ive always looked at it like this: if w=-p*v and *v=(v2-v1) then positive work must be done if we're going from a large space (v1) to a small space (v2) like with a car piston.
if a piston compresses a cylinder, then the pressure inside must be increasing. so the p from the equation w=-p*v, which represents external pressure, would most likely be decreasing, and thus, is negative.
not sure if this is the correct way of looking at it, but its the way i do. hope it helps.