Okay... so I think I figured it out. It appears to be an issue with OneDrive, which turned itself on recently. I don't use it, so when I saw the alert pop up, I just ignored it until I had time to look at it - which never came. This morning, a file I created last week was available to me, but not to our IT guy (and I haven't restarted since the last forced update).
Once I started poking around, I found the Word doc in the list of files that showed up when I hovered over the OneDrive icon in the active task bar. Once I unlinked my PC from OneDrive, re-synced offline files and placed the file back in the shared folder, he was able to see it.
I'll keep an eye on it, but I'm going to hope OneDrive was the issue.