How do you roll out of a set?

I wanted to start a little database here of ways to roll out of a set. Typically you want to do this at an emotional high point, which kind of plants a seed for something bigger later. Advice? Strategies? This is probably one of the weakest parts of my game, and I often find myself realizing that I should have rolled out a moment before the realization.

So: 1) How do you time your rollouts 2) How do you execute your rollouts?