According to https://streetepistemology.com/publications/street_epistemology_the_basics , street epistemology is a "conversational technique" which is intended to be "a more productive and positive alternative to debates and arguments." Street epistemologists assume a role similar to Socrates in Plato's dialogues, asking questions of his interlocutor to try to create a realisation of ignorance in them. The goal of street epistemology is to find incoherences in people's beliefs, and to convince them of the value of "scepticism."
A street epistemologist tries to remain calm and pleasant throughout the entire interaction, and to build rapport at the beginning in order to make their interlocutor comfortable with the exchange. After introductions and rapport are established,they can ask their interlocutor to identify a belief and give an approximate level of confidence in it (on a scale of 1 to 10). The early stages of the conversation, after identifying the belief, are devoted to making the belief clear and precise so that there is as little ambiguity as possible, and less wiggle room if and when incoherences are found. Terms are defined, clarifying questions are asked and answered. To confirm that the belief is understood, before trying to undermine it, the street epistemologist will try to give a paraphrase of the view that his interlocutor finds charitable and acceptable.
Having pinpointed what the claim is, the street epistemologist then asks which methods the interlocutor used to arrive at their confidence level in this belief. This is the very first question in what might be called the cross-examination stage, and it reveals what sort of incoherence is being sought in these conversations. Street epistemology is all about finding poorly articulated or unarticulated spots in people's epistemological views. One the interlocutor has given a few answers and it comes time to dive into them, the website recommends focusing only on "one or two" of the methods listed, ideally those that are identified as most important. The idea here is to ask many questions about the methods and sources of evidence, hoping that at some point there will be a stumper that causes the interlocutor to notice mistakes or incoherence in their thought. Whether the street epistemologist succeeds is identified partly by observing their body language during the interaction: the website mentions, for example, that looking up in thought to avoid eye contact might be a sign.
Crucially, during this whole process the street epistemologist is told to avoid talking about the content of the beliefs or the particulars of the evidence. Again, the point is to find holes in the interlocutor's epistemology, not per se with the belief itself. The conversation is a step removed from the belief, instead focusing on examining the epistemology on which the belief is supposedly based. For that reason, street epistemologists are also instructed to avoid presenting additional evidence or advancing arguments against the interlocutor's position. To do any of this is described on the website as getting "pulled in the weeds" and "sidetracked." The questions and of the conversation should only be about the one or two methods chosen earlier.
That's enough of a sketch that I can dive into my thoughts. Street epistemology strikes me as misguided in a couple of ways. First, because it treats scepticism as a positive position or worldivew, abstracted from the intentional content , rather than an attitude toward particular beliefs or proposals. ("Sceptical about what?" "Oh, just sceptical in general.") Second, because it assumes that people's ability to articulate and defend epistemological methods has any special bearing on the warrant for their belief.
On the first, we've already seen that people who practice street epistemology have the explicit aim of spreading scepticism, and that in doing so they consider dealing with the particular content of the beliefs "getting stuck in the weeds." The mode of conversation, the Socratic chain of questions and answers, is abused in order to avoid having to deal with the particular evidence or content. Usually, someone is sceptical toward some belief for some reason. Those reasons will normally have to do with the content of the belief, the associated evidence or arguments, and so forth. Yet street epistemology suggests, by what it chooses to ask about and through the premises of the questions, that people should be sceptical that they can know anything. It suggests that the methods they use are so faulty that knowing the particulars of the belief is extraneous information.
It is only after the series of questions successfully undermine the interlocutor's sense of their epistemic foundations, not just for the belief in question, but in general, that the conversation ever goes back to the particulars and context of the initial belief. And then, it is only to point out that the interlocutor's responses to the questions imply that it is unwarranted. The problem with this is that in any earnest form of enquiry, the relevant context of the particular judgements has to be considered from the very beginning. A claim, even if successful, that one of several methods was faulty or unreliable does not itself touch on the veracity of the belief.
The point here is analogous to one often made about logical fallacies. While it may be true that affirming the consequent is invalid, it does not follow that any instance of affirming the consequent is unsound. In order to determine that, we would have to consider the content of the premises and the balance of the evidence for or against them. Indeed, going into those details is also necessary to determine whether the particular method in this case was faulty. Reconstructing an argument presented in natural language into a symbolic form requires grappling with the meaning of the claims. Logical structure can be discerned only by knowing the meaning and content.
On the second issue, it may be the case that the interlocutor has never made their methods of knowing sufficiently explicit to articulate them accurately in a conversation, if they are even aware of vaguely what those methods are. It depends on how experienced they are at thinking about the particular topic at hand. Because of this, they might mischaracterise the relevant methods in order to provide a enough detail to satisfy the norms of the conversation. Asking a relatively intellectually inexperienced person (on the topic at hand) to elaborate on their methods is a bit like trying to ask a novice at the gym why he leaned forward when going down into a squat, and whether that was good or bad. There are definite reasons that any more experienced powerlifter will perceive right away, but the novice won't know where to look in his experience to find the answer (although it is there, in his experience).
Rather than asking them outright to give explicit reasons for a belief for the purpose of questioning them, it would be much better to have them give several minutes of uninterrupted, free-association thoughts about the subject, and then try to tease out their reasoning from there. This closely resembles the best practices in witness interviews developed by forensic psychologists. It's the best way to ensure that you are not relying on a potentially non-existent explicit understanding in your questions, and to avoid biasing their statement about the beliefs and evidence with the wording and direction of your questions.
This gets at a broader point which people tend not to consider, which is that most forms of theoretical knowledge are more like the knowledge of how to play the piano than they are like knowledge of what you ate for breakfast. They are driven by craft, which is passed down by both written and oral traditions through training and schooling.
Training in biology, for example, involves spending time having the best techniques, mnemonics, and interpretations of the relevant material or activity explained to you by experts who have already mastered them to some degree. Learning and remembering facts is part of it, but there is also skill and experienced judgement in how a biologist designs an experiment, in how they set up the laboratory equipment to conduct it, and in how they interpret and organise the results for publication. There needs to be a sense, at every step, of what's appropriate, what's relevant, what's fruitful, and so forth. This also applies to our ability to use the five senses in extremely normal ways. Something as quintessential as noticing what's in your visual field is an activity which you can spend your entire lifetime honing and teaching, as visual artists do.
Street epistemology tries very hard to be neutral in several ways: with respect to evidence, arguments, the tone and tenor of the conversation, and even the particular methods that are called into question. One motivation behind this is that the conversation is not about the street epistemologists' views, whether epistemic or in terms of the content of the belief in question. The conversation is supposed to be exclusively about the interlocutor's epistemic methods relative to one of their views, methods which are explored in such a way that their internal contradictions reveal themselves over the course of impartial questions.
What I've tried to argue, though, is that street street epistemology smuggles in many assumptions about epistemology. It is hardly neutral about it in the way it assumes and requires. By avoiding the context and content of the beliefs, street epistemology adopts a view in which knowledge is a nexus of propositions connected by chains of reasoning. These chains are formed by "epistemic methods" (analogous with proposed rules of inference) which may or may not be reliable (analogous with valid). Someone is warranted to believe a proposition only if they can show that they arrived at it by a reliable method. Because of this, people of varying levels of skill and practice in the relevant activities are held to the same epistemic expectations. They are all equally expected to articulate their beliefs in such a way that they can identify, not only the evidence for them, but also some methods used to obtain and assess the evidence. They must also be able to defend these methods as generally reliable, when abstracted from the context of the particular belief. Even if this standard were good, which I hope I have at least called into question, this would be unreasonable. People with little to no ability to engage in epistemological discourse may still be warranted to have beliefs.
Street epistemology tries to characterise the conversation as conceptually neutral. Yet its take on the Socratic method bakes in so many assumptions about epistemology that it is very easy to disagree, in at least four ways: a) with the implicit epistemology, b) with the characterisation of the discourse implicit in the premises of the questions, c) with the aim and structure of the line of questioning, and d) with the content of the questions, including the content excluded by them. I provided examples of disagreement along all these lines in the discussion of craft above. To address any of these problems, though, requires stepping outside of the framework of street epistemology, because it requires that the street epistemologist, the questioner, express positive views. This ends the Socratic mode of a series of questions and answers, and gets "stuck in the weeds" of discussing the content of beliefs.
In order to seek, in good faith, to help improve an interlocutor's beliefs, I would suggest doing exactly what street epistemologists are advised against in the online guide. Go to the particulars of the belief and the relevant context. Engage directly in argument. Look at varying examples of evidence. Do not be afraid of frustration or heated exchanges, since often that is an important sign for both people that they have reached a crucial problem in the discussion that needs to be resolved. Teach relevant skills if the other person lacks them. Perhaps most important, expect the conversation to last off and on for a long time in the context of acquaintance or friendship, rather than as a one-off exchange with a stranger.