It seems that The Stone‘s contributors’ responses to readers’ comments are often better than their original posts themselves:
Philosophers typically try to illuminate with a combination of argument and (re-)conceptualization. But the most careful and perspicuous argumentation, as indispensable as care and perspicuity are, will not convince someone who is disinclined to accept a philosopher’s way of framing a problem or phenomenon. And, as the philosopher Stanley Cavell has stressed repeatedly, nothing guarantees that the arrogation of philosophical authority, no matter how well intended, will not turn out to be an act of mere arrogance. In this way, in fact, philosophical expression and young women’s sexualized attempts at self-expression have something in common: neither can be fully controlled by an author’s intentions, and nothing guarantees that they will come off in the way their authors hope they will. –Nancy Bauer, “Authority and Arrogance: A Response”
Which, if you think about it, is what ails all human communication, but i think the problem is even more exaggerated when it comes to doing philosophy. Philosophy is best done dialogically (because every argument requires counter-arguments to move forward, and the best counter-arguments come from those who have had different experiences than you have), and if your opponent cannot accept your way of approaching a problem or understand your intentions in communicating your ideas, the argument falls flat. This is why philosophers, more than anyone else, need to find people who can understand the way they think and communicate in order to do their job.
Which makes me wonder, can real philosophy only be done between people who can “click” in this way? I’ve spent many philosophy recitations frustrated and impatient because everyone had their own way of thinking, and each think-system was so disparate to the point where we were all on different wavelengths, trying to intersect somewhere, but usually failing miserably. One person would require real life examples to contemplate any philosophical issue, and another would find such examples cumbersome and dangerously restrictive. One would be engrossed in analysis, while another would constantly divert to meta-analysis. One would subscribe to dualism, and another, to monism, and yet another, to pluralism. No one would think to budge. And why should they? Their individual frameworks were the ones that helped them think about these issues. But do you know what happens when such disparate individual frameworks gather in one room? A question is raised, a claim is made, and a silence follows while everybody tries to evaluate the claim-maker’s think-system, ultimately rejecting it in favor of their own. Repeat until time’s up. You’re lucky if you get a single counter-argument.