“Can you do it in 4 weeks?”. “Can you do it in 2 weeks?”. In tech you are always crunched for time. Crunched to deliver more quickly.
Working with my Dev teams though I know that there is a limit. Corners get cut to deliver. More risk is assumed. Perhaps quality is compromised.
The job of a great Product Manager is to realize how much you can push boundaries to get things more quickly without sacrificing too much in other areas. That’s why when management asks for more (whether delivering more, or delivering in less time, or providing more status updates), my answer is always some variant of “how badly do you want it?” (because doing more sometimes means doing it badly).
Of course, how you phrase that question should depend on who you are talking with (CEO versus peer). 😉 Sometimes I try to be funny.