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What does your manager say to your philosophy?
She's known, but really has never said anything. I just know that she wants yes people and that's just not me and I don't want my reports to be yes people either.
Depending on their personality they may just need to hear yes to their request straight away. Once out of that situation if you come back to them and say something along the lines of “I’ve been working on your request and a few items come up, in regards to X Y Z and impact 123… my suggestion to is ….” This way your boss feels they have initial direction and you are now including them in the solution and having your say. Works well with the driver type personality.