Not necessarily. If there is a scratch or rust pit or whatever defect, very small, less than the length of the piston stroke, that has not torn the seal, the leak would only occur as the piston is in motion past the defect. So, only a tiny bit of fluid gets pushed out. But hydraulic pressure is not what it should be at the end of the stroke because a bubble of air is displacing the space that should be occupied by fluid. Every time you pump the pedal, more air is introduced into the system. All those bubbles are rising in the system to escape through the vent hole in the cap. You've got to compress all of them to build pressure.

Try double or triple pumping the clutch and see if it shifts a bit better.
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Mr. Shannon DeWolfe -- (I've taken to using Mr. because my name tends to mislead folks on the WWW. I am a 51 year old fat man ;-) -- KD5QBL