The following excerpt summarizes this ladder to humility.
From "Steps to Humility":
Brethren, the Holy Scripture cries to us saying: "Every one that exalts himself shall be humbled; and he that humbles himself shall be exalted."
"The first degree of humility, then, is that a man always have the fear of God before his eyes shunning all forgetfulness and that he be ever mindful of all that God hath commanded… .
"The second degree of humility is, when a man loveth not his own will, nor is pleased to fulfill his own desires but by his deeds carrieth out that word of the Lord which saith: 'I came not to do My own will but the will of Him that sent Me.'
"The third degree of humility is, that for the love of God a man subject himself to a Superior in all obedience, imitating the Lord, of whom the Apostle saith: 'He became obedient unto death.'
"The fourth degree of humility is, that, if hard and distasteful things are commanded, nay, even though injuries are inflicted, he accept them with patience and even temper, and not grow weary or give up… .
"The fifth degree of humility is, when one hideth from his Abbot none of the evil thoughts which rise in his heart or the evils committed by him in secret, but humbly confesseth them.
"The sixth degree of humility is, when a monk is content with the meanest and worst of everything, and in all that is enjoined him holdeth himself as a bad and worthless workman, saying with the Prophet: 'I am brought to nothing and I knew it not; I am become as a beast before Thee, and I am always with Thee.'
"The seventh degree of humility is, when, not only with his tongue he declareth, but also in his inmost soul believeth, that he is the lowest and vilest of men, humbling himself and saying with the Prophet: 'But I am a worm and no man, the reproach of men and the outcast of the people.'
"The eighth degree of humility is, when a monk doeth nothing but what is sanctioned by the common rule of the monastery and the example of his elders.
"The ninth degree of humility is, when a monk withholdeth his tongue from speaking, and keeping silence doth not speak until he is asked; for the Scripture showeth that 'in a multitude of words there shall not want sin.'
"The tenth degree of humility is, when a monk is not easily moved and quick for laughter, for it is written: 'The fool exalteth his voice in laughter.'
"The eleventh degree of humility is, that, when a monk speaketh, he speak gently and without laughter, humbly and with gravity, with few and sensible words, and that he be not loud of voice, as it is written: 'The wise man is known by the fewness of his words.'
"The twelfth degree of humility is, when a monk is not only humble of heart, but always letteth it appear also in his whole exterior to all that see him; namely, at the Work of God, in the garden, on a journey, in the field, or wherever he may be, sitting, walking, or standing, let him always have his head bowed down, his eyes fixed on the ground, ever holding himself guilty of his sins, thinking that he is already standing before the dread judgment seat of God, and always saying to himself in his heart what the publican in the Gospel said, with his eyes fixed on the ground: 'Lord, I am a sinner and not worthy to lift up mine eyes to heaven'; and again with the Prophet: 'I am bowed down and humbled exceedingly.'
"Having, therefore, ascended all these degrees of humility, the monk will presently arrive at that love of God, which being perfect, casteth out fear. In virtue of this love all things which at first he observed not without fear, he will now begin to keep without any effort, and as it were, naturally by force of habit, no longer from the fear of hell, but from the love of Christ, from the very habit of good and the pleasure in virtue. May the Lord be pleased to manifest all this by His Holy Spirit in His laborer now cleansed from vice and sin."The strange thing for me is finding that the more I strive to be humble, the more confident God seems to make me, which I guess is a fulfilment of His above promise "and he that humbles himself shall be exalted"