As I was working my way through one of the missions/achievements in mafia wars 2 I noticed that if done properly you can help more than the 5 times you have energy for. It made doing this achievement just a bit easier :)
Anyway all you have to do is queue up your actions as quickly as possible, anything you have selected to perform before he finishes his first task will be performed. And as you can see it counts!
I seem to average getting an additional 1 or 2 tasks in, but it helps in the long run! and helps your firend too!