If I'm ever a Pyramid contestant and I make the Winner's Circle, I'm giving the clues, no questions asked.
With that in mind, let's go with pHvHounds' scenario, where I need $800 to tie, and I'm having a rough WC. I have :15 to nail the last two categories, and the chances of winning $10K are pretty slim. Since I'll already know my mission going into the Circle, doing an immediate skip to to the top spot is not a bad idea, as long as I can remember to utilize that strategy under pressure.
I'd much rather want to go into the final box tied, as opposed to being down $50 and now banking on pulling a miracle out my rear.