When I’ve read about these philosophers it seems often like they’re there to affirm whatever needs to be affirmed, rather than doing the philosopher’s actual role of finding extreme fault in whatever you’re doing and showing how unsound the thinking is and how the task being carried out won’t lead to the results desired etc etc

Philosophy isn't about finding fault. It's about searching for answers. Sure faults may be found, but it's somewhat meaningless without the proposition of - hopefully better - alternatives.