From the American Philosophical Association's Committee on the Status of Women report on CU-Boulder philosophy department, this paragraph on page 7 really jumped out at me:
The Department uses pseudo-philosophical analyses to avoid directly addressing the situation. Their faculty discussions revolve around the letter rather than the spirit of proposed regulations and standards. They spend too much time articulating (or trying to articulate) the line between acceptable and unacceptable behavior instead of instilling higher expectations for professional behavior. They spend significant time time debating footnotes and "what if" scenarios instead of discussing what they want their department to look and feel like. In other words, they spend time figuring out how to get around regulations rather than focusing on how to make the department supportive of women and family-friendly.
(Bold emphasis in original.)
What the report is pointing to here is the chronic rules-lawyering, the looking for an exception to defeat any attempts at formulating useful descriptions, the valorization of the critical project to the exclusion of even a glance towards the positive project -- in short, the kind of stuff that makes people hate being around a certain kind of philosopher (or "skeptic," or debate team champion).
The complicated hypotheticals and counterfactuals and Devil's advocacy get in the way of acknowledging actual things happening to actual people and working out something like a strategy (even if it's an imperfect one) to change things so people don't have to experience that sort of bad thing so much going forward.
Also, maybe not coincidentally, such pseudo-philosophical analyses keep the people engaging in them in their comfort zone (framing arguments, looking for counterexamples) rather than making them do the uncomfortable work of changing how they treat each other.
We can do better than that.