* Wear on the lens mount - lenses do wear, it's inevitable and often the wear looks worse than you think, but one that is properly bashed around may have been dropped or suchlike.
* Check the contacts are clean(ish) and are all there or if spring-loaded like on Nikons, that they pop out when pressed.
* General damage such as marks the body don't neccessarily means a poor lens but marked optics can mean big problems, as can chips in the body around the front element. It could have been dropped.
* Look through the lens into the light; dust specks will show, although they don't always means the lens will perform badly (all my lenses have some specks in and work fine). Misting or mould will show up doing this.
* Check the zoom and focu rings move smoothly and don't feel gritty. Also check the rubber on these zoom rings to see if they're firmly in place.
* If the lens is high-end it may have a rubber gromit (wether seal) around the lens mount - check this is intact and not all broken and cracked.
* Check it works on your camera - the usual like stopping down, pressing the DoF preview button, taking a few shots ate different apertures and distances, zooming. Check the AF/MF slider works.
* If it's a Nikon AF-D lens you're looking at, check the aperture ring works AND locks so it can be used.
* Check it has a serial number
* If it comes with a lens hood then it should work (i.e fit on the lens). If not, knock down the price....
* If there's a filter on the front them check it comes off just to see that the thread isn't buggered.
* Check the rear element for scratches.
* Check all the screws are in the lens mount - missing screws could mean someone's been fiddling and that it could have been (badly) repaired.