Leadership

Quote from Letter 9.20 to Urbicus, abbot. October 598

I see how the monastic rule has been broken, when no monks in that monastery are ready to obey you, and you have been unable to arrange anything with consistency.
For that reason, I lament very greatly that I find out our monastery very different from what I thought. And that could not have arisen in any other way, except that your Beloved has been irregular in your rule, and you are incapable of arranging anything with dignity. At one time you are keen to flatter the sinner a little, at another, to be excessively angry with them, without order or moderation. For if you could have held yourself to some rational plan, your maturity itself could have been treated with reverence, and the order of discipline could have been preserved in the monastery.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 557

Saving Souls

Quote from Letter 9.18 to Victor, bishop of Palermo. October 598

A desire that is shown to involve a religious appointment and the saving of souls should be fulfilled without any delay, with God's authority. Thus the community of monks living in the monastery of Praetoria is clearly in need of a priest, for the celebration go solemn Mass, and they ask that one of their own community should be ordained for them with this rank.
Therefore, we exhort your Fraternity with this letter, that your should ordain in the aforesaid monastery the one whom they agree unanimously should be chosen from their community.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 556

Practicalities

Quote from Letter 9.17 to Maurentius, general. October 598

Your Glory should know that we have written to Anthelm, our sub-deacon, asking him to pay attention to sending us some wickerwork chairs, or, if he cannot find any ready-made, to make the artisan himself into his place to work in his home, and weave at least twenty-four really good seats. They are absolutely necessary for us, so your Glory must therefore ensure that this can be done.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 

Spirituality

Quote from Letter 9.15 Jovinus, an illustrious man from Catana. October 598

I rejoice in your quietness, just as much as I groan over my own occupations. And I strongly suggest to you that, if the sweetness of inner delight has touched the palate of your heart, your mind should be drawn inwards, so that all the fine sounds outside, all external delights, are bitter.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 554

Eye to Eye

Quote from Letter 9.14 to John, an illustrious man from Palermo. October 598

We (also) accept your complaint now somewhat less, because we cannot see the man of love. But a person was here to tell me that it was impossible for your Glory to make a voyage now, and for that reason I retained what I loved and spared what had angered me. 
May almighty God guard you with his protection and defend you from all evils with his continual grace.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 554

Allegory

Quote from Letter 9.13 to Venantius, a patrician from Palermo. October 598

I have received the writings of your most beloved Excellency, in which I rejoiced as much in the conversation of an absent friend, as I desire that he who has spoken should always be present with me too.
However, you want me to provide an allegorical interpretation of the deeds of Sampson. But such great bodily weakness has come upon me that, even if some ideas should occur to me, my mind would not rise to follow them up.
Even so, I rejoice in your worthy desire. For in looking for an explanation of holy words, you show how closely you are seeking the author of those words.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 554

Good Qualities and a Vice

Quote from Letter 9.12 to Fortunatus, bishop of Naples. October 598

For the present, we decree that het has been put in charge, so that, if his way of life pleases your Fraternity, you should ordain him after a short period of time as their abbot. For he has good qualities that would please you, but there is this dreadful vice in him also, that he considers himself extremely wise. It is well known how may branches of sin can grow from this root.
Therefore, let your Holiness keep a careful watch over him, and if you find that he has become circumspect in his command and humble in his own disposition, then you should promote him to the rank of abbot, with God's blessing. But if he makes little progress in humility, you should put off his ordination and report back to me.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 553

Talents

Quote from Letter 9.11 to Januarius, bishop of the Sardinians. September-October 598

For that reason, I exhort you to consider the office that you bear with a concerned mind, and shun totally whatever can harm either your reputation or your soul. Realize that you have undertaken the care not of earthly things, but of men's souls. And so you should fix your heart there, show concern there, pay all your attention there and think more diligently about winning souls.
Thus, when the Lord comes, you would return the talents which he handed over to you multiplied, and would deserve to obtain from him the fruit of retribution, and to be exalted among his faithful servants for eternal glory.
But know that my criticism and censure derive not from bitterness, but from brotherly love.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 552

Recommedation

Quote from Letter 9.9 to Gennadius, exarch of Africa. September-October 598

Droctulf [a Lombard] has come from the enemy of the republic, inspired by the goodness of your reputation, that spreads far and wide, and as he has hastened to serve your Excellency with the greatest desire.
And since he had asked for himself to be recommended to you in our letter, we greet you with paternal affection and ask that your Excellency should deign to appoint him, just as God will inspire your heart and it will seem advantageous.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 551

Wise Advise

Quote from Letter 9.6 to Quertinus, ex-praetor. September-October 598

For the administration itself has been offered to  one person prior to him, and to another of lower rank, and they were not at all willing to take part in it, knowing that undertaking this administration is extremely demanding, and especially at this time. 
And so, if it was demanding for them, how much more difficult should it be for that man, who is new to the task? And there is the additional fact that it is useless and extremely laborious for a man of letters to take on cases of financial decisions, and making himself liable for them, which is not expedient.
But besides this, we are put off by the fact that we recall nobody having come well from this activity except your Glory, and for this we pray almighty God to guard you with his protection until the very end. 

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 550

A Dream Message

Quote from Letter 9.5 to Amandinus. September-October 598

And as for what we found in the letters of your Glory, you took those matters badly, which you should not have done, since we cannot remember having written anything harsh, but we encouraged you to feel love and gratitude for him. 
But since you wrote that you were prevented by a dream from sending that letter to us, as you replied to these harsh remarks, we thank almighty God, who guards you while awake so as to warn you even when you are asleep. 
But as you write that in the same dream you were also criticized by me for the same reason, gather even from this what sort of person I am towards you, and when I address you with a fatherly encouragement, you ought not to receive it with ill grace, since, as I am pure to those asleep, I clearly cannot be two-faced to those who are awake.

Cited from: The Letters of Gregory the Great, trans. John R.C. Martyn (Toronto: PIMS, 2004), II, 549