pnp Shadow Thief hierarchy:
Grandmaster of Shadow: the ultimate leader of the Shadow Thieves is the Grandmaster of Shadow, the commander of the Shade Council.
Shades: the eight lesser members of the Shade Council, who act as the guildmasters of a particular sect of the Shadow Thieves in certain cities in Amn and Tethyr: Athkatla, Esmeltaran, Velen, Zazesspur, Myratma, and Riatavin. There are also two separate Shades for all foreign activities and intelligence. One is based in Saerloon and manages all intelligence in the Heartlands (east of Amn), and the other, currently residing in Baldur's Gate, handles the guild information network for the Sword Coast north of Amn.
Shadowmasters: at least two per sect of Shadow Thieves (so there's a minimum of 16 Shadowmasters). One oversees activities within each city of 10,000+ natives, while another handles activities in the surrounding rural areas and towns. Major cities might have multiple Shadowmasters and sects; Zazesspur, for example, has a Shadowmaster for each district, numbering eight in all.
Cloakmasters: a special, additional Shadowmaster who coordinates any work or information passing between foreign powers and the guild. These Cloakmasters report only to the Shades of Saerloon or Baldur's Gate,though many give duplicate reports to the local Shade as a courtesy.
Guildmasters / Silhouettes: each Shadowmaster command 10 sub-guilds (assassins, beggars, bounty hunters, burglars, con artists/tricksters, cutpurses/pickpockets, enforcers/thugs, racketeers, scouts/spies, and fences/smugglers/pirates), and the Silhouettes oversee these. Only higher ranking Shadow Thieves (Shadowmasters and up) use the title "Silhouette", lower ranking thieves know their leader as their "Guildmaster". This nomenclature works to mislead many law enforcers into stopping investigations after they catch a "Guildmaster", even though these 10 lieutenants are relatively low-ranked.
Below the rank of Guildmaster, the individual guilds and various affiliated groups (such as the Bilge Rats of Murann) are free to introduce their own titles and ranks as they see fit.
Shadow Thieves almost never don't know the identity of anyone more than 1 rank higher than themselves. If they do somehow manage to find out such information, they're usually promoted as a reward for their skills, and the person responsible for allowing the information leak will almost certainly be executed (unless of course the person responsible is the Grandmaster of Shadows himself
).