You could have a hundred painters paint the same subject. But only a handful will describe the essence of the subject that gives it life. Because the composition must be based on some metaphysical connection to the subject. Even if it's only speculative, but better if it is unconscious, or intuitive. A truly great portrait painter climbs inside the subject and finds the persona, and brings it out through the craft.
So the question is Booboo, can a teacher stir this up and out of the average bear? To seek the real meaning of the picnic basket. "Gee I don't know Yogi." I think it is the duty of a good instructor to consider this as part of the training. But there again we are talking about those teachers with enough creative feel to impart that magic beyond the craft. Again, few and far between.
Mark