Will had been a poacher before joining the Night's Watch, hunting in House Mallister's woods. After Lord Mallister's freeriders caught him skinning a buck, Will choose to taking the black instead of losing a hand.
Will is portrayed as a seasoned and cautious ranger, having spent four years ranging beyond the Wall.
Shortly before the series starts, Will, Gared, and Ser Waymar Royce were sent ranging into the haunted forest by Jeor Mormont, Lord Commander of the Night's Watch, in search of a band of wildling raiders. Jeor gave the command to Waymar, although he was the least experienced of the three, whereas Jeor counted Gared and Will among his best men. However, Waymar felt it was his due to have a command because he was a knight, and the Lord Commander accepted because he did not want to offend Waymar's father, Lord Yohn Royce. Will's negative perspective on Waymar Royce is influenced by this, who describes him in his chapter as a pompous and stuck up person. In the end, Sir Waymar Royce dies facing the Others with great valor while Will stays in the tree which he climbed to overseee the lands beyond the Wall.