How to Approach a Linguistic Item

When I encounter a word, phrase, or grammatical construction in need of philosophical explanation or clarification, what do I do? Sometimes the item derives its interest from its relation to something I already find interesting, but sometimes the interest is somehow intrinsic to the item itself. I’m more interested in what I do when the latter happens. What are the questions I have to bear in mind on my first encounter, as a philosopher, with a linguistic item of self-luminescent interest?

First, I think of examples. I look for seemingly typical or non-distinctive instances of the item. I try to situate it in a handful of different sentential and pragmatic contexts.

The next question I ask is: What is useful about this item? I think there are two ways of approaching this from the armchair. The first is to ask how things change after a sentence containing the item of interest is uttered in the intuitively typical or non-distinctive pragmatic contexts. What do I imagine would happen after the utterance? How might an interlocutor respond? What is true now of speaker and listener that was not true before?

The second approach is to ask what we would lose if we were not to allow this (or any heteronymous substitute) into our speech. On this approach, what I imagine is more a whole linguistic and theoretical world than a set of particular speech situations. For instance, would we fail to mark an important distinction? Would we lose some pragmatic tool, some ability (very broadly speaking) to change the social status of people or things? Would we not be able to express an interesting theory?

The first approach to the question of usefulness tells us what actual linguistic facts there are for an analysis or explication of the item to capture. The second approach tells us why it is worth capturing it. Both of these approaches are profitably initiated and conducted from the armchair, but both are also susceptible to experimental and observational test.

Is this it? What am I missing?