During the Office Worker job, one of the tasks you'll get toward the end of the job is to shred documents and a floating shredder will appear. You're also asked to shred 5 items of your choice from your office area.
At some point during this section (whether it is one of the 5 items or not), you need to grab the toy of the JobBot and throw it in the active shredder. The toy is sitting on top of the coffee maker, to the right of the computer.