Plans should be evaluated for likelihood of success before you try them.

But most of the time when PCs are involved a post mortem will just have to do.

Transcript

{on board a star destroyer}
Lieutenant Cabbel: Sir, Rebel ships are coming into our sector.
Captain Lennox: Good. Our first catch of the day.
Captain Lennox: Wait... Did you say our sector?
{a Rebel transport with two X-wing fighter escorts flies right past the star destroyer}
Captain Lennox: Recalibrate the guns! Recalibrate!!
[SFX]: Whooooooooosssshhhh!!!
Lieutenant Cabbel: Aaaaand that's them going into hyperspace...
{Rebel hangar}
Rebel PA System: The first transport is away!
Rebel pilots: Yaayyy!!
Han: Fly straight at them... What kind of ridiculous plan was that?!
Chewbacca: The sort that actually works, my good fellow.
Han: Exactly!