they want.

But even then, I would manage one or two Windows PCs (for a couple of C suite execs) by hand, than a full organization full. And you would save the organization a boatload of money.