Training Effectiveness - What Are You Most Proud Of?

Hi everyone! I'm trying to build a comprehensive method of developing continuous cycles of measuring training effectiveness.

This is for ramping people up before they experience a huge shift to a new software system from a legacy system (think ERP solution). I want to have enough opportunities to get folks digging into the system through some role-based/problem-based scenarios. But I want to know how to keep the cycle going on a continuous basis and not after every long cycle.

So I wanna know -- what training effectiveness exercises/surveys have you done? Why are you proud of it? What did it look like? And can I copy it :)