First of all, Augustine of Canterbury must not be confused with Saint Augustine of Hippo, Augustine of Hippo in Northern Egypt is probably the better known of the two having been a prolific writer, exploring many of the doctrines of the early church.
Augustine of Canterbury was a much more timid man who, in the situations he found himself, sought to do the best that he could, but often had to play "outside his comfort zone."
Augustine was born in Italy and studied under Bishop Felix of Messana then, in 573, when Gregory the Great founded his monastery in Rome, which he dedicated to Saint Andrew, Augustine was among the first to join. It was here that he not only began his training as a Benedictine Monk, he also became a close companion of Gregory himself.
In 590, Gregory was chosen to become the new Pope, an office he took up with great zeal, but, as it prevented him engaging in mission, he chose others to carry out his missions for him. Thus, in 595, Gregory chose Augustine to head up a mission to Britain.
Augustine was not the most confident of men, and it has been said that he lacked the imagination needed for such a great task. In fact, as his small team of thirteen monks reached France, they wanted to turn back and had to be encouraged by Gregory to continue. Finally they landed in England and were cautiously welcomed by Ethelberht, King of Kent. Ethelberht was married to Bertha, the daughter of King Charibert of Paris and, as part of their marriage agreement, Bertha had her own chaplain, a monk named Luidhard. Although he knew of the Christian Faith, Ethelberht was not ready to embrace it yet, he did, however, grant Augustine and his monks a piece of land at Canterbury where they quickly started building a church and a school: an approach which was very similar to the one taken by the Celtic Saints in the north.
Augustine's approach was one of caution, seeking to consolidate at every opportunity, rather than go for a sudden expansion and build something which he felt he could not maintain. He continuously exchanged letters with Gregory asking for advice, sometimes on the most mundane matters, and because of this it is Gregory who is often called "The Apostle to the English" rather than Augustine. It was his cautious approach that led to a process known as "Christianisation" whereby, whenever a pagan practise was uncovered, instead of confronting it, it was given anew Christian meaning. In this way, many of the early English Churches were built on former pagan sites so that the new believers could continue to worship in the same place. Their festivals, such as the winter solstice, were replaced with Christian ones, like Christmas.
Augustine's cautious approach did reap dividends as he succeeded in planting Churches in both Rochester and London, and in 600 Ethelberht himself became a Christian and was baptised on Christmas day, after which the King and the Bishop worked closely together in drafting the first set of Christian laws in England. In 601, Gregory sent a second group of monks to reinforce Augustine's mission team and in 604 Augustine died: he may not have been the best man for the task of evangelising England but, with the encouragement of Gregory, he did the best that he could.