It's because once the glycerol chain leaves, the O's want to abstract the H's from the OH that attacked the carbonyl in order to become more stable. The negative charge on the O can be better resonated with the double bonded O than if the negative charges remained on the glycerol O's. Basically, the alkoxide (glycerol without the H's) functions as a stronger base than the carboxylic acid's conjugate base, so a rapid acid-base reaction occurs.