why riddle the caller? Just have some voice controlled computer asking the basics like "did you try to turn it off and on again" with the shortcut of saying "yes" before the sentence is completed (a computer is not annoyed by this). Then you will enter enough information like "yes, it says 'timeout' every time" for the real support guy.
Voice controlled tools are nice gadgets, but can't beat a good troubleshooter, even on the phone.
user: Yes the application says 'timeout' every time.
Support: That ticking sound I hear in the background 'tick..tick..tick..tick' does it come from you're computer
Support: If this is recent behavior, you're hard disk is probably crashing. You need to visit a hardware store and come back for applicative support after fixing that.