You are assigned targets at random, without regard to the number of jobs that you've already taken in a particular hold. Completing all four reputation jobs is a prerequisite to becoming the Guild Master. You may start taking these jobs at any time after officially joining the guild (completing Taking Care of Business). Once you have completed five jobs in a particular hold (except the Rift, where the Guild already has influence), Delvin will offer you a special 'reputation' job to increase the Thieves Guild's influence there. To get an improvement job, talk to Delvin Mallory or Vex you can have one quest active from each. In order to restore the Thieves Guild to its former glory and assume the title of Guild Master, you must perform small jobs in four holds of Skyrim: Haafingar, the Reach, Whiterun, and Eastmarch. The quest will not begin until you complete all prerequisites. Note: This section only describes prerequisites for this quest.
The members of the guild awaiting their new guildmaster