Usually they'll leak if the shaft itself is worn by the old seal.
If a groove forms in the shaft, a new seal won't be very effective.
If that's the case you can put a spedi-sleeve on the shaft to fix the problem.
Other than that - the shaft has to be shiny clean and free of any pitting, scratches, rust, etc.
The viscosity of the fluid you're trying to seal in plays a big role too. Any old seal/shaft will hold in 140 weight gear oil, but might leak like a sieve with engine oil. The thinner the viscosity, the more perfect the seal and surface have to be.
I hear seals can tear very easily putting them on, but I've yet to ever tear one myself even during some less than perfect installation practices.
I'd assume you're putting it on in the right direction - the lip pointing in towards the oil side.
Tap them in very gently and evenly, make sure they're not crooked.
If they're double seals, you can sometimes pack some grease between them to help seal better.
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