This Achievement can be earned after about 20 minutes of simulating.
Begin a new General Manager Mode game. Select Schedule from the interface menu, and select the current week's event. Press the X button to use a predefined bout card, then press the LB button to switch to the list of matches and choose "Confirm".
If you have any wrestlers under contract on your roster, you will then need to simulate the matches with the Y button. Otherwise, just press A to continue to the next week in the schedule.
You won't win the Manager of the Year award with this method, but it will give you a quick 50 points if you need them for a 360voice challenge or just to keep your Achievement streak alive for another day.
The Achievement will unlock following the Manager of the Year award presentation by Vince McMahon.