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.

  • Onno (VK6FLAB)
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    247 months ago

    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.

    • lolpostslol
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      7 months ago

      I’m not in tech anymore but must comment that I work at a major company in a dynamic field with young, ultra-qualified, ultra-smart personnel that is not horribly computer-unsavvy but I still think I’m the only one in the whole company who opens IT support tickets via a system instead of caling, even though IT pushes the system and even though you get good support via the system and horrible people by calling

      • Onno (VK6FLAB)
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        37 months ago

        I see this everyday.

        The ticket system is for the IT department, allowing it to track activities, keep abreast of open tickets, build a knowledge base and share information with colleagues.

        Users benefit from this indirectly.

        Of course, some managers use ticket systems to manage performance metrics. That doesn’t work, but they’ll never learn.

  • @[email protected]
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    167 months ago

    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.

    • @[email protected]
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      137 months ago

      Or Office 365. Yeah, I know people hate SaaS, but businesses love it. Licensing is flexible and scales up and down as you need it. And you get major updates as long as you have a license, unlike when you buy 2021 Pro Plus or whatever, where you’ll always be on 2021.

      • @[email protected]OP
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        37 months ago

        We recently had discussion on this too and 365 is also a possibility. Nobody wants to deal with MS and their licensing though :-D

          • @[email protected]OP
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            87 months ago

            That’s what we’re using now and where quite some problems come from. I don’t have anything against it, it’s awesome suite for personal use, but running it in company we constantly run into problems with compatibility. Every partner we’re dealing with is using MS Office and when they’re exchanging spreadsheets or documents with us it’s often pain in the a*s to make it work. And MS is not helping in this…

        • m-p{3}
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          7 months ago

          If you clearly define your needs, it won’t be hard to figure out which version you’ll want. Then you don’t really have to manage those office installations as long as you have enough licenses in the pool.

          That’s just the tip of the iceberg, you’ll likely want to have something to centrally manage these computers, so something like Intune + EntraID to deploy softwares, manage the user account, etc will be an added cost.

  • @MrPoopyButthole
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    107 months ago

    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.

    • @[email protected]OP
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      107 months ago

      It’s small grocery store chain in the middle of European nowhere, with about hundred of stores run mostly in small villages. Some of those ancient software was made in-house decades ago for internal ordering from wholesaler (also run by the company) to individual shops. Everything in wholesale warehouse runs on the same DOS thing too, with stock inventory, invoice, ordering, … There’s already plan to (finally!!) put it to sleep and replace with something newer and more flexible, but given how low on resources and manpower the company is, it’s not going to happen fast.

  • @SMillerNL
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    77 months ago

    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.

    • @[email protected]
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      27 months ago

      MD is a great idea to promote during this transition.

      I’ve found you also need a company system that is independent of system management tools - some places use a help desk ticketing system, some use a change management system.

      Some friends in the SMB space use a single system for their company (IT consulting firms) to track their clients, client hardware purchase dates, contracts, warranty, every change they make, Admin accounts, device ID’s, their billable time, etc.

      This way all info on a client is maintained in a single place in case (this is the important bit) you get hit by a bus.

      That’s a common refrain - “what happens if bob gets hit by a bus?”. Can’t have any knowledge dependent upon a single person, everything needs to be maintained in a single, accessible form, hosted on company servers and backed up.

      Being a small operation, this could be a hard sell. Maybe an open-source help desk solution that you can host internally would be acceptible. The hardest part with that is defining roles and who has access to what.

      Something you may consider - small orgs have difficulty documenting their systems (basically it’s a lack of manpower, you got shit to do, and documentation seems unimportant). Since there’s a transition, it would be incredibly useful to introduce requirements gathering and documentation. A typical model defines Business Requirements, which are mapped to System Requirements, which are then mapped to Technical Requirements (e.g. One Business Requirement will often map to several System Requirements, which usually map to multiple Technical Requirements).

      Look into Business Systems Analysis, there’s some intro docs out there for how to do this, it’s pretty straightforward, and you don’t have to do all the detail, just having some documentation is better than none.

      • @[email protected]OP
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        17 months ago

        Thanks for deep reply. I’ll chew through it.

        Documentation is non-existent now and that’s what bothers me the most. I, at least, started to put my agenda and acquired how-tos to plain txt files for future, because with so much shit going on I tend to forget stuff. I’d like to extend it and make it system-wide to cover all the IT related stuff in the company with some proper software to do it in (no idea which). But there’s virtually no way this lack of documentation will change dramatically anytime soon. There’s simply no will from higher ups and even if there was, there would be no manpower to do it :-( We’re barely holding things running.

        • @[email protected]
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          6 months ago

          Here’s an idea, since you’re an MS shop - OneNote.

          My SMB consultant friends use it as a secondary, shared, more comprehensive and free-form way to track system docs, changes, etc.

          It’s so easy to use, just using it yourself will sell it to other people in the company, besides giving you a single place to store stuff (that can easily be shared or copied elsewhere when needed).

          When someone asks “where’s this” and you can pull it up in seconds in OneNote, they’ll be impressed.

          Just don’t use the Universal app version of OneNote, or use OneDrive - use the full version included with Office. I’m still using OneNote 2016,though I think there’s a 2022 version (I keep all notebooks in the 2016 version just in case)

          Store your OneNote files on a file share (that gets backed up, and that you can control access), so it only syncs locally. You won’t get mobile device sync this way, but it never leaves the premises, and it’s not sensitive to OneDrive issues (I’ve seen OneDrive hose a notebook). (You can do mobile device sync if you store notebooks on a SharePoint server).

          I have a personal notebook I work from, plus a work notebook (which is just mine, not shared). I then create other notebooks as needed - I have an IT Reference notebook with saved web pages and docs of how to fix problems. My personal notebook has a section for a current laptop rebuild, with a spreadsheet embedded that I open every day to track changes and problems.

          OneNote auto syncs between all devices using a given notebook. You can copy anything into it, even zip files or executables (don’t do this, since OneNote keeps 3 copies of a notebook locally - working version, cache, and backup).

          Last year I started using the PARA model for my notebooks, and it’s a huge help with business stuff: one notebook with section groups (Tabs) for Projects, Area of responsibility, Resources, Archive. I’ve added a fifth section, Reference, to my work notebook.

          I do things like share emails from outlook to OneNote - it puts the email in there with all it’s info, then I can add notes as needed for reference. Great for tracking Approvals.

          If you start using OneNote, there are numerous paid and free add-ons for it that really extend its ability to sort, search, layout, edit, etc, such as OneMore and NoteGem. Just the calendar showing notebook changes is worth installing either one, but the section and page sorting is a massive help.

          I have 15 years of nitebooksbat this point - be judicious in setting up and organizing your notebooks. I’ve found the idea of Archiving to be hugely helpful.

  • @[email protected]
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    7 months ago

    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.

    • @[email protected]OP
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      27 months ago

      There are multitude of OS & software in running. Some people still use DOS, but most of those were already upgraded - to windows XP. These machines are currently being replaced with Win10 ones. But due to some specific old SW there still need to be some DOS machines running, at least for couple upcoming years. Linux is sadly not an option for typical office workers, again due to some software in use. There’s at least open source in places where possible with more (Firefox, Thunderbird, tightVNC, …) or less (LibreOffice) success.

        • @[email protected]OP
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          27 months ago

          I haven’t tried, but given how quirky it is (in house development decades ago with patches and hotfixes stuck to it over years) I highly doubt it would work. The main problem is that there’s no will to use Linux in office environment…

          We’re at least running it on POS machines - about 150 openSUSE installs - where there’s nothing fancy needed.

          • @[email protected]
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            37 months ago

            DOSBox runs on both Linux and Windows (and probably Mac too?); I was suggesting it since you might be able to replace the dying DOS computers with a modern system and just launch the legacy system as an application under it. (You might be able to do the same with a VM as well, but DOSBox came to mind first and may be easier to setup and distribute.)

            Just a thought. If it’s not useful, feel free to disregard.

            • Nougat
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              37 months ago

              Hell, DOS is open source now. Run it in a Hyper-V on Windows 10.

      • @[email protected]
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        27 months ago

        I haven’t tried to run DOS on Win10, but I haven’t been able to get my old DOS programs to run on anything Windows XP or newer, myself. XP at least had some compatibility options to try. I don’t think I’ve seen those options in Win7 or newer.

        It will vary by program, but I’ve needed DosBox on Windows, as well as on Linux, for anything DOS based that I have run anytime recently.