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 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.
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.