The new Apple era has strayed considerably from "it just works," except for AirDrop, which has been nothing but a pleasure to work with.
And I assume you are all using Mac?
Because In Cooperate World it is pretty much Windows Only.
The last two companies I worked for — a creative agency with ~50 people, and a larger more anonymous company with ~2,000 employees in 10 states — both were 100% Mac. The first one, because that's how creative agencies have always been. The second for security. The IT dept's policy was no Microsoft hardware or software allowed other than Office: Mac.
As for the workflow, it's like this:
- See file on desktop. - Right-click and select "Airdrop" - Choose destination computer - Notification appears on target computer stating that someone wants to send a file - Destination user clicks "Accept" - File transmits super-duper fast in the background and lands in the destination computer's download folder
Or if you're sending a file to yourself (both devices have the same iCloud/.mac/.me ID) skip everything after the third step.