You can’t help those who won’t help themselves. Most people aren’t really interested in improving their workflow — they don’t see the value of it — so they’re basically unhelpable when it comes to this stuff. They’ll keep doing what they do until either they retire or changes in the software ecosystem forces it (like when people used to store their data directly on the C drive before Windows security stepped it up). I’ve decided it’s not worth spending any energy on these people. You’ll recognize them when you give them a tiny bit of advice (“There’s a shortcut key for that, so you don’t need to dig through three menus all the time.”) and they completely ignore it. This wouldn’t bother me much, but unfortunately it’s usually the people that have these awful workflows that get to decide the standard corporate system configuration (like buying WinZip licenses in 2015).

Where I’ve had the most success is when someone who is interested in improving gets to watch me in my workflow. They’ll see me do wizardry with Emacs (or some other thing I use) and start asking questions because they hadn’t realized how much easier some particular task can be (I’ve seen people spend hours doing things that should take about one minute). That’s exactly why I like following Emacs blogs and such. I pick up all sorts of new tricks from other people that makes productive work easier and faster.

@ Dr. Azrael Tod:

Network shares do have their own peculiar drawbacks:

– Office files getting locked when someone is editing them
– Some asshole accidentally deleting shared folder
– Version hell when people try to collaborate “New”, “New New”, “Updated”, “Updated New”…

Also executives love to circumvent this by asking their assistant to email them the file, then mail it back to be put in the right place because they can’t be bothered to navigate a file system.

But yeah, I think cloud based apps do solve this problem by abstracting the file-system and enabling concurrent collaboration. You do trade off local storage, control and responsiveness of a native application for a flaky web interface that you have no direct control over. :(

some bigger companies/organisations did try to circumvent that whole “send me that file in outlook”-workflow by introducing network-shares/web-tools where documents _have_ to be stored.
(even going as far as introducing office-plugins that make this the default save/load-location)

And then there is that whole cloud-bullshit-stuff, where people even sometimes have a finer control about who changed what in which version. So we kinda see the situation getting better.. but in the worst possible way.

@ Robert:

I did have some luck training users to “Save to the Desktop” because files just show up there, and can be found easily. Somehow the Desktop is a more real place than “My Documents” because it can be observed directly I guess. Next step of course is teaching them to keep stuff organized.

And yes, ten thousand files piled on the desktop without any kind of organization quickly becomes a brand new issue, but at least it is a step in the right direction.

For almost all users the file system is a horrible place full of dragons and terror. The only way they can deal with it is by double-clicking on files they see in their email or on their desktop, or through the File, Open dialogue in Word and Excel. Ask where their files are saved and you’re likely to get a response like, “In Word,” in a ‘duh, where else?’ tone.