Gregory and monasticism
Although the first monk to become pope, Gregory was in no sense an original contributor to monastic ideals or practice. He took monasticism as he found it established by St. Benedict, and his efforts and influence were given to strengthening and enforcing the prescriptions of that greatest of monastic legislators. His position did indeed tend to modify St. Benedict's work by drawing it into a closer connection with the organization of the Church, and with the papacy in particular, but this was not deliberately aimed at by Gregory. Rather he was himself convinced that the monastic system had a very special value for the Church, and so he did everything in his power to diffuse and propagate it. His own property was consecrated to this end, he urged many wealthy people to establish or support monasteries, and he used the revenues of the patrimony for the same purpose.
He was relentless in correcting abuses and enforcing discipline, the letters on such matters being far too numerous for mention here, and the points on which he insists most are precisely those, such as stability and poverty, on which St. Benedict's recent legislation had laid special stress. Twice only do we find anything like direct legislation by the pope. The first point is that of the age at which a nun might be made abbess, which he fixes at "not less than sixty years" (Epistle 4.11). The second is his lengthening of the period of novitiate. St. Benedict had prescribed at least one year (Reg. Ben., lviii); Gregory (Epistle 10.9) orders two years, with special precautions in the case of slaves who wished to become monks.
More important was his line of action in the difficult question of the relation between monks and their bishop. There is plenty of evidence to show that many bishops took advantage of their position to oppress and burden the monasteries in their diocese, with the result that the monks appealed to the pope for protection. Gregory, while always upholding the spiritual jurisdiction of the bishop, was firm in support of the monks against any illegal aggression. All attempts on the part of a bishop to assume new powers over the monks in his diocese were condemned, while at times the pope issued documents, called Privilegia, in which he definitely set forth certain points on which the monks were exempt from episcopal control (Epistles 5.49; 7.12; 8.17; 12.11; 12.12; 12.13). This action on Gregory's part undoubtedly began the long progress by which the monastic bodies have come to be under the direct control of the Holy See.
It should be mentioned that in Gregory's day the current view was that ecclesiastical work, such as the cure of souls, preaching, administering the sacraments, etc., was not compatible with the monastic state, and in this view the pope concurred. On the other hand a passage in Epistle 12.4, where he directs that a certain layman "should be tonsured either as a monk or a subdeacon", would suggest that the pope held the monastic state as in some way equivalent to the ecclesiastical; for his ultimate intention in this case was to promote the layman in question to the episcopate.
Conclave Begins on Feast of Pope St. Gregory the Great
The Transalpine Redemptorists have noted that the conclave is set to begin on March 12th, the feast of Pope St. Gregory the Great. I have included an excerpt from the Catholic Encyclopedia entry on Pope St. Gregory the Great. I encourage you to read the article in its entirety.