Aside from Montaigne and perhaps Plato, few philosophers have reflected deeply on conversation, especially the one-to-one, heart-to-heart exchange of thoughts between friend and friend. A shining exception is Ralph Waldo Emerson, who wrote as follows in his essay on friendship:
Friendship may be said to require natures so rare and costly, each so well tempered and so happily adapted, and withal so circumstanced (for even in that particular, a poet says, love demands that the parties be altogether paired), that its satisfaction can very seldom be assured. It cannot subsist in its perfection, say some of those who are learned in this warm lore of the heart, betwixt more than two. I am not quite so strict in my terms, perhaps because I have never known so high a fellowship as others. I please my imagination more with a circle of godlike men and women variously related to each other and between whom subsists a lofty intelligence. But I find this law of one to one peremptory for conversation, which is the practice and consummation of friendship. Do not mix waters too much. The best mix as ill as good and bad. You shall have very useful and cheering discourse at several times with two several men, but let all three of you come together and you shall not have one new and hearty word. Two may talk and one may hear, but three cannot take part in a conversation of the most sincere and searching sort. In good company there is never such discourse between two, across the table, as takes place when you leave them alone. In good company the individuals merge their egotism into a social soul exactly co-extensive with the several consciousnesses there present. No partialities of friend to friend, no fondnesses of brother to sister, of wife to husband, are there pertinent, but quite otherwise. Only he may then speak who can sail on the common thought of the party, and not poorly limited to his own. Now this convention, which good sense demands, destroys the high freedom of great conversation, which requires an absolute running of two souls into one.
Can conversation with your coach, counselor, or personal philosopher reach this same height? Although some might argue that conversation requires a long-term relationship to flower so beautifully, I posit that a deep connection between two persons is more a matter of affinity and aspiration than of mere time. Yet there is much wrapped up in these words “affinity” and “aspiration”; we don’t understand these phenomena very well because they involve aspects of life that are both vague and fragile, such as values, idealism, personality, character, thinking styles, openness to experience, vulnerability, attunement, fellow-feeling, true listening, trust in self and other, yearnings for self-knowledge and interpersonal connection, etc.
When a deep rapport takes root, conversation and consideration are not forced but utterly natural; as the Taoist philosopher Chuang-Tzu wrote many centuries ago, no special effort is required:
Tzu Sang-hu, Meng Tzu-fan, and Tzu Ch’in-chang were friends. They said to each other: “Who can live together without any special effort to live together and help each other without any special effort to help each other?” ….The three looked at each other and smiled, completely understood each other, and thus became friends.
Even though such rapport might seem magical, I suspect that there are specific skills and practices involved, which can be deliberately honed over time. Although some of these are fairly well defined (e.g., listening skills), others have been barely explored and rarely analyzed. The work of the soul is neverending and endlessly fascinating.