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After you receive your first Hero Doll, either from winning at a tavern game, or receiving it by any other method, the next time you visit Bowerstone South, a little kid will run up to you and tell you about this quest.

This is an on-going quest with many parts throughout the game, so it will be broken down to each point in time where you can earn another doll.

Hero Doll Acquired
Briar Rose Beat 30 seconds on Card Pairs.
Whisper Score 11 or less while playing Coin Golf.
Twinblade Beat Spot the Addition in under 25 seconds.
Thunder At the Arena, if you're evil, steal the doll, but if you're good, just purchase it from the vendor. If you have already done the Arena quest, the Thunder doll can also be purchased from the store in Northern Bowerstone.
Scarlet Robe Beat the Card Sorting game in less than 25 seconds in Knothole Glade.
Maze Score 30 or more at Shove Ha'Penny.
Scythe Beat the Coin Golf game in Snowspire village using 10 strokes or less.
Jack Once you've obtained the seven Hero Dolls the teacher from Bowerstone South will find you about the dolls. Speak to him to complete the quest. When you beat this quest you will lose the seven dolls you had but you will get a new one in return.
Bonus doll This doll is not needed to finish the Collect The Hero Dolls quest. However, during the Assassin Attack side quest, you will receive a Hero Doll of yourself after killing one of the assassins.