If you're like me you might be confused and wondering where your special reward is for being Guild Master. RELATED: Skyrim: Every Thieves Guild Shadowmark (& What They Mean). The Thieves Guild, Dark Brotherhood, the Companions. After i'm done with thieves guild stuff i'll try and go back to being all about heavy armor, being a master of healing spells, and purging skyrim of filthy heretics with my dwarven warhammer. Now you only have to do ONE quest in each Hold to get the corresponding quest and the levels for the items at the Guild Master's desk are: 5,6,7,8,9,10,11,12. This trophy will be a bit of a grind, as it requires the player to reach level 50. The Elder Scrolls V: Skyrim (Skyrim) PC … You have to do more to get there.