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by grvdrm 1402 days ago
This is all about context.

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.