A graduate student in philosophy writes:
Would it be possible to pose the questions in the subject line to the blog? Some questions: how much tailoring to the department is necessary? How cheesy does tailoring (period) come off? Do you need to mention that you'd be excited to "collaborate" with people in the department? How do you say that without still sounding like a grad student fan? Do hiring committees really care if we mention that we want to advise the Philosophy Club? It'd be nice to hear from established academics whether they really matter, and if so, why. After all, all the information they contain could be gleaned from the CV and the research and teaching statement. And that just leads me to think that they are meant to carry all the relevant information that would let someone decide on their basis alone whether to continue looking at the rest of your dossier. If that is the case, and they are that important, then we could use a little more guidance.
To be clear, placement officers in my program have given some advice on this, but not much. Many of the faculty in my program come from a time when cover letters were not even a thing.
There are some jobs--"open" positions at research-intensive departments, for example--where cover letters don't really matter. But for the vast majority of positions, they are important and should be responsive to the ad, especially with regard to areas the department looks to hire in. (If the ad doesn't mention the "Philosophy Club" don't mention it in the cover letter! But if you created the "Philosophy Club" for undergraduates, and you're applying to an institution where the main job is teaching undergraduates, you might mention it.) Anyway, comments are open for advice from faculty who have been involved in hiring. Submit your comment only once.