If I inform you now about the risk of missing the deadline, I look weak, ineffective, etc (even if it is better for the team) but if I wait and some situation develop which I can say will prevent us from reaching the deadline, I don't look nearly as weak.
I don't think it makes you look weak at all — putting the success of the team first shows leadership and maturity. Waiting for a situation that covers your ass but hurts the project is not likely to bode well for one's career.
I don't think it makes you look weak at all — putting the success of the team first shows leadership and maturity. Waiting for a situation that covers your ass but hurts the project is not likely to bode well for one's career.