The organosilane is activated with  fluoride (as some sort of salt such as TBAF or TASF) or a base to form a pentavalent silicon center which is labile enough to allow for the breaking of a C-Si bond during the transmetalation step. The general scheme to form this key intermediate is shown below. This step occurs in situ or at the same time as the catalytic cycle in the reaction. 
The mechanism for the Hiyama coupling follows a catalytic cycle, including an A) oxidative addition step, in which the organic halide adds to the palladium oxidizing the metal from palladium(0) to palladium(II); a B) transmetalation step, in which the C-Si bond is broken and the second carbon fragment is bound to the palladium center; and finally C) a reductive elimination step, in which the C-C bond is formed and the palladium returns to its zero-valent state to start the cycle over again. The catalytic cycle is shown below.