This list is amazing, great job. Would be great to understand your rationale about 1-on1's? Also, do you guys use a tool where I can use these questions?
Very helpful list. But it would be good to see a list that is organized around objectives than the current set of categories. Ultimately, one asks these questions to get a certain outcome or information. Starting from there would be better.
From a brief skimming, this seems like a good list.
Only big asterisk is that it seems to paper over that you need a strong and trustworthy relationship to have these questions be answered sincerely and honestly. Otherwise you'll get shrugs and/or non-answers to keep you happy.
The hard part isn't what to ask, it's how to build and maintain an environment where people feel secure enough to speak their mind.