How often does a team member reach out and say “hey, this feature is not working out?”
It really depends on the studio culture and the dev team leadership. The leadership and direction establish the environment that encourages or discourages individual devs from speaking out critically. When the leadership pushes back against feedback or visibly overrules it, the working environment becomes inhospitable for that feedback. When the leadership visibly encourages and acts on feedback and criticism, the working environment encourages more.
In a studio and culture that fosters an environment where asking questions and constructive criticism is encouraged, critical feedback happens quite often. I'm currently working on one of those sort of teams - we've got our design pillars and core theme and everything we're building is in service to those pillars and theme. There have been many cases along the way where we have pivoted on specific features and systems because team members have said "this feature isn't working". We have regular play tests and regularly collect feedback from team members and others at the studio so we can gauge our direction overall. The old proverb "As iron sharpens iron, so one person sharpens another" applies - the more you have to defend your ideas and the more open you are to new ones, the better the overall result becomes.
Some studios have a very top-down structure where the leadership essentially dictates to the devs what to do and how to do it. The environment allows little room for feedback or for the recognition of mistakes. This is often when the leadership doesn't allow the workers to function autonomously or trust them to make their own choices along the way. The leaders have all the ideas and the workers execute those ideas. These studios can work when the leadership holds strong ideas from the start, but it hurts morale which can make retaining talent difficult.
Another type of studio where negative feedback is discouraged is the "toxic positivity" studio culture. This is where negative feedback is essentially ignored or dismissed, only the good things are shared and focused on. Criticism gets handwaved away and the consensus from the group encourages praise and encouragement instead. These studios are typically the "dream job" studios for new hires, working there can feel amazing because morale is high and everybody is happy. These kind of studios cultivate a false sense of security in the developers that cracks when reality inevitably strikes. In this kind of situation, everyone internally thinks everything is going great and then a project "suddenly" gets cancelled or the game fails at launch and mass layoffs ensue. This often comes as a shock to the less veteran devs in question, but makes perfect sense in hindsight.
While this may not have been the kind of answer you thought you'd get, it's helpful to understand why this is the answer I give. "This feature isn't working" is inevitable feedback as we build more and more things. We're not always going to get things right the first time around so iteration and improvement is always necessary. The working environment plays an incredibly important role in encouraging or discouraging that kind of feedback among the team members, so it makes sense that we should be able to identify the kind of environment we're in and understand the ramifications of that environment.
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