The record Windows keeps of USBMemory sticks and portable disks are logged by Windows as they go in, serial number and all, together with the length of time each stayed connected. A stick first seen on a Sunday evening, days before a resignation, needs explaining.
Webmail, and the sync clientsTraces stay on the machine whichever service it was. OneDrive, Dropbox, Google Drive, or a browser tab of webmail: sync databases, cached tokens, history, uploads that halted part-way. Almost none of it goes when somebody signs out and tidies up.
Wiping tools, and mass deletionMore evidence, not less, is what destroying evidence tends to produce. The name of the tool stays behind, so does the time it ran, and so — this being the detail that usually decides matters — does everything it did not reach.
The sequence is what proves itOn its own, each of these comes with an innocent explanation ready. Set them against the clock, though — files gathered, stick in, upload done, wiper run — and coincidence is no longer the natural explanation.