Gotcha! I decide on a constellation, then what might be there or the near vicinity. eg. Messier object or double stars, and then work to that. Saves time spent re-orienting myself. If I get 6 to 8 objects for a 2 hour session I'm more than happy. Even happier if I get to see them all.
If I can't get enough from the one constellation, then I choose a second to go with the first. I then explore the one that's closest to setting to explore first.
I'm sure there are many ways of organizing an evening's session, but this works for me.
Another way might be to just explore a single quadrant of sky. In Astroplanner this can be done easily by picking everything which you might want to see that night then clicking on the top of the column that will sort them into say, RA, then choose a group in a particular region to explore and forget the rest until tomorrow. (Dangerous if you live in Melbourne where the nights' conditions are so variable)
Astroplanner is very good in that you can sort the hit-list data on whatever is of immediate interest just at the click of a button.
Hope that's of some help.