[JumpCrisscross]

> I can very easily rattle off lists of "why that won't work" or "what's wrong with that", but it's a challenge for me to come up with lists of "why that would work"

A framework I have found to temper this instinct involves shifting from predicting whether something will or won’t work to finding the smallest, most-plausible set of assumptions which need to be true (or false) for the idea to work. You’re still identifying potential weaknesses. But instead of resolving the question around that weakness with flippant dismissal or a gut-feel guess , you’re considering how to solve it and being explicit about the boundaries between what you know, what you could learn, and what you cannot know.

[AwaAwa]

Well said. I had much the same problem, and all it took to appear more positive, was to distill the message down to "This is how it will work", rather than "This won't work no way, no how".

(I cringe inside, but my paycheck thanks me)