Those aren't bad or uncomfortable questions. Having as much clarity as possible helps ensure plans are on track, need adjusting, etc. right? Some folks stress over questions like this, but I think it's important to ask them, and to provide context to the folks on the receiving end.
So, I think you ask these questions with a few basic rules:
(1) Don't send an email/message with a question like that without being clear about how urgent the response is
(2) Send the question or have the conversation during the course of a "normal" work-day - instead of in the middle of someone's night/etc.
(3) Keep the emotions out of the question, hopefully helping to keep them out of the response
(4) Just always think about what might be involved in answering the question. Are you needlessly grinding someone for an answer or do you really need it?
That last one really hits home for me. Was most recently in analytics/product at a large financial services company (insurance) and am now in a start-up. But I see a common thread across the two: senior folks sometimes asking for answers/work without spending much or any time thinking about the time the receiver will spend trying to figure out that answer/work.
You want stable operations with some slack for the cases something goes wrong, you don't want ops that are constantly under stress.
Having slack and not being stressed are important, but they have nothing to do with asking uncomfortable questions.
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?
Stopping bothering me with damn fool questions would be a good start … ;-)
It's often really helpful for someone to ask these questions, especially when they have higher level context you weren't aware of.
I think those questions are good. One benefit is that it can reveal potential organisation-wide blockers:
*Getting design changes could be slow (and hence the design department may be understaffed, or inefficient communication channels)
*Maybe some processes can be ran in parallel. Someone can build the login form while the other does the database.
*They might require git access for another department that could take a while to come through.
Considering engineers' time is often the greatest cost for a technology startup, you can bet they'd be incentivised to maximise the efficiency of it.
Not only might they reveal potential blockers, but answering it also helps both parties understand they're on the same page regarding what the task entails. If the task is building a login form and the response is 'It will take two days to train the neural network', you can nip that in the bud.