In the School of War game, each player is paired with a TA who works exclusively with that player on formulating strategy, discussing moves, and generally acts as a mentor for the player throughout the game. Each player and their TA should be constantly communicating with questions, observations, and ideas, with the idea being that the TA serves as a source of experience and knowledge while the beginning player learns about the game from someone who knows how to play well.
During the game itself, we keep a discussion thread going in the forum where third parties or TAs are welcome to ask questions and discuss the ongoing game, ideally without affecting gameplay too much. Each game also has two or three Professors, usually some of the top players on the site, who will post thoughts and observations on the game each turn based on what they see. Professors, for example, may post their "power rankings" of each country, critique moves, answer questions, discuss possible moves and builds, and generally talk Diplomacy strategy within the context of the ongoing game.