The Church Fathers, pt (vi). From ‘The Story of Christian Theology’, Olsen, (IVP).

Roman Catholicism consider him to be one of the 4 great doctors of the church (with Ambrose, Jerome, and Augustine). In a time of weak Empire, Gregory provided authority; he contributed great missionary effort to Britain and others. He was significant not for his originality but for his influence.
He created a hybrid of Augustine and Cassian – he read Augustine through Cassian. In emphasising God’s sovereignty and man’s sin, he sounded Augustinian; in emphasising Christian discipleship and responsibility, he sounded Pelagian. This created a balance of warning and comfort:
Even the predestination itself to the eternal kingdom is so arranged by the omnipotent God that the elect attain it from their own effort.
He also said that preaching involved two tasks: comforting the afflicted, and afflicting the comfortable.
Essentially he was a synergist: he believed that Christ didn’t fulfill everything, and so penitential acts of self-sacrifice were needed. This undermined assurance, or security, about salvation. Luther was taught Gregory’s version of Augustinianism and was plagued by guilt.