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Assuming you do know how hired workers are supposed to work in this game, my best advice is the start the job yourself. Once the tractor and tool are partway onto the field doing their job, then switching to the hired worker should just work. If you start back a little ways off of the field, sometimes the game doesn't know what you want the hired worker to do.
You might be out of money..
Go to the controlls and hit reset to default...
Not really sure what else might cause it