You will get a small tutorial of the Virtual Training Program when you first access it. The game will explain what it is, and after that point you can do it whenever you want by hitting . To earn this achievement, you must earn a gold medal on at least 3 different challenges (but they can all be in the same category). These categories are as follows:
- Free Run
- Stealth Assassination
The first 3 Free Run Challenges are the easiest to get gold in. Just run the courses to get the gold medals (probably attempting each a few times).