You don't want unconfortable people, you want people being comfortable doing whatvthey are doing. Getting out of your comfort zone every once in a while is good, pushing it too hard is just increasing the risk of errors.
You want stable operations with some slack for the cases something goes wrong, you don't want ops that are constantly under stress.
To ask uncomfortable questions is, inherently, to make someone uncomfortable talking to you. It’s in the definition. If you ask uncomfortable questions repeatedly, people will avoid talking to you. This is normal human behaviour.
If you make people talk to you despite being uncomfortable - for example, because you are their manager - they will find a job where they are comfortable.
Potentially your business runs on destroying people. I don’t think that’s a reasonable way we want to run society.
The way /normal/ companies handle this is things like agile retrospectives - what went wrong, how can we fix it. Did we have enough people? How did /management/ fail /the people doing the work/?
If I answer “we would need X more people to get this done tomorrow instead of next week”, does that actually change anything, or do you just respond some nonsense about how you can’t afford that and we should just work harder? Basically: are /you/ willing to make sacrifices for /me/, or is it a one way street?
Hard disagree here. Being constantly asked uncomfortable questions by your manager is making you uncomfortable. In short, it is creating a toxic environment of stressed out people. And that ops org is not the most recilient one. And you want recilient ops, even if you don't care about the people.
