Here's a sample of St Gregory's pastoral wisdom and discernment, from his classic work on Pastoral Rule:
Every teacher, that he may edify all in the one virtue of charity, ought to touch the hearts of his hearers out of one doctrine, but not with one and the same exhortation.
Differently to be admonished are these that follow:
Men and women.
The poor and the rich.
The joyful and the sad.
Prelates and subordinates.
Servants and masters.
The wise of this world and the dull.
The impudent and the bashful.
The forward and the faint-hearted.
The impatient and the patient.
The kindly disposed and the envious.
The simple and the insincere.
The whole and the sick.
Those who fear scourges, and therefore live innocently; and those who have grown so hard in iniquity as not to be corrected even by scourges.
The too silent, and those who spend time in much speaking.
The slothful and the hasty.
The meek and the passionate.
The humble and the haughty.
The obstinate and the fickle.
The gluttonous and the abstinent.
Those who mercifully give of their own, and those who would fain seize what belongs to others.
Those who neither seize the things of others nor are bountiful with their own; and those who both give away the things they have, and yet cease not to seize the things of others.
Those who are at variance, and those who are at peace.
Lovers of strife and peacemakers.
Those who understand not aright the words of sacred law; and those who understand them indeed aright, but speak them without humility.
Those who, though able to preach worthily, are afraid through excessive humility; and those whom imperfection or age debars from preaching, and yet rashness impels to it....
Differently to be admonished are the wise of this world and the dull. For the wise are to be admonished that they leave off knowing what they know; the dull also are to be admonished that they seek to know what they know not. In the former this thing first, that they think themselves wise, is to be overcome; in the latter, whatsoever is already known of heavenly wisdom is to be built up; since, being in no wise proud, they have, as it were, prepared their hearts for supporting a building. With those we should labor that they become more wisely foolish, leave foolish wisdom, and learn the wise foolishness of God: to these we should preach that from what is accounted foolishness they should pass, as from a nearer neighborhood, to true wisdom.
Every teacher, that he may edify all in the one virtue of charity, ought to touch the hearts of his hearers out of one doctrine, but not with one and the same exhortation.
Differently to be admonished are these that follow:
Men and women.
The poor and the rich.
The joyful and the sad.
Prelates and subordinates.
Servants and masters.
The wise of this world and the dull.
The impudent and the bashful.
The forward and the faint-hearted.
The impatient and the patient.
The kindly disposed and the envious.
The simple and the insincere.
The whole and the sick.
Those who fear scourges, and therefore live innocently; and those who have grown so hard in iniquity as not to be corrected even by scourges.
The too silent, and those who spend time in much speaking.
The slothful and the hasty.
The meek and the passionate.
The humble and the haughty.
The obstinate and the fickle.
The gluttonous and the abstinent.
Those who mercifully give of their own, and those who would fain seize what belongs to others.
Those who neither seize the things of others nor are bountiful with their own; and those who both give away the things they have, and yet cease not to seize the things of others.
Those who are at variance, and those who are at peace.
Lovers of strife and peacemakers.
Those who understand not aright the words of sacred law; and those who understand them indeed aright, but speak them without humility.
Those who, though able to preach worthily, are afraid through excessive humility; and those whom imperfection or age debars from preaching, and yet rashness impels to it....
Differently to be admonished are the wise of this world and the dull. For the wise are to be admonished that they leave off knowing what they know; the dull also are to be admonished that they seek to know what they know not. In the former this thing first, that they think themselves wise, is to be overcome; in the latter, whatsoever is already known of heavenly wisdom is to be built up; since, being in no wise proud, they have, as it were, prepared their hearts for supporting a building. With those we should labor that they become more wisely foolish, leave foolish wisdom, and learn the wise foolishness of God: to these we should preach that from what is accounted foolishness they should pass, as from a nearer neighborhood, to true wisdom.