I like the idea of more transparency, and I think that opening processes can often help to reduce surprises and increase the quality of decisions.
I wonder whether a reason that people hide information, including drafts and plans, is that they are afraid that if they share information then someone will criticize them bluntly for perceived shortcomings.
I think that some courage is necessary to publish work while knowing that the work may be criticized. Public speaking is a common fear, and I wonder whether we should do more to encourage people and to train people how to present in public even when there is a risk of criticism. I have drafted some additional comments regarding this point that I may share later.
At the same time, I understand that the level of frustration in the Wikiverse can be high, and it's easy to snap at someone else who may be generally competent and have had good intentions when they share something, make a comment, or ask a question. (My guess is that if I review my own emails then I will find a few emails that I wish that I had worded differently.)
I also wonder if, collectively, we should work on improving our listening and one on one conversation skills. By listening I do not necessarily mean "create a survey and obtain analytics", although surveys and analytics can be useful tools. Listening includes hearing comments that are unpleasant, and hearing criticism that may be delivered coldly. Listening may difficult, but my guess is that improving our collective listening skills would decrease the average level of stress and frustration in the Wikiverse. People who feel heard and are given a chance to shape decisions, in my experience, sometimes become more understanding and accepting, while people who feel ignored may also feel frustrated and resentful.
Regarding WMF specifically, I think that some teams in WMF do a good job of listening, while others seem to regard listening as something that is best done exclusively through surveys and analytics. I think that surveys and analytics can be good, but also that one on one conversations are often necessary for enriching mutual understanding, for the greatest chance of producing good outcomes, and for decreasing the average level of frustration and stress in our shared environment.