The teacher must be skilled in tailoring his advice to each student based on a concerned and loving vision of what would be attractive versus what would be awkward and ill adapted to him or her. "Beautiful" and "ugly" are relative categories, a function of taste, preference, and style. What is attractive to one may be repugnant to another, and what is becoming on one may be unbecoming on another. Therefore the teacher must choose his advice–particularly spiritual advice–with the same deliberation he would use in choosing a dress, a suit, or some other garment for a loved one. What should he get? Where should he go shopping? What color? What size? What style and material? How expensive? All these factors must be considered. In both of these decision making processes–choosing what advice to give or selecting what item of clothing to give–the giver holds an affectionate image of the receiver in his mind's eye. The giver "enclothes" the receiver in each option, steps back and evaluates whether the result is in fact becoming, and selects the most attractive of the various possibilities.
This skill follows naturally from the three previously discussed. First, the educator reflects upon his own life and behavior so that his teachings come from a place of humility and self-awareness. Second, he makes a general assessment of the student's interests and intellectual ability, and adapts his approach and style of communication accordingly. Third, he devotes himself to collecting as much specific information as possible about each student, so as to strengthen the bond between them and enhance the flow of influence both qualitatively and quantitatively. Finally, in this fourth stage, the educator uses this reservoir of knowledge concerning the student as the basis for directing the student's growth in one direction or another. In so doing, the teacher must customize his approach. He must become infinitely sensitive to the student's individuality and offer advice that will harmonize with the student's temperament and personality.
Although the decision‑making process itself is quite complex, since many options are explored and only one is chosen, nevertheless, the teacher must express his advice firmly and unambiguously. While it should be clear that his instruction comes from love and concern, nevertheless he must be decisive and unambiguous in his delivery. For maximum clarity, the Talmud suggests that the educator express his advice in positive and negative terms, making explicit both what should and what should not be done.
The discrimination referred to here is not between the "forbidden" and the "permissible," for those are universal concepts which have uniform application. However, within the black-and-white boundaries of prohibited and obligatory, there is a huge sea of gray. This is the area where one may choose to be lenient or stringent, the area where financial, emotional, and health factors become relevant. A teacher must take all this into consideration when his students comes for advice regarding religious practice, for example–perhaps it is time that they be encouraged to go beyond the minimum requirements or perhaps they have taken on too much already and are over-occupied with outer details, neglecting the more difficult work of bringing their learning into their hearts.
For this reason, everyone (even the great spiritual leaders of each generation) is urged to find a spiritual advisor and to develop a relationship with him over time. As it the sages advise: "Make yourself a Rav" (Avot 1:16). The student should consult this advisor on major life choices, thereby incorporating an outside opinion on matters where the ego's vested interests tend to cloud his or her own judgment.