I've always been the "that won't work" person in whatever organization i've worked in for the last 35 years (fortunately for most organizations, I've been self-employed for the last 25 years). I think this article is needlessly negative. I view my "that won't work" contributions as the reason why it did work (eventually).

As others have noted, it's important that "that won't work" is accompanied by actual reasons (and reasoning). But it is often important to have a nattering nabob of negativity, especially with a younger cohort full of positivity and possibility and not a lot of battles fought. Most of the time, it can be made to work, but often that requires the injection of a voice mostly full of objections, problems, issues, overlooked items.