What Windows notes about USBWindows logs every memory stick and portable disk that goes into it, the serial number included, and how many hours it stayed connected. One appearing for the first time at two in the morning on a Sunday, a few days ahead of a resignation, wants explaining.
Webmail and cloud storageWhichever service was used — OneDrive, Dropbox, Google Drive, or webmail in a browser — traces stay behind on the machine: sync databases and cached tokens, the browsing history, uploads that stopped part-way. Signing out, then clearing up afterwards, removes hardly any of it.
Wipers and wholesale deletionDestroying evidence tends to create more of it. What is left behind is the name of the tool, the time at which it ran, and — usually the deciding detail — everything it could not reach.
The order is the evidenceTaken singly, each of these has an innocent explanation waiting for it. Lay them out against the clock — files gathered, stick in, upload completed, wiper run — and coincidence stops being the obvious reading.