Who would feel safe flying with someone who did not have an appropriate level of confidence? In my mind, developing a student’s self-confidence should be one of the main jobs of the instructor. During periods where pilots are not actively undergoing flight training, it needs to be something they work on themselves. I can think back to several experiences which taught me this firsthand.
I didn’t want to speak up right away (I didn’t want to undermine the instructor, or speak up before my buddy did), but finally the worsening weather became too much of a concern to keep quiet. I told them that the weather was clearly deteriorating. The next day at work, some of the employees seemed to think that I should have just kept my mouth shut.